Prop-1-en-2-ylbenzene (alpha-Methylstyrene) Ranking by Asch

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477 reactions in Reaxys

2016-05-12 11h:20m:12s (EST)

477 reactions in Reaxys

2016-05-12 11h:20m:36s (EST)

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Rx-ID: 278983 View in Reaxys 1/477 Yield 97 %

Conditions & References 1 :A cumene solution (containing 0 ppm by weight of propylene oxide) containing 25percent by weight of cumyl alcohol and hydrogen were passed through a fixed bed flow reactor in which activated alumina was packed, at a rate of 1.6g/minute and 105 Ncc/minute, respectively. In addition, LHSV(Liquid Hourly Space Velocity) was 9 h-1, the pressure was 1.0 MPaG, and the temperature was 200°C. The dehydration conversion of cumyl alcohol in the obtained reaction mixture was 97percent. With aluminum oxide in isopropyl-benzene, T= 200 °C , p= 7500.75Torr , Product distribution / selectivity Patent; Sumitomo Chemical Company, Limited; EP1674439; (2006); (A1) English View in Reaxys

83 %

With copper(II) sulfate in neat (no solvent), Time= 1h, T= 95 °C , p= 25Torr Hoffman, Robert V.; Bishop, Richard D.; Fitch, Patricia M.; Hardenstein, Richard; Journal of Organic Chemistry; vol. 45; nb. 5; (1980); p. 917 - 919 View in Reaxys

80 %

With chloro-trimethyl-silane, acetic anhydride in acetonitrile, Time= 3h Kumareswaran; Gupta, Anuradha; Vankar, Yashwant D.; Synthetic Communications; vol. 27; nb. 2; (1997); p. 277 - 282 View in Reaxys

78 %

With tetrachlorosilane in chloroform, Time= 5h, Heating Firouzabadi, Habib; Iranpoor, Naser; Hazarkhani, Hassan; Karimi, Babak; Synthetic Communications; vol. 33; nb. 21; (2003); p. 3653 - 3660 View in Reaxys

75 %

With sulfuric acid, Heating Amelichev, V. A.; Nosovskii, M. V.; Saidov, G. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 51; nb. 8; (1981); p. 1879 - 1885,1613 - 1619 View in Reaxys

68 - 97 %

2; 3; 1 :It was carried out in the same manner as in Example 1 except that a cumene solution (containing 110 ppm by weight of propylene oxide) containing 25percent by weight of cumyl alcohol was used. The dehydration conversion of cumyl alcohol in the obtained reaction mixture was 97percent.; It was carried out in the same manner as in Example 1 except that a cumene solution (containing 1200 ppm by weight of propylene oxide) containing 25percent by weight of cumyl alcohol was used. The dehydration conversion of cumyl alcohol in the obtained reaction mixture was 96percent.; It was carried out in the same manner as in Example 1 except that a cumene solution (containing 12500 ppm by weight of propylene oxide) containing 25percent by weight of cumyl alcohol was used. The dehydration conversion of cumyl alcohol in the obtained reaction mixture was 68percent. With methyloxirane, aluminum oxide in isopropyl-benzene, T= 200 °C , p= 7500.75Torr , Product distribution / selectivity Patent; Sumitomo Chemical Company, Limited; EP1674439; (2006); (A1) English View in Reaxys

46 %

With methyltrioxorhenium (VII) in benzene, Time= 72h Zhu, Zuolin; Espenson, James H.; Journal of Organic Chemistry; vol. 61; nb. 1; (1996); p. 324 - 328 View in Reaxys With 1,2-benzenedicarboxylic acid, phenol Patent; Soc. Usines Chim. Rhone-Poulenc; US2866832; (1956) View in Reaxys With kieselguhr

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Sabetay; Bulletin de la Societe Chimique de France; vol. <4> 47; (1930); p. 614,617 View in Reaxys With iodine Woronkow; Broun; Karpenko; Zhurnal Obshchei Khimii; vol. 19; (1949); p. 1927,1939; ; (1950); p. 1955 View in Reaxys With organic acids, phenol Patent; Soc. Usines Chim. Rhone-Poulenc; US2866832; (1956) View in Reaxys Tissier; Grignard; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 132; (1901); p. 685 View in Reaxys With potassium peroxodisulfate Matsubara; Perkin; Journal of the Chemical Society; vol. 87; (1905); p. 671 View in Reaxys T= 250 °C , durch Ueberleiten ueber Kupfer Tiffeneau; Annales de Chimie (Cachan, France); vol. <8>10; (1907); p. 190; Annales de Chimie (Cachan, France); vol. <8>11; (1907); p. 144 View in Reaxys With acetic anhydride Danilow; Venus-Danilowa; Chemische Berichte; vol. 60; (1927); p. 1062; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 59; (1927); p. 204 View in Reaxys Tiffeneau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 134; (1902); p. 846; Annales de Chimie (Cachan, France); vol. <8> 10; (1907); p. 166 View in Reaxys Staudinger; Breusch; Chemische Berichte; vol. 62; (1929); p. 455 View in Reaxys Hurd; Webb; Journal of the American Chemical Society; vol. 49; (1927); p. 557 View in Reaxys With oxalic acid Tiffeneau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 134; (1902); p. 846; Annales de Chimie (Cachan, France); vol. <8> 10; (1907); p. 166 View in Reaxys With oxalic acid Danilow; Venus-Danilowa; Chemische Berichte; vol. 60; (1927); p. 1062; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 59; (1927); p. 204 View in Reaxys Staudinger; Breusch; Chemische Berichte; vol. 62; (1929); p. 455 View in Reaxys Hurd; Webb; Journal of the American Chemical Society; vol. 49; (1927); p. 557 View in Reaxys With hydrogenchloride, T= 120 °C , Behandeln mit Pyridin im Einschlussrohr Harries; Justus Liebigs Annalen der Chemie; vol. 390; (1912); p. 264 View in Reaxys With 3-chloro-benzenecarboperoxoic acid in dichloromethane, 1.) -60 deg C, 3.5 h, 2.) room temperature, 20 h Hino, Tohru; Yamaguchi, Hitoshi; Matsuki, Kenji; Nakano, Kumiko; Sodeoka, Mikiko; Nakagawa, Masako; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 1; (1983); p. 141 - 146

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View in Reaxys With sulfuric acid in water, T= 25 °C Moodie, Roy B.; Richards, Stuart N.; Thorne, Melanie P.; Journal of the Chemical Society, Chemical Communications; (1987); p. 870 - 871 View in Reaxys With 2,6-Di-tert-butyl-4-methylphenyl-2-hydroxyphenyl-phosphatphosphol in chlorobenzene, Rate constant Schwertlick, K.; Rueger, C.; Noack, R.; Journal fuer Praktische Chemie (Leipzig); vol. 324; nb. 5; (1982); p. 697 705 View in Reaxys With sulfuric acid in water, T= 25 °C , Equilibrium constant, Rate constant Moodie, Roy B.; Richards, Stuart N.; Thorne, Melanie P.; Journal of the Chemical Society, Chemical Communications; (1987); p. 870 - 871 View in Reaxys With sulfuric acid in various solvent(s), T= 80 °C , Kinetics, Further Variations: Temperatures Gagarin; Mamedov; Kharlampidi; Petroleum Chemistry; vol. 42; nb. 3; (2002); p. 187 - 191 View in Reaxys With isopropyl-benzene, sulfuric acid, T= 110 °C , Kinetics, Further Variations: Reagents, Temperatures Mamedov; Gagarin; Kharlampidi; Russian Journal of Applied Chemistry; vol. 75; nb. 4; (2002); p. 585 - 588 View in Reaxys With toluene-4-sulfonic acid in benzene Peppe, Clovis; Lang, Ernesto Schulz; De Andrade, Fabiano Molinos; De Castro, Lierson Borges; Synlett; nb. 10; (2004); p. 1723 - 1726 View in Reaxys With hydrogenchloride, T= 325.2 - 386.2 °C , Kinetics, Further Variations: HCl pressure; initial pressure of title comp. Rasse, Rafael J.; Dominguez, Rosa M.; Herize, Armando; Tosta, Maria; Brusco, Doris; Chuchani, Gabriel; Journal of Physical Organic Chemistry; vol. 20; nb. 1; (2007); p. 44 - 48 View in Reaxys 43.9 % Chromat.

With hydrogenchloride, Time= 0.266667h, T= 340.5 °C Rasse, Rafael J.; Dominguez, Rosa M.; Herize, Armando; Tosta, Maria; Brusco, Doris; Chuchani, Gabriel; Journal of Physical Organic Chemistry; vol. 20; nb. 1; (2007); p. 44 - 48 View in Reaxys Reaction Steps: 2 1: HCl gas 2: pyridine / acetonitrile / 55 °C With pyridine, hydrogenchloride in acetonitrile Balachandran; Santhosh Kumar; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 44; nb. 8; (2005); p. 1731 - 1734 View in Reaxys Reaction Steps: 2 1: 1.) KH / 1.) ether, mineral oil, 15 min, 2.) ether, up to r.t. 2: 15 percent / BF3*Et2O / pentane / 1.) -5 deg C, 15 min, 2.) up to r.t. With boron trifluoride diethyl etherate, potassium hydride in pentane Bourgeois; Montaudon; Maillard; Tetrahedron; vol. 49; nb. 12; (1993); p. 2477 - 2484 View in Reaxys Reaction Steps: 2 1: HCl / Eingiessen des Reaktionsproduktes in Eiswasser

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2: pyridine With pyridine, hydrogenchloride Klages; Chemische Berichte; vol. 35; (1902); p. 2649; Chemische Berichte; vol. 39; (1906); p. 2591 View in Reaxys 0.1 - 11.8 %

1; 2; 3 : Example 1 40 Grams of a mixed solution composed of 5percent by weight of cumyl alcohol and 95 percent by weight of cumene as a raw material were charged in an autoclave, then stirred and heated at 136°C for 60 minutes. α-Methyl styrene was produced by dehydration of cumyl alcohol. The result is shown in Table 1.Example 2 It was carried out in the same manner as in Example 1 except that the temperature is 155°C. The result is shown in Table 1.Example 3 It was carried out in the same manner as in Example 1 except that the temperature is 184°C. The result is shown in Table 1.Comparative Example 1 It was carried out in the same manner as in Example 1 except that the temperature is 194°C. The result is shown in Table 1. [Table 1] Example 1Example 2Example 3Comparative Example 1Temperature heated (°C)136155184194α-MS yield(percent) *10.11.33.511.8* 1: α-Methyl styrene yield (percent) = [Amount of α-methyl styrene produced(mol)/amount of cumyl alcohol in raw material(mol)] x 100 The above Examples and Comparative Example were carried out by using the raw material described above as a bottom liquid, respectively, and it is found that when the temperature heated became 190°C orhigher, production of α -methyl styrene, in other words, production of water was remarkable. in isopropyl-benzene, Time= 1h, T= 136 - 194 °C Patent; Sumitomo Chemical Company, Limited; EP1484326; (2004); (A1) English View in Reaxys 1; 2; 3; 4 :A cumene solution (containing 200 ppm of formic acid) containing 25percent by weight of cumyl alcohol and hydrogen were passed through a fixed bed flow reactor in which an activated alumina was packed, at a rate of 1.6g/minute and 105 Ncc/minute, respectively. At this time, LHSV(Liquid Hourly Space Velocity) was 9/hour, the pressure was 1.0 MPaG, and the temperature was 200°C. The dehydration conversion of cumyl alcohol in the obtained reaction mixture was 97percent.; Example 2; It was carried out in the same manner as in Example 1 except that a cumene solution (containing 130 ppm of formic acid) containing 25percent by weight of cumyl alcohol was used. The dehydration conversion of cumyl alcohol in the obtained reaction mixture was 93percent.; Example 3; It was carried out in the same manner as in Example 1 except that a cumene solution (containing 60 ppm of formic acid) containing 25percent by weight of cumyl alcohol was used. The dehydration conversion of cumyl alcohol in the obtained reaction mixture was 85percent.; Example 4; It was carried out in the same manner as in Example 1 except that a cumene solution (containing 30 ppm of formic acid) containing 25percent by weight of cumyl alcohol was used. The dehydration conversion of cumyl alcohol in the obtained reaction mixture was 74percent.; Comparative Example 1; It was carried out in the same manner as in Example 1 except that a cumene solution (containing 5 ppm of formic acid) containing 25percent by weight of cumyl alcohol was used. The dehydration conversion of cumyl alcohol in the obtained reaction mixture was 46percent. With aluminum oxide, formic acid in isopropyl-benzene, T= 200 °C , Conversion of starting material Patent; Sumitomo Chemical Company, Limited; EP1621527; (2006); (A1) English View in Reaxys 9 : EXAMPLE 9 EXAMPLE 9 A cumene solution containing 40.2percent w/w cumene hydroperoxide, 0.65percent w/w acetophenone and 2.44percent w/w phenyldimethyl carbinol was fed at 400 ml/h to the reactor illustrated in FIG. 1 packed with 3 mm stainless steel gauze rings, the reactor being maintained at a pressure of 500 mm absolute. A solution of 1.0percent w/w sulphuric acid in acetophenone was fed as a separate stream through a common inlet with the cumene solution at such a rate that the sulphuric acid concentration in the total feed was 365 ppm. The products distilled at 140° C. and the distillate accounted for 96.7percent of the total weight fed. The phenol and acetone yields were 86.4 mole percent and 90.7 mole percent respectively and the yield of alphamethylstyrene was 3.8 mole percent. A tar containing acid was drained from the bottom of the reactor. With sulfuric acid, isopropylbenzene hydroperoxide in acetophenone Patent; BP Chemicals Limited; US4246203; (1981); (A1) English View in Reaxys

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1 :Example 1; According to the method described in the specification, an oxidization reaction solution (1) containing 31percent by weight of cumene hydroperoxide was obtained by oxidizing cumene with an oxygen-containing gas (air) in an oxidation step. An epoxidation reaction solution (2) containing mainly propylene oxide, cumyl alcohol, unreacted propylene, and cumene was obtained by passing the oxidization reaction solution and propylene through a reactor filled with a titanium-containing silicon oxide catalyst in an epoxidation step. The unreacted propylene (3) was separated and removed from the resulting reaction solution (2) to obtain a reaction solution (4) after recovering propylene. The reaction solution (4) after recovering propylene was used in the following Example 3 and Comparative Example 1.First, the reaction solution (4) after recovering propylene was separated into a fraction of a solution (5) containing mainly cumyl alcohol and cumene and a fraction containing mainly propylene oxide in a propylene oxide purification step, and then the fraction containing mainly <n="27"/>propylene oxide was distilled with a plurality of distillation columns including extraction and distillation so as to satisfy product quality to obtain a propylene oxide product. Regarding the fraction of the solution (5) containing mainly cumyl alcohol and cumene, cumyl alcohol was subjected to a dehydration reaction and a hydrogenation reaction in a hydrogenation step to obtain cumene, which was recycled to the oxidization step.Fig. 1 is a schematic flow chart described in the specification. , Dehydration Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2008/123384; (2008); (A1) English View in Reaxys With phosphorous pentoxide, vacuum distillation Prusek, Ondrej; Bures, Filip; Pytela, Oldrich; Collection of Czechoslovak Chemical Communications; vol. 74; nb. 1; (2009); p. 85 - 99 View in Reaxys 1 :Example 1 Using the apparatus as shown in FIG. 1, Example 1 was carried out. A liquid (2) (a cumene solution containing about 25percent by weight of cumyl alcohol) and a gas (3) (hydrogen) were fed through the bottom of the column (1), and the resulting mixed fluid of the gas and the liquid was flowed upward through the column. Within the column, there was provided the gas-liquid dispersing device according to the present invention comprising the plate (4) which was arranged perpendicular to the flow direction of the fluid and blocked the flow of the fluid. The plate had holes (5) for gas-liquid mixed fluid, the holes were connected to the conduits (6) extending downward from the plate, and three passages (7) for the gas per one conduit were provided through the side surface of the conduit. As was described above, in order that the positional relationship in the levels of the passages for the gas through the conduit flexibly accommodates the change in the height of the space of the gas in accordance with the change of the operation conditions and the throughput, the first passage for the gas was provided at the level of 75 mm downward from the plate, the second one was at the level of additionally 40 mm downward from the first passage and the third one was at the level of further additionally 40 mm downward from the second passage. The ratio of H/L was about 12.7, wherein height of the column (1) was H and length of conduits (6) was L.The structure of the end (8) of the lower part of the conduit had a structure which was closed by a cap. And, two small holes as the passages for the liquid per one conduit were provided through the conduit at the same level of 45 mm upward from the lower end of the conduit.The diameter of the hole of the plate was generally the same as that of the conduit.The ratio of N/S was 15/m2 wherein N is the number of the holes of the plate and S is an area [m2] of the lower surface of the plate.The linear velocity (v) of the gas-liquid mixed fluid flowing through the hole of the plate was about 2 m/s which is based on the volume of the fluid of the entrance (lower) side of the hole for the gas-liquid mixed fluid.The velocity (g) of the gas flowing through the passage for the gas provided through the side surface of the conduit was about 54 m/s which is based on the volume of the gas of the entrance side of the passage for the gas.The velocity (h) of the liquid flowing through the passage for the liquid provided through the conduit was about 6 m/s.Thus, it was confirmed that a space (with a thickness of 380 mm) containing the gas was formed by flowing the liquid and the gas at a predetermined ratio through the conduit from the down side to the upper side of the plate. The value of dPG-dPL was 8.7 kPa at this point.Above the gas-liquid dispersion device, there was provided a bed (10) of packing comprising spherical alumina catalysts (partially supporting a noble metal). Under the conditions of a catalyst bed temperature of about 200° C. to 230° C. and a column top pressure of about 1.5 MPaG to 2 MPaG, cumyl alcohol was intra-molecularly dehydrated to α-methylstylene, and α-methylstylene was successively converted to cumene by reacting with hydrogen. When the state of the gas-liquid dispersion is insufficient, there would be caused channeling in the reactor, and thereby an insufficient hydrogenation zone and an excessive hydrogenation zone would be partially formed. The formation of such zones is one of factors which worsen the loss of cumene in the hydrogenation step. Then, the state of the dispersion was evaluated by the following index. The index for the insufficient hydrogenation was a concentration of αmethylstylene at the outlet of the column (referred to as a leak-concentration of α-methylstylene). As a result, the obtained reaction product had the leak-concentration of α-methylstylene (the index for the insufficient hydrogenation) was 323 ppm by weight. In Table 1, the results of Example 1 are shown with "with dispersion plate".

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With spherical alumina catalysts (partially supporting a noble metal) in isopropyl-benzene, T= 200 - 230 °C , the gas-liquid dispersion device, Industry scale, Product distribution / selectivity Patent; Sumitomo Chemical Company, Limited; US2011/4009; (2011); (A1) English View in Reaxys Reaction Steps: 3 1: copper(l) chloride / 20 °C 2: dichloromethane / -30 °C 3: toluene / 1 h / 110 °C With copper(l) chloride in dichloromethane, toluene, 3: Chugaev type reaction Schur, Christine; Becker, Nina; Bergstraesser, Uwe; Gottwald, Thomas; Hartung, Jens; Tetrahedron; vol. 67; nb. 12; (2011); p. 2338 - 2347 View in Reaxys With C30H29N7ORu(2+)*2F6P(1-) in acetonitrile, T= 20 °C , Inert atmosphere, Irradiation Kojima, Takahiko; Nakayama, Kazuya; Sakaguchi, Miyuki; Ogura, Takashi; Ohkubo, Kei; Fukuzumi, Shunichi; Journal of the American Chemical Society; vol. 133; nb. 44; (2011); p. 17901 - 17911 View in Reaxys With dichloro bis(acetonitrile) palladium(II), p-benozquinone in hexadeuterioacetone, Time= 72h, T= 20 °C Dong, Jia Jia; Harvey, Emma C.; Faans-Mastral, Martn; Browne, Wesley R.; Feringa, Ben L.; Journal of the American Chemical Society; vol. 136; nb. 49; (2014); p. 17302 - 17307 View in Reaxys

Rx-ID: 36727416 View in Reaxys 2/477 Yield 50 %, 5 %

Conditions & References General procedure for the catalytic decarbonylation process General procedure: A mixture of freshly distilled aldehyde (1 mmol which amountsto ca. 0.8 wt.percent of the expected microemulsion), TDW (15–20 ml,90.1 wt.percent), cetyltrimethylammonium bromide (CTAB, 0.4–0.8 g, ca.2.5 wt.percent) and 1-propanol (1.2 ml, 6.6 wt. percent) was stirrer magneticallyat room temperature (25 C) until a clear transparent mixture thatscatters laser beams was formed. In some cases the addition of afew drops of 1-propanol was necessary.The sol–gel entrapped catalyst (10–200 mg) was roughly groundand placed together with 2,5-di-tertbutylhydroquinone (10 mg)and a freshly prepared microemulsion of an aldehyde in a miniautoclave equipped with a sampler through which small samplescould been removed periodically. The reaction mixture wasparched with nitrogen, stirred magnetically and heated with a controllablethermostat at the required temperature for the desiredlength of time. The reaction mixture was cooled to 20 C. With 2,5-dihydroxy-1,4-di-tert-butyl benzene, N-hexadecyl-N,N,N-trimethylammonium bromide in propan-1-ol, water, Time= 45h, T= 180 °C , Autoclave, Inert atmosphere, Green chemistry Dahoah, Shirel; Nairoukh, Zackaria; Fanun, Monzer; Schwarze, Michael; Schomaecker, Reinhard; Blum, Jochanan; Journal of Molecular Catalysis A: Chemical; vol. 380; (2013); p. 90 - 93 View in Reaxys

Rx-ID: 108067 View in Reaxys 3/477 Yield 98 %

Conditions & References With bromine in tetrachloromethane, Solvent Delgado-Abad, Thais; Martnez-Ferrer, Jaime; Reig-Lpez, Javier; Mello, Rossella; Acerete, Rafael; Asensio, Gregorio; Gonzlez-Nez, Mara Elena; RSC Advances; vol. 4; nb. 92; (2014); p. 51016 - 51021 View in Reaxys

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59 %

General procedure: Reactions were performed in a single 1'' (2.5 cm) diameter tubular reactor, 24'' (61 cm) long, with two electrically heated temperature zones of equal length. An internal thermocouple array monitored the reactor temperature at five equally spaced points. The reactor was fed via a vaporizer/preheater of similar configuration in 1/2'' (1.25 cm) diameter. The reactor was charged with CrF3-on-carbon pellets that had been previously used to exhaustion in chlorofluorination reactions. This "spent" CrF3-on-carbon was chosen for the reactor bed as it was expected to be resistant to degradation by NF3 and devoid of any oxidizing power (a control experiment on toluene, absent NF3, yielded unchanged toluene with no oxidation or disproportionation observed). The reactor bed was pre-heated to 385 °C under a flow of 50 ml/min N2. This N2 flow was maintained throughout the experiments as a precaution against pooling of reagents within the preheating system in the event of flow stoppages. A backpressure of 1 atm was maintained. The vaporizer/preheater temperature was controlled to maintain a vapor temperature 10 °C above the boiling point of the organic feedstock. The feedstock (i.e. toluene), NF3 and N2 were all fed together to the vaporizer/ preheater and through the reactor. An exotherm was always observed and the NF3 feed was controlled so as to keep the temperature of all internal thermocouples under 425 °C. Typically NF3 feeds did not exceed 50 molepercent. Generally there would be one or two thermocouples indicating the exotherm and hence the location of the reaction. Product was collected through a cold water condenser, washed with water to remove HF, neutralized with saturated NaHCO3 and dried over Na2SO4. Unreacted starting material and product fractions were separated by fractional distillation and sometimes silica gel column chromatography. With nitrogen trifluoride, T= 385 - 425 °C , p= 760.051Torr , Inert atmosphere Belter, Randolph K.; Journal of Fluorine Chemistry; vol. 132; nb. 5; (2011); p. 318 - 322 View in Reaxys

20 %

With sulfuryl dichloride, Co(II)(5,10,15,20-tetra-4-anisylporphyrin) in benzene, T= 85 °C Khanna, Vibha; Tamilselvan, Pitchiah; Kalra, Swinder Jeet Singh; Iqbal, Javed; Tetrahedron Letters; vol. 35; nb. 32; (1994); p. 5935 - 5938 View in Reaxys With steam, T= 600 °C , Leiten ueber Eisen, Kupfer, Kalium und Magnesium enthaltender Oxyd-Katalysator Patent; Standard Oil Devel. Co.; US2449004; (1944) View in Reaxys Patent; Dow Chem. Co.; US2443217; (1945) View in Reaxys Nickels et al.; Industrial and Engineering Chemistry; vol. 41; (1949); p. 563,565 View in Reaxys T= 600 - 750 °C Patent; Stanley; Minkoff; Youell; US2198185; (1937) View in Reaxys Patent; Dow Chem. Co.; US2110830; (1937) View in Reaxys Balandin; Marukjan; Doklady Akademii Nauk SSSR; vol. 48; (1945); p. 482; ; (1946); p. 4686 View in Reaxys Nickels et al.; Industrial and Engineering Chemistry; vol. 41; (1949); p. 563,565 View in Reaxys With steam, T= 600 °C , Leiten ueber Zinkoxyd-Calciumoxyd-Kontakte Patent; I.G. Farbenind.; DE550055; (1931); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 19; p. 611,613 View in Reaxys With steam, T= 600 °C , Leiten ueber Vanadin(V)-oxyd und Aluminiumoxyd Patent; Distiller Co.; US2342980; (1942) View in Reaxys With Catalyst M-Chromium oxide, T= 600 °C Nicolescu; Modestinu; Revue de Chimie, Academie de la Republique Populaire Roumaine; vol. 1; nb. 1; (1956); p. 143 View in Reaxys

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Nicolescu; Modestinu; ; nb. 9; (1956); p. 103; ; (1958); p. 19985 View in Reaxys With zinc oxide, T= 630 - 640 °C Modestinu-Nicolescu; ; vol. 7; (1959); p. 305; ; (1960); p. 14157 View in Reaxys With aluminum oxide, molybdenum, T= 400 °C , var. hydrorefining catalysts, Rate constant Lopez, Rafael; Collection of Czechoslovak Chemical Communications; vol. 48; nb. 8; (1983); p. 2269 - 2272 View in Reaxys With monoaluminum phosphate, rhodium, T= 419.9 - 579.9 °C , Ea, ΔH(excit.), ΔS(excit.), Kinetics, Thermodynamic data, Mechanism Bautista; Campelo; Garcia; Luna; Marinas; Bulletin of the Chemical Society of Japan; vol. 62; nb. 11; (1989); p. 3670 - 3674 View in Reaxys With Fe/Cr/K, T= 499.9 °C , p= 200266000Torr , selectivity and formation rate; var. temperature and pressure Smirnov; Kondrat'yev; Safronov Maltese Cross Sign; Petroleum Chemistry; vol. 37; nb. 1; (1997); p. 44 - 50 View in Reaxys 78.0 % Chromat.

With sulfur dioxide, water, magnesium o-vanadate, T= 500 °C , oxidative dehydrogenation Isagulyants; Belomestnykh; Petroleum Chemistry; vol. 39; nb. 5; (1999); p. 306 - 309 View in Reaxys Reaction Steps: 2 1: NBS, benzoyl peroxide / CCl4 / 18 h / Heating 2: p-toluolsulphonic acid With N-bromosuccinmide, meta-chloroperoxybenzoic acid, toluene-4-sulfonic acid in tetrachloromethane Ravindranath, B.; Srinivas, P.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 22; nb. 6; (1983); p. 592 - 594 View in Reaxys Reaction Steps: 2 1: dibenzoyl peroxide; dilauroyl peroxide; SO2Cl2 With sulfuryl dichloride, didodecanoyl peroxide, dibenzoyl peroxide Kharasch; Brown; Journal of the American Chemical Society; vol. 61; (1939); p. 2142,2146 View in Reaxys Reaction Steps: 2 1: benzene; dibenzoyl peroxide; dilauroyl peroxide; SO2Cl2 With sulfuryl dichloride, didodecanoyl peroxide, benzene, dibenzoyl peroxide Kharasch; Brown; Journal of the American Chemical Society; vol. 61; (1939); p. 2142,2146 View in Reaxys With tantalum containing Y zeolite, T= 349.84 °C , Inert atmosphere Trejda; Wojtaszek; Floch; Wojcieszak; Gaigneaux; Ziolek; Catalysis Today; vol. 158; nb. 1-2; (2010); p. 170 177 View in Reaxys 2.3. Catalytic measurements Cumene decomposition tests were performed for the activatedcarbon catalysts obtained from brown coal from “Konin” colliery.This process was realised by the pulse method in a glass reactorwith a fixed bed catalysts (0.05 g) at 623 K. After reaching a desiredtemperature, cumene was dosed by a microsyringe in the amountof 1 l to the reactor. The outlet of the reactor was connected to thechromatograph. The products were analysed using a FID detectorand a 3 m column packed with 5percent SE-30 deposited on ChromosorbG AW-DMCS. Helium was used as a carrier gas.

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With ammonia, carbon, Time= 4h, T= 649.84 °C , Catalytic behavior, Temperature, Reagent/catalyst Krzyzyska, Beata; Malaika, Anna; Rechnia, Paulina; Kozlowski, Mieczyslaw; Journal of Molecular Catalysis A: Chemical; vol. 395; (2014); p. 523 - 533 View in Reaxys

Rx-ID: 23426135 View in Reaxys 4/477 Yield

Conditions & References II.IIB :20.0 cc of the above Cu/Zn/Zr catalyst from IIA was crushed and sized into 6-20 mesh particles. The catalyst was mixed with 45 grams of 80 mesh silicon carbide and centered inside a 69 cm long stainless steel reactor tube between beds of 20 mesh SiC and glass wool. The reactor tube had an internal diameter of 1. 5cm. The catalyst was slowly reduced by heating the catalyst particles at a rate of 3°C per minute from 20°C to 180°C while flowing 0.05 wt. percent hydrogen in nitrogen at a rate of 10 L/Hr. The catalyst was allowed to reduce at 180°C for 2 hours and then the hydrogen content in the nitrogen was doubled every 2 hours until the gas was 3.2 wt. percent hydrogen in nitrogen. The catalyst was reduced for a final two-hour period after which the gas was switched to 99.999percent hydrogen and the reactor was pressurized with hydrogen to a gauge pressure of 290 psig (20 bar) while the catalyst bed was maintained at 180OC. The hydrogen flow rate was adjusted to 2 L/Hr. A mixture containing about 25.5 wt. percent of 2-phenyl-2-propanol (obtained from AVOCADO CHEMICAL) AND 74.5 WTpercent OF CUMENE (OBTAINED FROM ALDRICH CHEMICAL CO. ) WAS fed the reactor at a feed rate of 33.5 g/hr. while maintaining the hydrogen flow rate and a bed temperature of 180°C. After a week of operation, a sample of the reactor product was collected, dried of water and analyzed by gas chromatography. The product contained 8.1 wt. percent 2-phenyl-2propanol, 91.2 wt. percent OF CUMENE, 0.1 wt. percent alpha-methyl styrene, 0.1 wt. percent of i-propylcyclohexane and 0.5 wt. percent of cumene dimers. Stage 1: With α6H-SiC, hydrogen, Cu/Zn/Zr catalyst, T= 20 - 180 °C Stage 2: With hydrogen, T= 180 °C , p= 15001.5Torr Patent; SHELL OIL COMPANY; WO2005/5350; (2005); (A2) English View in Reaxys II.IIE :A feedstock containing about 25 wt. percent cumyl alcohol* (>98percent purity, obtained from Avocado Chemical) in 75 wt. percent cumene (>99percent purity obtained from Aldrich Chemical) was made by blending. The hydrogenolysis reaction was conducted under the conditions provided in the Table 4 below. Two hydrogen flowrates were used during the testing, 2L/Hr or 4/Hr. The results of the testing are shown in Table 5 and Table 6. As demonstrated, this fixed bed process produces a cumene product stream of about 91 wt. percent purity having 7.9 wt. percent of unconverted cumyl alcohol, 0.6 wt. percent of cumene dimers and 0.1 wt. percent OF ISOPROPYLCYCLOHEXANE as side products. With hydrogen, reduced copper chromite catalyst (G-22/2), Time= 600 - 800h, T= 180 °C , p= 15001.5Torr Patent; SHELL OIL COMPANY; WO2005/5350; (2005); (A2) English View in Reaxys II.IIC :The experiment of IIB was repeated using the copper on silica catalyst described in Example 1B (T-366) obtained from Sud Chemie. 20 cc of the catalyst was used. Due to the higher activity of the reduced T-366 catalyst, the testing was conducted at a temperature of 150°C. After 200 hours of operation, the dried product contained 9.7 wt. percent 2-phenyl-2- propanol, 88.4 WT. percent of cumene, 0.1 wt. percent alpha-methyl styrene, 0.1 wt. percent of iPROPYLCYCLOHEXANE and 1.7 wt. percent of cumene dimers. When operated at 180°C, the product contained less than 5 wt. percent 2-phenyl-2-propanol. With hydrogen, reduced copper on silica (T-366) catalyst, T= 150 °C , p= 15001.5Torr Patent; SHELL OIL COMPANY; WO2005/5350; (2005); (A2) English View in Reaxys

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Br–

P+ O

Rx-ID: 3383182 View in Reaxys 5/477 Yield 89 %

Conditions & References Stage 1: With potassium tert-butylate in tetrahydrofuran, Time= 0.75h, T= 0 °C , Inert atmosphere Stage 2: in tetrahydrofuran, Time= 16h, T= 0 - 20 °C , Inert atmosphere Tripathi, Chandra Bhushan; Mukherjee, Santanu; Angewandte Chemie - International Edition; vol. 52; nb. 32; (2013); p. 8450 - 8453; Angew. Chem.; vol. 125; nb. 32; (2013); p. 8608 - 8611,4 View in Reaxys

53 %

With potassium tert-butylate in benzene, 1.) 0 deg C - 4 deg C, 2 h, 2.) r.t., 72 h Dehmlow, Eckehard V.; Barahona-Naranjo, Simon; Journal of Chemical Research, Miniprint; nb. 5; (1981); p. 1748 - 1762 View in Reaxys With sodium hydride, dimethyl sulfoxide, 1) 1 h, r.t. 2) overnight, r.t., Yield given. Multistep reaction Pine; Shen; Hoang; Synthesis; nb. 2; (1991); p. 165 - 167 View in Reaxys With n-butyllithium, 1.) ether, room temperature, 2.) room temperature, 15 h, Yield given. Multistep reaction Adlercreutz, Patrick; Magnusson, Goeran; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 34; nb. 9; (1980); p. 647 - 652 View in Reaxys Stage 1: With potassium tert-butylate in diethyl ether, Time= 1h, Inert atmosphere Stage 2: in diethyl ether, Inert atmosphere Phan, Diem H. T.; Kou, Kevin G. M.; Dong, Vy M.; Journal of the American Chemical Society; vol. 132; nb. 46; (2010); p. 16354 - 16355 View in Reaxys Stage 1: With n-butyllithium in diethyl ether, Time= 3h, T= 0 °C , Inert atmosphere Stage 2: in diethyl ether, Reflux, Inert atmosphere, Wittig reaction Schneider, Jakob F.; Lauber, Markus B.; Muhr, Vanessa; Kratzer, Domenic; Paradies, Jan; Organic and Biomolecular Chemistry; vol. 9; nb. 11; (2011); p. 4323 - 4327 View in Reaxys Stage 1: With n-butyllithium in diethyl ether, hexane, Time= 1h, Inert atmosphere Stage 2: in diethyl ether, hexane, Time= 24h, T= 20 °C , Inert atmosphere, Wittig reaction Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576 View in Reaxys With potassium tert-butylate in tetrahydrofuran, Time= 16h, T= 0 - 20 °C , Inert atmosphere Tripathi, Chandra Bhushan; Mukherjee, Santanu; Organic Letters; vol. 16; nb. 12; (2014); p. 3368 - 3371 View in Reaxys With n-butyllithium in tetrahydrofuran, Time= 48h, T= 0 - 20 °C Zhang, Hang; Wang, Bo; Yi, Heng; Zhang, Yan; Wang, Jianbo; Organic Letters; vol. 17; nb. 13; (2015); p. 3322 3325 View in Reaxys Stage 1: With n-butyllithium in tetrahydrofuran, hexane, Time= 0.5h, T= -78 °C Stage 2: in tetrahydrofuran, T= -78 - 20 °C

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Vom Stein, Thorsten; Perz, Manuel; Dobrovetsky, Roman; Winkelhaus, Daniel; Caputo, Christopher B.; Stephan, Douglas W.; Angewandte Chemie - International Edition; vol. 54; nb. 35; (2015); p. 10178 - 10182; Angew. Chem.; vol. 54; (2015); p. 10178 - 10182,5 View in Reaxys With potassium tert-butylate Müller, Daniel S.; Marek, Ilan; Journal of the American Chemical Society; vol. 137; nb. 49; (2015); p. 15414 15417 View in Reaxys Stage 1: With potassium tert-butylate in tetrahydrofuran, Time= 0.75h, T= 0 °C , Inert atmosphere Stage 2: in tetrahydrofuran, T= 0 - 20 °C Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879 View in Reaxys

O O

Rx-ID: 2071796 View in Reaxys 6/477 Yield

Conditions & References

30 %, 23 %, 33 %, 26 %

30 %, 26 %, 33 %, 23 %

With trimethylhexadecylammonium chloride, copper dichloride in water, T= 20 - 25 °C , Irradiation, Further byproducts given Turro, Nicholas J.; Mattay, Jochen; Journal of the American Chemical Society; vol. 103; nb. 14; (1981); p. 4200 4204 View in Reaxys With copper dichloride in water, Irradiation, Further byproducts given. Title compound not separated from byproducts Turro, J. Nicholas; Mattay, Jochen; Tetrahedron Letters; vol. 21; nb. 19; (1980); p. 1799 - 1802 View in Reaxys With copper dichloride in water, Irradiation, Further byproducts given. Title compound not separated from byproducts Turro, J. Nicholas; Mattay, Jochen; Tetrahedron Letters; vol. 21; nb. 19; (1980); p. 1799 - 1802 View in Reaxys With copper dichloride in water, Irradiation, Further byproducts given. Title compound not separated from byproducts Turro, J. Nicholas; Mattay, Jochen; Tetrahedron Letters; vol. 21; nb. 19; (1980); p. 1799 - 1802 View in Reaxys

Rx-ID: 4927924 View in Reaxys 7/477 Yield 76 %, 17 %

Conditions & References With hydrogen, HRh(CO)lt;P(NC6H4)3gt;3, Time= 1.66667h, T= 79.9 °C , p= 3750.3Torr

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Trzeciak, Anna M.; Glowiak, Tadeusz; Ziolkowski, Jozef J.; Journal of Organometallic Chemistry; vol. 552; nb. 1-2; (1998); p. 159 - 164 View in Reaxys 17 %, 76 %

With hydrogen, HRh(CO)lt;P(NC6H4)3gt;3, Time= 1.66667h, T= 79.9 °C , p= 3750.3Torr Trzeciak, Anna M.; Glowiak, Tadeusz; Ziolkowski, Jozef J.; Journal of Organometallic Chemistry; vol. 552; nb. 1-2; (1998); p. 159 - 164 View in Reaxys

Rx-ID: 2011786 View in Reaxys 8/477 Yield

Conditions & References

31 %, 57 %

With phosphorus tribromide in chloroform, Time= 2h, T= 40 °C , Title compound not separated from byproducts Kamer, Paul C. J.; Nolte, Roeland J. M.; Drenth, Wiendelt; Journal of the American Chemical Society; vol. 110; nb. 20; (1988); p. 6818 - 6825 View in Reaxys

67 % Spectr., 30 % Spectr.

With triphenylphosphine in dichloromethane, Time= 0.25h, T= 20 °C Tongkate, Pratoomrat; Pluempanupat, Wanchai; Chavasiri, Warinthorn; Tetrahedron Letters; vol. 49; nb. 7; (2008); p. 1146 - 1148 View in Reaxys

O S O

Rx-ID: 24810327 View in Reaxys 9/477 Yield

Conditions & References I.a.1.2 :9.62 g of toluene-4-sulfonic acid (S)-2-phenyl-propyl ester (33.13 mmol) were dissolved in 80 ml of polyethylenglycol 400. 9.62 g of potassium fluoride (165.6 mmol) were added and the reaction mixture was stirred at 50°C for 3 days and another 2 days at 55-700C. The reaction was treated with 150 ml of saturated aqueous sodium chloride solution, extracted three times with diethyl ether, and the combined organic layers were dried over magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure. The crude product was purified via silica gel chromatography using cyclohexyane/ethyl acetate 15percent as eluent. 2.85 g of the desired product were isolated, containing ~ 25percent of the elimination side product.1H-NMR (CDCI3, 400 Hz): δ [ppm] 7.2-7.4 (m, 5H), 4.3-4.6 (several m, 2H), 3.15 (m, 1 H).1.3 (m, 3H). With potassium fluoride in polyethylenglycol 400, Time= 192h, T= 50 - 70 °C Patent; ABBOTT GMBH and CO.KG; WO2006/40177; (2006); (A1) English View in Reaxys

O O

O N H

S N

S S

S O

Rx-ID: 30461673 View in Reaxys 10/477

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Yield

Conditions & References

27 %, 78 %, 6 %

4.1 Thermal decomposition of 3-cumyloxythiazolethione 1d. A solution of 3-cumyloxythiazolethione 1d (185 mg, 0.50 mmol) in dry toluene (6 mL) was heated under reflux for 1 h. The solution was subjected to GC-analysis for identification of volatile products. α-Methylstyrene 6. Yield: 46.1 mg (78percent). Phenyl methyl ketone (7). Yield: 1.8 mg (3percent). Concentration of the solution under reduced pressure (100 --> 20 mbar, 40 °C) afforded an oil that was purified by column chromatography [elution gradient tert-butyl methyl ether:pentane = 1:1 --> tert-butyl methyl ether:acetone = 1:1 (v/v)]. 1,2-Bis-[5-(4-methoxyphenyl)-4-methylthiaz-3-yl]-disulfane (5).8 Yield: 65.0 mg (27percent), yellow solid, mp 87 °C. Rf = 0.30 for tert-butyl methyl ether:pentane = 1:1 (v/v). 1H NMR (CDCl3, 400 MHz) δ 2.44 (s, 6H), 3.83 (s, 6H), 6.93 (d, 4H, J = 9.0 Hz), 7.32 (d, 4H, J = 8.7 Hz), 13C NMR (CDCl3, 101 MHz) δ 16.1, 55.3, 114.2, 123.5, 130.4, 136.0, 149.0, 159.6, 160.4. 5-(4-Methoxyphenyl)-4-methylthiazole-2(3H)-thione8.9 Yield 6.6 mg (6percent), colorless crystals. Rf = 0.53 for tert-butyl methyl ether:acetone = 1:1 (v/v). 1H NMR (CDCl3, 400 MHz) δ 2.18 (s, 3H), 3.82 (s, 3H), 6.91 (d, 2H, J = 8.6 Hz), 7.25 (d, 2H, J = 6.6 Hz), 9.98 (s, 1H). 13C NMR (CDCl3, 101 MHz) δ 12.7, 55.3, 113.9, 114.2, 124.1, 124.8, 129.9, 159.1, 174.2. in toluene, Time= 1h, T= 110 °C , Chugaev type reaction Schur, Christine; Becker, Nina; Bergstraesser, Uwe; Gottwald, Thomas; Hartung, Jens; Tetrahedron; vol. 67; nb. 12; (2011); p. 2338 - 2347 View in Reaxys

P O

Rx-ID: 3125680 View in Reaxys 11/477 Yield

Conditions & References

76 %

With cesium fluoride in N,N-dimethyl-formamide, Time= 9h, T= 80 °C Kawashima, Takayuki; Ishii, Takafumi; Inamoto, Naoki; Chemistry Letters; (1983); p. 1375 - 1378 View in Reaxys

76 %

With water, cesium fluoride in N,N-dimethyl-formamide, Time= 9h, T= 80 °C , Elimination Kawashima, Takayuki; Ishii, Takafumi; Inamoto, Naoki; Tokitoh, Norihiro; Okazaki, Renji; Bulletin of the Chemical Society of Japan; vol. 71; nb. 1; (1998); p. 209 - 219 View in Reaxys

I O

Rx-ID: 3382492 View in Reaxys 12/477 Yield 90 %

Conditions & References With titanium tetrachloride, zinc in tetrahydrofuran, Time= 0.5h, T= 25 °C Hibino, Jun-ichi; Okazoe, Takashi; Takai, Kazuhiko; Nozaki, Hitosi; Tetrahedron Letters; vol. 26; nb. 45; (1985); p. 5579 - 5580 View in Reaxys

8 % Chromat.

With zinc in tetrahydrofuran, Time= 5h, Ambient temperature, Irradiation Yamashita; Inoue; Kondo; Hashimoto; Bulletin of the Chemical Society of Japan; vol. 57; nb. 8; (1984); p. 2335 2336 View in Reaxys

Mg Cl Br

Rx-ID: 4933840 View in Reaxys 13/477

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Yield

Conditions & References

60 %

With 1-methyl-pyrrolidin-2-one, iron (III) acetylacetonate in tetrahydrofuran, Time= 0.25h, T= 15 - 20 °C Cahiez, Gerard; Avedissian, Hovsep; Synthesis; nb. 8; (1998); p. 1199 - 1205 View in Reaxys

Rx-ID: 8734927 View in Reaxys 14/477 Yield

Conditions & References

75 %, 12 % Chromat.

With 1,4-diaza-bicyclo[2.2.2]octane, tetrabutyl-ammonium chloride, bis(dibenzylideneacetone)-palladium(0) in acetonitrile, Time= 24h, T= 20 °C , Heck-type reaction Jeffery; Tetrahedron Letters; vol. 41; nb. 44; (2000); p. 8445 - 8449 View in Reaxys

Si O

Rx-ID: 9116159 View in Reaxys 15/477 Yield 63 %

Conditions & References With tetra-N-butylammonium borohydride, zinc(II) iodide, CoBr2(1,2-bis(diphenylphosphino)ethane) in dichloromethane, Time= 0.5h, T= 20 °C , neutral Diels-Alder reaction Hilt, Gerhard; Smolko, Konstantin I.; Lotsch, Bettina V.; Synlett; nb. 7; (2002); p. 1081 - 1084 View in Reaxys

Rx-ID: 27834621 View in Reaxys 16/477 Yield 83.6 %

Conditions & References 4 :Example 4: In Runs 19 to 30, the catalyst samples made using conventional extrusion technology in order to screen various acidic species as potential candidates for the layering process, set forth in Table 4 below, were screened for activity and selectivity..Zeolite beta was synthesized in accordance with the disclosure in US 5,723,710. The as synthesized beta was acid washed in the presence of ammonium salt to lower sodium below250-wppm with minimal de-alumination.[0051] UZM-4 was synthesized using the procedure described in US 6,419,895, and modified to UZM-4M in accordance with the procedure described in US 6,776,975.Specifically, the UZM-4 was treated with a ammonium hexafluorosilicate (AFS) treatment, in an ammonium ion exchange reactor, to increase the silica to alumina ratio. The effluent from the ion exchange was treated by steaming and acid extraction in the presence of ammonium nitrate to further increase the silica to alumina ratio to 15.5 to greatly improve the thermal stability of the catalyst to form UZM-4M.[0052] UZM-5 was synthesized in accordance with US 6,613,302, and then subjected to an ammonium exchange to remove sodium and formed into an extrudate.[0053] UZM-8 was synthesized in accordance with the disclosure of US 6,756,030 having a silica to alumina ratio of 20. The as synthesized UZM-8 was subjected to an ammonium ion exchange to lower the sodium contents below 250-wppm on a volatile free basis, before being formed into an extrudate. [0054] Mordenite was obtained from PQ Corporation, and was directly formulated into catalyst.[0055] MTW was synthesized in accordance with the disclosure of US 6,872,866 to obtain a catalyst with a silica to alumina ratios ranging from 20 to 45. The MTW was then formed into an extrudate, calcined, and subjected to an ammonium ion exchange. Then this product was calcined again to lower the sodium content to convert the catalyst from an ammonium salt form to an acid form.[0056] MFI with a silica to alumina ratio of 38 is commercially available from UOP.MFI with a silica to alumina ratio of 23 and 80 were obtained from PQ Corporation.[0057] Zeolite X is a commercially available from the Dow Chemical Company. The acquired material was treated to an ammonium ion exchange to lower the sodium content of the starting material. <n="20"/>[0058] Zeolite Y starting material having a silica to alumina ratio of 5.0 was obtained from the PQ Corporation. The starting material was treated to an ammonium ion exchange to remove approximately 75percent sodium. The reduced sodium product was treated by steaming at 6000C and then acid extracted in the presence of ammonium ion to increase the bulk silica alumina ratio to 8.5 and the framework silica to alumina ratio to 10 as determined by XRD. [0059] Solid phosphoric acid ready for testing can be obtained from the Innophos Corporation located in Kentucky or Houston, Texas.[0060] The zeolites were pre-

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pared for testing in the following typical manner. An amount OfAl2O3 equivalent to 15 wtpercent of total powder blend on a volatile free basis was peptized using 70 wtpercent HNO3 using a HNO3 to Al2O3 ratio (w/w) of 0.17, to form a gelatin binder. The binder was added to a powder blend consisting of one of the zeolites described above, Al2O3 and Methocel, in an amount of 0.5 wtpercent of the total powder blend as an extrusion aid in a muller. Additional water was added to the mixture Of Al2O3 binder and the powder, while mixing. Mixing was continued until a doughy consistency, suitable for extrusion, was achieved. The dough formed was extruded into 1/16" diameter pellets which were then calcined in a flowing air at approximately 550 to 6000C over a period of 1 to 4 hours. [0061] In the case of zeolite X and Y, Ludox silica was used as a binder to form extrudate. The formed extrudate was dried, calcined, ammonium exchanged to remove residual sodium inherent from Ludox silica. This material was calcined again to convert the zeolite from an ammonium form to an acidic form (proton).[0062] In the case of MFI(38), the zeolite was formed into a sphere using AlPO4 binder at 67/33 zeolite/binder formulation following an oil dropping technique. [0063] Run 19 utilized a zeolite beta having a composition as specified in Table 4. Runs 20-30 utilized acidic materials other than beta zeolite as specified in Table 4. The catalysts were tested using the following experimental set up. Approximately 4 gms of a 20-40 mesh catalyst was added to 36 cc of a 1 :1 molar mixture of acetone/phenol in a 50 cc stirred glass vessel operating as a continuous stirred tank reactor (CSTR) system to simulate the environment of a commercial decomposer reactor. The temperature of the mixture is then raised to 55°C to 7O0C and approximately 4 gms of an 85 wtpercent CHP concentrate solution derived from a commercial phenol unit (see reference numeral 21 of FIG. 1) was fed as a source of fresh CHP into the reaction mixture in 30 seconds. Reaction products and <n="21"/>temperatures were monitored during the course of the runs to determine the extent of the reaction and the product selectivity over approximately 25 minutes of total reaction time. Continuous circulation of the reaction products was maintained throughout the course of the run to control the strong exothermic heat of reaction that occurs and to simulate CSTR reactor conditions. Results obtained are described as followed with detailed catalysts and product yields and selectivities shown in the Table 4 at a reaction time of 25 minutes. [0064] Run 19 utilizing beta zeolite showed good activity and selectivity as an unlayered material which was subjected to further enhancement using the layering process demonstrated in Example 3. Runs 20 to 24 also showed good activity and selectivity as unlayered materials and is expected to be further enhanced using the layering process demonstrated in Example 3. [0065] Run 20 utilizing a material known as solid phosphoric acid or SPA is a non- zeolitic material that, when layered, would further enhance its performance. Runs 25-30 utilizing MFI, X and Y zeolites are alternative acidic materials such as SAPO-11 described previously in Example 3 that would not likely be enhanced sufficiently by the layering process to be acceptable candidates for the CHP decomposition process due to low activity and selectivity demonstrated in the screening process of Example 4.[0066] Best results observed in this testing are better than any known commercial decomposer operation using trace sulfuric acid with AMS yields ranging from 78 to 81percent and <n="22"/>an overall cumene/ phenol consumption ratio of 1.31. Note that Run 5 showed an AMS yield in excess of 86percent which is equivalent to an overall cumene/phenol consumption ratio of 1.29 if the resultant AMS is hydrogenated and recycled as cumene back to the oxidation section of the process which is typically what is practiced in commercial operation. The only way, known to the inventors hereof, to achieve such a yield with the conventional sulfuric acid technology is to use acetone recycled as a diluent in the decomposer section (at molar ratio significantly greater than 1) which would be at an added cost and is typically difficult to justify. With UZM-4M layered γ-alumina, Time= 0.416667h, T= 55.1 °C , Product distribution / selectivity Patent; UOP LLC; WO2008/83064; (2008); (A1) English View in Reaxys 82.9 %

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lyst from an ammonium salt form to an acid form.[0056] MFI with a silica to alumina ratio of 38 is commercially available from UOP.MFI with a silica to alumina ratio of 23 and 80 were obtained from PQ Corporation.[0057] Zeolite X is a commercially available from the Dow Chemical Company. The acquired material was treated to an ammonium ion exchange to lower the sodium content of the starting material. <n="20"/>[0058] Zeolite Y starting material having a silica to alumina ratio of 5.0 was obtained from the PQ Corporation. The starting material was treated to an ammonium ion exchange to remove approximately 75percent sodium. The reduced sodium product was treated by steaming at 6000C and then acid extracted in the presence of ammonium ion to increase the bulk silica alumina ratio to 8.5 and the framework silica to alumina ratio to 10 as determined by XRD. [0059] Solid phosphoric acid ready for testing can be obtained from the Innophos Corporation located in Kentucky or Houston, Texas.[0060] The zeolites were prepared for testing in the following typical manner. An amount OfAl2O3 equivalent to 15 wtpercent of total powder blend on a volatile free basis was peptized using 70 wtpercent HNO3 using a HNO3 to Al2O3 ratio (w/w) of 0.17, to form a gelatin binder. The binder was added to a powder blend consisting of one of the zeolites described above, Al2O3 and Methocel, in an amount of 0.5 wtpercent of the total powder blend as an extrusion aid in a muller. Additional water was added to the mixture Of Al2O3 binder and the powder, while mixing. Mixing was continued until a doughy consistency, suitable for extrusion, was achieved. The dough formed was extruded into 1/16" diameter pellets which were then calcined in a flowing air at approximately 550 to 6000C over a period of 1 to 4 hours. [0061] In the case of zeolite X and Y, Ludox silica was used as a binder to form extrudate. The formed extrudate was dried, calcined, ammonium exchanged to remove residual sodium inherent from Ludox silica. This material was calcined again to convert the zeolite from an ammonium form to an acidic form (proton).[0062] In the case of MFI(38), the zeolite was formed into a sphere using AlPO4 binder at 67/33 zeolite/binder formulation following an oil dropping technique. [0063] Run 19 utilized a zeolite beta having a composition as specified in Table 4. Runs 20-30 utilized acidic materials other than beta zeolite as specified in Table 4. The catalysts were tested using the following experimental set up. Approximately 4 gms of a 20-40 mesh catalyst was added to 36 cc of a 1 :1 molar mixture of acetone/phenol in a 50 cc stirred glass vessel operating as a continuous stirred tank reactor (CSTR) system to simulate the environment of a commercial decomposer reactor. The temperature of the mixture is then raised to 55°C to 7O0C and approximately 4 gms of an 85 wtpercent CHP concentrate solution derived from a commercial phenol unit (see reference numeral 21 of FIG. 1) was fed as a source of fresh CHP into the reaction mixture in 30 seconds. Reaction products and <n="21"/>temperatures were monitored during the course of the runs to determine the extent of the reaction and the product selectivity over approximately 25 minutes of total reaction time. Continuous circulation of the reaction products was maintained throughout the course of the run to control the strong exothermic heat of reaction that occurs and to simulate CSTR reactor conditions. Results obtained are described as followed with detailed catalysts and product yields and selectivities shown in the Table 4 at a reaction time of 25 minutes. [0064] Run 19 utilizing beta zeolite showed good activity and selectivity as an unlayered material which was subjected to further enhancement using the layering process demonstrated in Example 3. Runs 20 to 24 also showed good activity and selectivity as unlayered materials and is expected to be further enhanced using the layering process demonstrated in Example 3. [0065] Run 20 utilizing a material known as solid phosphoric acid or SPA is a non- zeolitic material that, when layered, would further enhance its performance. Runs 25-30 utilizing MFI, X and Y zeolites are alternative acidic materials such as SAPO-11 described previously in Example 3 that would not likely be enhanced sufficiently by the layering process to be acceptable candidates for the CHP decomposition process due to low activity and selectivity demonstrated in the screening process of Example 4.[0066] Best results observed in this testing are better than any known commercial decomposer operation using trace sulfuric acid with AMS yields ranging from 78 to 81percent and <n="22"/>an overall cumene/ phenol consumption ratio of 1.31. Note that Run 5 showed an AMS yield in excess of 86percent which is equivalent to an overall cumene/phenol consumption ratio of 1.29 if the resultant AMS is hydrogenated and recycled as cumene back to the oxidation section of the process which is typically what is practiced in commercial operation. The only way, known to the inventors hereof, to achieve such a yield with the conventional sulfuric acid technology is to use acetone recycled as a diluent in the decomposer section (at molar ratio significantly greater than 1) which would be at an added cost and is typically difficult to justify. With mordenite layered γ-alumina, Time= 0.416667h, T= 60.8 °C , Product distribution / selectivity Patent; UOP LLC; WO2008/83064; (2008); (A1) English View in Reaxys 72.3 %

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ammonium nitrate to further increase the silica to alumina ratio to 15.5 to greatly improve the thermal stability of the catalyst to form UZM-4M.[0052] UZM-5 was synthesized in accordance with US 6,613,302, and then subjected to an ammonium exchange to remove sodium and formed into an extrudate.[0053] UZM-8 was synthesized in accordance with the disclosure of US 6,756,030 having a silica to alumina ratio of 20. The as synthesized UZM-8 was subjected to an ammonium ion exchange to lower the sodium contents below 250-wppm on a volatile free basis, before being formed into an extrudate. [0054] Mordenite was obtained from PQ Corporation, and was directly formulated into catalyst.[0055] MTW was synthesized in accordance with the disclosure of US 6,872,866 to obtain a catalyst with a silica to alumina ratios ranging from 20 to 45. The MTW was then formed into an extrudate, calcined, and subjected to an ammonium ion exchange. Then this product was calcined again to lower the sodium content to convert the catalyst from an ammonium salt form to an acid form.[0056] MFI with a silica to alumina ratio of 38 is commercially available from UOP.MFI with a silica to alumina ratio of 23 and 80 were obtained from PQ Corporation.[0057] Zeolite X is a commercially available from the Dow Chemical Company. The acquired material was treated to an ammonium ion exchange to lower the sodium content of the starting material. <n="20"/>[0058] Zeolite Y starting material having a silica to alumina ratio of 5.0 was obtained from the PQ Corporation. The starting material was treated to an ammonium ion exchange to remove approximately 75percent sodium. The reduced sodium product was treated by steaming at 6000C and then acid extracted in the presence of ammonium ion to increase the bulk silica alumina ratio to 8.5 and the framework silica to alumina ratio to 10 as determined by XRD. [0059] Solid phosphoric acid ready for testing can be obtained from the Innophos Corporation located in Kentucky or Houston, Texas.[0060] The zeolites were prepared for testing in the following typical manner. An amount OfAl2O3 equivalent to 15 wtpercent of total powder blend on a volatile free basis was peptized using 70 wtpercent HNO3 using a HNO3 to Al2O3 ratio (w/w) of 0.17, to form a gelatin binder. The binder was added to a powder blend consisting of one of the zeolites described above, Al2O3 and Methocel, in an amount of 0.5 wtpercent of the total powder blend as an extrusion aid in a muller. Additional water was added to the mixture Of Al2O3 binder and the powder, while mixing. Mixing was continued until a doughy consistency, suitable for extrusion, was achieved. The dough formed was extruded into 1/16" diameter pellets which were then calcined in a flowing air at approximately 550 to 6000C over a period of 1 to 4 hours. [0061] In the case of zeolite X and Y, Ludox silica was used as a binder to form extrudate. The formed extrudate was dried, calcined, ammonium exchanged to remove residual sodium inherent from Ludox silica. This material was calcined again to convert the zeolite from an ammonium form to an acidic form (proton).[0062] In the case of MFI(38), the zeolite was formed into a sphere using AlPO4 binder at 67/33 zeolite/binder formulation following an oil dropping technique. [0063] Run 19 utilized a zeolite beta having a composition as specified in Table 4. Runs 20-30 utilized acidic materials other than beta zeolite as specified in Table 4. The catalysts were tested using the following experimental set up. Approximately 4 gms of a 20-40 mesh catalyst was added to 36 cc of a 1 :1 molar mixture of acetone/phenol in a 50 cc stirred glass vessel operating as a continuous stirred tank reactor (CSTR) system to simulate the environment of a commercial decomposer reactor. The temperature of the mixture is then raised to 55°C to 7O0C and approximately 4 gms of an 85 wtpercent CHP concentrate solution derived from a commercial phenol unit (see reference numeral 21 of FIG. 1) was fed as a source of fresh CHP into the reaction mixture in 30 seconds. Reaction products and <n="21"/>temperatures were monitored during the course of the runs to determine the extent of the reaction and the product selectivity over approximately 25 minutes of total reaction time. Continuous circulation of the reaction products was maintained throughout the course of the run to control the strong exothermic heat of reaction that occurs and to simulate CSTR reactor conditions. Results obtained are described as followed with detailed catalysts and product yields and selectivities shown in the Table 4 at a reaction time of 25 minutes. [0064] Run 19 utilizing beta zeolite showed good activity and selectivity as an unlayered material which was subjected to further enhancement using the layering process demonstrated in Example 3. Runs 20 to 24 also showed good activity and selectivity as unlayered materials and is expected to be further enhanced using the layering process demonstrated in Example 3. [0065] Run 20 utilizing a material known as solid phosphoric acid or SPA is a non- zeolitic material that, when layered, would further enhance its performance. Runs 25-30 utilizing MFI, X and Y zeolites are alternative acidic materials such as SAPO-11 described previously in Example 3 that would not likely be enhanced sufficiently by the layering process to be acceptable candidates for the CHP decomposition process due to low activity and selectivity demonstrated in the screening process of Example 4.[0066] Best results observed in this testing are better than any known commercial decomposer operation using trace sulfuric acid with AMS yields ranging from 78 to 81percent and <n="22"/>an overall cumene/ phenol consumption ratio of 1.31. Note that Run 5 showed an AMS yield in excess of 86percent which is equivalent to an overall cumene/phenol consumption ratio of 1.29 if the resultant AMS is hydrogenated and recycled as cumene back to the oxidation section of the process which is typically what is practiced in commercial operation. The only way, known to the inventors hereof, to achieve such a yield with the conventional sulfuric acid technology is to use acetone recycled as a diluent in the decomposer section (at molar ratio significantly greater than 1) which would be at an added cost and is typically difficult to justify. With UZM-8/β (70/30) layered γ-alumina, Time= 0.416667h, T= 55.1 °C , Product distribution / selectivity Patent; UOP LLC; WO2008/83064; (2008); (A1) English View in Reaxys

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66.0 %

4 :Example 4: In Runs 19 to 30, the catalyst samples made using conventional extrusion technology in order to screen various acidic species as potential candidates for the layering process, set forth in Table 4 below, were screened for activity and selectivity..Zeolite beta was synthesized in accordance with the disclosure in US 5,723,710. The as synthesized beta was acid washed in the presence of ammonium salt to lower sodium below250-wppm with minimal de-alumination.[0051] UZM-4 was synthesized using the procedure described in US 6,419,895, and modified to UZM-4M in accordance with the procedure described in US 6,776,975.Specifically, the UZM-4 was treated with a ammonium hexafluorosilicate (AFS) treatment, in an ammonium ion exchange reactor, to increase the silica to alumina ratio. The effluent from the ion exchange was treated by steaming and acid extraction in the presence of ammonium nitrate to further increase the silica to alumina ratio to 15.5 to greatly improve the thermal stability of the catalyst to form UZM-4M.[0052] UZM-5 was synthesized in accordance with US 6,613,302, and then subjected to an ammonium exchange to remove sodium and formed into an extrudate.[0053] UZM-8 was synthesized in accordance with the disclosure of US 6,756,030 having a silica to alumina ratio of 20. The as synthesized UZM-8 was subjected to an ammonium ion exchange to lower the sodium contents below 250-wppm on a volatile free basis, before being formed into an extrudate. [0054] Mordenite was obtained from PQ Corporation, and was directly formulated into catalyst.[0055] MTW was synthesized in accordance with the disclosure of US 6,872,866 to obtain a catalyst with a silica to alumina ratios ranging from 20 to 45. The MTW was then formed into an extrudate, calcined, and subjected to an ammonium ion exchange. Then this product was calcined again to lower the sodium content to convert the catalyst from an ammonium salt form to an acid form.[0056] MFI with a silica to alumina ratio of 38 is commercially available from UOP.MFI with a silica to alumina ratio of 23 and 80 were obtained from PQ Corporation.[0057] Zeolite X is a commercially available from the Dow Chemical Company. The acquired material was treated to an ammonium ion exchange to lower the sodium content of the starting material. <n="20"/>[0058] Zeolite Y starting material having a silica to alumina ratio of 5.0 was obtained from the PQ Corporation. The starting material was treated to an ammonium ion exchange to remove approximately 75percent sodium. The reduced sodium product was treated by steaming at 6000C and then acid extracted in the presence of ammonium ion to increase the bulk silica alumina ratio to 8.5 and the framework silica to alumina ratio to 10 as determined by XRD. [0059] Solid phosphoric acid ready for testing can be obtained from the Innophos Corporation located in Kentucky or Houston, Texas.[0060] The zeolites were prepared for testing in the following typical manner. An amount OfAl2O3 equivalent to 15 wtpercent of total powder blend on a volatile free basis was peptized using 70 wtpercent HNO3 using a HNO3 to Al2O3 ratio (w/w) of 0.17, to form a gelatin binder. The binder was added to a powder blend consisting of one of the zeolites described above, Al2O3 and Methocel, in an amount of 0.5 wtpercent of the total powder blend as an extrusion aid in a muller. Additional water was added to the mixture Of Al2O3 binder and the powder, while mixing. Mixing was continued until a doughy consistency, suitable for extrusion, was achieved. The dough formed was extruded into 1/16" diameter pellets which were then calcined in a flowing air at approximately 550 to 6000C over a period of 1 to 4 hours. [0061] In the case of zeolite X and Y, Ludox silica was used as a binder to form extrudate. The formed extrudate was dried, calcined, ammonium exchanged to remove residual sodium inherent from Ludox silica. This material was calcined again to convert the zeolite from an ammonium form to an acidic form (proton).[0062] In the case of MFI(38), the zeolite was formed into a sphere using AlPO4 binder at 67/33 zeolite/binder formulation following an oil dropping technique. [0063] Run 19 utilized a zeolite beta having a composition as specified in Table 4. Runs 20-30 utilized acidic materials other than beta zeolite as specified in Table 4. The catalysts were tested using the following experimental set up. Approximately 4 gms of a 20-40 mesh catalyst was added to 36 cc of a 1 :1 molar mixture of acetone/phenol in a 50 cc stirred glass vessel operating as a continuous stirred tank reactor (CSTR) system to simulate the environment of a commercial decomposer reactor. The temperature of the mixture is then raised to 55°C to 7O0C and approximately 4 gms of an 85 wtpercent CHP concentrate solution derived from a commercial phenol unit (see reference numeral 21 of FIG. 1) was fed as a source of fresh CHP into the reaction mixture in 30 seconds. Reaction products and <n="21"/>temperatures were monitored during the course of the runs to determine the extent of the reaction and the product selectivity over approximately 25 minutes of total reaction time. Continuous circulation of the reaction products was maintained throughout the course of the run to control the strong exothermic heat of reaction that occurs and to simulate CSTR reactor conditions. Results obtained are described as followed with detailed catalysts and product yields and selectivities shown in the Table 4 at a reaction time of 25 minutes. [0064] Run 19 utilizing beta zeolite showed good activity and selectivity as an unlayered material which was subjected to further enhancement using the layering process demonstrated in Example 3. Runs 20 to 24 also showed good activity and selectivity as unlayered materials and is expected to be further enhanced using the layering process demonstrated in Example 3. [0065] Run 20 utilizing a material known as solid phosphoric acid or SPA is a non- zeolitic material that, when layered, would further enhance its performance. Runs 25-30 utilizing MFI, X and Y zeolites are alternative acidic materials such as SAPO-11 described previously in Example 3 that would not likely be enhanced sufficiently by the layering process to be acceptable candidates for the CHP decomposition process due to low activity and selectivity demonstrated in the screening process of Example 4.[0066] Best results observed in this testing are better than any known commercial decomposer operation using trace sulfuric acid with AMS yields ranging from 78 to 81percent and <n="22"/>an overall cumene/ phenol consumption ratio of 1.31. Note that Run 5 showed an AMS yield in excess of 86percent which is equivalent to an overall cumene/phenol consumption ratio of 1.29 if the resultant AMS is hydrogenated and recycled as cumene

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back to the oxidation section of the process which is typically what is practiced in commercial operation. The only way, known to the inventors hereof, to achieve such a yield with the conventional sulfuric acid technology is to use acetone recycled as a diluent in the decomposer section (at molar ratio significantly greater than 1) which would be at an added cost and is typically difficult to justify. With H3PO4 layered silica phosphate, Time= 0.416667h, T= 55.1 °C , Product distribution / selectivity Patent; UOP LLC; WO2008/83064; (2008); (A1) English View in Reaxys 55.6 %

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expected to be further enhanced using the layering process demonstrated in Example 3. [0065] Run 20 utilizing a material known as solid phosphoric acid or SPA is a non- zeolitic material that, when layered, would further enhance its performance. Runs 25-30 utilizing MFI, X and Y zeolites are alternative acidic materials such as SAPO-11 described previously in Example 3 that would not likely be enhanced sufficiently by the layering process to be acceptable candidates for the CHP decomposition process due to low activity and selectivity demonstrated in the screening process of Example 4.[0066] Best results observed in this testing are better than any known commercial decomposer operation using trace sulfuric acid with AMS yields ranging from 78 to 81percent and <n="22"/>an overall cumene/ phenol consumption ratio of 1.31. Note that Run 5 showed an AMS yield in excess of 86percent which is equivalent to an overall cumene/phenol consumption ratio of 1.29 if the resultant AMS is hydrogenated and recycled as cumene back to the oxidation section of the process which is typically what is practiced in commercial operation. The only way, known to the inventors hereof, to achieve such a yield with the conventional sulfuric acid technology is to use acetone recycled as a diluent in the decomposer section (at molar ratio significantly greater than 1) which would be at an added cost and is typically difficult to justify. With Y zeolite layered silica, Time= 0.416667h, T= 55.1 °C , Product distribution / selectivity Patent; UOP LLC; WO2008/83064; (2008); (A1) English View in Reaxys 34.4 %

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85 wtpercent CHP concentrate solution derived from a commercial phenol unit (see reference numeral 21 of FIG. 1) was fed as a source of fresh CHP into the reaction mixture in 30 seconds. Reaction products and <n="21"/>temperatures were monitored during the course of the runs to determine the extent of the reaction and the product selectivity over approximately 25 minutes of total reaction time. Continuous circulation of the reaction products was maintained throughout the course of the run to control the strong exothermic heat of reaction that occurs and to simulate CSTR reactor conditions. Results obtained are described as followed with detailed catalysts and product yields and selectivities shown in the Table 4 at a reaction time of 25 minutes. [0064] Run 19 utilizing beta zeolite showed good activity and selectivity as an unlayered material which was subjected to further enhancement using the layering process demonstrated in Example 3. Runs 20 to 24 also showed good activity and selectivity as unlayered materials and is expected to be further enhanced using the layering process demonstrated in Example 3. [0065] Run 20 utilizing a material known as solid phosphoric acid or SPA is a non- zeolitic material that, when layered, would further enhance its performance. Runs 25-30 utilizing MFI, X and Y zeolites are alternative acidic materials such as SAPO-11 described previously in Example 3 that would not likely be enhanced sufficiently by the layering process to be acceptable candidates for the CHP decomposition process due to low activity and selectivity demonstrated in the screening process of Example 4.[0066] Best results observed in this testing are better than any known commercial decomposer operation using trace sulfuric acid with AMS yields ranging from 78 to 81percent and <n="22"/>an overall cumene/ phenol consumption ratio of 1.31. Note that Run 5 showed an AMS yield in excess of 86percent which is equivalent to an overall cumene/phenol consumption ratio of 1.29 if the resultant AMS is hydrogenated and recycled as cumene back to the oxidation section of the process which is typically what is practiced in commercial operation. The only way, known to the inventors hereof, to achieve such a yield with the conventional sulfuric acid technology is to use acetone recycled as a diluent in the decomposer section (at molar ratio significantly greater than 1) which would be at an added cost and is typically difficult to justify. With MTW layered γ-alumina, Time= 0.416667h, T= 80.3 °C , Product distribution / selectivity Patent; UOP LLC; WO2008/83064; (2008); (A1) English View in Reaxys 24.1 %

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nium exchanged to remove residual sodium inherent from Ludox silica. This material was calcined again to convert the zeolite from an ammonium form to an acidic form (proton).[0062] In the case of MFI(38), the zeolite was formed into a sphere using AlPO4 binder at 67/33 zeolite/binder formulation following an oil dropping technique. [0063] Run 19 utilized a zeolite beta having a composition as specified in Table 4. Runs 20-30 utilized acidic materials other than beta zeolite as specified in Table 4. The catalysts were tested using the following experimental set up. Approximately 4 gms of a 20-40 mesh catalyst was added to 36 cc of a 1 :1 molar mixture of acetone/phenol in a 50 cc stirred glass vessel operating as a continuous stirred tank reactor (CSTR) system to simulate the environment of a commercial decomposer reactor. The temperature of the mixture is then raised to 55°C to 7O0C and approximately 4 gms of an 85 wtpercent CHP concentrate solution derived from a commercial phenol unit (see reference numeral 21 of FIG. 1) was fed as a source of fresh CHP into the reaction mixture in 30 seconds. Reaction products and <n="21"/>temperatures were monitored during the course of the runs to determine the extent of the reaction and the product selectivity over approximately 25 minutes of total reaction time. Continuous circulation of the reaction products was maintained throughout the course of the run to control the strong exothermic heat of reaction that occurs and to simulate CSTR reactor conditions. Results obtained are described as followed with detailed catalysts and product yields and selectivities shown in the Table 4 at a reaction time of 25 minutes. [0064] Run 19 utilizing beta zeolite showed good activity and selectivity as an unlayered material which was subjected to further enhancement using the layering process demonstrated in Example 3. Runs 20 to 24 also showed good activity and selectivity as unlayered materials and is expected to be further enhanced using the layering process demonstrated in Example 3. [0065] Run 20 utilizing a material known as solid phosphoric acid or SPA is a non- zeolitic material that, when layered, would further enhance its performance. Runs 25-30 utilizing MFI, X and Y zeolites are alternative acidic materials such as SAPO-11 described previously in Example 3 that would not likely be enhanced sufficiently by the layering process to be acceptable candidates for the CHP decomposition process due to low activity and selectivity demonstrated in the screening process of Example 4.[0066] Best results observed in this testing are better than any known commercial decomposer operation using trace sulfuric acid with AMS yields ranging from 78 to 81percent and <n="22"/>an overall cumene/ phenol consumption ratio of 1.31. Note that Run 5 showed an AMS yield in excess of 86percent which is equivalent to an overall cumene/phenol consumption ratio of 1.29 if the resultant AMS is hydrogenated and recycled as cumene back to the oxidation section of the process which is typically what is practiced in commercial operation. The only way, known to the inventors hereof, to achieve such a yield with the conventional sulfuric acid technology is to use acetone recycled as a diluent in the decomposer section (at molar ratio significantly greater than 1) which would be at an added cost and is typically difficult to justify. With X zeolite layered silica, Time= 0.416667h, T= 55.1 °C , Product distribution / selectivity Patent; UOP LLC; WO2008/83064; (2008); (A1) English View in Reaxys 21.6 - 86.9 %

3; 4 :Example 3: In Runs 1 to 18, the catalyst samples made in accordance with Examples 1 and 2 and having outer layers of varying thicknesses, set forth in Table 1 below, were screened for activity and selectivity. Runs 1-12 utilized a zeolite beta outer layer having a thickness specified in Table 1. Runs 13-16 and 18 utilized a SAPO-1 1 outer layer having a thickness specified in Table 1. Run 17 utilized an SM-3 outer layer having the thickness specified Table 1. The catalysts were tested using the following experimental set up. Approximately 4 gms of catalyst were added to 36 cc of a 1 :1 molar mixture of acetone/phenol in a 50 cc stirred glass vessel operating as a continuous stirred tank reactor (CSTR) system to simulate the environment of a commercial decomposer reactor. The temperature of the mixture is then raised to 55°C to 700C and approximately 4 gms of an 85 wtpercent CHP concentrate solution derived from a commercial phenol unit (see reference numeral 21 of FIG. 1) as a source of fresh CHP feed is injected into the reaction mixture in 30 seconds. Reaction products and temperature were monitored during the course of the runs to determine the extent of reaction and the product selectivity over an approximately 25 min of total reaction time. A continuous circulation of the reaction products was maintained throughout the course of the run to control the strong exothermic heat of reaction that occurs <n="17"/>and to simulate CSTR reactor conditions. Results obtained are described as followed with detailed catalysts and product yields and selectivities shown in the Table 1 at a reaction time of 25 minutes.The zeolite beta layered catalysts are active (Runs 1 to 12) for CHP decomposition whereas the layered SAPO-1 1 and SM-3 catalysts are inactive (Runs 13 to 18) under conditions similar to what is currently being practiced for a state-of-the-art decomposer design (e.g., 55 to 70 0C (131-158 0F) and 25 min residence time using trace sulfuric acid). It has been determined there is a minimum catalyst acidity, as measured by NH3-TPD (See Table 2), needed to catalyze the CHP decomposition reaction. The catalyst acidity should be equal to or greater than 0.36 mmoles NH3 per gram catalyst at 150 to 550 0C based on using a powder form of the outer layer material.; Example 4: In Runs 19 to 30, the catalyst samples made using conventional extrusion technology in order to screen various acidic species as potential candidates for the layering process, set forth in Table 4 below, were screened for activity and selectivity..Zeolite beta was synthesized in accordance with the disclosure in US 5,723,710. The as synthesized beta was acid washed in the presence of ammonium salt to lower sodium below250-wppm with minimal dealumination.[0051] UZM-4 was synthesized using the procedure described in US 6,419,895, and modified to

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UZM-4M in accordance with the procedure described in US 6,776,975.Specifically, the UZM-4 was treated with a ammonium hexafluorosilicate (AFS) treatment, in an ammonium ion exchange reactor, to increase the silica to alumina ratio. The effluent from the ion exchange was treated by steaming and acid extraction in the presence of ammonium nitrate to further increase the silica to alumina ratio to 15.5 to greatly improve the thermal stability of the catalyst to form UZM-4M.[0052] UZM-5 was synthesized in accordance with US 6,613,302, and then subjected to an ammonium exchange to remove sodium and formed into an extrudate.[0053] UZM-8 was synthesized in accordance with the disclosure of US 6,756,030 having a silica to alumina ratio of 20. The as synthesized UZM-8 was subjected to an ammonium ion exchange to lower the sodium contents below 250-wppm on a volatile free basis, before being formed into an extrudate. [0054] Mordenite was obtained from PQ Corporation, and was directly formulated into catalyst.[0055] MTW was synthesized in accordance with the disclosure of US 6,872,866 to obtain a catalyst with a silica to alumina ratios ranging from 20 to 45. The MTW was then formed into an extrudate, calcined, and subjected to an ammonium ion exchange. Then this product was calcined again to lower the sodium content to convert the catalyst from an ammonium salt form to an acid form.[0056] MFI with a silica to alumina ratio of 38 is commercially available from UOP.MFI with a silica to alumina ratio of 23 and 80 were obtained from PQ Corporation.[0057] Zeolite X is a commercially available from the Dow Chemical Company. The acquired material was treated to an ammonium ion exchange to lower the sodium content of the starting material. <n="20"/>[0058] Zeolite Y starting material having a silica to alumina ratio of 5.0 was obtained from the PQ Corporation. The starting material was treated to an ammonium ion exchange to remove approximately 75percent sodium. The reduced sodium product was treated by steaming at 6000C and then acid extracted in the presence of ammonium ion to increase the bulk silica alumina ratio to 8.5 and the framework silica to alumina ratio to 10 as determined by XRD. [0059] Solid phosphoric acid ready for testing can be obtained from the Innophos Corporation located in Kentucky or Houston, Texas.[0060] The zeolites were prepared for testing in the following typical manner. An amount OfAl2O3 equivalent to 15 wtpercent of total powder blend on a volatile free basis was peptized using 70 wtpercent HNO3 using a HNO3 to Al2O3 ratio (w/w) of 0.17, to form a gelatin binder. The binder was added to a powder blend consisting of one of the zeolites described above, Al2O3 and Methocel, in an amount of 0.5 wtpercent of the total powder blend as an extrusion aid in a muller. Additional water was added to the mixture Of Al2O3 binder and the powder, while mixing. Mixing was continued until a doughy consistency, suitable for extrusion, was achieved. The dough formed was extruded into 1/16" diameter pellets which were then calcined in a flowing air at approximately 550 to 6000C over a period of 1 to 4 hours. [0061] In the case of zeolite X and Y, Ludox silica was used as a binder to form extrudate. The formed extrudate was dried, calcined, ammonium exchanged to remove residual sodium inherent from Ludox silica. This material was calcined again to convert the zeolite from an ammonium form to an acidic form (proton).[0062] In the case of MFI(38), the zeolite was formed into a sphere using AlPO4 binder at 67/33 zeolite/binder formulation following an oil dropping technique. [0063] Run 19 utilized a zeolite beta having a composition as specified in Table 4. Runs 20-30 utilized acidic materials other than beta zeolite as specified in Table 4. The catalysts were tested using the following experimental set up. Approximately 4 gms of a 20-40 mesh catalyst was added to 36 cc of a 1 :1 molar mixture of acetone/phenol in a 50 cc stirred glass vessel operating as a continuous stirred tank reactor (CSTR) system to simulate the environment of a commercial decomposer reactor. The temperature of the mixture is then raised to 55°C to 7O0C and approximately 4 gms of an 85 wtpercent CHP concentrate solution derived from a commercial phenol unit (see reference numeral 21 of FIG. 1) was fed as a source of fresh CHP into the reaction mixture in 30 seconds. Reaction products and <n="21"/>temperatures were monitored during the course of the runs to determine the extent of the reaction and the product selectivity over approximately 25 minutes of total reaction time. Continuous circulation of the reaction products was maintained throughout the course of the run to control the strong exothermic heat of reaction that occurs and to simulate CSTR reactor conditions. Results obtained are described as followed with detailed catalysts and product yields and selectivities shown in the Table 4 at a reaction time of 25 minutes. [0064] Run 19 utilizing beta zeolite showed good activity and selectivity as an unlayered material which was subjected to further enhancement using the layering process demonstrated in Example 3. Runs 20 to 24 also showed good activity and selectivity as unlayered materials and is expected to be further enhanced using the layering process demonstrated in Example 3. [0065] Run 20 utilizing a material known as solid phosphoric acid or SPA is a non- zeolitic material that, when layered, would further enhance its performance. Runs 25-30 utilizing MFI, X and Y zeolites are alternative acidic materials such as SAPO-11 described previously in Example 3 that would not likely be enhanced sufficiently by the layering process to be acceptable candidates for the CHP decomposition process due to low activity and selectivity demonstrated in the screening process of Example 4.[0066] Best results observed in this testing are better than any known commercial decomposer operation using trace sulfuric acid with AMS yields ranging from 78 to 81percent and <n="22"/>an overall cumene/ phenol consumption ratio of 1.31. Note that Run 5 showed an AMS yield in excess of 86percent which is equivalent to an overall cumene/phenol consumption ratio of 1.29 if the resultant AMS is hydrogenated and recycled as cumene back to the oxidation section of the process which is typically what is practiced in commercial operation. The only way, known to the inventors hereof, to achieve such a yield with the conventional sulfuric acid technology is to use acetone recycled as a diluent in the decomposer section (at molar ratio significantly greater than 1) which would be at an added cost and is typically difficult to justify. With zeolite β layered alumina, Time= 0.416667h, T= 55 - 70 °C , Product distribution / selectivity

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Patent; UOP LLC; WO2008/83064; (2008); (A1) English View in Reaxys 6.1 - 16.3 %

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phenol consumption ratio of 1.31. Note that Run 5 showed an AMS yield in excess of 86percent which is equivalent to an overall cumene/phenol consumption ratio of 1.29 if the resultant AMS is hydrogenated and recycled as cumene back to the oxidation section of the process which is typically what is practiced in commercial operation. The only way, known to the inventors hereof, to achieve such a yield with the conventional sulfuric acid technology is to use acetone recycled as a diluent in the decomposer section (at molar ratio significantly greater than 1) which would be at an added cost and is typically difficult to justify. With MFI layered γ-alumina, Time= 0.416667h, T= 80.3 °C , Product distribution / selectivity Patent; UOP LLC; WO2008/83064; (2008); (A1) English View in Reaxys 4.4 %

3 :Example 3: In Runs 1 to 18, the catalyst samples made in accordance with Examples 1 and 2 and having outer layers of varying thicknesses, set forth in Table 1 below, were screened for activity and selectivity. Runs 1-12 utilized a zeolite beta outer layer having a thickness specified in Table 1. Runs 13-16 and 18 utilized a SAPO-1 1 outer layer having a thickness specified in Table 1. Run 17 utilized an SM-3 outer layer having the thickness specified Table 1. The catalysts were tested using the following experimental set up. Approximately 4 gms of catalyst were added to 36 cc of a 1 :1 molar mixture of acetone/phenol in a 50 cc stirred glass vessel operating as a continuous stirred tank reactor (CSTR) system to simulate the environment of a commercial decomposer reactor. The temperature of the mixture is then raised to 55°C to 700C and approximately 4 gms of an 85 wtpercent CHP concentrate solution derived from a commercial phenol unit (see reference numeral 21 of FIG. 1) as a source of fresh CHP feed is injected into the reaction mixture in 30 seconds. Reaction products and temperature were monitored during the course of the runs to determine the extent of reaction and the product selectivity over an approximately 25 min of total reaction time. A continuous circulation of the reaction products was maintained throughout the course of the run to control the strong exothermic heat of reaction that occurs <n="17"/>and to simulate CSTR reactor conditions. Results obtained are described as followed with detailed catalysts and product yields and selectivities shown in the Table 1 at a reaction time of 25 minutes.The zeolite beta layered catalysts are active (Runs 1 to 12) for CHP decomposition whereas the layered SAPO-1 1 and SM-3 catalysts are inactive (Runs 13 to 18) under conditions similar to what is currently being practiced for a state-of-the-art decomposer design (e.g., 55 to 70 0C (131-158 0F) and 25 min residence time using trace sulfuric acid). It has been determined there is a minimum catalyst acidity, as measured by NH3-TPD (See Table 2), needed to catalyze the CHP decomposition reaction. The catalyst acidity should be equal to or greater than 0.36 mmoles NH3 per gram catalyst at 150 to 550 0C based on using a powder form of the outer layer material. With zeolite SM-3 layered alumina, Time= 0.416667h, T= 55 - 70 °C , Product distribution / selectivity Patent; UOP LLC; WO2008/83064; (2008); (A1) English View in Reaxys

3.4 %

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and the framework silica to alumina ratio to 10 as determined by XRD. [0059] Solid phosphoric acid ready for testing can be obtained from the Innophos Corporation located in Kentucky or Houston, Texas.[0060] The zeolites were prepared for testing in the following typical manner. An amount OfAl2O3 equivalent to 15 wtpercent of total powder blend on a volatile free basis was peptized using 70 wtpercent HNO3 using a HNO3 to Al2O3 ratio (w/w) of 0.17, to form a gelatin binder. The binder was added to a powder blend consisting of one of the zeolites described above, Al2O3 and Methocel, in an amount of 0.5 wtpercent of the total powder blend as an extrusion aid in a muller. Additional water was added to the mixture Of Al2O3 binder and the powder, while mixing. Mixing was continued until a doughy consistency, suitable for extrusion, was achieved. The dough formed was extruded into 1/16" diameter pellets which were then calcined in a flowing air at approximately 550 to 6000C over a period of 1 to 4 hours. [0061] In the case of zeolite X and Y, Ludox silica was used as a binder to form extrudate. The formed extrudate was dried, calcined, ammonium exchanged to remove residual sodium inherent from Ludox silica. This material was calcined again to convert the zeolite from an ammonium form to an acidic form (proton).[0062] In the case of MFI(38), the zeolite was formed into a sphere using AlPO4 binder at 67/33 zeolite/binder formulation following an oil dropping technique. [0063] Run 19 utilized a zeolite beta having a composition as specified in Table 4. Runs 20-30 utilized acidic materials other than beta zeolite as specified in Table 4. The catalysts were tested using the following experimental set up. Approximately 4 gms of a 20-40 mesh catalyst was added to 36 cc of a 1 :1 molar mixture of acetone/phenol in a 50 cc stirred glass vessel operating as a continuous stirred tank reactor (CSTR) system to simulate the environment of a commercial decomposer reactor. The temperature of the mixture is then raised to 55°C to 7O0C and approximately 4 gms of an 85 wtpercent CHP concentrate solution derived from a commercial phenol unit (see reference numeral 21 of FIG. 1) was fed as a source of fresh CHP into the reaction mixture in 30 seconds. Reaction products and <n="21"/>temperatures were monitored during the course of the runs to determine the extent of the reaction and the product selectivity over approximately 25 minutes of total reaction time. Continuous circulation of the reaction products was maintained throughout the course of the run to control the strong exothermic heat of reaction that occurs and to simulate CSTR reactor conditions. Results obtained are described as followed with detailed catalysts and product yields and selectivities shown in the Table 4 at a reaction time of 25 minutes. [0064] Run 19 utilizing beta zeolite showed good activity and selectivity as an unlayered material which was subjected to further enhancement using the layering process demonstrated in Example 3. Runs 20 to 24 also showed good activity and selectivity as unlayered materials and is expected to be further enhanced using the layering process demonstrated in Example 3. [0065] Run 20 utilizing a material known as solid phosphoric acid or SPA is a non- zeolitic material that, when layered, would further enhance its performance. Runs 25-30 utilizing MFI, X and Y zeolites are alternative acidic materials such as SAPO-11 described previously in Example 3 that would not likely be enhanced sufficiently by the layering process to be acceptable candidates for the CHP decomposition process due to low activity and selectivity demonstrated in the screening process of Example 4.[0066] Best results observed in this testing are better than any known commercial decomposer operation using trace sulfuric acid with AMS yields ranging from 78 to 81percent and <n="22"/>an overall cumene/ phenol consumption ratio of 1.31. Note that Run 5 showed an AMS yield in excess of 86percent which is equivalent to an overall cumene/phenol consumption ratio of 1.29 if the resultant AMS is hydrogenated and recycled as cumene back to the oxidation section of the process which is typically what is practiced in commercial operation. The only way, known to the inventors hereof, to achieve such a yield with the conventional sulfuric acid technology is to use acetone recycled as a diluent in the decomposer section (at molar ratio significantly greater than 1) which would be at an added cost and is typically difficult to justify. With MFI layered AlPO4, Time= 0.416667h, T= 80.3 °C , Product distribution / selectivity Patent; UOP LLC; WO2008/83064; (2008); (A1) English View in Reaxys 2.5 - 3.7 % 3 :Example 3: In Runs 1 to 18, the catalyst samples made in accordance with Examples 1 and 2 and having outer layers of varying thicknesses, set forth in Table 1 below, were screened for activity and selectivity. Runs 1-12 utilized a zeolite beta outer layer having a thickness specified in Table 1. Runs 13-16 and 18 utilized a SAPO-1 1 outer layer having a thickness specified in Table 1. Run 17 utilized an SM-3 outer layer having the thickness specified Table 1. The catalysts were tested using the following experimental set up. Approximately 4 gms of catalyst were added to 36 cc of a 1 :1 molar mixture of acetone/phenol in a 50 cc stirred glass vessel operating as a continuous stirred tank reactor (CSTR) system to simulate the environment of a commercial decomposer reactor. The temperature of the mixture is then raised to 55°C to 700C and approximately 4 gms of an 85 wtpercent CHP concentrate solution derived from a commercial phenol unit (see reference numeral 21 of FIG. 1) as a source of fresh CHP feed is injected into the reaction mixture in 30 seconds. Reaction products and temperature were monitored during the course of the runs to determine the extent of reaction and the product selectivity over an approximately 25 min of total reaction time. A continuous circulation of the reaction products was maintained throughout the course of the run to control the strong exothermic heat of reaction that occurs <n="17"/>and to simulate CSTR reactor conditions. Results obtained are described as followed with detailed catalysts and product yields and selectivities shown in the Table 1 at a reaction time of 25 minutes.The zeolite beta layered catalysts are active (Runs 1 to 12) for CHP decomposition whereas

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the layered SAPO-1 1 and SM-3 catalysts are inactive (Runs 13 to 18) under conditions similar to what is currently being practiced for a state-of-the-art decomposer design (e.g., 55 to 70 0C (131-158 0F) and 25 min residence time using trace sulfuric acid). It has been determined there is a minimum catalyst acidity, as measured by NH3-TPD (See Table 2), needed to catalyze the CHP decomposition reaction. The catalyst acidity should be equal to or greater than 0.36 mmoles NH3 per gram catalyst at 150 to 550 0C based on using a powder form of the outer layer material. With zeolite SAPO-11 layered alumina, Time= 0.416667h, T= 55 - 70 °C , Product distribution / selectivity Patent; UOP LLC; WO2008/83064; (2008); (A1) English View in Reaxys

Rx-ID: 32226413 View in Reaxys 17/477 Yield

Conditions & References

82.1 %

3 :Example 3 Conditions were as in example 2 with 1.5 wt. percent additional water added ahead of the second stage. An optimal average AMS yield of 82.1percent was obtained at 122° C. with 0.02 to 0.04percent DCP, and 0.16 to 0.18 wt. percent DMBA exiting the second stage. With sulfuric acid, water, acetophenone, T= 78 - 122 °C , p= 550 - 600Torr , Product distribution / selectivity Patent; Keenan, Scott Roy; Hagans, Michael Keith; US2011/306800; (2011); (A1) English View in Reaxys OH Se

Rx-ID: 2089960 View in Reaxys 18/477 Yield 4 % Chromat., 85 %

Conditions & References With pyridine, 3-(4-nitrophenyl)-2-(phenylsulfonyl)-1,2-oxaziridine in chloroform, Time= 18h, T= 25 °C Davis, Franklin A.; Stringer, Orum D.; Billmers, Joanne M.; Tetrahedron Letters; vol. 24; nb. 12; (1983); p. 1213 1216 View in Reaxys

43 % Chromat., 39 %

With 3-(4-nitrophenyl)-2-(phenylsulfonyl)-1,2-oxaziridine in chloroform, Time= 1h, T= 25 °C Davis, Franklin A.; Stringer, Orum D.; Billmers, Joanne M.; Tetrahedron Letters; vol. 24; nb. 12; (1983); p. 1213 1216 View in Reaxys

Si O

Rx-ID: 10431660 View in Reaxys 19/477 Yield 78 %

Conditions & References With (iPr)CuCl, triphenylphosphine, isopropyl alcohol in tetrahydrofuran, diethyl ether, Time= 16h, T= 60 °C Lebel, Helene; Davi, Michael; Diez-Gonzalez, Silvia; Nolan, Steven P.; Journal of Organic Chemistry; vol. 72; nb. 1; (2007); p. 144 - 149 View in Reaxys

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Rx-ID: 23409495 View in Reaxys 20/477 Yield

Conditions & References I.IB :Illustrative Embodiments 1. Illustrative Embodiment I: I (A) Preparation OF HYDROCRACKING Catalyst PdMordenite Catalyst A mixture of 1500 grams of sodium mordenite, (having the following properties: a surface area of 430 square meters per gram; an average crystallite size of around 1 micron; a cyclohexane adsorption uptake of 7.6 cc/g; and a molar silica to alumina ratio of 11. 1), 9000 grams of ammonium nitrate and 15 liters of 1.5 M nitric acid was heated to 50 °C. and stirred for five hours. The solid material was filtered off and washed with 25 liters of deionized water. This treatment of the Mordenite with ammonium nitrate in nitric acid was repeated twice with fresh ammonium nitrate and nitric acid each time. After each treatment the solid material was filtered off and washed with water and dried overnight at 120 °C. Palladium was added to the zeolite to a level of 0.35 percent by weight by treatment with an aqueous solution containing Tetraamine palladium nitrate and an excess of ammonium nitrate prepared by dissolving 6.55 grams of tetramine palladium nitrate in 308 grams of deionized water and adding to this solution 4.92 grams of ammonium nitrate. The palladium solution was then co-mulled with 1083 grams of DEALUMINATED mordenite having an LOI (loss of iginition at 750 °C for 2 hours) of 10.6percent. The palladium- containing mordenite was uniformly mixed and then 338 grams of PSEUDOBOEHMITE alumina (Catapal B which is commercially available from Vista Chemical Company) having an LOI of 28.4percent was added and allowed to mix. The mixture was extruded and the 1.6 mm extrudates were dried in air for 16 hours at 125 °C, and then calcined in flowing air at 500°C. for two hours. The catalyst was crushed and sized to 6-20 mesh particles and then reduced using the procedure as described in IIA below. IB. HYDROCRACKING of Cumene Dimer Using Pd on H-Mordenite Catalyst The bottom stream from a catalytic distillation column, for the catalytic distillation of cumyl alcohol to produce cumene, was distilled to yield a cumene dimer rich mixture that was diluted with cumene and fed into a fixed bed hydrogenation loaded with the acidic palladium on H-Mordenite catalyst as described in I (A) for hydrocracking under the condition as provided in TABLE 1 below. The results are shown in TABLE 2 below. Table 1 Feedrate 33.5 g/hr Reaction Temperature 220°C Pressure 10 bar Hydrogen Flowrate 4 L/Hr Catalyst Weight 33.5 g (before reduction) Table 2 Fixed Bed Cumene Dimers To Cumene Results With Palladium On H-Mordenite Catalyst At 220°C Component Cumene dimers in cumene Fixed Bed Product (FEED) 2,3-Dimethyl-2, 3- 1. 94 0.06 diphenylbutane, (wtpercent) 2methyl-2,4-diphenylpentane, 1. 03 0. 02 (wtpercent) Cumene, (wtpercent) 96. 75 99. 82 Isopropylcyclohexane, (wtpercent) 0.08 0.08 Alpha-Methyl styrene, (wtpercent) 0. 20 0. 02 With hydrogen, palladium on H-mordenite, T= 220 °C , p= 7500.75Torr , Gas phase, Product distribution / selectivity Patent; SHELL OIL COMPANY; WO2005/5351; (2005); (A2) English View in Reaxys III.A :The bottom stream from II (B) (I) above was distilled to yield a cumene dimer rich mixture that was diluted with cumene and fed into a fixed bed hydrogenation loaded with the T-366 catalyst as described in II (A) (i) above for hydrocracking under the condition as provided in TABLE 4 below. The results are shown in TABLE 5 below. With hydrogen, hydrogenated copper on silica (T-366), T= 260 °C , p= 7500.75Torr , Product distribution / selectivity Patent; SHELL OIL COMPANY; WO2005/5402; (2005); (A2) English View in Reaxys 3.B :The bottom stream from II (B) (i) above was distilled to yield a cumene dimer rich mixture that was diluted with cumene and fed into a fixed bed hydrogenation loaded with the acidic palladium on H-Mordenite catalyst as described in II (B) (i) above for hydrocracking under the condition as provided in TABLE 6 below. The results are shown in TABLE 7 below. With hydrogen, palladium on H-Mordenite, T= 220 °C , p= 7500.75Torr , Product distribution / selectivity Patent; SHELL OIL COMPANY; WO2005/5402; (2005); (A2) English View in Reaxys III.IIIB :III. Comparative Example IIIA. Preparation OF HYDROGENATION CATALYST Palladium on Carbon Pressed granules of 0.5 wt. percent of palladium on carbon, available from the Calsicat division of Mallinckrodt Incorporated was mixed with silicon carbide and reduced according the same procedure as described in IIA above. IIIB. HYDROCRACKING OF CUMENE Dimers with Palladium on Carbon Catalyst The bottom stream from a catalytic distillation

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column, for the catalytic distillation of cumyl alcohol to produce cumene, was distilled to yield a cumene dimer rich mixture that was diluted with cumene and fed into a fixed bed hydrogenation loaded with the acidic palladium on carbon catalyst as described in III (A) for hydrocracking under the condition as provided in TABLE 5 below. The results are shown in TABLE 6 below. Table 5 Feedrate 33.5 g/hr Reaction Temperature 220 °C Pressure 10 bar Hydrogen Flowrate 4 L/Hr Catalyst Weight 33.5 g (before reduction) Table 6 Fixed Bed Cumene Dimers To Cumene Results With Palladium on Carbon Catalyst at 220°C Component Cumene dimers in cumene Fixed Bed Product (FEED) 2,3-Dimethyl-2, 3- 1. 94 0.10 diphenylbutane, (wtpercent) 2-methyl-2,4-diphenylpentane, 1. 03 0. 10 (wtpercent) Cumene, (wtpercent) 96. 75 99. 60 Isopropylcyclohexane, (wtpercent) 0. 08 0.16 Alp11a-Methyl styrene, (wtpercent) 0. 20 0. 04 With hydrogen, 5 Pd/C, T= 220 °C , p= 7500.75Torr , Gas phase, Product distribution / selectivity Patent; SHELL OIL COMPANY; WO2005/5351; (2005); (A2) English View in Reaxys II.IIB :II. Illustrative Embodiment II IIA Preparation of Hydrocracking Catalyst T-366 Catalyst A commercially available copper on silica catalyst, T-366, available from Sud Chemie, having 54 wt. percent of Cu on silica extruded into 3.2 mm extrudate, is further processed using the following procedure for the catalytic cracking experiments. Five grams of Sud Chemie T-366 copper on silica catalyst (3mm tablets) was crushed and sized into 6-20 mesh particles. The catalyst was mixed with 45 grams of 80 mesh silicon carbide and centered inside a 69 cm long stainless steel reactor tube between beds of 20 mesh SiC and glass wool. The reactor tube had an internal diameter of 1. 5CM. The catalyst was slowly reduced by heating the catalyst particles at a rate of 3°C per minute from 20°C to 180°C while flowing 0.05 wt. percent hydrogen in nitrogen at a rate of 10 L/Hr. The catalyst was allowed to reduce at 180°C for 2 hours and then the hydrogen content in the nitrogen was doubled every 2 hours until the gas was 3.2 wt. percent hydrogen in nitrogen. The catalyst was reduced for a final two-hour period and then cooled while maintaining gas flow. After cooling, the reactor was capped without allowing any air to enter and the gas flow was stopped. The reactor was opened in a nitrogen filled glove box and the catalyst and silicon carbide were separated by screen sieve. IIB. HYDROCRACKING of Cumene Dimers Using T-366 Copper on Silica Catalyst The bottom stream from a catalytic distillation column, for the catalytic distillation of cumyl alcohol to produce cumene, was distilled to yield a cumene dimer rich mixture that was diluted with cumene and fed into a fixed bed hydrogenation loaded with the T-366 catalyst as described in II (A) for hydrocracking under the condition as provided in TABLE 3 below. The results are shown in TABLE 4 below. Table 3 Feedrate 33.5 g/hr Reaction Temperature 260°C Pressure 10 bar Hydrogen Flowrate 4 L/Hr Catalyst Weight 33. 5 g (before reduction) Table 4 Fixed Bed Cumene Dimer To Cumene Results With T-366 Catalyst At 260°C Component Cumene dimers in Fixed Bed Product cumene (FEED) 2,3-Dimethyl-2, 31. 94 0.05 diphenylbutane, (wtpercent) 2-methyl-2,4-diphenylpentane, 1. 03 0. 09 (wtpercent) Cumene, (wtpercent) 96. 75 99. 54 Isopropylcyclohexane, (wtpercent) 0. 08 0.18 alpha-Methyl styrene, (wtpercent) 0. 20 0. 09 With hydrogen, T= 260 °C , p= 7500.75Torr , Gas phase, Product distribution / selectivity Patent; SHELL OIL COMPANY; WO2005/5351; (2005); (A2) English View in Reaxys

Rx-ID: 39050266 View in Reaxys 21/477 Yield

Conditions & References 2.3. Catalytic measurements Cumene decomposition tests were performed for the activatedcarbon catalysts obtained from brown coal from “Konin” colliery.This process was realised by the pulse method in a glass reactorwith a fixed bed catalysts (0.05 g) at 623 K. After reaching a desiredtemperature, cumene was dosed by a microsyringe in the amountof 1 l to the reactor. The outlet of the reactor was connected to thechromatograph. The products were analysed using a FID detectorand a 3 m column packed with 5percent SE-30 deposited on ChromosorbG AW-DMCS. Helium was used as a carrier gas. With peracetic acid, carbon, Time= 8h, T= 59.84 °C Krzyzyska, Beata; Malaika, Anna; Rechnia, Paulina; Kozlowski, Mieczyslaw; Journal of Molecular Catalysis A: Chemical; vol. 395; (2014); p. 523 - 533 View in Reaxys

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Rx-ID: 39050267 View in Reaxys 22/477 Yield

Conditions & References 2.3. Catalytic measurements Cumene decomposition tests were performed for the activatedcarbon catalysts obtained from brown coal from “Konin” colliery.This process was realised by the pulse method in a glass reactorwith a fixed bed catalysts (0.05 g) at 623 K. After reaching a desiredtemperature, cumene was dosed by a microsyringe in the amountof 1 l to the reactor. The outlet of the reactor was connected to thechromatograph. The products were analysed using a FID detectorand a 3 m column packed with 5percent SE-30 deposited on ChromosorbG AW-DMCS. Helium was used as a carrier gas. With peracetic acid, carbon, Time= 4h, T= 59.84 °C Krzyzyska, Beata; Malaika, Anna; Rechnia, Paulina; Kozlowski, Mieczyslaw; Journal of Molecular Catalysis A: Chemical; vol. 395; (2014); p. 523 - 533 View in Reaxys

Rx-ID: 1627774 View in Reaxys 23/477 Yield

Conditions & References

90 %

With zirconium tetrachloride, sodium iodide in acetonitrile, Time= 0.0166667h, Heating Firouzabadi, Habib; Iranpoor, Nasser; Jafarpour, Maasoumeh; Tetrahedron Letters; vol. 46; nb. 23; (2005); p. 4107 - 4110 View in Reaxys

71 %

With manganese bromide tetrahydrate, methyllithium in diethyl ether, from -30 deg C up to 20 deg C, 18 h Kauffmann, Thomas; Neiteler, Christel; Neiteler, Gabriele; Chemische Berichte; vol. 127; nb. 4; (1994); p. 659 666 View in Reaxys With Titanium(IV) oxide in isopropyl alcohol, acetonitrile, Time= 12h, T= 29.84 °C , Photolysis Shiraishi, Yasuhiro; Hirakawa, Hiroaki; Togawa, Yoshiki; Hirai, Takayuki; ACS Catalysis; vol. 4; nb. 6; (2014); p. 1642 - 1649 View in Reaxys

cyclodibromodi-μ-methylene<μ-(tetrahydrofuran)>trizinc O

Rx-ID: 6712326 View in Reaxys 24/477 Yield

Conditions & References

76 %

With boron trifluoride diethyl etherate, titanium(III) chloride in tetrahydrofuran, T= 0 - 20 °C Matsubara, Seijiro; Sugihara, Masakazu; Utimoto, Kiitiro; Synlett; nb. 3; (1998); p. 313 - 315 View in Reaxys

Rx-ID: 28725543 View in Reaxys 25/477 Yield 39 %

Conditions & References With palladium diacetate, CsO2CCMe3, bis(1,1-diphenylphosphino)methane in N,N-dimethyl-formamide, Time= 24h, T= 110 °C , Inert atmosphere

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Kesharwani, Tanay; Verma, Akhilesh K.; Emrich, Daniel; Ward, Jeffrey A.; Larock, Richard C.; Organic Letters; vol. 11; nb. 12; (2009); p. 2591 - 2593 View in Reaxys

Rx-ID: 39050264 View in Reaxys 26/477 Yield

Conditions & References 2.3. Catalytic measurements Cumene decomposition tests were performed for the activatedcarbon catalysts obtained from brown coal from “Konin” colliery.This process was realised by the pulse method in a glass reactorwith a fixed bed catalysts (0.05 g) at 623 K. After reaching a desiredtemperature, cumene was dosed by a microsyringe in the amountof 1 l to the reactor. The outlet of the reactor was connected to thechromatograph. The products were analysed using a FID detectorand a 3 m column packed with 5percent SE-30 deposited on ChromosorbG AW-DMCS. Helium was used as a carrier gas. With dihydrogen peroxide, carbon, Time= 24h, T= 59.84 °C Krzyzyska, Beata; Malaika, Anna; Rechnia, Paulina; Kozlowski, Mieczyslaw; Journal of Molecular Catalysis A: Chemical; vol. 395; (2014); p. 523 - 533 View in Reaxys

Rx-ID: 25930492 View in Reaxys 27/477 Yield

Conditions & References

53 %

With 4-(N,N-dimethlyamino)pyridine, Time= 24h, T= 100 °C Sakakura, Akira; Kawajiri, Kimio; Ohkubo, Takuro; Kosugi, Yuji; Ishihara, Kazuaki; Journal of the American Chemical Society; vol. 129; nb. 47; (2007); p. 14775 - 14779 View in Reaxys

Rx-ID: 1990033 View in Reaxys 28/477 Yield

Conditions & References

85 %

With nitrogen(IV) oxide, Time= 2h, T= -78 °C , Irradiation Bosch, E.; Kochi, J. K.; Journal of Organic Chemistry; vol. 59; nb. 12; (1994); p. 3314 - 3325 View in Reaxys

P O

OH O–

O P

Rx-ID: 3125681 View in Reaxys 29/477 Yield 75 %

Conditions & References With water, potassium carbonate in N,N-dimethyl-formamide, Time= 40h, T= 85 °C Kawashima, Takayuki; Ishii, Takafumi; Inamoto, Naoki; Chemistry Letters; (1984); p. 1097 - 1100 View in Reaxys

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-1 F F (v6) F F P F F

(v2)

S+

Rx-ID: 4875006 View in Reaxys 30/477 Yield

Conditions & References

97 % Chromat.

With 1,1'-bis(diphenylphosphanyl)ferrocenenickel(II) chloride in tetrahydrofuran, Time= 8h, T= 45 °C Srogl, Jiri; Allred, Gary D.; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 119; nb. 50; (1997); p. 12376 - 12377 View in Reaxys

Cp2Ti(Cl)CH2Al(CH3)2

Rx-ID: 6712325 View in Reaxys 31/477 Yield

Conditions & References

88 %

in tetrahydrofuran, Time= 0.5h, T= 0 °C Pine, Stanley H.; Pettit, Robert J.; Geib, Gregory D.; Cruz, Susana G.; Gallego, Claudio H.; et al.; Journal of Organic Chemistry; vol. 50; nb. 8; (1985); p. 1212 - 1216 View in Reaxys

Rx-ID: 9719797 View in Reaxys 32/477 Yield

Conditions & References

71 %, 9 %, With nickel dichloride in tetrahydrofuran, Time= 1h, T= 25 °C 3% Terao, Jun; Watabe, Hiroyasu; Watanabe, Hiroyuki; Kambe, Nobuaki; Advanced Synthesis and Catalysis; vol. 346; nb. 13-15; (2004); p. 1674 - 1678 View in Reaxys

S O F

Rx-ID: 11175458 View in Reaxys 33/477 Yield 115 mg

Conditions & References With formic acid, tributyl-amine, [Pd(PPh3)2(OAc)2] in N,N-dimethyl-formamide, Time= 0.5h, T= 35 °C Pandey, Sushil K.; Greene, Andrew E.; Poisson, Jean-Francois; Journal of Organic Chemistry; vol. 72; nb. 20; (2007); p. 7769 - 7770 View in Reaxys

Rx-ID: 23148853 View in Reaxys 34/477

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Yield

Conditions & References

0.01 - 0.40 %

4; 5; 6; 2 : Example 4 40 Grams of a cumene mixed solution containing 3percent by weight of propylene oxide and 24percent by weight of cumyl alcohol were charged in an autoclave, then stirred and heated at 136°C for 60 minutes. α-Methyl styrene was produced by dehydration of cumyl alcohol. Further, propylene glycol was produced through a reaction of water with propylene oxide. The result is shown in Table 2.Example 5 It was carried out in the same manner as in Example 4 except that the temperature is 155°C. The result is shown in Table 2.Example 6 It was carried out in the same manner as in Example 4 except that the temperature is 174°C. The result is shown in Table 2.Comparative Example 2 It was carried out in the same manner as in Example 4 except that the temperature is 194°C. The result is shown in Table 2. [Table 2] Example 4Example 5Example 6Comparative Example 2Temperature heated (°C)136155174194αMS yield(percent)0.010.020.070.40PG concentration (ppm by weight) *218354277*2: Concentration of propylene glycol in mixture after heating In each of the above Examples 4-6 and Comparative Example 2, a liquid in which a small amount of propylene oxide was added to cumyl alcohol and cumene, was used, and it is found that when the temperature heated became 190°C or higher, production of α-methyl styrene remarkably increases, and propylene glycol also increases together with the increases of α-methyl styrene. in isopropyl-benzene, Time= 1h, T= 136 - 194 °C Patent; Sumitomo Chemical Company, Limited; EP1484326; (2004); (A1) English View in Reaxys

Rx-ID: 30958623 View in Reaxys 35/477 Yield

Conditions & References

76 %

With 2BF4 (1+)*C27H50P2*2H(1+), palladium diacetate, caesium carbonate in toluene, Time= 14h, T= 110 °C , Inert atmosphere Flores-Gaspar, Areli; Martin, Ruben; Advanced Synthesis and Catalysis; vol. 353; nb. 8; (2011); p. 1223 - 1228 View in Reaxys O

O S

Mg Br

Rx-ID: 34054874 View in Reaxys 36/477 Yield

Conditions & References

96 %

With [NiI2(PPh3)], tri-cyclo-hexyl-phosphine in tetrahydrofuran, T= 70 °C , Inert atmosphere, Kumada Cross-Coupling, chemoselective reaction Wu, Ji-Cheng; Gong, Lu-Bing; Xia, Yuanzhi; Song, Ren-Jie; Xie, Ye-Xiang; Li, Jin-Heng; Angewandte Chemie International Edition; vol. 51; nb. 39; (2012); p. 9909 - 9913 View in Reaxys

O P+ –

Rx-ID: 41482746 View in Reaxys 37/477 Yield 100 %

Conditions & References in 2-methyltetrahydrofuran, Time= 23h, T= 80 °C , p= 760.051Torr , Inert atmosphere Cattelan, Lisa; No, Marco; Selva, Maurizio; Demitri, Nicola; Perosa, Alvise; ChemSusChem; vol. 8; nb. 23; (2015); p. 3963 - 3966

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View in Reaxys

Rx-ID: 1970389 View in Reaxys 38/477 Yield

Conditions & References

10 %, 72 %

With bromine, mercury(II) oxide in tribromo methane, Time= 0.25h, T= 8 °C Sychkova, L. D.; Shabarov, Yu. S.; Journal of Organic Chemistry USSR (English Translation); vol. 16; nb. 10; (1980); p. 1775 - 1779; Zhurnal Organicheskoi Khimii; vol. 16; nb. 10; (1980); p. 2086 - 2091 View in Reaxys

72 %, 10 %

Rx-ID: 2185833 View in Reaxys 39/477 Yield 84 %

Conditions & References With hydrogen fluoride in acetonitrile, Ambient temperature Johnson, Carl R.; Tait, Bradley D.; Journal of Organic Chemistry; vol. 52; nb. 2; (1987); p. 281 - 283 View in Reaxys

E Mg Cl

Rx-ID: 3364746 View in Reaxys 40/477 Yield 98 %

Conditions & References With copper(I) bromide, lithium bromide in tetrahydrofuran, Time= 2h, T= 0 °C , Yields of byproduct given Westmijze, H.; Kleijn, H.; Meijer, J.; Vermeer, P.; Recueil: Journal of the Royal Netherlands Chemical Society; vol. 100; nb. 3; (1981); p. 98 - 102 View in Reaxys

Rx-ID: 9068953 View in Reaxys 41/477 Yield

Conditions & References

54 % Chromat., 29 % Chromat., 13 % Chromat.

With copper(l) iodide, chloro-trimethyl-silane, iodine, lanthanum in acetonitrile, Time= 1h, T= 82 °C

54 % Chromat., 13 % Chromat.,

With lanthanum, chloro-trimethyl-silane, iodine, copper(l) iodide in acetonitrile, Time= 1h, T= 82 °C

Nishino, Toshiki; Nishiyama, Yutaka; Sonoda, Noboru; Tetrahedron Letters; vol. 43; nb. 20; (2002); p. 3689 3691 View in Reaxys

Nishino, Toshiki; Nishiyama, Yutaka; Sonoda, Noboru; Bulletin of the Chemical Society of Japan; vol. 76; nb. 3; (2003); p. 635 - 641 View in Reaxys

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29 % Chromat. 36 % Chromat., 6 % Chromat., 29 % Chromat.

With lanthanum, chloro-trimethyl-silane, iodine, CoI2 in acetonitrile, Time= 1h, T= 82 °C Nishino, Toshiki; Nishiyama, Yutaka; Sonoda, Noboru; Bulletin of the Chemical Society of Japan; vol. 76; nb. 3; (2003); p. 635 - 641 View in Reaxys

Rx-ID: 9146955 View in Reaxys 42/477 Yield 17 %

Conditions & References With styrene and bis(4-vinylbenzylcyclopentadienyl)ZrCl2 copolym in hexane, dichloromethane, Time= 96h, T= 20 °C Hok, Saphon; Vassilian, Jenny; Schore, Neil E.; Organic Letters; vol. 4; nb. 14; (2002); p. 2365 - 2368 View in Reaxys

Rx-ID: 23672914 View in Reaxys 43/477 Yield

Conditions & References 1 :A cumene solution containing 25percent by weight of cumyl alcohol and hydrogen were passed upwardly through a single reactor, in which activated alumina as a dehydration catalyst and 60 wtpercent copper/silica as a hydrogenation catalyst were packed in this order, from the dehydration catalyst side. At this time, the pressure was 1 MpaG, the temperature was 205 DEG C at the inlet of the reactor, hydrogen of 1.5 times by mole of cumyl alcohol was used and the gas linear velocity was 14 cm/sec (converted under the normal temperature and pressure). The conversion of cumyl alcohol at the outlet of activated alumina was 99percent, the conversion of α-methyl styrene at the outlet of the copper/silica was 99percent and the overall selectivity of cumene was 99percent. With aluminum oxide, T= 205 °C , p= 7500.75Torr , Product distribution / selectivity Patent; Sumitomo Chemical Company, Limited; EP1598330; (2005); (A1) English View in Reaxys 2 :It was carried out in the same manner as in Example 1 except that the pressure was changed to 1.4 MPaG and hydrogen was used 2.0 times by mole of cumyl alcohol. The conversion of cumyl alcohol at the outlet of activated alumina was 99percent, the conversion of α-methyl styrene at the outlet of the copper/silica was 99percent and the overall selectivity of cumene was 99percent. With aluminum oxide, T= 205 °C , p= 10501.1Torr , Product distribution / selectivity Patent; Sumitomo Chemical Company, Limited; EP1598330; (2005); (A1) English View in Reaxys 3 :A cumene solution containing 25percent by weight of cumyl alcohol and hydrogen were passed upwardly through a single reactor in which activated alumina as a dehydration catalyst and 0.05 wtpercent palladium/alumina as a hydrogenation catalyst were packed in this order, from the dehydration side. At this time, the pressure was 1.4 MPaG, the temperature was 205 DEG C at the inlet of the reactor, hydrogen of 1.5 times by mole of cumyl alcohol was used and the gas linear velocity was 14 cm/sec (converted under the normal temperature and pressure). The conversion of cumyl alcohol at the outlet of activated alumina was 99percent, the conversion of α-methyl styrene at the outlet of the palladium/alumina was 99percent and the overall selectivity of cumene was 99percent. With aluminum oxide, T= 205 °C , p= 10501.1Torr , Product distribution / selectivity Patent; Sumitomo Chemical Company, Limited; EP1598330; (2005); (A1) English View in Reaxys

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Rx-ID: 23755686 View in Reaxys 44/477 Yield

Conditions & References 1; 1 :The catalyst A of 3 m-thick as a first layer and the catalyst B of 1.2 m-thick as a second layer were packed in a reactor having an inner diameter of 4 mm. The first layer and second layer were heated to 230 °C and 190°C, respectively, and 0.1 liter/minute of hydrogen and 1.6 g/minute of a cumene solution having a cumyl alcohol concentration of 23 percent by weight under a pressure of 4 MPa-G, were simultaneously fed to the reactor, continuously. After the reaction of 106 hours, a cumyl alcohol conversion was 99.8percent and a selectivity of a cumene dimer (hydrogenated product of an α-methyl styrene dimer) was 0.9percent. Further, a concentration of α-methyl styrene in cumene obtained was less than 0.01 percent by weight.; The catalyst B of 0.1 m-thick as a first layer, the catalyst A of 0.2 m-thick as a second layer, the catalyst B of 0.4 m-thick as a third layer, the catalyst A of 0.4 m-thick as a fourth layer, the catalyst B of 0.4 m-thick as a fifth layer, the catalyst A of 2.4 m-thick as a sixth layer and the catalyst B of 0.4 m-thick as a seventh layer (catalyst A: 3 m-thick in total, catalyst B: 1. 3 m-thick in total) were packed in a reactor having an inner diameter of 4 mm OE. The first and second layers, the third to fifth layers, and the sixth and sevens layers were heated to 180°C, 200°C and 230°C, respectively, and 0.1 normal liter/minute of hydrogen and 1.6 g/ minute of a cumene solution having a cumyl alcohol concentration of 23 percent by weight under a pressure of 4 MPa-G, were simultaneously fed to the reactor, continuously. After the reaction of 88 hours, a cumyl alcohol conversion was 99.9percent and a selectivity of a cumene dimer (hydrogenated product of an α-methyl styrene dimer) was 0.2percent. Further, a concentration of α-methyl styrene in cumene obtained was less than 0.01 percent by weight. With hydrogen, aluminum oxide, 0.05 palladium/alumina, Time= 88 - 106h, T= 180 - 230 °C , p= 30003Torr , Product distribution / selectivity Patent; Sumitomo Chemical Company, Limited; EP1666442; (2006); (A1) English View in Reaxys

O HO

Rx-ID: 24794773 View in Reaxys 45/477 Yield 85.5 %

Conditions & References DETAILED DESCRIPTION OF THE DRAWINGSA cumene oxidation product mixture is introduced into the process via line 1 into decomposing vessel 2. A circulating stream comprising cumene hydroperoxide, an acid catalyst, phenol and acetone is introduced into decomposing vessel 2 via line 8. The two hereinabove described streams which are introduced into decomposing vessel 2 pass through decomposing vessel 2 while contacting indirect heat exchange surfaces 3. A resulting admixed and cooled inventory in decomposing vessel 2 is removed therefrom via line 4. A coolant is introduced into chamber 16 via line 15 and flows into indirect heat exchange surfaces 3. A resulting coolant which has been heated by the flowing contents of decomposing vessel 2 is passed from indirect heat exchange surfaces 3 into chamber 17. A resulting heated coolant is removed from chamber 17 via line 18 and recovered. The heated coolant may be cooled and recycled to indirect heat exchange surfaces 3. The reacted flowing stream which was removed from decomposing vessel 2 via line 4 is carried via lines 5 and 19 and introduced into pump 6. The resulting pressurized stream is carried from pump 6 via line 7 and a portion is further carried via line 8 and introduced into decomposing vessel 2 as described hereinabove. Another portion of the pressurized circulating stream from pump 6 and carried via line 7 is carried via line 10 and is admixed with an acid catalyst which is introduced via line 11. The resulting mixture containing the acid catalyst is carried via line 12 and introduced into calorimeter 13 which is used to monitor and control the operating conditions for the decomposition of the CHP. A resulting stream is removed from calorimeter 13 via lines 14, 5 and 19 and is passed into pump 6 as hereinabove described. Another portion of the pressurized stream from pump 6 is carried via lines 7 and 9 and introduced into heat exchanger 20 to be heated. A resulting heated stream is removed from heat exchanger 20 via line 21 and introduced into flash drum 22. A vapor stream comprising acetone is removed from flash drum 22 via line 24 and introduced into heat exchanger 25 for cooling. A resulting cooled and condensed stream comprising acetone is removed from heat exchanger 25 via line 26 and is introduced into pump 6 via lines 26 and 19. A resulting stream comprising acetone and phenol is removed from flash drum 22 via line 23 and recovered.; ILLUSTRATIVE EMBODIMENTA cumene oxidation product mixture containing an 88.5 weight percent cumene hydroperoxide (CHP) in an amount of 26 m3/hr is

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introduced into a decomposer vessel containing heat exchange surfaces sufficient to maintain a desired temperature during the exothermic decomposition of CHP to produce phenol and acetone. The contents of the decomposer include CHP, an acid catalyst, phenol and acetone and are circulated in an external flowing loop and re-introduced into the decomposer. The external flowing loop is circulated at a flow rate of about 26 m3/hr and contains a sulfuric acid level of about 6 wppm and maintained at a temperature of about 75° C. (167° F.). The residence time of the cumene oxidation product mixture in the decomposer and the external flowing loop is about 15 minutes. A decomposer product stream containing a CHP concentration of about 3 weight percent is removed from the external flowing loop and is passed through a dehydrator operated at a temperature of 135° C. (275° F.). The resulting AMS yield is 85.5 mol percent and the feed cumene/phenol yield weight ratio is 1.290. Thus, the weight yield ratio is now very close to the theoretical limit for this type of chemistry of 1.277. The feed cumene/phenol yield mol ratio is 0.989. Stage 1: With sulfuric acid, Time= 0.25h, T= 75 °C Stage 2:, T= 135 °C , in dehydrator Patent; UOP LLC; US7141700; (2006); (B1) English View in Reaxys 72.7 - 85.5 %

DETAILED DESCRIPTION OF THE DRAWINGSIn FIG. 1, a cumene oxidation product stream containing CHP is introduced into the process via line 1 and enters metering vessel 2. A resulting stream containing cumene oxidation product is removed from metering vessel 2 via line 3 and a portion thereof is transported via line 4 and joins a flowing circulating loop carried in line 33 and the resulting admixture is transported via line 6 and introduced into vertical heat exchanger 7. A cooling medium is provided via line 8 and is introduced into vertical heat exchanger 7 and a resulting heated medium is removed via line 9 and recovered. The cooling medium may be recirculated after cooling, if desired. A cooled process stream is removed from vertical heat exchanger 7 via line 10 and is admixed with another portion of the cumene oxidation product stream provided via lines 3 and 5, and a make-up acetone stream provided via line 11. The resulting mixture is transported via line 12 and is admixed with an acetone recycle stream provided via line 29 and the resulting admixture is carried via line 14 and introduced into pump 15. A resulting stream is transported from pump 15 via lines 16 and 17. At least a portion of the flowing stream in line 17 is carried via line 21 and introduced into vertical heat exchanger 30. A cooling medium is provided via line 31 and introduced into vertical heat exchanger 30 and a resulting heated medium is removed from vertical heat exchanger 30 via line 32. A cooled flowing stream is removed from vertical heat exchanger 30 via line 33 and is admixed with cumene oxidation product as hereinabove described. A portion of the flowing stream in line 15 is transported via line 18 and introduced into calorimeter 20 which is used to monitor and control the operating conditions for the decomposition of the CHP. A sulfuric acid stream is carried via line 19 and introduced into calorimeter 20. The resulting admixture from calorimeter 20 is introduced into line 14 via line 13. Another portion of the flowing stream in line 17 is carried via line 22 and introduced into heat exchanger 23 to be heated. A resulting heated stream is removed from heat exchanger 23 via line 24 and introduced into flash drum 25. A stream rich in acetone is removed from flash drum 25 via line 27 and introduced into heat exchanger 28. A resulting cooled stream is removed from heat exchanger 28 via line 29 and introduced into line 14. A stream containing acetone and phenol is removed from flash drum 25 via line 26 and recovered.In FIG. 2, three data points, (A, B and C) from the Illustrative Embodiment are plotted in a graph showing alphamethylstyrene (AMS) yield as a function of a decomposer residence time.; Illustrative EmbodimentA cumene oxidation product mixture containing 79 weight percent cumene hydroperoxide at a rate of 41.8 m3/hr is passed through a metering vessel maintained at a temperature of about 60° C. (140° F.) and at a liquid hourly space velocity of 30 hr-1 with an average residence time of 26 minutes. The resulting effluent in an amount of 41.8 m3/hr from the metering vessel is introduced into a circulating decomposer loop having a volume of 18.1 m3. The circulating decomposer loop is operated at a residence time of 26 minutes, a sulfuric acid level of 54 wppm and temperature of 60° C. to produce a decomposer product containing a CHP concentration of 0.63 weight percent. The resulting decomposer effluent is passed through a dehydrator operated at a temperature of 120° C. The resulting AMS yield is 72.7 mol percent and the cumene/phenol yield ratio is 1.322. This run is in accordance with the present invention. The results are summarized and presented in Table 1 as Run A. The AMS yield result is plotted in FIG. 2 and is identified as point "A".; A cumene oxidation product mixture containing an 83 weight percent cumene hydroperoxide at a rate of 39.8 m3/hr is passed through a metering vessel maintained at a temperature of about 60° C. (140° F.) and at a liquid hourly space velocity of 30 hr-1 with an average residence time of 20 minutes. The resulting effluent in an amount of 39.8 m3/hr from the vessel is introduced into circulating decomposer loop having a volume of 13.3 m3. This lower volume in the circulating decomposer loop is made possible by the use of two vertically oriented heat exchangers. The circulating decomposer loop is operated at a residence time of 20 minutes, a sulfuric acid level of 40 wppm and a temperature of 60° C. to produce a decomposer product containing a CHP concentration of 1.5 weight percent. The resulting decomposer effluent is passed through a dehydrator operated at a temperature of 135° C. The resulting AMS yield is 80.6 mol percent and the cumene/phenol yield ratio is 1.311. This run is in accordance with the present invention. The results are summarized and presented in Table 1 as Run A. The AMS yield result is plotted in FIG. 2 and is identified as point "B".; A cumene oxidation product mixture containing an 88.5 weight percent cumene hydroperoxide at a rate of 26 m3/hr is passed through a metering vessel maintained at temperature of about 75° C.

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(167° F.) and at a liquid hourly space velocity of 30 hr-1 with an average residence time of 15 minutes. The resulting effluent at a rate of 26 m3/hr from the vessel is introduced into a circulating decomposer loop having a volume of 12.5 m3. Two vertically oriented heat exchangers are used in this run along with an acetone recycle in an amount of 8.6 m3/hr. the circulating decomposer loop is operated at a residence time of 15 minutes, a sulfuric acid level of 6 wppm and a temperature of 75° C. to produce a decomposer product containing a CHP concentration of 3.0 weight percent. The resulting decomposer effluent is passed through a dehydrator operated at a temperature of 135° C. The resulting AMS yield is 85.5 mol percent and the cumene/phenol yield ratio is 1.290. Thus the yield ratio has improved using the process of this invention to a level where it is now very close to the theoretical limit for this type of chemistry of 1.277. This run is in accordance with the present invention. The results are summarized and presented in Table 1 as Run C. The AMS yield result is plotted in FIG. 2 and is identified as point "C". TABLE 1 Operation Summary RUN A B C CLIP Concentration, wt percent 79 83 88.5 Predecomposer vessel, LHSV 30 30 30Decomposer feed rate, m3/hr. 41.8 39.8 2.6Decomposer volume, m3 18.1 13.3 12.5 Decomposer residence time, min. 26 20 15 Decomposer acid level, wppm 54 40 6 Decomposer temperature, ° C. 60 60 75 Decomposer product CLIP level, wt percent 0.63 1.5 3.0 Dehydrator temperature, ° C. 120 135 135 Cumene Feed/phenol yield ratio, wt/wt 1.322 1.311 1.290 AMS Yield, mol percent 72.7 80.6 85.5 Cumene feed/phenol yield ratio, mol/mol 0.966 0.974 0.989 Stage 1: With sulfuric acid, Time= 0.25 - 0.433333h, T= 60 - 75 °C Stage 2:, T= 120 - 135 °C , in dehydrator, Product distribution / selectivity Patent; UOP LLC; US7141701; (2006); (B1) English View in Reaxys

P P

(v4)

(v4) P (v6) (v4) P (v4)

(v4)P

(v4)

(v6) (v4)(v4)

Rx-ID: 26858052 View in Reaxys 46/477 Yield >99, 96 %

Conditions & References With CO2 in benzene-d6, CO2 added by vacuum transfer; not isolated; NMR Hartwig, John F.; Bergman, Robert G.; Andersen, Richard A.; Organometallics; vol. 10; (1991); p. 3344 - 3362 ; (from Gmelin) View in Reaxys 1

Rx-ID: 1599698 View in Reaxys 47/477 Yield 87 %

Conditions & References With Ledwith–Weitz salt in dichloromethane, T= -20.1 °C , ΔH(excit), ΔS(excit), Thermodynamic data Maslak, Przemyslaw; Asel, Stacey L.; Journal of the American Chemical Society; vol. 110; nb. 24; (1988); p. 8260 - 8261 View in Reaxys

Rx-ID: 2943475 View in Reaxys 48/477 Yield 20 %, 8.5 %

Conditions & References With sodium azide in water, 1.) 80 deg C, 1 h, 2.) room temperature, overnight Kyba, Evan P.; Abramovitch, Rudolph A.; Journal of the American Chemical Society; vol. 102; nb. 2; (1980); p. 735 - 740 View in Reaxys

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O HO

Rx-ID: 4522627 View in Reaxys 49/477 Yield

Conditions & References

95 %

With scandium tris(trifluoromethanesulfonate), Time= 1.3h, T= -40 °C , Yields of byproduct given Ishihara, Kazuaki; Kubota, Manabu; Kurihara, Hideki; Yamamoto, Hisashi; Journal of Organic Chemistry; vol. 61; nb. 14; (1996); p. 4560 - 4567 View in Reaxys

O O

racemate

Rx-ID: 4683276 View in Reaxys 50/477 Yield

Conditions & References

46 %, 18 %, 11 %, 42 %

(v4)

With triphenylphosphine in benzene, Time= 8h, T= 60 °C Abe, Manabu; Sumida, Yohko; Nojima, Masatomo; Journal of Organic Chemistry; vol. 62; nb. 3; (1997); p. 752 754 View in Reaxys

O P Ru (v4)(v4) P (v6) P

(v4)

(v4) P (v6) O (v4)Ru P O (v4)

(v4)

Rx-ID: 26743126 View in Reaxys 51/477 Yield

Conditions & References

83 %, 84 %

With CO2 in benzene-d6, CO2 added by vacuum transfer to a soln. of Ru-compound; not isolated; NMR Hartwig, John F.; Bergman, Robert G.; Andersen, Richard A.; Organometallics; vol. 10; (1991); p. 3344 - 3362 ; (from Gmelin) View in Reaxys

O O

Rx-ID: 2011780 View in Reaxys 52/477 Yield

Conditions & References

35 %, 10 %, 40 %

With acetic anhydride, cobalt(II) chloride in acetonitrile, Time= 8h, T= 25 °C Iqbal, Javed; Srivastava, Rajiv Ranjan; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2001 - 2007 View in Reaxys

O S Cl

Rx-ID: 2915965 View in Reaxys 53/477 Yield 19 %

Conditions & References With potassium fluoride, 18-crown-6 ether in N,N-dimethyl-formamide, Time= 24h, T= 153 °C

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Nader, Bassam S.; Cordova, Jody A.; Reese, Karen E.; Powell, Cynthia L.; Journal of Organic Chemistry; vol. 59; nb. 10; (1994); p. 2898 - 2901 View in Reaxys

Rx-ID: 23573045 View in Reaxys 54/477 Yield 45.73 51.50 %

Conditions & References 1; 2; 3 :In these Examples, the analysis of hydroxyacetone was carried out on an Agilent 6890 Gas chromatograph (GC). GC separation was carried out on glass column with a length 24 inches 1/4 inch outer diameter, configured for on column injection, packed with chromsorb 102 80/100 mesh, with helium as carrier gas at 30 milliliters per minute (ml/min). The injector temperature was maintained at 160° C. and the detector temperature was maintained at 250° C. The initial column temperature was kept at 110° C. for 3 minutes hold time, this was followed by a temperature increase at 7° C. per minute to reach 150° C., held for 2 minutes, at 150° C., followed by a temperature increase at 10° C. per minute to reach 200° C. and held at 200° C. for 15 minutes. The column was calibrated with standard hydroxyacetone (obtained from Aldrich Chemical Company, 97percent pure) at a concentration ranging from 5 parts per million (ppm) to 244 ppm made in a 50:50 mixture of cumene and phenol. Hydroxyacetone in the reaction mixture was analyzed by neutralizing a test sample with anhydrous sodium carbonate (around 1.5 g of sodium carbonate is utilized to neutralize 10 g of sample reaction mixture). The sample reaction mixture was directly injected into the GC without dilution to obtain maximum intensity of the HA peak in the sample. The analysis of cumene, AMS, acetophenone, DMBA, and DCP was carried out on an Agilent 6890 column Gas chromatograph. GC separation was carried out on SBP-1 liquid phase, 30 meter length, 0.53 millimeter inner diameter and a film thickness of 3.0 micrometer. The GC was initially calibrated using standard Aldrich samples of cumene, AMS, acetophenone, DMBA, and DCP diluted in 50:50 acetone and phenol mixture. The diluted standard samples were injected into GC with an on-column injector. About 10 grams of sample reaction mixture was neutralized with anhydrous sodium carbonate (1.5 grams) to avoid degradation and further reaction of cleavage products. The stabilized reaction mixture was then weighed accurately and diluted with an equal weight of acetone. The solution was than injected into an on-column GC. Samples at specific time intervals were analyzed and compared to the GC chromatogram of a standard to determine the cleavage of CHP to corresponding products. The analysis of phenol was carried out on a Shimadzu GC. The GC separation was carried out on HP-50 column, 30 meter length, 0.25 millimeter inner diameter and 0.25 micrometer film thickness. The injector and detector temperature were kept at 290° C., split ratio of 1:100 was used to avoid saturation of column. The initial column temperature was kept at 50° C., which was followed by a temperature increase of 8° C. per minute to 240° C. and then held at 240° C. for 10 minutes. The GC was initially calibrated with phenol obtained from Aldrich. The phenol standard was prepared by diluting phenol in acetonitrile to obtain various concentration levels of phenol. The diluted standard samples were then injected into the GC. Samples were analyzed by weighing about 100 milligrams of reaction mixture and diluting the reaction mixture with acetonitrile to a homogeneous mixture of 10 milliliters, and injecting into a GC with HP-50 Column. Samples at specific time intervals during reaction were analyzed and compared to the GC chromatogram of the standard sample to determine percentage of phenol formed by cleavage of CHP. Comparative Examples 1, 2, and 3 In these comparative examples, CHP was decomposed in a prior art two-step continuous process to obtain a phenol product, wherein the molar ratio of the phenol to acetone was maintained at 0.77:1 as in Comparative Example 1 or 1:1 as in Comparative Examples 2 and 3. The process generally included adding CHP to an agitated mixture of phenol, acetone, and sulfuric acid. The composition of the feed stream entering the reactor is illustrated in Table 1. In the first step of the continuous process, a typical synthetic feed stream comprising phenol, acetone, and CHP was fed to a glass reactor fitted with a condenser having a capacity of about 150 milliliters through the respective inlets for the feed stream and acid catalyst. The reactor was also fitted with a temperature probe to monitor the temperature and external heating/cooling jacket to maintain the temperature. The contents of the reactor were continuously stirred with a magnetic stirrer. The composition of the feed stream and amount of catalyst added is illustrated in Table I below. The reactor in the first step was maintained at 50° C. The residence time of the feed stream was monitored and maintained at 1 minute in the first step of the process. Sulfuric acid (98percent) was added separately and simultaneously with the feed stream to the reactor. The resultant effluent was analyzed for residual CHP, DMBA, hydroxyacetone, DCP and phenol. Results of the analysis are included in Table 2 below. The resulting effluent was then neutralized using 1percent aqueous ammonia solution, to result in a mixture containing 100 ppm acid catalyst, in a neutralizer. This neutralized effluent was then fed to the second step reactor. The reactor used in the second step was a stainless steel chamber

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having a capacity of 300 ml and is fitted with criss-cross baffles to ensure efficient mixing of the reactor contents. The second step reactor is maintained at 130° C. and under a pressure of 90 psig. The residence time maintained in the second step was 17 minutes. The resulting mixture from second step was analyzed using gas chromatographic techniques. The results of the analysis are included in Table 2 below. In these examples, CHP was decomposed in a continuous 2-STEP process to obtain a phenol product, wherein the molar ratio of phenol to acetone was greater than or equal to 1.2:1, and the effluent produced from the first step contained at least 1percent residual CHP. Table 3 illustrates the composition of the feed stream. The process generally included adding CHP to an agitated mixture of phenol, acetone, and sulfuric acid. In the first step of the continuous process, a typical synthetic feed composition having phenol, acetone, and CHP was fed to a glass reactor fitted with a condenser having a capacity of about 150 milliliters through the respective inlets for the feed stream and acid catalyst. The reactor was also fitted with a temperature probe to monitor the temperature and external heating/cooling jacket to maintain the temperature. The contents of the reactor were continuously stirred with a magnetic stirrer. The composition of the feed stream and amount of catalyst added is illustrated in Table II below. The reactor in the first step was maintained at 50° C. The residence time of the feed stream was monitored and maintained at 1 minute in the first step of the process. Sulfuric acid (98percent) of concentration was added separately and simultaneously with the feed stream to the reactor. The resultant effluent was analyzed for residual CHP, DMBA, hydroxyacetone, DCP and phenol. Results of the analysis are included in Table 4 below. The resulting mixture was the neutralized using 1percent aqueous ammonia solution to result in a mixture containing 100 ppm acid catalyst, in a neutralizer. This neutralized effluent was then fed to the second step reactor. The reactor used in the second step was a stainless steel chamber having a capacity of 300 ml and is fitted with criss-cross baffles to ensure efficient mixing of the reactor contents. The second step reactor is maintained at 130° C. and under a pressure of 90 psig. The residence time maintained in the second step was 17 minutes. The resulting mixture from second step was analyzed using gas chromatographic techniques. The results of the analysis are included in Table 4 below. With sulfuric acid in water, T= 50 - 200 °C , Product distribution / selectivity Patent; Tatake, Prashant Anil; Kumbhar, Pramod Shankar; Singh, Bharat; Fulmer, John William; Mandal, Sabyasachi; Kumar, Arun N.; Pawar, Rupesh; US2005/222466; (2005); (A1) English View in Reaxys

–O

Na +

Rx-ID: 28112923 View in Reaxys 55/477 Yield

Conditions & References 1-2 :EXAMPLE 1 [0047] The comparative example 1 was repeated with the difference that in the cleavage product 1.0 wt.-percent sodium phenolate were dissolved. The sodium phenolate was added by means of 42 wt.-percent aqueous sodium phenolate solution, whereby the water content of the cleavage product was increased to 2.4 wt.percent. The mixture of cleavage product and aqueous phenolate solution remained homogeneous. The homogeneous mixture was saturated with air by applying air at a pressure of 3 barabs. The mixture was held for 2 hours at 80° C. under constant air pressure. The cleavage product comprised 42 wt.-percent phenol, 26 wt.-percent acetone, 3.1 wt.-percent alpha-methylstyrene, and 300 wppm hydroxyacetone. All concentrations are related to the total amount of organic components (water-free).; EXAMPLE 2 [0048] The comparative example 1 was repeated with the difference that in the cleavage product 1.5 wt.-percent sodium phenolate were dissolved. The sodium phenolate was added by means of 42 wt.-percent aqueous sodium phenolate solution, whereby the water content of the cleavage product was increased to 3.1 wt.-percent. The mixture of cleavage product and aqueous phenolate solution remained homogeneous. The homogeneous mixture was saturated with air by applying air at a pressure of 5 barabs. The mixture was held for 2 hours at 80° C. under constant air pressure. The cleavage product comprised 42 wt.-percent phenol, 26 wt.-percent acetone, 3.1 wt.-percent alpha-methylstyrene, and less than 50 wppm hydroxyacetone. All concentrations are related to the total amount of organic components (water-free). Stage 1:, T= 40 °C , pH= 7 Stage 2: With oxygen in water, Time= 2h, T= 80 °C , p= 2250.23 - 3750.38Torr , Product distribution / selectivity Patent; Weber, Manfred; Sigg, Reinhard; Lausmann, Michael; Greschek, Siegmund; US2003/220528; (2003); (A1) English View in Reaxys

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H O

Rx-ID: 2071794 View in Reaxys 56/477 Yield

Conditions & References

17 %, 2.8 %, 1.3 %, 30 %

With sodium lauryl sulfate in water, Irradiation, Title compound not separated from byproducts

30 %, 17 %, 2.8 %, 1.3 %

With sodium lauryl sulfate in water, Irradiation, further detergents, Quantum yield, Product distribution

30 %, 30 %, 2.0 %, 1%

With trimethylhexadecylammonium chloride in water, T= 20 - 25 °C , Irradiation, cage effect, Quantum yield, Product distribution

Turro, J. Nicholas; Mattay, Jochen; Tetrahedron Letters; vol. 21; nb. 19; (1980); p. 1799 - 1802 View in Reaxys

Turro, Nicholas J.; Mattay, Jochen; Journal of the American Chemical Society; vol. 103; nb. 14; (1981); p. 4200 4204 View in Reaxys 22 %, 2.2 %, 0.8 %, 23 %

With trimethylhexadecylammonium chloride in water, Irradiation, Title compound not separated from byproducts Turro, J. Nicholas; Mattay, Jochen; Tetrahedron Letters; vol. 21; nb. 19; (1980); p. 1799 - 1802 View in Reaxys

Rx-ID: 2085044 View in Reaxys 57/477 Yield

Conditions & References

73 %

With sodium sulfide, Aliquatreg; 336 in water, pentane, Time= 0.5h, Ambient temperature Nakayama, Juzo; Machida, Haruki; Hoshino, Masamatsu; Tetrahedron Letters; vol. 24; nb. 29; (1983); p. 3001 3004 View in Reaxys

Rx-ID: 2085780 View in Reaxys 58/477 Yield

Conditions & References With tetrakis(triphenylphosphine) palladium(0), carbon monoxide, 2,6-di-tert-butyl-4-methyl-phenol, trimethyl(1-methylethenyl)stannane in toluene, Time= 1h, T= 100 °C , p= 760Torr Renaldo, A. F.; Ito, Hiroshi; Synthetic Communications; vol. 17; nb. 15; (1987); p. 1823 - 1830 View in Reaxys O Se

Rx-ID: 2089961 View in Reaxys 59/477 Yield 51 %

Conditions & References With dipotassium hydrogenphosphate, 3-chloro-benzenecarboperoxoic acid in tetrahydrofuran, Time= 1h, T= 0 °C , Title compound not separated from byproducts Tiecco, Marcello; Testaferri, Lorenzo; Tingoli, Marco; Chianelli, Donatella; Bartoli, Donatella; Gazzetta Chimica Italiana; vol. 117; nb. 7; (1987); p. 423 - 428

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View in Reaxys

dimethyl-<α.α-dimethyl-benzyl>-amine oxide

Rx-ID: 7067052 View in Reaxys 60/477 Yield

Conditions & References T= 75 - 85 °C , p= 3 - 5Torr Cope; Foster; Towle; Journal of the American Chemical Society; vol. 71; (1949); p. 3929,3933 View in Reaxys

terphenylsuccinic acid dinitrile

9,10-dioxo-9,10-dihydro-anthracene-1-sulfenyl bromide Rx-ID: 16951042 View in Reaxys 61/477 Yield

Conditions & References Reaction Steps: 2 2: 97 percent Chromat. / Ni(dppf)Cl2 / tetrahydrofuran / 8 h / 45 °C With 1,1'-bis(diphenylphosphanyl)ferrocenenickel(II) chloride in tetrahydrofuran Srogl, Jiri; Allred, Gary D.; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 119; nb. 50; (1997); p. 12376 - 12377 View in Reaxys

(v4)

P (v4) P P (v4) P(v4)Ru (v6) (v4) O

O P Ru (v4)(v4) P (v6) P

(v4)

Rx-ID: 26517677 View in Reaxys 62/477 Yield 61 %, 58 %

Conditions & References With acetophenone in benzene-d6, inert gas, pumped and sealed under vacuum, heated to 45°C for 8 h; not isolated; NMR Hartwig, John F.; Bergman, Robert G.; Andersen, Richard A.; Organometallics; vol. 10; (1991); p. 3344 - 3362 ; (from Gmelin) View in Reaxys

Rx-ID: 28269867 View in Reaxys 63/477 Yield

Conditions & References 22 :EXAMPLES 22 (COMPARATIVE) AND 23-27Catalysts were prepared according to the process of Examples 1-17. The ingredients were used in different amounts and the catalyst composition after calcination is shown in Table 3. The catalysts of Examples 22-27 were tested according to the same method of the above examples. The amount of α-methyl styrene (AMS) in the product was measured and is shown in Table 3 as ppmw relative to the weight of the condensed product stream from the dehydrogenation reactor. The α-methyl styrene levels were tested by gas chromatograph at the T70 temperature. Example 22 depicts the average results for three catalysts with the same composition. TABLE 3 Composition, millimoles/mole Exam- iron oxide Calc T70 S70 AMS ple Ag Mo Ce Ca K T ° C. ° C. percent ppmw 22 0 18 122 25 623 950 595.9 95.5 260 (Comp) 23 70 18 125 25 623 975 588.1 95.8 226 24 70 18 125 25 623 1035 590.0 96.4 248 25 100 18 150 25 623 1035 592.8 95.8 218 26 150 18 150 25 623 1035 594.9 95.8 235 27 200 18 150 25 623 1035 588.7 96.2 225 As can be seen from Examples 22-27, an iron oxide based dehydrogenation catalyst containing silver can result in the production of a reduced amount of alpha-methyl styrene impurity in an ethylbenzene dehydrogenation process.One skilled in the art can vary many of the variables shown above in addition to other variables to achieve a dehydrogenation catalyst that is most effective for a particular application. Additional catalyst components may also be added to affect the properties and performance of the catalyst.

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The catalyst manufacturing process may be altered with respect to such variables as drying times and temperatures, calcination times and temperatures, and processing speed to affect the properties and performance of the catalyst. With CaCO3; Ce2(CO3)2; Fe2O3; FeOOH; K2CO3; MoO3; mixture of, calcined, Time= 120 - 240h, T= 595 - 600 °C , p= 570.057Torr , Product distribution / selectivity Patent; KOWALESKI, Ruth Mary; US2009/62588; (2009); (A1) English View in Reaxys 23; 24; 25; 26; 27 :EXAMPLES 22 (COMPARATIVE) AND 23-27Catalysts were prepared according to the process of Examples 1-17. The ingredients were used in different amounts and the catalyst composition after calcination is shown in Table 3. The catalysts of Examples 22-27 were tested according to the same method of the above examples. The amount of α-methyl styrene (AMS) in the product was measured and is shown in Table 3 as ppmw relative to the weight of the condensed product stream from the dehydrogenation reactor. The α-methyl styrene levels were tested by gas chromatograph at the T70 temperature. Example 22 depicts the average results for three catalysts with the same composition. TABLE 3 Composition, millimoles/mole Exam- iron oxide Calc T70 S70 AMS ple Ag Mo Ce Ca K T ° C. ° C. percent ppmw 22 0 18 122 25 623 950 595.9 95.5 260 (Comp) 23 70 18 125 25 623 975 588.1 95.8 226 24 70 18 125 25 623 1035 590.0 96.4 248 25 100 18 150 25 623 1035 592.8 95.8 218 26 150 18 150 25 623 1035 594.9 95.8 235 27 200 18 150 25 623 1035 588.7 96.2 225 As can be seen from Examples 22-27, an iron oxide based dehydrogenation catalyst containing silver can result in the production of a reduced amount of alphamethyl styrene impurity in an ethylbenzene dehydrogenation process.One skilled in the art can vary many of the variables shown above in addition to other variables to achieve a dehydrogenation catalyst that is most effective for a particular application. Additional catalyst components may also be added to affect the properties and performance of the catalyst. The catalyst manufacturing process may be altered with respect to such variables as drying times and temperatures, calcination times and temperatures, and processing speed to affect the properties and performance of the catalyst. With Ag2O; CaCO3; Ce2(CO3)2; Fe2O3; FeOOH; K2CO3; MoO3; mixture of, calcined, Time= 120 - 240h, T= 595 - 600 °C , p= 570.057Torr , Product distribution / selectivity Patent; KOWALESKI, Ruth Mary; US2009/62588; (2009); (A1) English View in Reaxys

O HO

O O O

Rx-ID: 30687454 View in Reaxys 64/477 Yield

Conditions & References

64 %

With trans-[RuCl2(η3:η3-2,7-dimethylocta-2,6-diene-1,8-diyl)(PPh3)] in water, Time= 24h, T= 60 °C , Sealed tube, Inert atmosphere Cadierno, Victorio; Francos, Javier; Gimeno, Jose; Organometallics; vol. 30; nb. 4; (2011); p. 852 - 862 View in Reaxys

Rx-ID: 1627776 View in Reaxys 65/477 Yield 1 %, 99 %

Conditions & References With niobium bromide in toluene, Time= 25h, T= 50 °C Miyashita, Akira; Shimada, Takeshi; Sugawara, Atsushi; Nohira, Hiroyuki; Chemistry Letters; (1986); p. 1323 1326 View in Reaxys

20 %, 60 %

With bis(cyclopentadienyl)titanium dichloride, magnesium in tetrahydrofuran, Time= 12h, Ambient temperature Schobert, Rainer; Angewandte Chemie; vol. 100; nb. 6; (1988); p. 869 - 871 View in Reaxys

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With Ni(PPh3)4 in toluene, Time= 2h, T= 50 °C , Yield given. Yields of byproduct given Miyashita, Akira; Shimada, Takeshi; Sugawara, Atsushi; Nohira, Hiroyuki; Chemistry Letters; (1986); p. 1323 1326 View in Reaxys

Rx-ID: 2032902 View in Reaxys 66/477 Yield

Conditions & References in ethanol, T= 75 °C , hydrogen isotope effect, primary chlorine isotope effect, Rate constant Koch, H. F.; Koch, J. G.; Tumas, W.; McLennan, D. J.; Dobson, B.; Lodder, G.; Journal of the American Chemical Society; vol. 102; nb. 27; (1980); p. 7955 - 7956 View in Reaxys With sodium ethanolate in ethanol, T= 75 °C , chlorine and hydrogen isotope effects, and element effect, Mechanism Koch, Heinz F.; McLennan, Duncan J.; Koch, Judith G.; Tumas, William; Dobson, Brian; Koch, Nanci H.; Journal of the American Chemical Society; vol. 105; nb. 7; (1983); p. 1930 - 1937 View in Reaxys With potassium hydroxide in diethylene glycol, Time= 1.5h, Reflux Magerramov; Aliev; Mustafaev; Askerova; Russian Journal of Organic Chemistry; vol. 48; nb. 2; (2012); p. 293 295 View in Reaxys

S Br–+Mg

Rx-ID: 2059302 View in Reaxys 67/477 Yield 70 %

Conditions & References With [1,3-bis(diphenylphosphino) propane] dichloronickel(II) in diethyl ether, Time= 36h, Ambient temperature Fiandanese, V.; Marchese, G.; Naso, F.; Ronzini, L.; Synthesis; nb. 11; (1987); p. 1034 - 1036 View in Reaxys

N+ C–

Rx-ID: 2432013 View in Reaxys 68/477 Yield 77 %, 20 %

Conditions & References T= 520 - 550 °C , p= 0.01Torr Meier, Michael; Ruechardt, Christoph; Chemische Berichte; vol. 120; (1987); p. 1 - 4 View in Reaxys

20 %, 77 %

T= 520 - 550 °C , p= 0.01Torr Meier, Michael; Ruechardt, Christoph; Chemische Berichte; vol. 120; (1987); p. 1 - 4 View in Reaxys

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Rx-ID: 2556340 View in Reaxys 69/477 Yield

Conditions & References

76.6 %

With toluene-4-sulfonic acid, T= 105 °C Takano, Seiichi; Iwabuchi, Yoshiharu; Takahashi, Michiyasu; Ogasawara, Kunio; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 8; (1986); p. 3445 - 3446 View in Reaxys

O HN

N N

Rx-ID: 3219263 View in Reaxys 70/477 Yield

Conditions & References

95 %, 98 %

in dimethyl sulfoxide, T= 60 °C , decomposition, other solvent, other temperature, Rate constant Mitsuhashi Tsutomu; Journal of the American Chemical Society; vol. 108; nb. 9; (1986); p. 2394 - 2400 View in Reaxys

O O

racemate

Rx-ID: 4683279 View in Reaxys 71/477 Yield

Conditions & References

48 % Chromat., 20 %, 12 % Chromat., 44 % Chromat.

With triphenylphosphine in benzene, Time= 8h, T= 60 °C Abe, Manabu; Sumida, Yohko; Nojima, Masatomo; Journal of Organic Chemistry; vol. 62; nb. 3; (1997); p. 752 754 View in Reaxys

Rx-ID: 5086067 View in Reaxys 72/477 Yield

Conditions & References With mer,trans-[(CH3CH2CH2N(CH2CH2PPh2)2)RuCl2(PPh3)], water, 1.) THF, reflux, 2.) THF, Multistep reaction Bianchini, Claudio; Peruzzini, Maurizio; Zanobini, Fabrizio; Lopez, Carlos; De Los Rios, Isaac; Romerosa, Antonio; Chemical Communications; nb. 5; (1999); p. 443 - 444 View in Reaxys With cis-[Ru(κ2-OAc)2(PPh3)2] in dichloromethane-d2, T= 20 °C , Inert atmosphere

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Welby, Christine E.; Eschemann, Thomas O.; Unsworth, Christopher A.; Smith, Elizabeth J.; Thatcher, Robert J.; Whitwood, Adrian C.; Lynam, Jason M.; European Journal of Inorganic Chemistry; nb. 9; (2012); p. 1493 1506 View in Reaxys

<(Me3Si)2N>2U<*>CH2SiMe2NSiMe3

Rx-ID: 6712324 View in Reaxys 73/477 Yield 85 %

Conditions & References in pentane, Time= 0.0333333h, Ambient temperature Dormond, Alain; Bouadili, Abdelaziz El; Moise, Claude; Journal of Organic Chemistry; vol. 52; nb. 4; (1987); p. 688 - 689 View in Reaxys

Rx-ID: 9874531 View in Reaxys 74/477 Yield

Conditions & References With dicyclohexyl(2,4,6-triisopropylphenyl)phosphine, potassium carbonate, bis(dibenzylideneacetone)-palladium(0) in isopropyl alcohol, Time= 21.5h, T= 80 °C Bei, Xiaohong; Hagemeyer, Alfred; Volpe, Anthony; Saxton, Robert; Turner, Howard; Guram, Anil S.; Journal of Organic Chemistry; vol. 69; nb. 25; (2004); p. 8626 - 8633 View in Reaxys

Rx-ID: 11324492 View in Reaxys 75/477 Yield

Conditions & References Reaction Steps: 2 1: 2,6-di-tert-butyl-4-methylpyridine / 1,2-dichloro-ethane / 1 h / 70 °C 2: 115 mg / formic acid; tributylamine / Pd(OAc)2(PPh3)2 / dimethylformamide / 0.5 h / 35 °C With formic acid, 2,6-di-tert-butyl-4-methylpyridine, tributyl-amine, [Pd(PPh3)2(OAc)2] in 1,2-dichloro-ethane, N,N-dimethyl-formamide Pandey, Sushil K.; Greene, Andrew E.; Poisson, Jean-Francois; Journal of Organic Chemistry; vol. 72; nb. 20; (2007); p. 7769 - 7770 View in Reaxys

HO O

Rx-ID: 27897451 View in Reaxys 76/477 Yield

Conditions & References 2 :Example 2; CHP decomposition was carried out in the same equipment as in Example 1, but the reactor for synthesis of the catalytic system had a volume of 20 μL, and a mixture having the composition shown in Table 3 was used as feedstock.The feedstock was fed to the reactor at a rate of 10 mL/h, concentrated (96percent) sulfuric acid was fed at a rate of 1.1 μL/h, which corresponded to a concentration of 0.02 wt. percent, and phenol for mixing with sulfuric acid was fed at a rate of 0.9 μL/h, which corresponded to a sulfuric acid/phenol ratio of 2:1. The mixture of phenol and sulfuric acid was held for 600 minutes at a temperature of 20° C. The circulation rate of the reaction mix-

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ture was 200 mL/h, and the temperature in the reactor was 70° C. As used herein, concentrated sulfuric acid means "commercially available usual sulfuric acid", which generally means about 93 to 96percent sulfuric acid (H2SO4). With sulfuric acid, phenol in water, T= 70 °C , Product distribution / selectivity Patent; Nelson, Mark; Sederel, Willem Lodewyk; Dyckman, Arkady Samuilovich; Grebenshchikov, Ilya Nikolaevich; Pinson, Viktor Vladimirovich; Zinenkov, Andrey Vladimirovich; US2008/214872; (2008); (A1) English View in Reaxys 6 :Example 6 (Comparative Example)The CHP cleavage reaction was carried out using the same equipment as in Example 1, but the feed of composition presented in Table 7 was used. CHP feed was pumped at rate of 26 ml/hr, and the sulfuric acid rate was 4 μL/h. Circulation rate and temperature regime used were the same as presented in Example 1.Reaction product discharged form the first stage reactor was passed to the second stage reactor together with a 5percent ammonia solution in water fed at rate of 8 μL/h. The composition of reaction mixture produced is presented in Table 8. Stage 1: With sulfuric acid in water, T= 40 - 125 °C Stage 2: With ammonia in water, T= 125 °C , Product distribution / selectivity Patent; Nelson, Mark; Sederel, Willem Lodewyk; Dyckman, Arkady Samuilovich; Grebenshchikov, Ilya Nikolaevich; Pinson, Viktor Vladimirovich; Zinenkov, Andrey Vladimirovich; US2008/214873; (2008); (A1) English View in Reaxys

Rx-ID: 28317558 View in Reaxys 77/477 Yield 45 %Chromat., 25 %Chromat., 20 %Chromat., 6 %

Conditions & References With palladium diacetate, CsO2CCMe3 in N,N-dimethyl-formamide, Time= 8h, T= 105 °C , Inert atmosphere Motti, Elena; Catellani, Marta; Advanced Synthesis and Catalysis; vol. 350; nb. 4; (2008); p. 565 - 569 View in Reaxys

Rx-ID: 267157 View in Reaxys 78/477 Yield

Conditions & References Chalezki; Zhurnal Obshchei Khimii; vol. 15; (1945); p. 524,525; ; (1946); p. 4696 View in Reaxys Kharasch; Brown; Journal of the American Chemical Society; vol. 61; (1939); p. 2142,2146 View in Reaxys With potassium hydroxide Tiffeneau; Annales de Chimie (Cachan, France); vol. <8>10; (1907); p. 190; Annales de Chimie (Cachan, France); vol. <8>11; (1907); p. 144 View in Reaxys With pyridine Klages; Chemische Berichte; vol. 35; (1902); p. 2649; Chemische Berichte; vol. 39; (1906); p. 2591 View in Reaxys With 1,3,5-trimethylverdazyl in acetonitrile, T= 25 °C , influence of var. salts on the rate of ionization, other verdazyls, Rate constant, Mechanism

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Dvorko, G.F.; Evtushenko, N.Yu.; J. Gen. Chem. USSR (Engl. Transl.); vol. 61; nb. 9.2; (1991); p. 2051 2059,1900 - 1907 View in Reaxys With 1,3,5-trimethylverdazyl in various solvent(s), T= 25 °C , influence of var. salts on the rate of ionization, Kinetics, Rate constant, Mechanism Dvorko, G.F.; Evtushenko, N.Yu.; J. Gen. Chem. USSR (Engl. Transl.); vol. 61; nb. 9.2; (1991); p. 2051 2059,1900 - 1907 View in Reaxys With 1,3,5-trimethylverdazyl in various solvent(s), T= 25 °C , influence of var. salts on the rate of ionization, Rate constant, Mechanism Dvorko, G.F.; Evtushenko, N.Yu.; J. Gen. Chem. USSR (Engl. Transl.); vol. 61; nb. 9.2; (1991); p. 2059 2067,1908 - 1915 View in Reaxys in acetonitrile, T= 45 °C , Kinetics Balachandran; Santhosh Kumar; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 44; nb. 8; (2005); p. 1731 - 1734 View in Reaxys With pyridine in acetonitrile, T= 55 °C , Kinetics, Further Variations: Temperatures Balachandran; Santhosh Kumar; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 44; nb. 8; (2005); p. 1731 - 1734 View in Reaxys 3 : EXAMPLE 3 EXAMPLE 3 In a flask fitted with a strirrer 500 ml of water is heated to 110° C., and 250 g of cumyl chloride is added dropwise over a period of 6 h. Continuous distillation is carried out through the column described in Example 1, yielding 166 g of alpha-methylstyrene and 190 ml of water. in water Patent; BASF Aktiengesellschaft; US4822946; (1989); (A1) English View in Reaxys

O O

Rx-ID: 2052023 View in Reaxys 79/477 Yield 94 % Chromat.

Conditions & References With tetrakis(triphenylphosphine) palladium(0), Time= 2h, T= 25 °C Takai, Kazuhiko; Oshima, Koichiro; Nozaki, Hitosi; Tetrahedron Letters; vol. 21; (1980); p. 2531 - 2534 View in Reaxys

94 % Chromat.

With tetrakis(triphenylphosphine) palladium(0) in hexane, 1,2-dichloro-ethane, Time= 2h, T= 25 °C Takai; Sato; Oshima; Nozaki; Bulletin of the Chemical Society of Japan; vol. 57; nb. 1; (1984); p. 108 - 115 View in Reaxys

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O W Cl (v6) Cl

Rx-ID: 3383789 View in Reaxys 80/477 Yield

Conditions & References

77 %

in tetrahydrofuran, Time= 1.5h, T= 20 °C Kauffmann, Thomas; Abeln, Renate; Welke, Siegfried; Wingbermuehle, Dorothea; Angewandte Chemie; vol. 98; nb. 10; (1986); p. 927 - 928 View in Reaxys

I–

N+

Rx-ID: 4080576 View in Reaxys 81/477 Yield

Conditions & References

25 %

With sodium tetrahydroborate in isopropyl alcohol, Heating Gupton, John T.; Layman, William J.; Journal of Organic Chemistry; vol. 52; nb. 16; (1987); p. 3683 - 3686 View in Reaxys

OMo(NNCMePh)(S2CN(Et)2)2

Rx-ID: 6712331 View in Reaxys 82/477 Yield 65 %

Conditions & References Time= 24h, Ambient temperature Smegal, John A.; Meier, Ingrid K.; Schwartz, Jeffrey; Journal of the American Chemical Society; vol. 108; nb. 6; (1986); p. 1322 - 1323 View in Reaxys

fac,cis[(PNP)RuCl2{C=CHC(Ph)=CH2}] Rx-ID: 8519215 View in Reaxys 83/477 Yield

Conditions & References With water in chloroform-d1, T= 20 °C , Hydrolysis Bianchini, Claudio; De los Rios, Isaac; Lopez, Carlos; Peruzzini, Maurizio; Romerosa, Antonio; Journal of Organometallic Chemistry; vol. 593-594; (2000); p. 485 - 488 View in Reaxys

Rx-ID: 9062270 View in Reaxys 84/477 Yield 55 %, 28 %, 13 %

Conditions & References With 2-hydroxy-1,3-isoindolinedione, air, nitrogen(IV) oxide, Time= 5h, T= 70 °C Nishiwaki, Yoshiki; Sakaguchi, Satoshi; Ishii, Yasutaka; Journal of Organic Chemistry; vol. 67; nb. 16; (2002); p. 5663 - 5668 View in Reaxys

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Rx-ID: 9721535 View in Reaxys 85/477 Yield

Conditions & References With hydrogen cation in water, T= 250 °C Hunter, Shawn E.; Savage, Phillip E.; Journal of Organic Chemistry; vol. 69; nb. 14; (2004); p. 4724 - 4731 View in Reaxys

O HO

Rx-ID: 29443976 View in Reaxys 86/477 Yield

Conditions & References

72 %, 23 %

With pentafluorophenyldihydroxyborane in toluene, Time= 16h, Reflux, Molecular sieve, Friedel-Crafts arylation McCubbin, J. Adam; Krokhin, Oleg V.; Tetrahedron Letters; vol. 51; nb. 18; (2010); p. 2447 - 2449 View in Reaxys

P+

I– O

Rx-ID: 34597824 View in Reaxys 87/477 Yield

Conditions & References Stage 1: With n-butyllithium in tetrahydrofuran, hexane, Time= 0.5h, T= 0 °C , Wittig Olefination Stage 2: in tetrahydrofuran, hexane, Time= 24h, T= 20 °C , Wittig Olefination Gong, Wanchun; Liu, Yun; Xue, Jijun; Xie, Zhixiang; Li, Ying; Chemistry Letters; vol. 41; nb. 12; (2012); p. 1597 - 1599 View in Reaxys With potassium tert-butylate in tetrahydrofuran, T= 20 °C , Inert atmosphere, Schlenk technique, Wittig Olefination Matsuda, Takanori; Yuihara, Itaru; Chemical Communications; vol. 51; nb. 34; (2015); p. 7393 - 7396 View in Reaxys With potassium tert-butylate in tetrahydrofuran, Wittig Olefination Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583 View in Reaxys

F F

HN S

S F

F F

Rx-ID: 34987185 View in Reaxys 88/477 Yield

Conditions & References With acetyl chloride in dichloromethane, Time= 10h, T= 20 °C , Overall yield = 37 percentSpectr. Liu, Jianbo; Chu, Lingling; Qing, Feng-Ling; Organic Letters; vol. 15; nb. 4; (2013); p. 894 - 897 View in Reaxys

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N O

Rx-ID: 41318781 View in Reaxys 89/477 Yield

Conditions & References

72 %

in neat (no solvent), Time= 24h, T= 120 °C , Sealed tube, Inert atmosphere, Schlenk technique Li, Gang; Yang, Suling; Lv, Bingjie; Han, Qingqing; Ma, Xingxing; Sun, Kai; Wang, Zhiyong; Zhao, Feng; Lv, Yunhe; Wu, Hankui; Organic and Biomolecular Chemistry; vol. 13; nb. 46; (2015); p. 11184 - 11188 View in Reaxys

Rx-ID: 1709983 View in Reaxys 90/477 Yield

Conditions & References With (NH4)2S2O8, copper diacetate in water, acetonitrile, T= 100 °C , Yield given. Yields of byproduct given Walling, Cheves; Zhao, Chengxue; El-Taliawi, Gamil M.; Journal of Organic Chemistry; vol. 48; nb. 25; (1983); p. 4910 - 4914 View in Reaxys

Rx-ID: 2011787 View in Reaxys 91/477 Yield

Conditions & References

60 %, 23 %

With phosphoric acid, acetic anhydride, Time= 48h, Ambient temperature Gurudutt, K. N.; Rao, L. Jagan Mohan; Rao, Sanjay; Srinivas, P.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 32; nb. 4; (1993); p. 468 - 470 View in Reaxys

31 %, 45 %

With 1,3,2-benzodithiazole 1,1,3,3-tetraoxide, acetic anhydride, T= 20 °C Barbero, Margherita; Cadamuro, Silvano; Dughera, Stefano; Venturello, Paolo; Synthesis; nb. 22; (2008); p. 3625 - 3632 View in Reaxys

Rx-ID: 2071792 View in Reaxys 92/477 Yield 29 %, 30 %, 26 %, 23 %, 33 %

Conditions & References With trimethylhexadecylammonium chloride, copper dichloride in water, T= 20 - 25 °C , Irradiation, cage effect, Quantum yield, Product distribution Turro, Nicholas J.; Mattay, Jochen; Journal of the American Chemical Society; vol. 103; nb. 14; (1981); p. 4200 4204 View in Reaxys With copper dichloride in water, Irradiation, micellar cage effects investigated, Product distribution Turro, J. Nicholas; Mattay, Jochen; Tetrahedron Letters; vol. 21; nb. 19; (1980); p. 1799 - 1802

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View in Reaxys

Rx-ID: 2503868 View in Reaxys 93/477 Yield

Conditions & References With (E)-1,2-diphenyl-ethene, cesium fluoride in N,N-dimethyl-formamide Pernez, Stephane; Hamelin, Jack; Tetrahedron Letters; vol. 30; nb. 26; (1989); p. 3419 - 3422 View in Reaxys

13C

H 13C

Rx-ID: 2834975 View in Reaxys 94/477 Yield

Conditions & References

41 %, 41 %, 1.4 %, 0.7 %

With trimethylhexadecylammonium chloride in water, T= 20 - 25 °C , Irradiation, isotope effect, cage effect, Quantum yield Turro, Nicholas J.; Mattay, Jochen; Journal of the American Chemical Society; vol. 103; nb. 14; (1981); p. 4200 4204 View in Reaxys

O F F

O F

Rx-ID: 3070192 View in Reaxys 95/477 Yield

Conditions & References With acetic acid, T= 25 °C , Rate constant Creary, Xavier; Hatoum, Holia N.; Barton, Angela; Aldridge, Timothy E.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1887 - 1897 View in Reaxys With sodium acetate, acetic acid in diethyl ether, water, T= 25 °C , Rate constant Creary, Xavier; Casingal, Vincent P.; Leahy, Charlene E.; Journal of the American Chemical Society; vol. 115; nb. 5; (1993); p. 1734 - 1738 View in Reaxys

Rx-ID: 4668208 View in Reaxys 96/477 Yield

Conditions & References

54 %, 6 %, With C28H26N6ORu(2+)*3F6P(1-)*H(1+) in acetonitrile-D3, T= 24.84 °C , Inert atmosphere, Kinetics 6% Kojima, Takahiko; Nakayama, Kazuya; Ikemura, Kenichiro; Ogura, Takashi; Fukuzumi, Shunichi; Journal of the American Chemical Society; vol. 133; nb. 30; (2011); p. 11692 - 11700 View in Reaxys 15 %, 13 %, 34 %

With C16H10Br4CoN2O2, oxygen, T= 60 °C , Inert atmosphere, Neat (no solvent) Ghanbari; Ferdosi; Tafazolian; Research on Chemical Intermediates; vol. 38; nb. 3-5; (2012); p. 871 - 883 View in Reaxys With lt;Fe2(μ-O)2(TPA)2gt;3+ in acetonitrile, T= -40 °C , Yield given. Yields of byproduct given

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Kim; Dong; Que L.; Journal of the American Chemical Society; vol. 119; nb. 15; (1997); p. 3635 - 3636 View in Reaxys

Me2Fe(CN)2Li2

Rx-ID: 6712328 View in Reaxys 97/477 Yield 89 %

Conditions & References in diethyl ether, Time= 18h, for -78 deg C to r.t. Kauffmann; Nienaber; Synthesis; nb. 2; (1995); p. 207 - 211 View in Reaxys

[(η3-2-phenylallyl)PdCl]2 Rx-ID: 8664237 View in Reaxys 98/477 Yield

Conditions & References With c-C6H11Co(DMG)2, triphenylphosphine in benzene, Photolysis, Demetallation Reid; Freeman; Baird; Chemical Communications; nb. 18; (2000); p. 1777 - 1778 View in Reaxys

I HO

Rx-ID: 9793957 View in Reaxys 99/477 Yield 16 %, 52 %, 20 %

Conditions & References Stage 1: With strontium in tetrahydrofuran Stage 2: in tetrahydrofuran, Time= 19h, T= 20 °C Miyoshi, Norikazu; Kamiura, Koji; Oka, Hiromi; Kita, Akiko; Kuwata, Rika; Ikehara, Daitetsu; Wada, Makoto; Bulletin of the Chemical Society of Japan; vol. 77; nb. 2; (2004); p. 341 - 345 View in Reaxys

Rx-ID: 23426134 View in Reaxys 100/477 Yield

Conditions & References II.B.i :The 6-20 mesh particles of reduced T-366 catalyst, prepared by the procedure of Illustrative Embodiment II (A) (i), were loaded into the reflux zone of a thick walled 31 cm long Vigreux column with an internal diameter of 1.5 cm while inside a nitrogen filled glove box. A small, piece of glass wool was used to support the catalyst particles. The column was attached to a thick walled 250 ml round bottom flask which served as the bottom segment of the reactor for catalytic distillation. Hydrogen gas was added via a regulator to the apparatus to maintain a pressure between 1 and 10 bar. The flow rate was adjusted to maintain twice the amount of hydrogen required for the reaction stoichiometry. 50 grams of 2-phenyl-2-propanol (cumyl alcohol) from Avacado Chemical was added to the 250 mL flask which contained a magnetic stir bar at the bottom of the round bottom flask. The flask containing the cumyl alcohol was lowered into a heater and then the temperature was raised until the liquid refluxed in the Vigreux column containing the catalyst. Lower boiling cumene and water were distilled out from the top of the column. Additional cumyl alcohol was continually added with a slight molar excess of hydrogen to replace the amount of cumyl alcohol that was converted to cumene and distilled off. The cumene product easily separated from the denser water phase. It was optionally dried further with 3A molecular sieves. The results are provided in TABLE 2 below. As shown, the top product stream produced, (after removal of the water), had a purity of cumene of >99.5 wt. percent. No measurable cumyl alcohol (<0. 1 wt. percent) was found in the cumene product. When desired, the bottoms can be removed, optionally diluted with cumene and sent to a fixed bed hydrogenation reactor to make additional cumene. With hydrogen, hydrogenated copper on silica (T-366), p= 750.075 - 7500.75Torr , Product distribution / selectivity Patent; SHELL OIL COMPANY; WO2005/5402; (2005); (A2) English View in Reaxys

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2,4-dibenzoyl-3-ferrocenyl-1,5-diphenylpentane-1,5-dione Rx-ID: 26039598 View in Reaxys 101/477

Yield

Conditions & References

62 %

in diethyl ether, benzene, Time= 6h, T= 20 °C Klimova; Berestneva, T. Klimova; Mendoza, J. M. Martinez; Stivalet, J. M. Mendez; Toscano; Garcia, M. Martinez; Synthetic Communications; vol. 38; nb. 14; (2008); p. 2299 - 2315 View in Reaxys

2,4-dibenzoyl-3-ferrocenyl-2-[(ferrocenyl)hydroxymethyl]-1,5diphenylpentane-1,5-dione Rx-ID: 26039599 View in Reaxys 102/477

Yield

Conditions & References

55 %

in diethyl ether, benzene, Time= 10h, T= 20 °C Klimova; Berestneva, T. Klimova; Mendoza, J. M. Martinez; Stivalet, J. M. Mendez; Toscano; Garcia, M. Martinez; Synthetic Communications; vol. 38; nb. 14; (2008); p. 2299 - 2315 View in Reaxys

2-ferrocenylmethylidene-1,3-diphenylpropane-1,3-dione Rx-ID: 26039601 View in Reaxys 103/477

Yield

Conditions & References

Stage 1: in diethyl ether, benzene, Time= 3h, T= 20 °C Stage 2: With acetic acid, Time= 0.0833333h, Heating, Further stages. Klimova; Berestneva, T. Klimova; Mendoza, J. M. Martinez; Stivalet, J. M. Mendez; Toscano; Garcia, M. Martinez; Synthetic Communications; vol. 38; nb. 14; (2008); p. 2299 - 2315 View in Reaxys

crushed scrap tires Rx-ID: 27958368 View in Reaxys 104/477 Yield

Conditions & References With synthetic air, T= 750 °C , Formation of xenobiotics Conesa, Juan A.; Martin-Gullon; Font; Jauhiainen; Environmental Science and Technology; vol. 38; nb. 11; (2004); p. 3189 - 3194 View in Reaxys T= 750 °C , Formation of xenobiotics Conesa, Juan A.; Martin-Gullon; Font; Jauhiainen; Environmental Science and Technology; vol. 38; nb. 11; (2004); p. 3189 - 3194 View in Reaxys

Rx-ID: 31902762 View in Reaxys 105/477 Yield

Conditions & References Experiments were carried out with formalin (37 wt percent formaldehyde, 15 wt percent methanol, and 48 wt percent water) and toluene over an X-type zeolite catalyst containing boron and cesium. A 0.75-inch outside diameter stainless steel tube was fitted with a 0.5-inch inside diameter ceramic liner. The tube was then filled with crushed quartz (to a height of about 13.5-inches), then filled with 10.2 grams (12.0 cc) of the catalyst, and then more crushed quartz is added to bring the quartz/catalyst/quartz bed to a height of about 17-inches. A pyropaint-coated thermowell was positioned in the middle of the bed. The reactor was installed in a 3-zone furnace and heated to 500° C. and held for

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2 hours while passing nitrogen through it at 150 cc/min. The reactor was then cooled to the reaction temperature of 375° C. The feed was toluene, formalin, and nitrogen. The inlet flow rates were not corrected for temperature. The effluent was monitored by an on-line gas chromatograph.The cesium ion-exchanged zeolite material was made by the following procedure: A glass cylinder (2 inside diameter), fitted with a sintered glass disk and stopcock at the lower end, was charged with 544-HP zeolite (100 g, W.C. Grace) and CsOH (400 mL, 1.0 M in water). The mixture was then brought to 90° C. and allowed to stand for 4 h. The liquid was drained from the zeolite material and another aliquot of CsOH (400 mL of 1.0 M solution in water) was added and allowed to stand for 3 hours at 90° C. The liquid was drained from the zeolite material and another aliquot of CsOH (400 mL of 1.0 M solution in water) was added and allowed to stand for 15 hours at 90° C. The liquid was drained from the zeolite material and dried at 150° C. for 1.5 hours.Deposition of 0.3 wt percent boron onto cesium ion-exchanged zeolite material: The cesium ion-exchanged zeolite material (100 g) was treated with a solution of boric acid (1.52 g) dissolved in acetone (500 mL) at room temperature for 2 hours. The (Cs, B)/X material was then dried at 150° C. for 12 hours. This catalyst was used for the example shown in Table 1.The information in Table 1 describes the results of the above reaction in producing styrene and ethylbenzene from toluene and formalin. It is seen that styrene selectivity decreases during the run and that the highest toluene conversion is at the beginning of the test and at a short contact time. A short contact time and fresh catalyst is seen to result in the highest toluene conversion. The first conversion reading was taken 20 minutes after the start of the run and the toluene conversion was 3.7 wt percent. The second conversion reading was taken 57 minutes into the run and the toluene conversion dropped to 1.9 wt percent. Increasing the contact time during the test improved the toluene conversion but did not bring it to the conversion level at the beginning of the run. Zero selectivity to o-xylene, cumene, phenylacetylene, 1,2,4-trimethylbenzene, and benzaldehyde was observed. The toluene conversion versus contact times from Table 1 is graphed in FIG. 4. The toluene conversion versus on stream time from Table 1 is graphed in FIG. 5. Referring to FIG. 4, the highest conversion of toluene (3.7 mol percent) is at a contact time of 0.71 seconds and at the start of the test when the catalyst is fresh and has not had the deleterious deactivation effects from an extended run time. The other data points show a lower rate of conversion of toluene at both shorter and longer contact times.Referring to FIG. 5, the highest conversion of toluene is at an on stream time of 20 minutes while the catalyst is fresh and has not had the deleterious deactivation effects from an extended run time. The other data points show a lower rate of conversion as the time on stream increases, indicating a benefit to having a restricted time on stream for the catalyst. With (Cs, B)/544-HP zeolite in methanol, water, Time= 0.000197222h, T= 375 °C , Inert atmosphere, Product distribution / selectivity Patent; Fina Technology, Inc.; US2011/257451; (2011); (A1) English View in Reaxys

Rx-ID: 39050265 View in Reaxys 106/477 Yield

Conditions & References 2.3. Catalytic measurements Cumene decomposition tests were performed for the activatedcarbon catalysts obtained from brown coal from “Konin” colliery.This process was realised by the pulse method in a glass reactorwith a fixed bed catalysts (0.05 g) at 623 K. After reaching a desiredtemperature, cumene was dosed by a microsyringe in the amountof 1 l to the reactor. The outlet of the reactor was connected to thechromatograph. The products were analysed using a FID detectorand a 3 m column packed with 5percent SE-30 deposited on ChromosorbG AW-DMCS. Helium was used as a carrier gas. With nitric acid, carbon, Time= 8h, T= 59.84 °C , Catalytic behavior, Temperature, Reagent/catalyst Krzyzyska, Beata; Malaika, Anna; Rechnia, Paulina; Kozlowski, Mieczyslaw; Journal of Molecular Catalysis A: Chemical; vol. 395; (2014); p. 523 - 533 View in Reaxys

Rx-ID: 1709982 View in Reaxys 107/477

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Yield

Conditions & References With (NH4)2S2O8, copper diacetate in water, acetic acid, T= 100 °C , Yield given. Further byproducts given. Yields of byproduct given Walling, Cheves; Zhao, Chengxue; El-Taliawi, Gamil M.; Journal of Organic Chemistry; vol. 48; nb. 25; (1983); p. 4910 - 4914 View in Reaxys

Rx-ID: 2011788 View in Reaxys 108/477 Yield

Conditions & References

39 %

With Lawesson's reagent in toluene, Time= 3h, Heating Nishio, Takehiko; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 10; (1993); p. 1113 - 1118 View in Reaxys

39 %

With Lawesson's reagent in toluene, Time= 3h, Heating Nishio, Takehiko; Journal of the Chemical Society, Chemical Communications; nb. 4; (1989); p. 205 - 206 View in Reaxys

O B

Rx-ID: 2057423 View in Reaxys 109/477 Yield

Conditions & References

96 % Chromat.

With sodium hydroxide, tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran, water, Time= 3h, Heating Soderquist; Santiago; Tetrahedron Letters; vol. 31; nb. 39; (1990); p. 5541 - 5542 View in Reaxys

O S O

Rx-ID: 4004434 View in Reaxys 110/477 Yield 5 %, 72 %

Conditions & References With lithium aluminium tetrahydride in tetrahydrofuran, Time= 1h, T= 19 °C Froehlich, Johannes; Sauter, Fritz; Blasl, Karin; Heterocycles; vol. 37; nb. 3; (1994); p. 1879 - 1892 View in Reaxys

O O

racemate

Rx-ID: 4683275 View in Reaxys 111/477 Yield 15 % Chromat.,

Conditions & References With water, triphenylphosphine in benzene, Time= 8h, T= 60 °C

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17 % Chromat., 3 % Chromat., 51 % Chromat.

Abe, Manabu; Sumida, Yohko; Nojima, Masatomo; Journal of Organic Chemistry; vol. 62; nb. 3; (1997); p. 752 754 View in Reaxys

O O

racemate

Rx-ID: 4683278 View in Reaxys 112/477 Yield

Conditions & References

14 % Chromat., 16 % Chromat., 5 % Chromat., 63 % Chromat.

With water, triphenylphosphine in benzene, Time= 8h, T= 60 °C Abe, Manabu; Sumida, Yohko; Nojima, Masatomo; Journal of Organic Chemistry; vol. 62; nb. 3; (1997); p. 752 754 View in Reaxys

(+-)-<β-chloro-isopropyl>-benzene Rx-ID: 6712321 View in Reaxys 113/477 Yield

Conditions & References With potassium hydroxide Bachman; Hellman; Journal of the American Chemical Society; vol. 70; (1948); p. 1772 View in Reaxys

Rx-ID: 10289693 View in Reaxys 114/477 Yield

Conditions & References With .alpha.,.alpha.,.alpha.-trichloroacetamide, triphenylphosphine in dichloromethane, Time= 0.25h, T= 30 °C Pluempanupat, Wanchai; Chavasiri, Warinthorn; Tetrahedron Letters; vol. 47; nb. 38; (2006); p. 6821 - 6823 View in Reaxys

2 Cl – (v5) (v5)

Pd (v2)

Cl (v5)

(v5)

(v2)

Pd (v5) (v5)

(v6) H P (v6) H HB B HB BH (v6) (v6) (v6) (v6) (v6) (v6) (v6) HB BH B (v6) H B HB B H (v6) H (v6)

H+

2 Pd2+

(v6) (v6) 2 (v6) (v6)

(v6)

HB HB

P (v6) C 2BHB

HB BBH HB (v6) B HB (v6)H

(v5) (v5) (v6)

(v6)

Rx-ID: 26554486 View in Reaxys 115/477 Yield 47 %

Conditions & References With acetic acid, lithium chloride in chloroform, Kinetics, addn. of acetic acid to soln. of Pd-complex and carborane in CHCl3 (presence of LiCl), standing (48 h, 80°C); filtration, washing (CHCl3-HOAc 1:1, HOAc, HOAc-H2O 1:1, pure water), drying (vac. over NaOH); isomer ratio B(3)/B(4) 64:36 (not sepd.)

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Ryabov, Alexander D.; Eliseev, Alexey V.; Sergeyenko, Ekaterina S.; Usatov, Alexander V.; Zakharkin, Leonid I.; Kalinin, Valery N.; Polyhedron; vol. 8; (1989); p. 1485 - 1496 ; (from Gmelin) View in Reaxys

(halomethyl)(triphenyl)-λ5-phosphane

Rx-ID: 29083872 View in Reaxys 116/477 Yield

Conditions & References With potassium carbonate in 1,4-dioxane, Inert atmosphere, Reflux Fan, Jinmin; Gao, Linfeng; Wang, Zhiyong; Chemical Communications; nb. 33; (2009); p. 5021 - 5023 View in Reaxys Br

Br–+Mg

Rx-ID: 213853 View in Reaxys 117/477 Yield

Conditions & References With diethyl ether Patent; E. Lilly and Co.; US2404235; (1945) View in Reaxys Kharasch; Fuchs; Journal of the American Chemical Society; vol. 65; (1943); p. 504; Journal of Organic Chemistry; vol. 10; (1945); p. 292,294 View in Reaxys

Rx-ID: 2011785 View in Reaxys 118/477 Yield

Conditions & References

28 %, 57 %

With triphenyl phosphite, tetraethylammonium bromide in acetonitrile, constant current electrolysis, 25 mA Maeda, Hatsuo; Maki, Toshihide; Eguchi, Kaoru; Koide, Takashi; Ohmori, Hidenobu; Tetrahedron Letters; vol. 35; nb. 24; (1994); p. 4129 - 4132 View in Reaxys

H Br

Rx-ID: 2032904 View in Reaxys 119/477 Yield

Conditions & References With sodium ethanolate in ethanol, T= 75 °C , element effect, Mechanism Koch, Heinz F.; McLennan, Duncan J.; Koch, Judith G.; Tumas, William; Dobson, Brian; Koch, Nanci H.; Journal of the American Chemical Society; vol. 105; nb. 7; (1983); p. 1930 - 1937 View in Reaxys

H O

Rx-ID: 2071791 View in Reaxys 120/477 Yield 15 %, 21 %, 8 %, 3.4 %

Conditions & References in benzene, T= 20 - 25 °C , Irradiation Turro, Nicholas J.; Mattay, Jochen; Journal of the American Chemical Society; vol. 103; nb. 14; (1981); p. 4200 4204 View in Reaxys

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3.4 %, 15 in benzene, Irradiation, Title compound not separated from byproducts %, 8 %, 21 Turro, J. Nicholas; Mattay, Jochen; Tetrahedron Letters; vol. 21; nb. 19; (1980); p. 1799 - 1802 % View in Reaxys 15 %, 3.4 in benzene, T= 20 - 25 °C , Irradiation %, 8 %, 21 Turro, Nicholas J.; Mattay, Jochen; Journal of the American Chemical Society; vol. 103; nb. 14; (1981); p. 4200 % 4204 View in Reaxys 21 %, 3.4 in benzene, T= 20 - 25 °C , Irradiation, other solvents, Quantum yield %, 8 %, 15 Turro, Nicholas J.; Mattay, Jochen; Journal of the American Chemical Society; vol. 103; nb. 14; (1981); p. 4200 % 4204 View in Reaxys 18 %, 6.1 %, 18 %, 7.1 %

in dichloromethane, Irradiation, further solvents, Quantum yield, Product distribution Turro, J. Nicholas; Mattay, Jochen; Tetrahedron Letters; vol. 21; nb. 19; (1980); p. 1799 - 1802 View in Reaxys

Rx-ID: 2116288 View in Reaxys 121/477 Yield

Conditions & References With sodium ethanolate in ethanol, T= 75 °C , hydrogen isotope effect, Mechanism Koch, Heinz F.; McLennan, Duncan J.; Koch, Judith G.; Tumas, William; Dobson, Brian; Koch, Nanci H.; Journal of the American Chemical Society; vol. 105; nb. 7; (1983); p. 1930 - 1937 View in Reaxys

Rx-ID: 2142026 View in Reaxys 122/477 Yield

Rx-ID: 2947070 View in Reaxys 123/477 Yield

37Cl

Rx-ID: 3115387 View in Reaxys 124/477 Yield

Conditions & References With sodium ethanolate in ethanol, T= 75 °C , chlorine isotope effect, Mechanism

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Koch, Heinz F.; McLennan, Duncan J.; Koch, Judith G.; Tumas, William; Dobson, Brian; Koch, Nanci H.; Journal of the American Chemical Society; vol. 105; nb. 7; (1983); p. 1930 - 1937 View in Reaxys

Rx-ID: 3115671 View in Reaxys 125/477 Yield

Conditions & References With sodium ethanolate in ethanol, T= 75 °C , chlorine and hydrogen isotope effects, and element effect, Mechanism Koch, Heinz F.; McLennan, Duncan J.; Koch, Judith G.; Tumas, William; Dobson, Brian; Koch, Nanci H.; Journal of the American Chemical Society; vol. 105; nb. 7; (1983); p. 1930 - 1937 View in Reaxys

37Cl

Rx-ID: 3116295 View in Reaxys 126/477 Yield

Conditions & References With sodium ethanolate in ethanol, T= 75 °C , chlorine isotope effect, Mechanism Koch, Heinz F.; McLennan, Duncan J.; Koch, Judith G.; Tumas, William; Dobson, Brian; Koch, Nanci H.; Journal of the American Chemical Society; vol. 105; nb. 7; (1983); p. 1930 - 1937 View in Reaxys

2H 37Cl

Rx-ID: 3120973 View in Reaxys 127/477 Yield

(+-)-2-phenyl-propyl bromide H 2N

Rx-ID: 8265086 View in Reaxys 128/477 Yield

Conditions & References With ethanol, ammonia Weston; Ruddy; Suter; Journal of the American Chemical Society; vol. 65; (1943); p. 675 View in Reaxys

Rx-ID: 25050273 View in Reaxys 129/477 Yield

Conditions & References 9 : PREPARATION 9 PREPARATION 9 Into a glass flask of 5 liters capacity were introduced 2700 g of ethyl benzene, 58 g of metallic sodium and 17 g of isopropyl alcohol to form a reaction mixture and then a mixture of 1100 g of α-methyl styrene and 300 g of ethyl benzene was added dropwise into the mixture in the flask heated at 120° C. under agitation gradually over a period of 5 hours followed by further continued agitation for additional 1 hour to complete the reaction.

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Patent; Idemitsu Kosan Company Limited; US4684754; (1987); (A1) English View in Reaxys

H 2H 2

H O

Rx-ID: 26019219 View in Reaxys 130/477 Yield 3.06 g, 0.14 g

Conditions & References With 1,3-bis-(diphenylphosphino)propane, bis(triphenylphosphine)carbonylrhodium(I) chloride in toluene, Time= 139h, Heating Baldwin, John E.; Singer, Stephanie R.; Canadian Journal of Chemistry; vol. 86; nb. 5; (2008); p. 395 - 400 View in Reaxys

(v4)

O Ru (v4) P OC-6 (v6)

O P Ru (v4)(v4) P (v6)

(v4)

Rx-ID: 26715579 View in Reaxys 131/477 Yield 74 %, 86 %

Conditions & References in benzene-d6, inert gas, soln. of p-cresol added dropwise to a soln. of Ru-compound; not isolated; NMR Hartwig, John F.; Bergman, Robert G.; Andersen, Richard A.; Organometallics; vol. 10; (1991); p. 3344 - 3362 ; (from Gmelin) View in Reaxys

P P P

(v4)

(v4)(v4) P

(v4) P Ru(v6) (v4) P (v4)

(v4)

O Ru OC-6 (v6) P

(v4)

racemate

Rx-ID: 26815389 View in Reaxys 132/477 Yield 74 %, >99

Conditions & References in benzene-d6, inert gas, p-cresol added as solid; not isolated; NMR Hartwig, John F.; Bergman, Robert G.; Andersen, Richard A.; Organometallics; vol. 10; (1991); p. 3344 - 3362 ; (from Gmelin) View in Reaxys

Rx-ID: 27897449 View in Reaxys 133/477 Yield

Conditions & References 3 :Example 1; Decomposition of cumene hydroperoxide was carried out on a pilot unit in the form of a reactor with a volume of 12 mL, equipped with a circulation loop to mix the reaction mass and a water jacket to maintain the assigned temperature. To prepare the catalyst, a reactor with a volume of 10 μL was used, and sulfuric acid and phenol

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were fed by pumps to the reactor. Catalyst and feedstock were fed to the stream of reaction mass at the input to the reactor. The composition of the feedstock is shown in Table 1. Sulfuric acid was also fed to the catalyst synthesis reactor at a rate of 3 μL/h, phenol was fed at a rate of 6 μL/h, which corresponds to a concentration in the reaction medium of 0.02 wt. percent, and the holding time in the reactor was 70 minutes at a temperature of 45° C. The rate at which the feedstock was fed to the CHP decomposition reactor was 27 mL/h. The rate of circulation of the reaction mass was 500 mL/h. The temperature in the reactor was maintained at 75° C. by supplying a heat transfer agent of the corresponding temperature to the jacket of the reactor.The stream emerging from the CHP decomposition reactor was cooled to room temperature and analyzed by GC. The composition of the reaction mass of CHP decomposition is shown in Table 2.; Example 2; CHP decomposition was carried out in the same equipment as in Example 1, but the reactor for synthesis of the catalytic system had a volume of 20 μL, and a mixture having the composition shown in Table 3 was used as feedstock.The feedstock was fed to the reactor at a rate of 10 mL/h, concentrated (96percent) sulfuric acid was fed at a rate of 1.1 μL/h, which corresponded to a concentration of 0.02 wt. percent, and phenol for mixing with sulfuric acid was fed at a rate of 0.9 μL/h, which corresponded to a sulfuric acid/phenol ratio of 2:1. The mixture of phenol and sulfuric acid was held for 600 minutes at a temperature of 20° C. The circulation rate of the reaction mixture was 200 mL/h, and the temperature in the reactor was 70° C. As used herein, concentrated sulfuric acid means "commercially available usual sulfuric acid", which generally means about 93 to 96percent sulfuric acid (H2SO4). With sulfuric acid, sulfur trioxide, phenol, T= 70 - 75 °C , Product distribution / selectivity Patent; Nelson, Mark; Sederel, Willem Lodewyk; Dyckman, Arkady Samuilovich; Grebenshchikov, Ilya Nikolaevich; Pinson, Viktor Vladimirovich; Zinenkov, Andrey Vladimirovich; US2008/214872; (2008); (A1) English View in Reaxys 2; 5 :Example 2; Decomposition of CHP was carried out in the same equipment as in Example 1, and a mixture having the composition shown in Table 3 was used as feedstock.The feedstock was supplied to the reactor at a rate of 10 mL/h, and concentrated (96percent) sulfuric acid was fed at a rate of 0.55 μL/h, which corresponded to a concentration of 0.009 wt. percent, and phenol for mixing with sulfuric was supplied at a rate of 0.45 μL/h, which corresponded to a sulfuric acid/phenol ratio of 2:1. The mixture of phenol and sulfuric acid was held for 600 minutes at a temperature of 20° C. The circulation rate of the reaction mass was 200 mL/h. The reaction mass emerging from the first stage reactor was mixed with acetone supplied at a rate of 3 mL/h, and was fed to the second stage reactor. The temperature was 50° C. in the first stage reactor, and 140° C. in the second stage reactor. Table 4 shows the composition of the reaction mass resulting from the CHP decomposition.; Example 5; Decomposition of CHP was carried out in the same equipment as in Example 1, except that a mixture having the composition shown in Table 5 was used as feedstock.The feedstock was fed to the reactor at a rate of 25 mL/h, concentrated (96percent) sulfuric acid was fed at a rate of 1.3 μL/h, which corresponded to a concentration of 0.009 wt. percent, and phenol for mixing with sulfuric acid was fed at a rate of 3.4 μL/h, (which corresponded to a sulfuric acid/phenol ratio of 1:1.5). The mixture of phenol and sulfuric acid were held for 140 minutes at a temperature of 42° C. The circulation rate of the reaction mass was 200 mL/h. The reaction mass emerging from the first stage reactor was mixed with acetone fed at a rate of 11 mL/h, and water fed at a rate of 0.2 mL/h. The obtained mixture was fed to the second stage reactor. The temperature was 40° C. in the first stage reactor, and 90° C. in the second stage reactor. The composition of the reaction mass resulting from the CHP decomposition is shown in Table 6. With sulfuric acid, phenol in water, T= 40 - 140 °C , Product distribution / selectivity Patent; Nelson, Mark; Sederel, Willem Lodewyk; Dyckman, Arkady Samuilovich; Grebenshchikov, Ilya Nikolaevich; Pinson, Viktor Vladimirovich; Zinenkov, Andrey Vladimirovich; US2008/214873; (2008); (A1) English View in Reaxys 3 :Example 3; Decomposition of CHP was carried out in the same equipment and under the same conditions as in Example 2, except that 0.3 μL/h of 30percent fuming sulfuric acid (oleum) was fed to the reactor, and phenol was fed at a rate of 600 μL/h (the ratio in terms of sulfuric acid to phenol in this Example was 1:1000) to prepare the catalyst. The residence time of the mixture in the reactor was 1 minute at a temperature of 80° C. Table 4 shows the composition of the reaction mass resulting from the CHP decomposition. With sulfuric acid, sulfur trioxide, phenol, T= 50 - 140 °C , Product distribution / selectivity Patent; Nelson, Mark; Sederel, Willem Lodewyk; Dyckman, Arkady Samuilovich; Grebenshchikov, Ilya Nikolaevich; Pinson, Viktor Vladimirovich; Zinenkov, Andrey Vladimirovich; US2008/214873; (2008); (A1) English View in Reaxys

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O O

Rx-ID: 34973416 View in Reaxys 134/477 Yield

Conditions & References

47 %, 18 %

With N,N,N',N'-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a;2',1'-c][1,4] diazepine-2,12-diamine in N,N-dimethyl-formamide, Time= 72h, Inert atmosphere, Glovebox, UV-irradiation Doni, Eswararao; O'Sullivan, Steven; Murphy, John A.; Angewandte Chemie - International Edition; vol. 52; nb. 8; (2013); p. 2239 - 2242; Angew. Chem.; vol. 125; nb. 8; (2013); p. 2295 - 2298,4 View in Reaxys

O Cl O

Rx-ID: 947276 View in Reaxys 135/477 Yield

Conditions & References With titanium tetrachloride in dichloromethane, T= 0 °C Mastagli,P.; de Nanteuil,M.; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 268; (1969); p. 1970 - 1972 View in Reaxys

–O

O Zn 2+

Rx-ID: 1981274 View in Reaxys 136/477 Yield

Conditions & References

2.9 g, 3.4 in acetic acid, Time= 2h, T= 10 - 15 °C g, 5.9 g, 72 Gurudutt, K. N.; Rao, L. Jagan Mohan; Rao, Sanjay; Srinivas, P.; Indian Journal of Chemistry, Section B: Organic % Chemistry Including Medicinal Chemistry; vol. 32; nb. 4; (1993); p. 468 - 470 View in Reaxys

Rx-ID: 4921202 View in Reaxys 137/477 Yield

Conditions & References With N-bromosuccinmide, 1.) CCl4, 130-140 deg C, 2.) THF, Yield given. Multistep reaction Von Doering; Benkhoff, Johannes; Carleton, Peter Smart; Pagnotta, Marco; Journal of the American Chemical Society; vol. 119; nb. 45; (1997); p. 10947 - 10955 View in Reaxys

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H N

(+-)-2-phenyl-propyl bromide

H 2N

Rx-ID: 8265087 View in Reaxys 138/477 Yield

Conditions & References With ethanol Weston; Ruddy; Suter; Journal of the American Chemical Society; vol. 65; (1943); p. 675 View in Reaxys

P+ O

I–

B O

Rx-ID: 9086455 View in Reaxys 139/477 Yield

Conditions & References

95 % Chromat.

Stage 1: With lithium hexamethyldisilazane in N,N,N',N',N'',N''-hexamethylphosphoric triamide, Time= 2h, T= 0 °C Stage 2: in N,N,N',N',N'',N''-hexamethylphosphoric triamide, T= -78 - 20 °C Al-Aziz Quntar, Abed; Srebnik, Morris; Synthetic Communications; vol. 32; nb. 16; (2002); p. 2575 - 2579 View in Reaxys

O F

Rx-ID: 10245773 View in Reaxys 140/477 Yield

Conditions & References With 2,6-dimethylpyridine, water in various solvent(s), T= 25 °C , Kinetics Creary, Xavier; Willis, Elizabeth D.; Gagnon, Madeleine; Journal of the American Chemical Society; vol. 127; nb. 51; (2005); p. 18114 - 18120 View in Reaxys

ZnCl2

phenylacetaldehyde ; benzaldehyde O

Rx-ID: 19084992 View in Reaxys 141/477 Yield

Conditions & References Reaction Steps: 2 1: lithium diisopropylamide / 1)THF, -78 deg C, 30 min, 2) THF, -78 to 0 deg C; 0 deg C, 20 min 2: 94 percent Chromat. / Pd(PPh3)4 / 1,2-dichloro-ethane; hexane / 2 h / 25 °C With tetrakis(triphenylphosphine) palladium(0), lithium diisopropyl amide in hexane, 1,2-dichloro-ethane Takai; Sato; Oshima; Nozaki; Bulletin of the Chemical Society of Japan; vol. 57; nb. 1; (1984); p. 108 - 115 View in Reaxys Reaction Steps: 2 1: 96 percent 2: 76 percent / CsF-H2O / dimethylformamide / 9 h / 80 °C With cesium fluoride in N,N-dimethyl-formamide Kawashima, Takayuki; Ishii, Takafumi; Inamoto, Naoki; Chemistry Letters; (1983); p. 1375 - 1378 View in Reaxys

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polymeric o-nitrophenyl benzoate O

Rx-ID: 20502265 View in Reaxys 142/477 Yield

Conditions & References Reaction Steps: 2 1: 1.) CeCl3 / 1.) THF, -78 deg C, 30 min, 2.) THF 2: 84 percent / 50percent aq. HF / acetonitrile / Ambient temperature With cerium(III) chloride, hydrogen fluoride in acetonitrile Johnson, Carl R.; Tait, Bradley D.; Journal of Organic Chemistry; vol. 52; nb. 2; (1987); p. 281 - 283 View in Reaxys

Rx-ID: 23140719 View in Reaxys 143/477 Yield

Conditions & References 1 : EXAMPLE 1 EXAMPLE 1; The catalyst was sieved between 100 and 400 mesh (0.149 mm to 0.037 mm) screens. A 91 ml sample of catalyst (1.17 g/ml packed, bulk density) was loaded into a 1 inch (2.5 cm) ID up-flow fluidized bed quartz reactor. A diluent gas was employed in the reaction, comprising ethane with a flow rate of 0.645 L/min (volume at 0° C., 1 atm (100 kPa) pressure). The reactor was heated to 550° C. as monitored and controlled from an internal thermocouple placed in the center of the reactor and two inches (5.50 cm) from the bottom of the catalyst bed. An ethylbenzene flow (0.68 ml/min) was initiated, mixed with the diluent, and vaporized at 195° C. prior to introduction to the reactor. The sum of ethane and ethylbenzene flows gave a gas hourly space velocity (GHSV) of 500 h-1, based on the packed volume of the catalyst and ideal gas volumes at normal conditions (0° C., 1 atm pressure). One evaluation cycle consisted of a reaction segment and a regeneration segment, which were separated by nitrogen purges. The reaction segment lasted for 10 min. Next, a nitrogen purge was passed through the reactor for 15 min. The liquid products were condensed in a liquid nitrogen trap, and the residual gaseous products were captured in a gas sampling bag. The nitrogen feed was switched to air at the same flow rate and the reactor temperature was increased to 650° C. for a catalyst regeneration segment. The regeneration segment was maintained for 30 min and followed by a second nitrogen purge. The gas stream was collected in a separate bag during the regeneration portion of the cycle and analyzed by gas chromatography (gc). The liquid sample was weighed and analyzed by gc. The results were quantified using external standards and normalization. Compilation of the three analyses allowed the calculation of an overall conversion and selectivity for the entire cycle. The main products were styrene, benzene, toluene, alpha-methyl styrene, tar, and coke. Tar is defined as the sum of peaks eluted after alpha-methyl styrene to the end of the temperature ramp of 230° C. The molecular weight of stilbene was used for the average molecular weight of tar. Coke was measured as CO2 formed during regeneration. The reactor was cooled to the next reaction temperature while purging with nitrogen. The temperature was set for the next cycle, and the entire process was repeated to generate another data point. Cycles were completed at selected temperatures between 550° C. and 600° C. The first six catalytic cycles were used as a break-in period, and the data were not recorded. The catalyst performance was stable through 200 cycles. The resulting data are shown in Table 1. , T= 550 - 600 °C , Product distribution / selectivity Patent; Pelati, Joseph E.; Gulotty JR., Robert J.; US2004/242945; (2004); (A1) English View in Reaxys 3; 4 : EXAMPLE 3; 4 EXAMPLE 3; Another embodiment of the catalyst was prepared comprised of gallium oxide (Ga2O3, 2.0 percent), potassium oxide (K2O, 0.6 percent), zinc oxide (ZnO, 0.5 percent), and manganese (0.17 percent), balance alumina support (100 m2/g) prepared hereinabove. The catalyst was prepared in the manner described in Example 1, with the exception that 3.6 g (12.1 millimole) of zinc nitrate hexahydrate were added in an initial impregnating solution. The resulting solid was dried in the manner of the previously described incipient wetness methods, then calcined at 950° C. for 6 hours. A second impregnation followed to add the gallium, potassium and manganese, and the resulting solid was subsequently dried and calcined at 750° C. for 4 hours. The catalyst was evaluated in the dehydrogenation of ethylbenzene in a manner closely similar to that described in Example 1, with the following changes. A 20percent ethylbenzene/80percent ethane reagent stream was used. The catalyst, 90 ml (packed) having a density of 1.02 g/packed ml, was loaded into the reactor. The ethane flow was 0.653 liters/min, and the liquid ethylbenzene flow was 0.90 ml/min. Results are shown in Tables 5 and 6. EXAMPLE 4; Another embodiment of the catalyst was

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prepared comprised of gallium oxide (Ga2O3, 2.0 percent), potassium oxide (K2O, 0.6 percent), zinc oxide (ZnO, 5.0 percent), and manganese (0.17 percent), balance alumina support (100 m2/g) prepared hereinabove. The catalyst was prepared in the manner described in Example 1, with the exception that 38.5 g (129 millimole) of zinc nitrate hexahydrate were added in an initial impregnating solution. The resulting solid was dried in the manner of the previously described incipient wetness methods, then calcined at 950° C. for 6 hours. A second impregnation followed to add the gallium, potassium and manganese, and the resulting solid was subsequently dried and calcined at 750° C. for 4 hours. The catalyst was evaluated in the dehydrogenation of ethylbenzene in a manner closely similar to that described in Example 1, with the following changes. A 20percent ethylbenzene/80percent ethane reagent stream was used. The catalyst, 90 ml (packed) having a density of 1.07 g/packed ml, was loaded into the reactor. The ethane flow was 0.653 liters/min, and the liquid ethylbenzene flow was 0.90 ml/min. Results are shown in Tables 6 and 7. , T= 575.4 - 611 °C , Product distribution / selectivity Patent; Pelati, Joseph E.; Gulotty JR., Robert J.; US2004/242945; (2004); (A1) English View in Reaxys 1 : EXAMPLE 2 EXAMPLE 2; A second embodiment of the catalyst was prepared comprised of gallium oxide (Ga2O3, 1.7 percent), potassium oxide (K2O, 0.6 percent), zinc oxide (ZnO, 0.5 percent), and platinum (100 ppm), balance alumina support (70 m2/g) prepared hereinabove. The catalyst was prepared in the manner described in Example 1, with the exception that 3.8 g (12.6 millimole) of zinc nitrate hexahydrate were added in the impregnating solution. The catalyst was evaluated in the dehydrogenation of ethylbenzene in a manner closely similar to that described in Example 1, with the following changes. The catalyst, 87 ml (packed) having a density of 1.21 g/packed ml, was loaded into the reactor. The ethane flow was 0.616 liters/min, and the liquid ethylbenzene flow was 0.65 ml/min. Results are shown in Table 3. , T= 550 - 600 °C , Product distribution / selectivity Patent; Pelati, Joseph E.; Gulotty JR., Robert J.; US2004/242945; (2004); (A1) English View in Reaxys CE-2 : Comparative Experiment CE-2 Comparative Experiment (CE-2); A comparative catalyst was prepared comprised of gallium oxide (Ga2O3, 2.0 percent), potassium oxide (K2O, 0.6 percent), and manganese (Mn, 0.17 percent) on the alumina (100 m2/g) described hereinabove. The preparation was similar to that of Example 1, with the exception that no zinc nitrate hexahydrate was impregnated onto the support. The comparative catalyst was evaluated in the dehydrogenation of ethylbenzene according to the procedure of Example 1, with the following changes. A catalyst sample of 89 ml (packed) and a density of 1.02 g/packed ml was loaded into the reactor. The ethane flow was 0.645 liters/min, and the liquid ethylbenzene flow was 0.89 ml/min. The results are shown in Tables 6 and 8. , T= 573.6 - 607.3 °C , Product distribution / selectivity Patent; Pelati, Joseph E.; Gulotty JR., Robert J.; US2004/242945; (2004); (A1) English View in Reaxys CE-1 : Comparative Experiment CE-1 Comparative Experiment CE-1; A comparative catalyst was prepared comprised of gallium oxide (Ga2O3, 1.7 percent), potassium oxide (K2O, 0.6 percent), and platinum oxide (PtO, 100 ppm) on the alumina (70 m2/g) described hereinabove. The preparation was similar to that of Example 1, with the exception that no zinc nitrate hexahydrate was impregnated onto the support. The comparative catalyst was evaluated in the dehydrogenation of ethylbenzene according to the procedure of Example 1, with the following changes. A catalyst sample of 389 ml (packed) and a density of 1.19 g/packed ml was loaded into the reactor. The ethane flow was 0.630 liters/min, and the liquid ethylbenzene flow was 0.67 ml/min. The results are shown in Tables 2 and 4. , T= 576 - 601 °C , Product distribution / selectivity Patent; Pelati, Joseph E.; Gulotty JR., Robert J.; US2004/242945; (2004); (A1) English View in Reaxys

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P P

(v4)

(v4) P (v6) (v4) P (v4)

O P

(v4) (v4)

P (v4) (v4) Ru OC-6 (v6) P H

Rx-ID: 26813022 View in Reaxys 144/477 Yield

Conditions & References

57 %, >99

in benzene-d6, (inert atm. in a vac.); heated to 110°C for 2 d; not isolated; NMR Hartwig, John F.; Bergman, Robert G.; Andersen, Richard A.; Organometallics; vol. 10; (1991); p. 3344 - 3362 ; (from Gmelin) View in Reaxys

(v4)

P O

P (v4) Ru (v4) P (v6) P

(v4) P (v4)

(v4)

(v6)

(v4)

Rx-ID: 26822192 View in Reaxys 145/477 Yield

Conditions & References

63 %

in pentane, inert gas, PhNCO in soln. added to the Ru-compound in soln.; filtered, washed (n-pentane), dried under vacuum; NMR Hartwig, John F.; Bergman, Robert G.; Andersen, Richard A.; Organometallics; vol. 10; (1991); p. 3344 - 3362 ; (from Gmelin) View in Reaxys Br

Rx-ID: 30958622 View in Reaxys 146/477 Yield

Conditions & References

41 %Chro- With 1,3-bis-(diphenylphosphino)propane, palladium diacetate, caesium carbonate in 1,4-dioxane, Time= 12h, T= mat., 22 110 °C , Inert atmosphere %Chromat. Flores-Gaspar, Areli; Martin, Ruben; Advanced Synthesis and Catalysis; vol. 353; nb. 8; (2011); p. 1223 - 1228 View in Reaxys

Rx-ID: 31323227 View in Reaxys 147/477 Yield

Conditions & References With dihydrogen peroxide in water, acetonitrile, Time= 24h, T= 80 °C Estrada, Ana C.; Simoes, Mario M. Q.; Santos, Isabel C. M. S.; Neves, M. Graca P. M. S.; Cavaleiro, Jose A. S.; Cavaleiro, Ana M. V.; Monatshefte fur Chemie; vol. 141; nb. 11; (2010); p. 1223 - 1235 View in Reaxys With dihydrogen peroxide in water, acetonitrile, Time= 24h, T= 80 °C Estrada, Ana C.; Simoes, Mario M. Q.; Santos, Isabel C. M. S.; Neves, M. Graca P. M. S.; Cavaleiro, Jose A. S.; Cavaleiro, Ana M. V.; Monatshefte fur Chemie; vol. 141; nb. 11; (2010); p. 1223 - 1235 View in Reaxys

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Rx-ID: 31323228 View in Reaxys 148/477 Yield

Rx-ID: 31323230 View in Reaxys 149/477 Yield

Conditions & References Reaction Steps: 3 1: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C 2: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C 3: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C With dihydrogen peroxide in water, acetonitrile Estrada, Ana C.; Simoes, Mario M. Q.; Santos, Isabel C. M. S.; Neves, M. Graca P. M. S.; Cavaleiro, Jose A. S.; Cavaleiro, Ana M. V.; Monatshefte fur Chemie; vol. 141; nb. 11; (2010); p. 1223 - 1235 View in Reaxys Reaction Steps: 2 1: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C 2: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C With dihydrogen peroxide in water, acetonitrile Estrada, Ana C.; Simoes, Mario M. Q.; Santos, Isabel C. M. S.; Neves, M. Graca P. M. S.; Cavaleiro, Jose A. S.; Cavaleiro, Ana M. V.; Monatshefte fur Chemie; vol. 141; nb. 11; (2010); p. 1223 - 1235 View in Reaxys Reaction Steps: 2 1: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C 2: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C With dihydrogen peroxide in water, acetonitrile Estrada, Ana C.; Simoes, Mario M. Q.; Santos, Isabel C. M. S.; Neves, M. Graca P. M. S.; Cavaleiro, Jose A. S.; Cavaleiro, Ana M. V.; Monatshefte fur Chemie; vol. 141; nb. 11; (2010); p. 1223 - 1235 View in Reaxys Reaction Steps: 2 1: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C 2: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C With dihydrogen peroxide in water, acetonitrile Estrada, Ana C.; Simoes, Mario M. Q.; Santos, Isabel C. M. S.; Neves, M. Graca P. M. S.; Cavaleiro, Jose A. S.; Cavaleiro, Ana M. V.; Monatshefte fur Chemie; vol. 141; nb. 11; (2010); p. 1223 - 1235 View in Reaxys Reaction Steps: 2 1: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C 2: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C With dihydrogen peroxide in water, acetonitrile Estrada, Ana C.; Simoes, Mario M. Q.; Santos, Isabel C. M. S.; Neves, M. Graca P. M. S.; Cavaleiro, Jose A. S.; Cavaleiro, Ana M. V.; Monatshefte fur Chemie; vol. 141; nb. 11; (2010); p. 1223 - 1235 View in Reaxys Reaction Steps: 2 1: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C

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2: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C With dihydrogen peroxide in water, acetonitrile Estrada, Ana C.; Simoes, Mario M. Q.; Santos, Isabel C. M. S.; Neves, M. Graca P. M. S.; Cavaleiro, Jose A. S.; Cavaleiro, Ana M. V.; Monatshefte fur Chemie; vol. 141; nb. 11; (2010); p. 1223 - 1235 View in Reaxys Reaction Steps: 2 1: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C 2: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C With dihydrogen peroxide in water, acetonitrile Estrada, Ana C.; Simoes, Mario M. Q.; Santos, Isabel C. M. S.; Neves, M. Graca P. M. S.; Cavaleiro, Jose A. S.; Cavaleiro, Ana M. V.; Monatshefte fur Chemie; vol. 141; nb. 11; (2010); p. 1223 - 1235 View in Reaxys Reaction Steps: 2 1: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C 2: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C With dihydrogen peroxide in water, acetonitrile Estrada, Ana C.; Simoes, Mario M. Q.; Santos, Isabel C. M. S.; Neves, M. Graca P. M. S.; Cavaleiro, Jose A. S.; Cavaleiro, Ana M. V.; Monatshefte fur Chemie; vol. 141; nb. 11; (2010); p. 1223 - 1235 View in Reaxys Reaction Steps: 3 1: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C 2: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C 3: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C With dihydrogen peroxide in water, acetonitrile Estrada, Ana C.; Simoes, Mario M. Q.; Santos, Isabel C. M. S.; Neves, M. Graca P. M. S.; Cavaleiro, Jose A. S.; Cavaleiro, Ana M. V.; Monatshefte fur Chemie; vol. 141; nb. 11; (2010); p. 1223 - 1235 View in Reaxys Reaction Steps: 3 1: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C 2: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C 3: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C With dihydrogen peroxide in water, acetonitrile Estrada, Ana C.; Simoes, Mario M. Q.; Santos, Isabel C. M. S.; Neves, M. Graca P. M. S.; Cavaleiro, Jose A. S.; Cavaleiro, Ana M. V.; Monatshefte fur Chemie; vol. 141; nb. 11; (2010); p. 1223 - 1235 View in Reaxys Reaction Steps: 3 1: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C 2: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C 3: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C With dihydrogen peroxide in water, acetonitrile Estrada, Ana C.; Simoes, Mario M. Q.; Santos, Isabel C. M. S.; Neves, M. Graca P. M. S.; Cavaleiro, Jose A. S.; Cavaleiro, Ana M. V.; Monatshefte fur Chemie; vol. 141; nb. 11; (2010); p. 1223 - 1235 View in Reaxys Reaction Steps: 3 1: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C 2: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C 3: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C With dihydrogen peroxide in water, acetonitrile Estrada, Ana C.; Simoes, Mario M. Q.; Santos, Isabel C. M. S.; Neves, M. Graca P. M. S.; Cavaleiro, Jose A. S.; Cavaleiro, Ana M. V.; Monatshefte fur Chemie; vol. 141; nb. 11; (2010); p. 1223 - 1235 View in Reaxys

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Reaction Steps: 3 1: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C 2: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C 3: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C With dihydrogen peroxide in water, acetonitrile Estrada, Ana C.; Simoes, Mario M. Q.; Santos, Isabel C. M. S.; Neves, M. Graca P. M. S.; Cavaleiro, Jose A. S.; Cavaleiro, Ana M. V.; Monatshefte fur Chemie; vol. 141; nb. 11; (2010); p. 1223 - 1235 View in Reaxys Reaction Steps: 3 1: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C 2: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C 3: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C With dihydrogen peroxide in water, acetonitrile Estrada, Ana C.; Simoes, Mario M. Q.; Santos, Isabel C. M. S.; Neves, M. Graca P. M. S.; Cavaleiro, Jose A. S.; Cavaleiro, Ana M. V.; Monatshefte fur Chemie; vol. 141; nb. 11; (2010); p. 1223 - 1235 View in Reaxys

Rx-ID: 31323241 View in Reaxys 150/477 Yield

Rx-ID: 32799224 View in Reaxys 151/477 Yield

Conditions & References

62 %Spectr.

Stage 1: With triethylamine tris(hydrogen fluoride), triethylamine in ethyl acetate, Time= 0.0833333h, T= 5 - 23 °C Stage 2: With TFFH in ethyl acetate, Time= 2h, T= 60 °C Bellavance, Gabriel; Dube, Pascal; Nguyen, Bao; Synlett; nb. 4; (2012); p. 569 - 572 View in Reaxys

P I

Rx-ID: 34518481 View in Reaxys 152/477 Yield

Conditions & References Stage 1: With potassium tert-butylate in tetrahydrofuran, Time= 2h, T= 20 °C Stage 2: in tetrahydrofuran, Time= 2.5h, T= 20 °C Liang, Zunjun; Ju, Long; Xie, Yongju; Huang, Lehao; Zhang, Yuhong; Chemistry - A European Journal; vol. 18; nb. 49; (2012); p. 15816 - 15821 View in Reaxys

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HN HO

Cl O

Rx-ID: 1609353 View in Reaxys 153/477 Yield

Conditions & References

15 %

With boron trifluoride diethyl etherate in pentane, 1.) -5 deg C, 15 min, 2.) up to r.t., Yield given Bourgeois; Montaudon; Maillard; Tetrahedron; vol. 49; nb. 12; (1993); p. 2477 - 2484 View in Reaxys

Rx-ID: 1627775 View in Reaxys 154/477 Yield

Conditions & References

25 %, 62 %

With methyllithium, iron(III) chloride in diethyl ether, from -78 deg C up to 20 deg C, 18 h Kauffmann, Thomas; Neiteler, Christel; Neiteler, Gabriele; Chemische Berichte; vol. 127; nb. 4; (1994); p. 659 666 View in Reaxys

Rx-ID: 1710289 View in Reaxys 155/477 Yield

Conditions & References With lithium perchlorate, triethylamine, triphenylphosphine in tetrahydrofuran, N,N,N',N',N'',N''-hexamethylphosphoric triamide, electrolysis Rollin, Yolande; Meyer, Gilbert; Troupel, Michel; Fauvarque, Jean-Francois; Perichon, Jacques; Journal of the Chemical Society, Chemical Communications; nb. 15; (1983); p. 793 - 794 View in Reaxys

O N

Rx-ID: 1915164 View in Reaxys 156/477 Yield 94 %, 4 %

Conditions & References T= 60 °C , decomposition, other solvent, Rate constant Mitsuhashi Tsutomu; Journal of the American Chemical Society; vol. 108; nb. 9; (1986); p. 2394 - 2400 View in Reaxys

Rx-ID: 1981280 View in Reaxys 157/477 Yield

Conditions & References With sodium azide in N,N,N',N',N'',N''-hexamethylphosphoric triamide, Time= 645h, Irradiation, Yield given. Yields of byproduct given Kornblum, Nathan; Ackermann, Peter; Manthey, Joseph W.; Musser, Michael T.; Pinnick, Harold W.; et al.; Journal of Organic Chemistry; vol. 53; nb. 7; (1988); p. 1475 - 1481 View in Reaxys

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O P

O OH

Rx-ID: 3383402 View in Reaxys 158/477 Yield

Conditions & References

67 %

Time= 5h, T= 120 °C Daniel, H.; le Corre, M.; Tetrahedron Letters; vol. 27; nb. 17; (1986); p. 1909 - 1912 View in Reaxys

P N

Rx-ID: 3383591 View in Reaxys 159/477 Yield

Conditions & References With pyridine, n-butyllithium, methyl iodide, 1.) THF, hexane, -78 deg C, 30 min, 2.) -78 deg C, 2 h; -78 deg C -> 0 deg C, 3.) acetone, room temperature, 16 h, Yield given. Multistep reaction Johnson,C.R.; Elliott,R.C.; Journal of the American Chemical Society; vol. 104; (1982); p. 7041 View in Reaxys

Rx-ID: 5048191 View in Reaxys 160/477 Yield

Conditions & References

51 % Chromat., 46 % Chromat., 3 % Chromat.

With Amberlite IRA-400, borohydride form, copper(II) sulfate in methanol, Time= 3h, T= 20 °C , Reduction Sim, Tae Bo; Yoon, Nung Min; Bulletin of the Chemical Society of Japan; vol. 70; nb. 5; (1997); p. 1101 - 1107 View in Reaxys

polystyrene O

Rx-ID: 5291394 View in Reaxys 161/477 Yield

Conditions & References With air, T= 400 - 650 °C , Formation of xenobiotics, Oxidation Park, Byung-Ik; Bozzelli, Joseph W.; Booty, Michael R.; Bernhard, Mary J.; Mesuere, Karel; Pettigrew, Charles A.; Shi, Ji-Chun; Simonich, Staci L.; Environmental Science and Technology; vol. 33; nb. 15; (1999); p. 2584 - 2592 View in Reaxys

Rx-ID: 9005084 View in Reaxys 162/477 Yield

Conditions & References With tetraethylammonium chloride in isopropyl alcohol, Time= 29h, T= 90 °C

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Maksyuta; Suprun; Opeida; Turovskii; Russian Journal of Organic Chemistry; vol. 37; nb. 6; (2001); p. 814 - 818 View in Reaxys

(v4)

P Ru (v4)(v4) P (v6) P

(v4)

H P (v4) Ru P OC-6 (v6)

(v4)

Rx-ID: 26906995 View in Reaxys 163/477 Yield 53 %, 76 %

Conditions & References in benzene-d6, (inert atm. in a vac.); stirred for 2 h; solid was removed; benzaldehyde was added at room temp.; heated to 45°C for 24 h; not isolated; NMR Hartwig, John F.; Bergman, Robert G.; Andersen, Richard A.; Organometallics; vol. 10; (1991); p. 3344 - 3362 ; (from Gmelin) View in Reaxys

HO O

Rx-ID: 27897450 View in Reaxys 164/477 Yield

Conditions & References 1 :Example 1; Decomposition of cumene hydroperoxide was carried out on a pilot unit in the form of a reactor with a volume of 12 mL, equipped with a circulation loop to mix the reaction mass and a water jacket to maintain the assigned temperature. To prepare the catalyst, a reactor with a volume of 10 μL was used, and sulfuric acid and phenol were fed by pumps to the reactor. Catalyst and feedstock were fed to the stream of reaction mass at the input to the reactor. The composition of the feedstock is shown in Table 1. Sulfuric acid was also fed to the catalyst synthesis reactor at a rate of 3 μL/h, phenol was fed at a rate of 6 μL/h, which corresponds to a concentration in the reaction medium of 0.02 wt. percent, and the holding time in the reactor was 70 minutes at a temperature of 45° C. The rate at which the feedstock was fed to the CHP decomposition reactor was 27 mL/h. The rate of circulation of the reaction mass was 500 mL/h. The temperature in the reactor was maintained at 75° C. by supplying a heat transfer agent of the corresponding temperature to the jacket of the reactor.The stream emerging from the CHP decomposition reactor was cooled to room temperature and analyzed by GC. The composition of the reaction mass of CHP decomposition is shown in Table 2. With sulfuric acid, phenol in water, T= 75 °C , Product distribution / selectivity Patent; Nelson, Mark; Sederel, Willem Lodewyk; Dyckman, Arkady Samuilovich; Grebenshchikov, Ilya Nikolaevich; Pinson, Viktor Vladimirovich; Zinenkov, Andrey Vladimirovich; US2008/214872; (2008); (A1) English View in Reaxys 5 :Example 5 (Comparative Example); The CHP cleavage reaction was carried out essentially the same as in Example 1, but in this case the feed of composition used was as presented in Table 5. Concentrated sulfuric acid catalyst was fed at a rate of 5 μL/h directly to the cleavage reactor. The produced reaction mixture was analyzed and the final composition is presented in Table 6. With sulfuric acid in water, T= 75 °C , Product distribution / selectivity Patent; Nelson, Mark; Sederel, Willem Lodewyk; Dyckman, Arkady Samuilovich; Grebenshchikov, Ilya Nikolaevich; Pinson, Viktor Vladimirovich; Zinenkov, Andrey Vladimirovich; US2008/214872; (2008); (A1) English View in Reaxys

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Rx-ID: 27897453 View in Reaxys 165/477 Yield

Conditions & References 4 :Example 4; Decomposition of CHP was carried out in the same equipment and under the same conditions as in Example 1, but 75percent sulfuric acid was supplied to the reactor at a rate of 2 μL/h, and phenol was supplied at a rate of 5 μL/h (the ratio in terms of sulfuric acid to phenol was 1:2). The residence time of the mixture in the reactor was about 80 minutes at a temperature of 60° C. The composition of the reaction mass is shown in Table 4. With sulfuric acid, phenol in water, T= 40 - 125 °C , Product distribution / selectivity Patent; Nelson, Mark; Sederel, Willem Lodewyk; Dyckman, Arkady Samuilovich; Grebenshchikov, Ilya Nikolaevich; Pinson, Viktor Vladimirovich; Zinenkov, Andrey Vladimirovich; US2008/214873; (2008); (A1) English View in Reaxys HO

Rx-ID: 28764093 View in Reaxys 166/477 Yield

Conditions & References

81 %Chromat., 10.5 %Chromat., 8.5 %Chromat.

With cytochrome P450BM3 CYP102A1 monooxygenase, NADPH, bovine liver catalase in dimethyl sulfoxide, T= 30 °C , pH= 7.4, aq. buffer, Enzymatic reaction Whitehouse, Christopher J.C.; Bell, Stephen G.; Wong, Luet-Lok; Chemistry - A European Journal; vol. 14; nb. 35; (2008); p. 10905 - 10908 View in Reaxys

Rx-ID: 29981752 View in Reaxys 167/477 Yield

Conditions & References With niobium containing Y zeolite, T= 349.84 °C , Inert atmosphere Trejda; Wojtaszek; Floch; Wojcieszak; Gaigneaux; Ziolek; Catalysis Today; vol. 158; nb. 1-2; (2010); p. 170 177 View in Reaxys With tantalum containing Y zeolite, T= 349.84 °C , Inert atmosphere Trejda; Wojtaszek; Floch; Wojcieszak; Gaigneaux; Ziolek; Catalysis Today; vol. 158; nb. 1-2; (2010); p. 170 177 View in Reaxys

S O

Rx-ID: 40013159 View in Reaxys 168/477 Yield

Conditions & References

63 With C24H20ClN2OPRu, potassium tert-butylate in 1,4-dioxane, Time= 5h, T= 125 °C , Inert atmosphere, Schlenk %Spectr., technique, Glovebox 8 %Spectr. Srimani, Dipankar; Leitus, Gregory; Ben-David, Yehoshoa; Milstein, David; Angewandte Chemie - International Edition; vol. 53; nb. 41; (2014); p. 11092 - 11095; Angew. Chem.; vol. 126; nb. 41; (2014); p. 11272 - 11275,4

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View in Reaxys

O HN

N N

Rx-ID: 1597534 View in Reaxys 169/477 Yield

Conditions & References

87 %, 7 %, T= 60 °C , decomposition, other solvent, Rate constant 83 % Mitsuhashi Tsutomu; Journal of the American Chemical Society; vol. 108; nb. 9; (1986); p. 2394 - 2400 View in Reaxys

Rx-ID: 1915183 View in Reaxys 170/477 Yield

Conditions & References

85 %, 5.5 %, 4 %

T= 60 °C , decomposition, other solvent, Rate constant Mitsuhashi Tsutomu; Journal of the American Chemical Society; vol. 108; nb. 9; (1986); p. 2394 - 2400 View in Reaxys

Rx-ID: 2037444 View in Reaxys 171/477 Yield 29 % Spectr., 30 % Spectr., 31 % Spectr., 9 % Spectr.

Conditions & References With sodium thiomethoxide in N,N,N',N',N'',N''-hexamethylphosphoric triamide, T= 90 °C , Product distribution Tanner, Dennis D.; Blackburn, Edward V.; Diaz, Gilberto E.; Journal of the American Chemical Society; vol. 103; nb. 6; (1981); p. 1557 - 1559 View in Reaxys

Rx-ID: 2124735 View in Reaxys 172/477 Yield 27.2 %

Conditions & References With zinc in tetrahydrofuran, 1.) reflux; 2.) 1 h, 50 deg C Kopp, Michael; Krauth, Luise R.; Ratka, Richard; Weidenhammer, Klaus; Ziegler, Manfred L.; Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie; vol. 35; nb. 7; (1980); p. 802 - 807 View in Reaxys

O O

Rx-ID: 2346793 View in Reaxys 173/477

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Yield

Conditions & References

35 %, 40 %, 10 %

With cobalt(II) chloride in acetonitrile, Time= 8h, T= 25 °C , other tertiary alcohols, other time, temperature, Product distribution, Mechanism Iqbal, Javed; Srivastava, Rajiv Ranjan; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2001 - 2007 View in Reaxys

40 %, 10 %, 35 %

With cobalt(II) chloride in acetonitrile, Time= 8h, T= 25 °C Iqbal, Javed; Srivastava, Rajiv Ranjan; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2001 - 2007 View in Reaxys

35 %, 40 %, 10 %

With cobalt(II) chloride in acetonitrile, Time= 8h, T= 25 °C Iqbal, Javed; Srivastava, Rajiv Ranjan; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2001 - 2007 View in Reaxys

Rx-ID: 2881553 View in Reaxys 174/477 Yield 15 % Chromat., 49 % Chromat., 20 % Chromat.

Conditions & References With sodium periodate in water, Time= 24h, T= 25 °C Hirai, Yasuyuki; Ohe, Kouichi; Toshimitsu, Akio; Uemura, Sakae; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 67; nb. 1-4; (1992); p. 173 - 176 View in Reaxys

Rx-ID: 3831646 View in Reaxys 175/477 Yield

Conditions & References With hydrogen, oxygen, T= 37 °C , p= 720Torr , Irradiation, variation of quantity of O2; effect of Me3N and pyridine, Product distribution Fornarini; Speranza; Attina; Cacace; Giacomello; Journal of the American Chemical Society; vol. 106; nb. 9; (1984); p. 2498 - 2501 View in Reaxys

Rx-ID: 3917178 View in Reaxys 176/477 Yield

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Rx-ID: 8945421 View in Reaxys 177/477 Yield

Conditions & References in carbon dioxide, T= 50 °C , p= 320330Torr , UV-irradiation, Product distribution, Further Variations: Pressures, Solvents Tanko; Pacut; Journal of the American Chemical Society; vol. 123; nb. 24; (2001); p. 5703 - 5709 View in Reaxys

Rx-ID: 9003974 View in Reaxys 178/477 Yield 40 % Chromat., 18 % Chromat., 14 % Chromat., 19 % Chromat.

Conditions & References With magnesium, T= 600 °C , p= 0.01 - 0.1Torr , Further byproducts. Title compound not separated from byproducts. Aitken, R. Alan; Hodgson, Philip K.G.; Morrison, John J.; Oyewale, Adebayo O.; Journal of the Chemical Society. Perkin Transactions 1; nb. 3; (2002); p. 402 - 415 View in Reaxys

n-Bu(t-Bu)2MgLi O

Rx-ID: 13436748 View in Reaxys 179/477 Yield

Conditions & References Reaction Steps: 2 1: diethyl ether 2: p-toluenesulfonic acid / benzene With toluene-4-sulfonic acid in diethyl ether, benzene Peppe, Clovis; Lang, Ernesto Schulz; De Andrade, Fabiano Molinos; De Castro, Lierson Borges; Synlett; nb. 10; (2004); p. 1723 - 1726 View in Reaxys

(cyclopentadienyl)(CO)2FeCH2S+(CH3)2*BF4

CH2=CH-CH2-Mg-Hlg

Rx-ID: 16568917 View in Reaxys 180/477 Yield

Conditions & References Reaction Steps: 2 1.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / -78 °C 1.2: 95 percent / tetrahydrofuran; hexane / 0.08 h / -78 °C 2.1: 76 percent / CsF; H2O / dimethylformamide / 9 h / 80 °C With n-butyllithium, water, cesium fluoride in tetrahydrofuran, hexane, N,N-dimethyl-formamide, 1.1: Metallation / 1.2: Addition / 2.1: Elimination Kawashima, Takayuki; Ishii, Takafumi; Inamoto, Naoki; Tokitoh, Norihiro; Okazaki, Renji; Bulletin of the Chemical Society of Japan; vol. 71; nb. 1; (1998); p. 209 - 219 View in Reaxys

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S N H

aqueous alkaline KMnO4

Rx-ID: 18484571 View in Reaxys 181/477 Yield

Conditions & References Reaction Steps: 2 1: sodium hydride / bis-(2-methoxy-ethyl) ether 2: bis-(2-methoxy-ethyl) ether / 115 - 160 °C / stereochemistry of carbenic decomposition With sodium hydride in diethylene glycol dimethyl ether Slack, W. E.; Taylor, W.; Moseley, C. G.; Chang, K. T.; Kraska, A.; et al.; Tetrahedron Letters; vol. 35; nb. 17; (1994); p. 2647 - 2650 View in Reaxys

Rx-ID: 27897452 View in Reaxys 182/477 Yield

Conditions & References 4 :Example 1; Decomposition of cumene hydroperoxide was carried out on a pilot unit in the form of a reactor with a volume of 12 mL, equipped with a circulation loop to mix the reaction mass and a water jacket to maintain the assigned temperature. To prepare the catalyst, a reactor with a volume of 10 μL was used, and sulfuric acid and phenol were fed by pumps to the reactor. Catalyst and feedstock were fed to the stream of reaction mass at the input to the reactor. The composition of the feedstock is shown in Table 1. Sulfuric acid was also fed to the catalyst synthesis reactor at a rate of 3 μL/h, phenol was fed at a rate of 6 μL/h, which corresponds to a concentration in the reaction medium of 0.02 wt. percent, and the holding time in the reactor was 70 minutes at a temperature of 45° C. The rate at which the feedstock was fed to the CHP decomposition reactor was 27 mL/h. The rate of circulation of the reaction mass was 500 mL/h. The temperature in the reactor was maintained at 75° C. by supplying a heat transfer agent of the corresponding temperature to the jacket of the reactor.The stream emerging from the CHP decomposition reactor was cooled to room temperature and analyzed by GC. The composition of the reaction mass of CHP decomposition is shown in Table 2.; Example 2; CHP decomposition was carried out in the same equipment as in Example 1, but the reactor for synthesis of the catalytic system had a volume of 20 μL, and a mixture having the composition shown in Table 3 was used as feedstock.The feedstock was fed to the reactor at a rate of 10 mL/h, concentrated (96percent) sulfuric acid was fed at a rate of 1.1 μL/h, which corresponded to a concentration of 0.02 wt. percent, and phenol for mixing with sulfuric acid was fed at a rate of 0.9 μL/h, which corresponded to a sulfuric acid/phenol ratio of 2:1. The mixture of phenol and sulfuric acid was held for 600 minutes at a temperature of 20° C. The circulation rate of the reaction mixture was 200 mL/h, and the temperature in the reactor was 70° C. As used herein, concentrated sulfuric acid means "commercially available usual sulfuric acid", which generally means about 93 to 96percent sulfuric acid (H2SO4). With sulfuric acid, phenol in water, T= 85 °C , Product distribution / selectivity Patent; Nelson, Mark; Sederel, Willem Lodewyk; Dyckman, Arkady Samuilovich; Grebenshchikov, Ilya Nikolaevich; Pinson, Viktor Vladimirovich; Zinenkov, Andrey Vladimirovich; US2008/214872; (2008); (A1) English View in Reaxys

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HO O

Rx-ID: 27897454 View in Reaxys 183/477 Yield

Conditions & References 1 :Example 1; Decomposition of cumene hydroperoxide was carried out on a pilot unit consisting of two reactors: the first stage was a CHP decomposition reactor that had a volume of 12 mL and was equipped with a circulation loop, and the second stage reactor was a displacement reactor that had a volume of 7 mL. The reaction mass from the first stage reactor was partially fed to the second reactor and partially returned to the input of the first reactor, thus accomplishing its circulation. Catalyst and feedstock, the composition of which is shown in Table 1, were fed to the stream of reaction mass at the input to the first stage reactor. The catalyst was prepared by mixing concentrated sulfuric acid with phenol, which were fed by two pumps into a constant-temperature reactor with a capacity of 10 μL, from which the mixture was directed to the CHP decomposition reactor. The feedstock having the composition shown in Table 1, as well as a catalyst obtained directly by mixing concentrated sulfuric acid at a rate of 1 μL/h and phenol at a rate of 9 μL/h (ratio 1:5), were fed to the CHP decomposition reactor, and the mixture was kept for 60 minutes at a temperature of 50° C. As used herein, concentrated sulfuric acid means "commercially available usual sulfuric acid", which generally means about 93 to 96percent sulfuric acid (H2SO4). This feed corresponds to a sulfuric acid concentration of 0.007 wt. percent in the reaction medium. The rate of circulation of the reaction mass was 500 mL/h. The temperature in the reactor was kept at a level of 40° C. by supplying a heat transfer agent of the corresponding temperature to the jacket of the reactor.The stream emerging from the first stage reactor was diluted with acetone supplied at a rate of 8 mL/h, and was fed to the second stage reactor heated to a temperature of 125° C. The stream emerging from the second stage reactor was cooled and analyzed by GC. The composition of the reaction mass of CHP decomposition is shown in Table 2. With sulfuric acid, phenol in water, T= 40 - 125 °C , Product distribution / selectivity Patent; Nelson, Mark; Sederel, Willem Lodewyk; Dyckman, Arkady Samuilovich; Grebenshchikov, Ilya Nikolaevich; Pinson, Viktor Vladimirovich; Zinenkov, Andrey Vladimirovich; US2008/214873; (2008); (A1) English View in Reaxys

S O

Rx-ID: 28168627 View in Reaxys 184/477 Yield

Conditions & References

28 %Chro- With 2,4,6-triphenylpyrylium-tetrafluoroborate, oxygen in acetonitrile, Irradiation mat., 5 %Chromat. Bonesi, Sergio M.; Fagnoni, Maurizio; Albini, Angelo; European Journal of Organic Chemistry; nb. 15; (2008); p. 2612 - 2620 View in Reaxys

Rx-ID: 31323226 View in Reaxys 185/477 Yield

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O O

HO O

Rx-ID: 34973413 View in Reaxys 186/477 Yield 21 %, 59 %

Conditions & References With N,N,N',N'-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a;2',1'-c][1,4] diazepine-2,12-diamine in N,N-dimethyl-formamide, Time= 72h, Inert atmosphere, Glovebox, UV-irradiation Doni, Eswararao; O'Sullivan, Steven; Murphy, John A.; Angewandte Chemie - International Edition; vol. 52; nb. 8; (2013); p. 2239 - 2242; Angew. Chem.; vol. 125; nb. 8; (2013); p. 2295 - 2298,4 View in Reaxys

Cl Cl Cl

O HN

N H

O O

Rx-ID: 39191784 View in Reaxys 187/477 Yield

Conditions & References With dichloro bis(acetonitrile) palladium(II), p-benozquinone in acetone, Time= 18h, T= 20 °C , Solvent Dong, Jia Jia; Harvey, Emma C.; Faans-Mastral, Martn; Browne, Wesley R.; Feringa, Ben L.; Journal of the American Chemical Society; vol. 136; nb. 49; (2014); p. 17302 - 17307 View in Reaxys

F Cl

Rx-ID: 1709894 View in Reaxys 188/477 Yield 60 %, 8 % Chromat., 10 % Chromat., 10 % Chromat. 60 %, 10 % Chromat., 11 % Chromat., 8 % Chromat. 60 %, 8 % Chromat., 11 % Chromat., 10 % Chromat. 8 % Chromat., 10 % Chromat., 11 % Chromat., 60 %

Conditions & References T= 200 - 250 °C , Further byproducts given Schmidt, H.; Burtzlaff, Ch.; Masuhr, H.'; Ohl, J.; Pehle, W.; et al.; Journal fuer Praktische Chemie (Leipzig); vol. 322; nb. 5; (1980); p. 751 - 760 View in Reaxys

T= 200 - 250 °C , Further byproducts given Schmidt, H.; Burtzlaff, Ch.; Masuhr, H.'; Ohl, J.; Pehle, W.; et al.; Journal fuer Praktische Chemie (Leipzig); vol. 322; nb. 5; (1980); p. 751 - 760 View in Reaxys T= 200 - 250 °C , Further byproducts given Schmidt, H.; Burtzlaff, Ch.; Masuhr, H.'; Ohl, J.; Pehle, W.; et al.; Journal fuer Praktische Chemie (Leipzig); vol. 322; nb. 5; (1980); p. 751 - 760 View in Reaxys

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F F

O S

Rx-ID: 1781086 View in Reaxys 189/477 Yield

Conditions & References

6 %, 58 %, With DPPH-H in chloroform-d1, T= -75 °C , chemiluminescence, other peroxides, Product distribution, Mechanism 2 %, 10 %, 5 %, 89 % Bartlett, Paul D.; Aida, Tetsuo; Chu, Hsien-Kun; Fang, Tai-Shan; Journal of the American Chemical Society; vol. 102; nb. 10; (1980); p. 3515 - 3524 View in Reaxys

Rx-ID: 1915182 View in Reaxys 190/477 Yield

Conditions & References

77 %, 5.5 %, 10 %

T= 60 °C , decomposition, other solvent, Rate constant Mitsuhashi Tsutomu; Journal of the American Chemical Society; vol. 108; nb. 9; (1986); p. 2394 - 2400 View in Reaxys

2H 2H

O N

Rx-ID: 1915185 View in Reaxys 191/477 Yield 82 %, 5.5 %, 6.5 %

Conditions & References T= 60 °C , decomposition, other solvent, Rate constant Mitsuhashi Tsutomu; Journal of the American Chemical Society; vol. 108; nb. 9; (1986); p. 2394 - 2400 View in Reaxys

Rx-ID: 2017893 View in Reaxys 192/477 Yield 43.41 %, 25.83 %, 10.2 %, 5.53 %

Conditions & References With magnesium 2-ethylhexanoate in chlorobenzene, Time= 6h, T= 130 °C , Kinetics Nurullina; Batyrshin; Kharlampidi, Kh. E.; Petroleum Chemistry; vol. 54; nb. 1; (2014); p. 65 - 68; Neftekhimiya; vol. 54; nb. 1; (2014); p. 66 - 69,4 View in Reaxys

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With bis(O,O'-diethyl dithiophosphato)nickel(II), T= 109.9 °C , investigation of decomposition promoted by different metal DDPs, Thermodynamic data, Product distribution, Mechanism Sexton, Michael D.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 11; (1984); p. 1771 - 1776 View in Reaxys With dihydrogen peroxide in water, acetonitrile, Time= 24h, T= 80 °C Estrada, Ana C.; Simoes, Mario M. Q.; Santos, Isabel C. M. S.; Neves, M. Graca P. M. S.; Cavaleiro, Jose A. S.; Cavaleiro, Ana M. V.; Monatshefte fur Chemie; vol. 141; nb. 11; (2010); p. 1223 - 1235 View in Reaxys N

Rx-ID: 2155406 View in Reaxys 193/477 Yield

Conditions & References

4 %, 96 %

in dimethyl sulfoxide, T= 33.5 °C Hirota, Hiroshi; Mitsuhashi, Tsutomu; Chemistry Letters; nb. 5; (1990); p. 803 - 806 View in Reaxys

96 %, 4 %

in dimethyl sulfoxide, T= 33.5 °C , Rate constant, Mechanism Hirota, Hiroshi; Mitsuhashi, Tsutomu; Chemistry Letters; nb. 5; (1990); p. 803 - 806 View in Reaxys

N C– N+ N

Rx-ID: 2313441 View in Reaxys 194/477 Yield

Conditions & References in pyridine, Time= 2h, T= 115 °C Hirota, Hiroshi; Mitsuhashi, Tsutomu; Chemistry Letters; nb. 5; (1990); p. 803 - 806 View in Reaxys

N N

Rx-ID: 4295712 View in Reaxys 195/477 Yield 28 % Spectr., 27 % Spectr., 45 % Spectr. 45 % Spectr., 27 % Spectr., 28 % Spectr.

Conditions & References in methanol, T= 15 °C , Irradiation Fehr; Fehr, Olaf C.; Grapenthin; Grapenthin, Olaf; Kilian; Kilian, Joerg; Kirmse; Kirmse, Wolfgang; Steenken; Steenken, Steen; Tetrahedron Letters; vol. 36; nb. 33; (1995); p. 5887 - 5890 View in Reaxys in methanol, T= 15 °C , Irradiation Fehr; Fehr, Olaf C.; Grapenthin; Grapenthin, Olaf; Kilian; Kilian, Joerg; Kirmse; Kirmse, Wolfgang; Steenken; Steenken, Steen; Tetrahedron Letters; vol. 36; nb. 33; (1995); p. 5887 - 5890 View in Reaxys

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Rx-ID: 10279025 View in Reaxys 196/477 Yield

Conditions & References

3.4 %, 1.0 %, 0.8 %

With di-tert-butyl peroxide, oxygen in acetonitrile, Time= 7h, UV-irradiation Baciocchi, Enrico; Del Giacco, Tiziana; Giombolini, Paolo; Lanzalunga, Osvaldo; Tetrahedron; vol. 62; nb. 27; (2006); p. 6566 - 6573 View in Reaxys

S Cl

N O

O O

S N

HO Cl

S Cl

Rx-ID: 11172809 View in Reaxys 197/477 Yield

Conditions & References

23 %, 19 %

in various solvent(s), Time= 0.166667h, T= 150 °C , microwave irradiation, Further byproducts. Hartung, Jens; Schneiders, Nina; Gottwald, Thomas; Tetrahedron Letters; vol. 48; nb. 34; (2007); p. 6027 - 6030 View in Reaxys

vanadium(V)-oxide

Rx-ID: 20050880 View in Reaxys 198/477 Yield

Conditions & References Reaction Steps: 3 1: 53 percent / iron(II) sulfate / H2O; acetic acid / 3 h / Ambient temperature 2: 85.6 percent / 10 percent potassium hydroxide / ethanol; H2O / 1 h / Ambient temperature 3: p-toluenesulfonic acid monohydrate / 105 °C With potassium hydroxide, toluene-4-sulfonic acid, iron(II) sulfate in ethanol, water, acetic acid Takano, Seiichi; Iwabuchi, Yoshiharu; Takahashi, Michiyasu; Ogasawara, Kunio; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 8; (1986); p. 3445 - 3446 View in Reaxys

O O

Rx-ID: 20053312 View in Reaxys 199/477

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Yield

Conditions & References Reaction Steps: 2 1: 85.6 percent / 10 percent potassium hydroxide / ethanol; H2O / 1 h / Ambient temperature 2: p-toluenesulfonic acid monohydrate / 105 °C With potassium hydroxide, toluene-4-sulfonic acid in ethanol, water Takano, Seiichi; Iwabuchi, Yoshiharu; Takahashi, Michiyasu; Ogasawara, Kunio; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 8; (1986); p. 3445 - 3446 View in Reaxys

tar

Rx-ID: 23233519 View in Reaxys 200/477 Yield

Conditions & References 1 : COMPARATIVE EXPERIMENT 1 For comparative purposes, a catalyst comprising iron oxide, yttrium oxide, and potassium oxide supported on alumina was evaluated for catalytic activity in the dehydrogenation of ethylbenzene to styrene. The catalyst comprised iron oxide (3 wtpercent Fe203), potassium oxide (3 wtpercent K20), and yttrium oxide (1.1 wtpercent Y203). The catalyst was prepared by impregnating the alumina support described in Example 1 (180 g) with an aqueous solution (72 mL) containing iron (III) nitrate nonahydrate (29.44 g, 0.07287 mol), potassium nitrate (12.47 g, 0.1233 MOL), yttrium nitrate tetrahydrate (6.32g, 0.01822 mol) and enough deionized water to make 72 ML of impregnating solution. The impregnating solution was added in 1 to 2 mL aliquots over the course of 45 min while the sample was continuously mixed at room temperature in a rotary tumbler. After being impregnated, the support was dried, with occasional mixing, for 4 h at room temperature. The impregnated sample was then dried for 3 h at 80°C, dried for 12 h at 120°C, and then calcined for 4 h at 750°C before cooling to room temperature to obtain the comparative catalyst. The sample of comparative catalyst (90 mL, 1.12 G/ML packed, bulk density) was tested for catalytic activity in the manner described in Example 2, with the exceptions that nitrogen gas was used in place of ethane and the sum of nitrogen and ethylbenzene flows gave a gas hourly space velocity of 400 IF 1. The resulting data are shown in Table 4. When Comparative Experiment 1 is compared with Example 2, it is seen that the presence of iron oxide in the catalyst lowers the selectivity to styrene and raises selectivities to cracking products, by-products, and tars. With iron(III) nitrate (3 wtpercent as Fe2O3); potassium nitrate (3 wtpercent as K2O); yttrium nitrate (1.1 wtpercent as Y2O3); alumina; mixture of, calcined, T= 548 - 598 °C , Continuous reaction, Product distribution / selectivity Patent; DOW GLOBAL TECHNOLOGIES INC.; WO2004/60839; (2004); (A1) English View in Reaxys

Rx-ID: 28764094 View in Reaxys 201/477 Yield 20 %, 21 %

Conditions & References With perchloric acid, C13H30N4*Fe(3+)*CF3O3S(1-)*C2H2F3O(1-)*C6H5IO in 2,2,2-trifluoroethanol, acetone, Time= 0.166667h, T= -40 °C , Inert atmosphere, Schlenk technique, Kinetics, Reagent/catalyst Hong, Seungwoo; Wang, Bin; Seo, Mi Sook; Lee, Yong-Min; Kim, Myoung Jin; Kim, Hyung Rok; Ogura, Takashi; Garcia-Serres, Ricardo; Clemancey, Martin; Latour, Jean-Marc; Nam, Wonwoo; Angewandte Chemie - International Edition; vol. 53; nb. 25; (2014); p. 6388 - 6392; Angew. Chem.; vol. 126; nb. 25; (2014); p. 6506 - 6510,5 View in Reaxys

79 %Chro- With cytochrome P450BM3 CYP102A1 variant KSK19 (F87A/H171L/Q307H/N319Y) monooxygenase, NADPH, bovine liver mat., 19.5 catalase in dimethyl sulfoxide, T= 30 °C , pH= 7.4, aq. buffer, Enzymatic reaction %Chromat. Whitehouse, Christopher J.C.; Bell, Stephen G.; Wong, Luet-Lok; Chemistry - A European Journal; vol. 14; nb. 35; (2008); p. 10905 - 10908 View in Reaxys

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45 %Chro- With [(1,4,7,10-tetramethyl-1,4,7,10-tetraazacyclotridecane)FeIII(OOC(O)CH3)]2+ in 2,2,2-trifluoroethanol, acetone, mat., 11 T= -60 °C , Inert atmosphere, Kinetics, Catalytic behavior, Reagent/catalyst, Time, Concentration, Temperature, che%Chromat. moselective reaction Wang, Bin; Lee, Yong-Min; Clmancey, Martin; Seo, Mi Sook; Sarangi, Ritimukta; Latour, Jean-Marc; Nam, Wonwoo; Journal of the American Chemical Society; vol. 138; nb. 7; (2016); p. 2426 - 2436 View in Reaxys

O HO

Rx-ID: 33242722 View in Reaxys 202/477 Yield

Conditions & References 1 :[Examples 1 and 2] Alpha methyl styrene was prepared according to the process flow diagram ofFig. 2. First, oxidation of cumene was progressed with an oxidizer under the following conditions using 3 oxidation reactors in a phenol process to prepare a stream including cumene hydroperoxide (CHP) of concentration of 25 wtpercent. (1) Condition of introducing first oxidizer supply (CHP 0.4percent + cumene 99.6percent) 1 ml/min, 02: 100 ml/min, pressure: 3bar, reaction temperature: 100 °C (2) Condition of introducing second oxidizer supply (CHP 8.42percent + cumene 91.58percent) 1 ml/min, 02: 100 ml/min, pressure:3bar, reaction temperature: 96 °C (3) Condition of introducing third oxidizer supply (CHP 16.27percent + cumene 83.73percent) 1 ml/min, 02: 100 ml/min, pressure: 3bar, reaction temperature: 94 °C The concentration of CHP stream was changed from 8.4 to 24 wtpercent while passing through 3 oxidation reactors as shown in the following Table 1. Then, 25 wtpercent of the stream of low concentration was separated and transferred to a receiver (20), and then, supplied to a catalytic hydrogenation reactor (30). The hydrogenation reactor was filled with a catalyst Pd/C, hydrogen was introduced and the reaction was progressed while maintaining internal temperature. And, the reactant of cumene hydroperoxide stream of 25 wtpercent concentration was introduced top-down of the reactor using a pressurization pump. The hydrogenation reaction was progressed under conditions of 150 g of cumene hydroperoxide (CHP) of 25 wtpercent concentration, 1 g of 1 wtpercent Pd/C, and hydrogen flow rate of 150 cc/min. And, the mole ratio of the cumene hydroperoxide stream and the introduced hydrogen was maintained 1 :8. The hydrogen reaction was progressed respectively for 7 hours and 3 hours in Examples 1 and 2. As the result, final product with cumene hydroperoxide (CHP) conversion rate of 99.97percent, CA increase rate of 960.5percent, and CA concentration of 25percent was obtained. After the reaction was completed, conversion rate of cumene hydroperoxied into cumyl alcohol was analyzed with liquid chromatography, and the result was shown in Table 2. After the hydrogenation reaction is completed, prepared cumyl alcohol is supplied to the receiver (20), and transferred to the stripper (40). Thereby, the stripper (40) is filled with a mixture of cumyl alcohol obtained by the hydrogenation reaction, and a stream including cumyl alcohol and cumene hydroperoxide which are not used in the hydrogen reaction. Then, the mixture is concentrated in the stripper (40), passed through a receiver (50) and transferred to a cleavage reactor (60), and the remainder is directly transferred to the cleavage reactor. And then, an acid catalyst is introduced in the cleavage reactor (60), and the mixture is continuously dehydrated so that the acid catalyst decomposes cumene hydroperoxide into phenol and acetone, and dehydrates cumyl alcohol into AMS. Into the cleavage reactor, 100 g of feedstock (CHP 72 wtpercent, CA 8 wtpercent, cumene 20 wtpercent) and 1 g of H2S04 were introduced to progress the reaction. And, the reaction temperature was maintained 65 °C , and raised to 1 10°C after conversion until the concentration of CHP became less than 1percent, so as to convert CA into AMS. The mixture of phenol, acetone and AMS produced in the cleavage reactor (60) was transferred to a neutralizer reactor (70), and a neutralization agent was introduced to progress a neutralization reaction. After neutralization, the product was transferred to a distillation reactor (80), and separated into phenol, AMS and acetone through distillation. By the above reaction, yield for conversion from CHP into phenol was 99.36percent, yield for conversion from CHP into aceton was 98.30percent, and yield for conversion from CA into AMS was 82.45percent. [Table 1 ]The above Table 1 shows that most of CHP was decomposed into phenol and acetone and the concentration decreased from 82 wtpercent to 1 wtpercent in the 1st cleavage reactor, and 1 wtpercent of CHP decreased to 1 wtpercent or less in the 2nd cleavage reactor. With sulfuric acid, T= 65 - 100 °C , Product distribution / selectivity Patent; LG CHEM, LTD.; HA, Seung-Back; YOO, Suk-Joon; CHO, Dong-Hyun; WO2012/74194; (2012); (A2) English View in Reaxys

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Rx-ID: 2011782 View in Reaxys 203/477 Yield

Conditions & References With tris(triphenylphosphine)ruthenium(II) chloride in various solvent(s), Time= 3h, T= 180 °C , Product distribution Pri-Bar, Ilan; Buchman, Ouri; Schumann, Hebert; Kroth, Heinz J.; Blum, Jochanan; Journal of Organic Chemistry; vol. 45; nb. 22; (1980); p. 4418 - 4428 View in Reaxys With 9,10-anthracenedicarbonitrile, benzyl-phenylsulphide in acetonitrile-D3, T= 40 °C , Irradiation, photoinduced oxidation of benzyl phenyl sulfides promoted by 9,10-dicyanoanthracene; stability of photoproducts or possible primary photoproducts, Product distribution Baciocchi, Enrico; Crescenzi, Cristina; Lanzalunga, Osvaldo; Tetrahedron; vol. 53; nb. 12; (1997); p. 4469 4478 View in Reaxys

Cl Mo Cl (v5) Cl

Rx-ID: 3383577 View in Reaxys 204/477 Yield

Conditions & References

53 %

in tetrahydrofuran, diethyl ether, 1) -70 deg C, 1-2 h, 2) -70 - 20 deg C, 15 h Kauffmann, Thomas; Ennen, Beate; Sander, Joerg; Wieschollek, Raphael; Angewandte Chemie; vol. 95; nb. 3; (1983); p. 237 - 238 View in Reaxys

Cl (v5)

Rx-ID: 3383788 View in Reaxys 205/477 Yield 87 %

Conditions & References in tetrahydrofuran, Time= 1.5h, T= 20 °C Kauffmann, Thomas; Abeln, Renate; Welke, Siegfried; Wingbermuehle, Dorothea; Angewandte Chemie; vol. 98; nb. 10; (1986); p. 927 - 928 View in Reaxys in tetrahydrofuran, Time= 1.5h, T= 20 °C , effect of use of var. carben-W-complexes, var. temp., or solvents, Product distribution Kauffmann, Thomas; Abeln, Renate; Welke, Siegfried; Wingbermuehle, Dorothea; Angewandte Chemie; vol. 98; nb. 10; (1986); p. 927 - 928 View in Reaxys

N N

Rx-ID: 3674991 View in Reaxys 206/477 Yield

Conditions & References in benzene, T= 25 °C , Irradiation, Yield given. Yields of byproduct given Slack, W. E.; Taylor, W.; Moseley, C. G.; Chang, K. T.; Kraska, A.; et al.; Tetrahedron Letters; vol. 35; nb. 17; (1994); p. 2647 - 2650 View in Reaxys

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Me2CuLi

Rx-ID: 6712327 View in Reaxys 207/477 Yield

Conditions & References

20 % Chromat.

in diethyl ether, Time= 5h, T= 0 °C Kauffmann, Thomas; Saelker, Reiner; Voss, Karl-Uwe; Chemische Berichte; vol. 126; nb. 6; (1993); p. 1447 1452 View in Reaxys

Me4CoLi2

Rx-ID: 6712329 View in Reaxys 208/477 Yield

Conditions & References

72 % Chromat.

in tetrahydrofuran, Time= 2h, T= -70 °C Kauffmann, Thomas; Saelker, Reiner; Voss, Karl-Uwe; Chemische Berichte; vol. 126; nb. 6; (1993); p. 1447 1452 View in Reaxys

Me4FeLi2

Rx-ID: 6712330 View in Reaxys 209/477 Yield

Conditions & References

70 % Chromat.

in tetrahydrofuran, Time= 4h, T= -50 °C Kauffmann, Thomas; Saelker, Reiner; Voss, Karl-Uwe; Chemische Berichte; vol. 126; nb. 6; (1993); p. 1447 1452 View in Reaxys

Poly(α-methyl styrene) Rx-ID: 8903047 View in Reaxys 210/477 Yield

Conditions & References With PMSNa in tetrahydrofuran, T= -60 - 15 °C , Equilibrium constant Kalninsh; Physical Chemistry Chemical Physics; vol. 3; nb. 20; (2001); p. 4542 - 4546 View in Reaxys O

Rx-ID: 9266026 View in Reaxys 211/477 Yield

Conditions & References Stage 1: With magnesium in diethyl ether Stage 2: With potassium hydrogensulfate, Heating Garner, Charles M.; Chiang, Shirley; Nething, Matthew; Monestel, Robert; Tetrahedron Letters; vol. 43; nb. 46; (2002); p. 8339 - 8342 View in Reaxys N

H20 HO

Rx-ID: 18199576 View in Reaxys 212/477

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Yield

Conditions & References Reaction Steps: 2 1: 54 percent / pyridine / Ambient temperature 2: 5 percent / LiAlH4 / tetrahydrofuran / 1 h / 19 °C With pyridine, lithium aluminium tetrahydride in tetrahydrofuran Froehlich, Johannes; Sauter, Fritz; Blasl, Karin; Heterocycles; vol. 37; nb. 3; (1994); p. 1879 - 1892 View in Reaxys

H20

Rx-ID: 18218101 View in Reaxys 213/477 Yield

Conditions & References Reaction Steps: 3 1: 1.) LDA / 1.) THF, hexane, -80 deg C, 1 h, 2.) THF, hexane, -40 deg C, 1 h 2: 54 percent / pyridine / Ambient temperature 3: 5 percent / LiAlH4 / tetrahydrofuran / 1 h / 19 °C With pyridine, lithium aluminium tetrahydride, lithium diisopropyl amide in tetrahydrofuran Froehlich, Johannes; Sauter, Fritz; Blasl, Karin; Heterocycles; vol. 37; nb. 3; (1994); p. 1879 - 1892 View in Reaxys

tar

Rx-ID: 23227659 View in Reaxys 214/477 Yield

Conditions & References 2 : EXAMPLE 2 A sample (93 mL; 1.11 G/ML packed, bulk density) of the catalyst prepared in Example 1 was loaded into a fluidized bed reactor (1 inch (2.5 cm) ID up-flow fluidized bed quartz reactor). The reactor was heated to 550°C as monitored and controlled from an internal thermocouple placed in the center of the reactor and two inches (5.0 cm) from the bottom of the catalyst bed. The ethylbenzene flow was 0.68 ML/MIN, and this stream was vaporized and mixed with ethane at 195°C prior to introduction to the reactor. The ethane gas had a flow rate of 0.645 L/min (0°C, 1 atm). The sum of ethane and ethylbenzene flows gave a gas hourly space velocity of 500 IFAPOS;, based on the packed volume of the catalyst and ideal gas volumes based on normal conditions described above for the diluent flow. One evaluation cycle consisted of a reaction segment and a regeneration segment that were separated by nitrogen purges used to sweep the reactor with an inert gas. The reaction segment lasted for 10 min. Thereafter, a nitrogen purge was passed through the reactor for 15 min. The liquid products were condensed in a liquid nitrogen trap and the residual gaseous products were captured in a gas sampling bag. The nitrogen feed was switched to air at the same flow rate, and the reactor temperature was increased to 650°C for the regeneration segment, which was maintained for 30 min and followed by a second nitrogen purge. The gas stream was collected in a separate bag during the regeneration portion of the cycle. The liquid sample was weighed and analyzed by GC; each of the gas sampling bags was also analyzed by GC. The results were quantified using external standards. Compilation of the three analyses allowed for the calculation of an overall conversion and selectivity for the entire cycle. The main products were styrene, benzene, toluene, alpha-methyl styrene, tar, and coke. Tar was defined as the sum of peaks eluted after alpha-methyl styrene to the end of the temperature ramp of 230°C. The molecular weight of stilbene was used for the average molecular weight of tar. Coke was measured as COx formed during the regeneration. The reactor was then cooled to the next reaction temperature while being purged with nitrogen. The temperature was then set for the next cycle and the above process was repeated again to generate another data point. Cycles were completed at selected reaction temperatures between 550°C and 605°C. The resulting data are shown in Table 2, with the exception that the first six catalytic cycles were used as a break-in period and the data are not recorded. Table 2. The data in Table 2 illustrate the activity of a rare earth catalyst of this invention, absent iron oxide and any platinum group metal, in the dehydrogenation of ethylbenzene to styrene in a feedstream containing ethane. The catalyst achieved high selectivity to styrene (>85 mole percent) and low selectivities to by-products and tar. Additionally, the activity of the catalyst, measured by ethylbenzene conversion, is acceptable at about 50 mole percent. The catalyst also showed activity for ethane dehydrogenation.

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With lanthanum nitrate (7 wtpercent as lanthanum metal); potassium nitrate (1 wtpercent as potassium metal); alumina; mixture of, calcined, T= 575 - 602 °C , Continuous reaction, Product distribution / selectivity Patent; DOW GLOBAL TECHNOLOGIES INC.; WO2004/60839; (2004); (A1) English View in Reaxys

Rx-ID: 31323243 View in Reaxys 215/477 Yield

Conditions & References Reaction Steps: 2 1: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C 2: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C With dihydrogen peroxide in water, acetonitrile Estrada, Ana C.; Simoes, Mario M. Q.; Santos, Isabel C. M. S.; Neves, M. Graca P. M. S.; Cavaleiro, Jose A. S.; Cavaleiro, Ana M. V.; Monatshefte fur Chemie; vol. 141; nb. 11; (2010); p. 1223 - 1235 View in Reaxys O O

Rx-ID: 33488034 View in Reaxys 216/477 Yield

Conditions & References Reaction Steps: 3 1.2: Acidic conditions 2.1: hydrogenchloride / pentane 3.1: water / acetone / 24.84 °C / Solvolysis With hydrogenchloride, water in acetone, pentane, 1.1: Grignard reaction / 1.2: Grignard reaction Taha, Ahmed A.; International Journal of Chemical Kinetics; vol. 44; nb. 8; (2012); p. 514 - 523 View in Reaxys

O OH

Rx-ID: 34973414 View in Reaxys 217/477 Yield

Conditions & References Reaction Steps: 2 1: pyridine / diethyl ether / 2 h / |Reflux; |Inert atmosphere 2: N,N,N',N'-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a;2',1'-c][1,4] diazepine-2,12-diamine / N,N-dimethyl-formamide / 72 h / |Inert atmosphere; |Glovebox; |UV-irradiation With pyridine, N,N,N',N'-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a;2',1'-c][1,4] diazepine-2,12-diamine in diethyl ether, N,N-dimethyl-formamide Doni, Eswararao; O'Sullivan, Steven; Murphy, John A.; Angewandte Chemie - International Edition; vol. 52; nb. 8; (2013); p. 2239 - 2242; Angew. Chem.; vol. 125; nb. 8; (2013); p. 2295 - 2298,4 View in Reaxys

Z Br

Rx-ID: 36555111 View in Reaxys 218/477 Yield

Conditions & References With dihydrogen peroxide, bromine in dichloromethane, water, Time= 4h, Reflux

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Amati, Alessandro; Dosualdo, Gabriele; Zhao, Lihua; Bravo, Anna; Fontana, Francesca; Minisci, Francesco; Bjorsvik, Hans-Rene; Organic Process Research and Development; vol. 2; nb. 4; (1998); p. 261 - 269 View in Reaxys

Rx-ID: 36875990 View in Reaxys 219/477 Yield

Conditions & References With Titanium(IV) oxide in isopropyl alcohol, Time= 15h, Irradiation, Inert atmosphere Li, Yue; Ji, Hongwei; Chen, Chuncheng; Ma, Wanhong; Zhao, Jincai; Angewandte Chemie - International Edition; vol. 52; nb. 48; (2013); p. 12636 - 12640; Angew. Chem.; vol. 125; nb. 48; (2013); p. 12868 - 12872,5 View in Reaxys

Rx-ID: 458044 View in Reaxys 220/477 Yield

Conditions & References T= 80 °C , p= 3Torr Cope; Foster; Towle; Journal of the American Chemical Society; vol. 71; (1949); p. 3929,3933 View in Reaxys

Rx-ID: 1709994 View in Reaxys 221/477 Yield

Conditions & References With N-bromosuccinmide, meta-chloroperoxybenzoic acid in tetrachloromethane, Time= 18h, Heating, Yield given. Yields of byproduct given Ravindranath, B.; Srinivas, P.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 22; nb. 6; (1983); p. 592 - 594 View in Reaxys

Rx-ID: 2480000 View in Reaxys 222/477 Yield

Conditions & References

49 % Chromat., 20 % Chromat., 15 % Chromat.

With sodium periodate, acetic acid, Time= 24h, T= 25 °C

15 % Chromat., 20 % Chromat., 49 % Chromat.

With sodium periodate, acetic acid, Time= 24h, T= 25 °C

Hirai, Yasuyuki; Ohe, Kouichi; Toshimitsu, Akio; Uemura, Sakae; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 67; nb. 1-4; (1992); p. 173 - 176 View in Reaxys

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Rx-ID: 2785990 View in Reaxys 223/477 Yield

Conditions & References With dimethylsulfide borane complex, dihydrogen peroxide, 1.) THF, 25 deg C, 2.) THF, 25-30 deg C (water bath cooling), Yield given. Multistep reaction Singaram, Bakthan; Goralski, Christian T.; Fisher, Gary B.; Journal of Organic Chemistry; vol. 56; nb. 19; (1991); p. 5691 - 5696 View in Reaxys

Rx-ID: 3383275 View in Reaxys 224/477 Yield

Conditions & References

35 %

in diethyl ether, Time= 4h, Ambient temperature Dzhemilev, U. M.; Ibragimov, A. G.; Morozov, A. B.; Muslukhov, R. R.; Tolstikov, G. A.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 38; nb. 11.2; (1989); p. 2350 2352; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 11; (1989); p. 2562 - 2565 View in Reaxys

Cl (v5)

Rx-ID: 3383329 View in Reaxys 225/477 Yield

Conditions & References With Cl-Mo(O)=CH2, 4-methoxy-benzaldehyde in tetrahydrofuran, ethanol, Time= 12h, -70 degC to room temp. Kauffmann, Thomas; Fiegenbaum, Petra; Wieschollek, Raphael; Angewandte Chemie; vol. 96; nb. 7; (1984); p. 500 - 501 View in Reaxys

Rx-ID: 3774646 View in Reaxys 226/477 Yield

Conditions & References With oxygen, bis(acetylacetonate)oxovanadium in chlorobenzene, T= 49.9 °C , Rate constant Howard, J. A.; Tait, J. C.; Yamada, T.; Chenier, H. B.; Canadian Journal of Chemistry; vol. 59; (1981); p. 2184 2190 View in Reaxys

Rx-ID: 3857435 View in Reaxys 227/477

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Yield

Conditions & References With triethylamine, palladium on activated charcoal in acetonitrile, Time= 8h, T= 100 °C , var. palladium catalysts; other vinyl compounds, Product distribution Andersson, Carl-Magnus; Karabelas, Kostas; Hallberg, Anders; Andersson, Carlaxel; Journal of Organic Chemistry; vol. 50; nb. 20; (1985); p. 3891 - 3895 View in Reaxys

N HO

Rx-ID: 4295708 View in Reaxys 228/477 Yield 28 % Spectr., 45 % Spectr., 27 % Spectr.

N N

N O

Rx-ID: 4564462 View in Reaxys 229/477 Yield

Conditions & References With oxygen, nitrogen(IV) oxide, iron (III) acetylacetonate in dichloromethane, Time= 1h, T= 0 °C , Yield given. Further byproducts given. Yields of byproduct given Suzuki, Hitomi; Yonezawa, Shuji; Nonoyama, Nobuaki; Mori, Tadashi; Journal of the Chemical Society - Perkin Transactions 1; nb. 19; (1996); p. 2385 - 2389 View in Reaxys With nitronium tetrafluoroborate in sulfolane, dichloromethane, Time= 10h, T= -20 °C , Product distribution Suzuki, Hitomi; Mori, Tadashi; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 7; (1997); p. 1265 - 1274 View in Reaxys

Me4(PrO)4(μ-PrO)2W2

Rx-ID: 6712334 View in Reaxys 230/477 Yield 22 %, 25 %, 26 %

Conditions & References in tetrahydrofuran Kauffmann, Thomas; Jordan, Jan; Voss, Karl-Uwe; Wilde, Heinz-Wilhelm; Chemische Berichte; vol. 126; nb. 9; (1993); p. 2083 - 2092 View in Reaxys

25 %, 26 %, 22 %

in tetrahydrofuran Kauffmann, Thomas; Jordan, Jan; Voss, Karl-Uwe; Wilde, Heinz-Wilhelm; Chemische Berichte; vol. 126; nb. 9; (1993); p. 2083 - 2092 View in Reaxys

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22 %, 26 %, 25 %

in tetrahydrofuran Kauffmann, Thomas; Jordan, Jan; Voss, Karl-Uwe; Wilde, Heinz-Wilhelm; Chemische Berichte; vol. 126; nb. 9; (1993); p. 2083 - 2092 View in Reaxys

Rx-ID: 10199107 View in Reaxys 231/477 Yield

Conditions & References With (CO)4(palladium)4(acetate)4, Time= 2h, T= 60 °C , Title compound not separated from byproducts Stolarov; Dobrokhotova; Kryukova; Kozitsyna; Gekhman; Vargaftik; Moiseev; Russian Chemical Bulletin; vol. 54; nb. 3; (2005); p. 803 - 806 View in Reaxys O

O S O

Rx-ID: 10294864 View in Reaxys 232/477 Yield

Conditions & References With oxygen, [NMQ][BF4] in acetonitrile, Photolysis, Further byproducts given Baciocchi, Enrico; Del Giacco, Tiziana; Giombolini, Paolo; Lanzalunga, Osvaldo; Tetrahedron; vol. 62; nb. 27; (2006); p. 6566 - 6573 View in Reaxys O

9,10-dioxo-9,10-dihydro-anthracene-1-sulfenyl bromide

Rx-ID: 17624197 View in Reaxys 233/477 Yield

Conditions & References Reaction Steps: 2 1: 1.) samarium(III) trifluoromethanesulfonate, s-butyllithium, hexamethylphosphoric triamide / 1.) THF, cyclohexane, room temperature, 1 h, 2.) THF, cyclohexane, room temperature, 1 h 2: 1.) samarium(III) trifluoromethanesulfonate, s-butyllithium, hexamethylphosphoric triamide / 1.) THF, cyclohexane, room temperature, 1 h, 2.) THF, cyclohexane, room temperature, 1 h With N,N,N',N',N'',N''-hexamethylphosphoric triamide, sec.-butyllithium, Sm(OTf)3 Fukuzawa, Shin-Ichi; Mutoh, Keisuke; Tsuchimoto, Teruhisa; Hiyama, Tamejiro; Journal of Organic Chemistry; vol. 61; nb. 16; (1996); p. 5400 - 5405 View in Reaxys

Rx-ID: 21282548 View in Reaxys 234/477 Yield

Conditions & References Reaction Steps: 2 1: 1.) LiCl, 2.) methanesulfonyl chloride / 1.) s-collidine, DMF, 0 deg C, 2.) 0 to 25 deg C, 8 h 2: 1.) Mg / 1.) THF, reflux, 2.) 0 deg C, 15 min With magnesium, methanesulfonyl chloride, lithium chloride Zimmerman, Howard E.; Bunce, Richard A.; Journal of Organic Chemistry; vol. 47; nb. 18; (1982); p. 3377 - 3396 View in Reaxys

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Rx-ID: 21288064 View in Reaxys 235/477 Yield

Conditions & References Reaction Steps: 3 1: 63.5 percent / 50 °C 2: 1.) LiCl, 2.) methanesulfonyl chloride / 1.) s-collidine, DMF, 0 deg C, 2.) 0 to 25 deg C, 8 h 3: 1.) Mg / 1.) THF, reflux, 2.) 0 deg C, 15 min With magnesium, methanesulfonyl chloride, lithium chloride Zimmerman, Howard E.; Bunce, Richard A.; Journal of Organic Chemistry; vol. 47; nb. 18; (1982); p. 3377 - 3396 View in Reaxys

S O

Rx-ID: 28168626 View in Reaxys 236/477 Yield 5 %Chromat., 40 %Chromat., 18 %Chromat., 2 %Chromat., 18 %Chromat.

Conditions & References With 2,4,6-triphenylpyrylium-tetrafluoroborate in acetonitrile, Irradiation, Inert atmosphere Bonesi, Sergio M.; Fagnoni, Maurizio; Albini, Angelo; European Journal of Organic Chemistry; nb. 15; (2008); p. 2612 - 2620 View in Reaxys

Rx-ID: 28225724 View in Reaxys 237/477 Yield

Conditions & References With C19H26N2PtS, Time= 21.2h, T= 110 °C , Inert atmosphere Luedtke, Avery T.; Goldberg, Karen I.; Angewandte Chemie - International Edition; vol. 47; nb. 40; (2008); p. 7694 - 7696 View in Reaxys With (3,5-dimethyl-2-(2-pyridyl)pyrrolide)PtPh(SMe2), Time= 120h, T= 100 °C , Inert atmosphere, Glovebox, Sealed tube, Catalytic behavior, Reagent/catalyst Clement, Marie L.; Grice, Kyle A.; Luedtke, Avery T.; Kaminsky, Werner; Goldberg, Karen I.; Chemistry - A European Journal; vol. 20; nb. 52; (2014); p. 17287 - 17291 View in Reaxys

Rx-ID: 33065388 View in Reaxys 238/477 Yield

Conditions & References With potassium hydroxide in diethylene glycol, Time= 1.5h, Reflux

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Magerramov; Aliev; Mustafaev; Askerova; Russian Journal of Organic Chemistry; vol. 48; nb. 2; (2012); p. 293 295 View in Reaxys

H E

Rx-ID: 33065394 View in Reaxys 239/477 Yield

Conditions & References With potassium hydroxide in diethylene glycol, Time= 1.5h, Reflux Magerramov; Aliev; Mustafaev; Askerova; Russian Journal of Organic Chemistry; vol. 48; nb. 2; (2012); p. 293 295 View in Reaxys

Si O

Rx-ID: 34466051 View in Reaxys 240/477 Yield

Conditions & References With SO3H silica gel, Time= 0.5h, T= 25 °C Fujii, Hideaki; Yamada, Takaaki; Hayashida, Kohei; Kuwada, Miki; Hamasaki, Atom; Nobuhara, Kazunori; Ozeki, Sumio; Nagase, Hiroshi; Heterocycles; vol. 85; nb. 11; (2012); p. 2685 - 2691 View in Reaxys Br

Rx-ID: 39113046 View in Reaxys 241/477 Yield

Conditions & References

32 %, 10 %, 23 %, 35 %

With bromine, acetic acid Delgado-Abad, Thais; Martnez-Ferrer, Jaime; Reig-Lpez, Javier; Mello, Rossella; Acerete, Rafael; Asensio, Gregorio; Gonzlez-Nez, Mara Elena; RSC Advances; vol. 4; nb. 92; (2014); p. 51016 - 51021 View in Reaxys

O O

Rx-ID: 519223 View in Reaxys 242/477 Yield

Conditions & References T= 550 °C Marvel; Gall; Journal of Organic Chemistry; vol. 24; (1959); p. 1494,1495 View in Reaxys

Rx-ID: 1990032 View in Reaxys 243/477

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Yield

Conditions & References With iron(II) diperchlorate, hexaoxo-.mu.-peroxodisulfate(2-), Cu(II) perchlorate in water, acetonitrile, Ambient temperature, Yield given. Yields of byproduct given. Title compound not separated from byproducts Camaioni, Donald M.; Franz, James A.; Journal of Organic Chemistry; vol. 49; nb. 9; (1984); p. 1607 - 1613 View in Reaxys With iron(II) diperchlorate, hexaoxo-.mu.-peroxodisulfate(2-), copper (I) perchlorate in water, acetonitrile, Ambient temperature, other reaction conditions, competitive oxidation with bibenzyl, Mechanism, Product distribution Camaioni, Donald M.; Franz, James A.; Journal of Organic Chemistry; vol. 49; nb. 9; (1984); p. 1607 - 1613 View in Reaxys

N HO

Rx-ID: 2143989 View in Reaxys 244/477 Yield

Conditions & References

93 %, 18 T= 800 °C , p= 0.001 - 0.01Torr , approximate contact time: 0.002-0.03 s %, 7 %, 80 Ohsawa, Akio; Kawaguchi Takayuki; Igeta Hiroshi; Chemical and Pharmaceutical Bulletin; vol. 30; nb. 12; % (1982); p. 4352 - 4358 View in Reaxys

Al E

Rx-ID: 3364744 View in Reaxys 245/477 Yield

Conditions & References With zirconocene dichloride in 1,2-dichloro-ethane, Time= 24h, Ambient temperature, further solvents, Product distribution, Mechanism Negishi,E.; Van Horn,D.E.; Yoshida,T.; Journal of the American Chemical Society; vol. 107; (1985); p. 6639 View in Reaxys

Mg Br

Rx-ID: 3364749 View in Reaxys 246/477 Yield

Conditions & References

24 %, 12 %

With copper(I) bromide in tetrahydrofuran, Time= 24h, T= -25 °C , other copper magmesium alkyls, Product distribution Ashby, E. C.; Smith, R. Scott; Goel, A. B.; Journal of Organometallic Chemistry; vol. 215; nb. 1; (1981); p. C1 - C5 View in Reaxys

S Si

Rx-ID: 3382792 View in Reaxys 247/477 Yield

Conditions & References With naphthalenyllithium, 1.) THF, -78 deg C, Yield given. Multistep reaction Ager, David J.; Tetrahedron Letters; vol. 22; nb. 30; (1981); p. 2923 - 2926 View in Reaxys With naphthalenyllithium, 1.) THF, -78 deg C, 0.5 h, 2.) THF, -78 deg C -> room temperature, Yield given. Multistep reaction

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Ager, David J.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 183 - 194 View in Reaxys

Li O

Rx-ID: 3383138 View in Reaxys 248/477 Yield

Conditions & References With [MoCl5], 1) ether, -70 degC, Yield given. Multistep reaction Kauffmann, Thomas; Kieper, Gudrun; Angewandte Chemie; vol. 96; nb. 7; (1984); p. 502 - 503 View in Reaxys With MoOCl3(THF)2, 1) THF, -70 deg C, 1 h, 2) THF, -70 -> 20 deg C, 18 h, Yield given. Multistep reaction Kauffmann, Thomas; Fiegenbaum, Petra; Papenberg, Michael; Wieschollek, Raphael; Wingbermuehle, Dorothea; Chemische Berichte; vol. 126; nb. 1; (1993); p. 79 - 88 View in Reaxys With (molybdenum pentachloride)2, 1.) THF, ether, -70 deg C, 1 h 2.) -70 -> 20 deg C, 16 h, Yield given. Multistep reaction Kauffmann, Thomas; Fiegenbaum, Petra; Papenberg, Michael; Wieschollek, Raphael; Sander, Joerg; Chemische Berichte; vol. 125; nb. 1; (1992); p. 143 - 148 View in Reaxys

Si O

Rx-ID: 4579332 View in Reaxys 249/477 Yield

Conditions & References With N,N,N',N',N'',N''-hexamethylphosphoric triamide, sec.-butyllithium, Sm(OTf)3, 1.) THF, cyclohexane, room temperature, 1 h, 2.) THF, cyclohexane, room temperature, 1 h, Yield given. Multistep reaction Fukuzawa, Shin-Ichi; Mutoh, Keisuke; Tsuchimoto, Teruhisa; Hiyama, Tamejiro; Journal of Organic Chemistry; vol. 61; nb. 16; (1996); p. 5400 - 5405 View in Reaxys

O HO

Rx-ID: 4615884 View in Reaxys 250/477 Yield

Conditions & References With water in acetonitrile, T= 60 °C , kinetic data for solvolysis reactions Thibblin, Alf; Saeki, Yoshihiro; Journal of Organic Chemistry; vol. 62; nb. 4; (1997); p. 1079 - 1082 View in Reaxys

N+

O– Cl O OO

Rx-ID: 4634103 View in Reaxys 251/477

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Yield

Conditions & References With water in acetonitrile, T= 60 °C , kinetic deuterium isotope effect; further temperatures and solvents, Rate constant, Mechanism Thibblin, Alf; Saeki, Yoshihiro; Journal of Organic Chemistry; vol. 62; nb. 4; (1997); p. 1079 - 1082 View in Reaxys N O– Cl O OO

N+

Rx-ID: 4654564 View in Reaxys 252/477 Yield

Conditions & References With water in acetonitrile, T= 60 °C , kinetic deuterium isotope effect; further temperatures, Rate constant Thibblin, Alf; Saeki, Yoshihiro; Journal of Organic Chemistry; vol. 62; nb. 4; (1997); p. 1079 - 1082 View in Reaxys N

O– N+ 2H

2H 2H

Cl OO

Rx-ID: 4655231 View in Reaxys 253/477 Yield

Conditions & References With water in acetonitrile, T= 60 °C , further temperatures and solvents, Rate constant Thibblin, Alf; Saeki, Yoshihiro; Journal of Organic Chemistry; vol. 62; nb. 4; (1997); p. 1079 - 1082 View in Reaxys

Br Br

Rx-ID: 8682799 View in Reaxys 254/477 Yield 15 % Chromat., 35 % Chromat.

Conditions & References With tetrakis(triphenylphosphine) palladium(0), tetrabutyl-ammonium chloride, potassium carbonate in xylene, Time= 2.5h, T= 80 - 85 °C , Product distribution Ma; Xu; Ni; Journal of Organic Chemistry; vol. 65; nb. 25; (2000); p. 8532 - 8543 View in Reaxys

Rx-ID: 348681 View in Reaxys 255/477 Yield

Conditions & References With potassium hydrogensulfate, high-boiling phenole Patent; Soc. Usines Chim. Rhone-Poulenc; US2806894; (1955) View in Reaxys Patent; Soc. Usines Chim. Rhone-Poulenc; DE1009176; (1955) View in Reaxys With high-boiling phenole, copper(II) sulfate

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Patent; Soc. Usines Chim. Rhone-Poulenc; US2806894; (1955) View in Reaxys Patent; Soc. Usines Chim. Rhone-Poulenc; DE1009176; (1955) View in Reaxys

O O

N N

O O

Rx-ID: 1867208 View in Reaxys 256/477 Yield

Conditions & References in dichloromethane, Time= 4h, Yield given Maslak, Przemyslaw; Chapman, William H.; Journal of Organic Chemistry; vol. 55; nb. 26; (1990); p. 6334 - 6347 View in Reaxys

N HN

N N

N N N

Rx-ID: 3219264 View in Reaxys 257/477 Yield

Conditions & References in acetonitrile, Time= 3h, T= 60 °C , decomposition, other solvent, Rate constant Mitsuhashi Tsutomu; Journal of the American Chemical Society; vol. 108; nb. 9; (1986); p. 2394 - 2400 View in Reaxys

Rx-ID: 3365804 View in Reaxys 258/477 Yield

Conditions & References With Cu6MgMe8, magnesium bromide in tetrahydrofuran, Time= 4h, T= -25 °C , other Mg-Me-cuprates, or with CH3MgBr/CuBr; or with addition of LiBr; other times and temp.; other conc.-ratio, Product distribution Ashby, E. C.; Smith, R. Scott; Goel, A. B.; Journal of Organic Chemistry; vol. 46; (1981); p. 5133 - 5139 View in Reaxys Cl Si

Cl Ti

(v4)

Rx-ID: 3383228 View in Reaxys 259/477 Yield 3%

Conditions & References in diethyl ether, Time= 20h, from -15 degC to 20 degC Kauffmann, Thomas; Koenig, Rolf; Pahde, Claudia; Tannert, Annegret; Tetrahedron Letters; vol. 22; nb. 50; (1981); p. 5031 - 5034 View in Reaxys

Rx-ID: 3384376 View in Reaxys 260/477

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Yield

Conditions & References With hydrogen, copperchromium (KGA-43), T= 80 - 100 °C , p= 15200 - 22800Torr , Product distribution, Kinetics Ziyatdinov, A. Sh.; Stepanenko, V. V.; Chernykh, I. S.; E. B. Leonova; Pisarenko, V. N.; Kafarov, V. V.; J. Appl. Chem. USSR (Engl. Transl.); vol. 61; nb. 3; (1988); p. 565 - 571,506 - 511 View in Reaxys

Rx-ID: 3774647 View in Reaxys 261/477 Yield

Conditions & References in chlorobenzene, T= 55 °C , p= 760Torr , various pressure, Product distribution Neuman, Robert C.; Amrich, Michael J.; Journal of Organic Chemistry; vol. 45; nb. 23; (1980); p. 4629 - 4636 View in Reaxys

Rx-ID: 4068745 View in Reaxys 262/477 Yield

Conditions & References

0.006 mmol, 0.012 mmol, 0.022 mmol

With (tBuOOCO)2, iodosylbenzene, [Fe(5,10,15,20-tetrakis-phenyl-porphyrinato)](1+) in benzene, Time= 3h, T= 50 °C , var. of reagent, catalyst, Product distribution Baciocchi, Enrico; d'Acunzo, Francesca; Galli, Carlo; Ioele, Marcella; Journal of the Chemical Society, Chemical Communications; nb. 4; (1995); p. 429 - 430 View in Reaxys

OH O

Rx-ID: 9004231 View in Reaxys 263/477 Yield

Conditions & References in isopropyl alcohol, Time= 60h, T= 90 °C Maksyuta; Suprun; Opeida; Turovskii; Russian Journal of Organic Chemistry; vol. 37; nb. 6; (2001); p. 814 - 818 View in Reaxys

Li+ O–

Rx-ID: 20678963 View in Reaxys 264/477 Yield

Conditions & References Reaction Steps: 2 2: 94 percent Chromat. / Pd(PPh3)4 / 2 h / 25 °C With tetrakis(triphenylphosphine) palladium(0) Takai, Kazuhiko; Oshima, Koichiro; Nozaki, Hitosi; Tetrahedron Letters; vol. 21; (1980); p. 2531 - 2534 View in Reaxys

O HO

Rx-ID: 23659891 View in Reaxys 265/477

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Yield

Conditions & References A cleavage product was produced from 70percent strength by weight cumene hydroperoxide. The cleavage product was cooled to 40° C. and subsequently neutralized (pH=7). The cleavage product comprised 42 wt.-percent phenol, 26 wt.-percent acetone, 3.1 wt.-percent alpha-methylstyrene, and 1200 wppm hydroxyacetone besides other organic components. All concentrations are related to the total amount of organic components (water-free). In addition, 1 wt. percent of water is present. , T= 40 °C , pH= 7, Product distribution / selectivity Patent; Weber, Manfred; Sigg, Reinhard; Lausmann, Michael; Greschek, Siegmund; US2003/220528; (2003); (A1) English View in Reaxys

NH O

Rx-ID: 30461685 View in Reaxys 266/477 Yield

Conditions & References Reaction Steps: 2 1: dichloromethane / -30 °C 2: toluene / 1 h / 110 °C in dichloromethane, toluene, 2: Chugaev type reaction Schur, Christine; Becker, Nina; Bergstraesser, Uwe; Gottwald, Thomas; Hartung, Jens; Tetrahedron; vol. 67; nb. 12; (2011); p. 2338 - 2347 View in Reaxys

HO O

Rx-ID: 37274927 View in Reaxys 267/477 Yield

Conditions & References

35.31 %, 26.37 %, 15.72 %, 11.03 %

With magnesium 2-ethylhexanoate in tetrachloromethane, Time= 4h, T= 130 °C , Kinetics Nurullina; Batyrshin; Kharlampidi, Kh. E.; Petroleum Chemistry; vol. 54; nb. 1; (2014); p. 65 - 68; Neftekhimiya; vol. 54; nb. 1; (2014); p. 66 - 69,4 View in Reaxys

HO O Z

O HO

Rx-ID: 469690 View in Reaxys 268/477 Yield

Conditions & References With sulfuric acid Thorpe; Wood; Journal of the Chemical Society; vol. 103; (1913); p. 1575; Journal of the Chemical Society; vol. 123; (1923); p. 63 View in Reaxys With hydrogenchloride Thorpe; Wood; Journal of the Chemical Society; vol. 103; (1913); p. 1575; Journal of the Chemical Society; vol. 123; (1923); p. 63

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View in Reaxys

I O

Rx-ID: 715528 View in Reaxys 269/477 Yield

Conditions & References With diethyl ether, Erhitzen des Reaktionsprodukts auf 100grad; Behandeln mit Wasser und anschliessend mit Schwefelsaeure Klages; Chemische Berichte; vol. 35; (1902); p. 2649; Chemische Berichte; vol. 39; (1906); p. 2591 View in Reaxys With diethyl ether, Behandeln mit trocknem Ammoniak anschliessend mit verd. Schwefelsaeure Klages; Chemische Berichte; vol. 35; (1902); p. 3507 View in Reaxys

Rx-ID: 1546614 View in Reaxys 270/477 Yield

Conditions & References With hydrogen, K doped ZnO, Time= 2h, T= 299.9 °C , p= 1500.1Torr , other temp., differently modified ZnO2; initial rate of hydrogenation, Product distribution Kijenski, Jacek; Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques; vol. 29; nb. 5-6; (1981); p. 225 - 230 View in Reaxys

Rx-ID: 1580253 View in Reaxys 271/477 Yield

Conditions & References With monofluoromethane, oxygen, T= 37.5 °C , Irradiation, 0.5 Torr substrate, 700 Torr bulk gas, 4 Torr O2 and 2.1 Torr methanol partial pressures, Product distribution Fornarini, Simonetta; Sparapani, Cinzia; Speranza, Maurizio; Journal of the American Chemical Society; vol. 110; nb. 1; (1988); p. 34 - 41 View in Reaxys

Rx-ID: 1580255 View in Reaxys 272/477 Yield

Conditions & References With oxygen, deuterium, T= 37.5 °C , Irradiation, 0.5 Torr substrate, 750 Torr bulk gas, 4 Torr O2 and 2.5 Torr methanol partial pressures, Product distribution Fornarini, Simonetta; Sparapani, Cinzia; Speranza, Maurizio; Journal of the American Chemical Society; vol. 110; nb. 1; (1988); p. 34 - 41 View in Reaxys

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Mg Br

Si O

Rx-ID: 1744396 View in Reaxys 273/477 Yield

Conditions & References With NiCl2((PPh3)P)2, 1.) ether, room temp., 2.) benzene, reflux, Yield given. Multistep reaction Hayashi, Tamio; Katsuro, Yoshio; Kumada, Makoto; Tetrahedron Letters; vol. 21; (1980); p. 3915 - 3918 View in Reaxys N

Rx-ID: 1784340 View in Reaxys 274/477 Yield

Conditions & References gaseous plasma of glow discharge, Yield given. Further byproducts given. Yields of byproduct given So, Y. H.; Miller, Larry L.; Journal of the American Chemical Society; vol. 103; nb. 14; (1981); p. 4204 - 4209 View in Reaxys N

Rx-ID: 1784341 View in Reaxys 275/477 Yield

O HO

Rx-ID: 2017896 View in Reaxys 276/477 Yield 51 % Chromat., 3 % Chromat., 39 % Chromat., 3 % Chromat.

Conditions & References With 2-(NHC6H13)-1,3,2-benzodioxaphospholen in chlorobenzene, T= 30 °C , other CHP-conc., further temp., further reag., Mechanism, Product distribution, Rate constant Rueger, C.; Arnold, D.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 324; nb. 5; (1982); p. 706 716 View in Reaxys With 1-(1,3,2-benzodioxaphospholan-2-yl)pyrolidine in chlorobenzene, T= -0.1 °C , other temp. (30 deg C), Rate constant Rueger, C.; Arnold, D.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 324; nb. 5; (1982); p. 706 716 View in Reaxys With 2-N(C6H11,C6H11)-1,3,2-benzodioxaphosphol in chlorobenzene, T= 0 °C , other temp. (30 deg C), Rate constant Rueger, C.; Arnold, D.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 324; nb. 5; (1982); p. 706 716 View in Reaxys

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With Brenzcatechyl-phosphorigsaureester-N-ethylanilid in chlorobenzene, T= 0 °C , other temp. (30 deg C), Rate constant Rueger, C.; Arnold, D.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 324; nb. 5; (1982); p. 706 716 View in Reaxys With Brenzcatechylphosphorigsaureester-anilid in chlorobenzene, T= 30 °C , Rate constant Rueger, C.; Arnold, D.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 324; nb. 5; (1982); p. 706 716 View in Reaxys With 2-N(C6H5,C6H5)-1,3,2-benzodioxaphosphol in chlorobenzene, T= 30 °C , Rate constant Rueger, C.; Arnold, D.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 324; nb. 5; (1982); p. 706 716 View in Reaxys

Rx-ID: 2868302 View in Reaxys 277/477 Yield

Conditions & References With magnesium, 1.) THF, reflux, 2.) 0 deg C, 15 min, Yield given. Multistep reaction Zimmerman, Howard E.; Bunce, Richard A.; Journal of Organic Chemistry; vol. 47; nb. 18; (1982); p. 3377 - 3396 View in Reaxys

Rx-ID: 3261595 View in Reaxys 278/477 Yield

Conditions & References in chloroform, T= 25 °C , p= 750.06Torr , Equilibrium constant Tsuzuki, Hideaki; Uosaki, Yasuhiro; Nakahara, Masaru; Sasaki, Muneo; Osugi, Jiro; Bulletin of the Chemical Society of Japan; vol. 55; nb. 5; (1982); p. 1348 - 1351 View in Reaxys

(v2)

2+Ti

H C– O

Rx-ID: 3383542 View in Reaxys 279/477 Yield

Conditions & References With sodium hydroxide, 1) THF, benzene or toluene a) 0 deg C to r.t. b) 15 min, r.t. 2) Et2O, Yield given. Multistep reaction Pine; Shen; Hoang; Synthesis; nb. 2; (1991); p. 165 - 167 View in Reaxys

(+-)-<β-hydroxy-isopropyl>-benzene Rx-ID: 6712322 View in Reaxys 280/477 Yield

Conditions & References With potassium hydroxide, Destillation

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Sabetay; Bulletin de la Societe Chimique de France; vol. <4> 47; (1930); p. 614,617 View in Reaxys

Rx-ID: 8874821 View in Reaxys 281/477 Yield

Conditions & References With sodium lauryl sulfate in chlorobenzene, T= 90 °C , Product distribution, Kinetics, Further Variations: Reagents, Temperatures Kartasheva; Koverzanova; Kashkai; Kasaikina; Petroleum Chemistry; vol. 41; nb. 3; (2001); p. 201 - 206 View in Reaxys Reaction Steps: 2 1: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C 2: dihydrogen peroxide / water; acetonitrile / 24 h / 80 °C With dihydrogen peroxide in water, acetonitrile Estrada, Ana C.; Simoes, Mario M. Q.; Santos, Isabel C. M. S.; Neves, M. Graca P. M. S.; Cavaleiro, Jose A. S.; Cavaleiro, Ana M. V.; Monatshefte fur Chemie; vol. 141; nb. 11; (2010); p. 1223 - 1235 View in Reaxys OH O

O HO

Rx-ID: 9017615 View in Reaxys 282/477 Yield

Conditions & References With tetraethylammonium bromide, Time= 60h, T= 90 °C , Further byproducts given Maksyuta; Suprun; Opeida; Turovskii; Russian Journal of Organic Chemistry; vol. 37; nb. 6; (2001); p. 814 - 818 View in Reaxys

OH O

O O HO

Rx-ID: 9017618 View in Reaxys 283/477 Yield

Conditions & References With tetraethylammonium bromide, Time= 29h, T= 90 °C Maksyuta; Suprun; Opeida; Turovskii; Russian Journal of Organic Chemistry; vol. 37; nb. 6; (2001); p. 814 - 818 View in Reaxys

F I

F B–

K+

Rx-ID: 37305887 View in Reaxys 284/477 Yield 17.1 %Chromat., 10.5 %Chromat., 1.2

Conditions & References With trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II), potassium carbonate, tris-(o-tolyl)phosphine in methanol, N,N-dimethyl acetamide, Time= 24h, T= 90 °C , Schlenk technique, Inert atmosphere, Catalytic behavior, Concentration Hartog, Tim Den; Toro, Juan Manuel Sarria; Chen, Peter; Organic Letters; vol. 16; nb. 4; (2014); p. 1100 - 1103

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%ChroView in Reaxys mat., 0.9 %Chromat., 5.9 %Chromat.

Rx-ID: 42024394 View in Reaxys 285/477 Yield

Conditions & References

33 %

With copper(l) iodide, DTBB, caesium carbonate in toluene, Time= 8h, T= 120 °C , Glovebox, Inert atmosphere, Catalytic behavior, Mechanism, Reagent/catalyst Chen, Hong-Jie; Tseng, Mei-Chun; Hsu, I.-Jui; Chen, Wei-Ting; Han, Chien-Chung; Shyu, Shin-Guang; Dalton Transactions; vol. 44; nb. 27; (2015); p. 12086 - 12090 View in Reaxys

Rx-ID: 1580254 View in Reaxys 286/477 Yield

Conditions & References With C3H8 bulk gas, oxygen, T= 37.5 °C , Irradiation, 0.5 Torr substrate, 690 Torr bulk gas, 4 Torr O2 and 2.4 Torr methanol partial pressures, Product distribution Fornarini, Simonetta; Sparapani, Cinzia; Speranza, Maurizio; Journal of the American Chemical Society; vol. 110; nb. 1; (1988); p. 34 - 41 View in Reaxys With methane, oxygen, T= 37.5 °C , Irradiation, different partial pressures of components and in the given case: in the presence of 4 Torr NMe3 partial pressure, Product distribution Fornarini, Simonetta; Sparapani, Cinzia; Speranza, Maurizio; Journal of the American Chemical Society; vol. 110; nb. 1; (1988); p. 34 - 41 View in Reaxys

Rx-ID: 1627777 View in Reaxys 287/477 Yield

Conditions & References in toluene, T= 50 °C , effect of the nickel catalyst and reaction temp., Product distribution Miyashita, Akira; Shimada, Takeshi; Sugawara, Atsushi; Nohira, Hiroyuki; Chemistry Letters; (1986); p. 1323 1326 View in Reaxys With NiBr2(PMe2Ph)2 in toluene, Time= 47h, T= 50 °C , Yield given. Yields of byproduct given Miyashita, Akira; Shimada, Takeshi; Sugawara, Atsushi; Nohira, Hiroyuki; Chemistry Letters; (1986); p. 1323 1326 View in Reaxys

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Rx-ID: 1981348 View in Reaxys 288/477 Yield

Conditions & References With toluene-4-sulfonic acid Ravindranath, B.; Srinivas, P.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 22; nb. 6; (1983); p. 592 - 594 View in Reaxys

O O

Rx-ID: 1992863 View in Reaxys 289/477 Yield

Conditions & References T= 290 °C , Yield given Ruechardt, Christoph; Gerst, Matthias; Noelke, Margot; Angewandte Chemie; vol. 104; nb. 11; (1992); p. 1516 1518 View in Reaxys

O HO

Rx-ID: 2017895 View in Reaxys 290/477 Yield

Conditions & References With "thiocarbonate" SM-1, T= 44.9 °C , other catalysts, other temperatures, Product distribution, Mechanism, Kinetics Kolesnikov, I. M.; J. Appl. Chem. USSR (Engl. Transl.); vol. 62; nb. 4.1; (1989); p. 818 - 824,758 - 763 View in Reaxys With 2-(C6H3(CH3)2,PO2C6H4)amino-1,3,2-benzodioxaphosphol in chlorobenzene, T= 30 °C , further temp., Rate constant, Product distribution Rueger, C.; Arnold, D.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 324; nb. 5; (1982); p. 706 716 View in Reaxys -1 F (v4)

B FF

Cl C+

Rx-ID: 2059322 View in Reaxys 291/477 Yield

Conditions & References With magnesium, 1.) THF, reflux, 2.) RT, 1.5 h, Yield given. Multistep reaction. Yields of byproduct given Zimmerman, Howard E.; Bunce, Richard A.; Journal of Organic Chemistry; vol. 47; nb. 18; (1982); p. 3377 - 3396

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View in Reaxys

H O

Rx-ID: 2071793 View in Reaxys 292/477 Yield

Conditions & References

41 %

in water, Ambient temperature, Irradiation, photolysis in aqueous micellar solutions of Na dodecyl sulfate; magnetic field; Isotope Separation Efficiency Coefficient α, Product distribution, Quantum yield Tarasov, V. F.; Step, E. N.; Margulis, L. A.; Buchachenko, A. L.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 38; nb. 2; (1989); p. 221 - 225; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; vol. 38; nb. 2; (1989); p. 264 - 268 View in Reaxys With HDTCl in water, Irradiation, magnetic field effects on cage effects investigated, Product distribution Turro, J. Nicholas; Mattay, Jochen; Tetrahedron Letters; vol. 21; nb. 19; (1980); p. 1799 - 1802 View in Reaxys Irradiation, magnetic field effect on cage reaction, Product distribution Turro, Nicholas J.; Chung, Chao-Jen; Jones, Guilford; Becker, William G.; Journal of Physical Chemistry; vol. 86; (1982); p. 3677 - 3679 View in Reaxys

Rx-ID: 3774648 View in Reaxys 293/477 Yield

Conditions & References With silica surface, T= 55 °C , energy data (ΔH(excit.), ΔS(excit.)); also photolysis at 25 deg C; labeling studies, Kinetics, Mechanism, Rate constant Leffler, J. E.; Zupancic, J. J.; Journal of the American Chemical Society; vol. 102; nb. 1; (1980); p. 259 - 267 View in Reaxys

C –

Rx-ID: 4018577 View in Reaxys 294/477 Yield

Conditions & References With 1-iodo-butane in N,N-dimethyl-formamide, T= 20 °C , velocity constants in N-methylpyrrolidine, Rate constant Grimshaw, James; Langan, John R.; Salmon, G. Arthur; Journal of the Chemical Society, Chemical Communications; nb. 16; (1988); p. 1115 - 1117 View in Reaxys

polymer-PPh2 (1+)-CH3*I(1-) Rx-ID: 6712332 View in Reaxys 295/477

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Yield

Conditions & References With HMDS, 1.) THF, r.t., 30 min, 2.) THF, r.t., 20 min, Yield given. Multistep reaction Bolli, Martin H.; Ley, Steven V.; Journal of the Chemical Society - Perkin Transactions 1; nb. 15; (1998); p. 2243 2246 View in Reaxys

CO, CO2 Rx-ID: 6727189 View in Reaxys 296/477 Yield

Conditions & References With oxygen, Erionite NaKE zeolite, T= 500 °C , temperature 400 to 550 deg C, different zeolites and calcium borate as catalyst, Product distribution Lashmanova, N.V.; Kolesnikov, V.A.; Efremov, R.V.; Danov, S.M.; J. Appl. Chem. USSR (Engl. Transl.); vol. 57; nb. 1; (1984); p. 199 - 201,188 - 189 View in Reaxys

<(η5C5H5)Fe(CO)2(CH2OSi(CH3)3)>

Rx-ID: 14875611 View in Reaxys 297/477 Yield

Conditions & References Reaction Steps: 2 1: 70 percent / PBr3 / 18 h / ice cooling 2: 14 percent Chromat. / Mg / 600 °C / 0.01 - 0.1 Torr With phosphorus tribromide, magnesium Aitken, R. Alan; Hodgson, Philip K.G.; Morrison, John J.; Oyewale, Adebayo O.; Journal of the Chemical Society. Perkin Transactions 1; nb. 3; (2002); p. 402 - 415 View in Reaxys

Rx-ID: 22203004 View in Reaxys 298/477 Yield

Conditions & References Reaction Steps: 3 2: HCl / Eingiessen des Reaktionsproduktes in Eiswasser 3: pyridine With pyridine, hydrogenchloride Klages; Chemische Berichte; vol. 35; (1902); p. 2649; Chemische Berichte; vol. 39; (1906); p. 2591 View in Reaxys

(v3)

Rx-ID: 31442775 View in Reaxys 299/477 Yield

Conditions & References T= 35 - 150 °C , Vacuo Haiss, Peter; Kuhn, Annette; Kuhn, Norbert; Maichle-Moessmer, Caecilia; Laufer, Stefan; Steimann, Manfred; Zeller, Klaus-Peter; European Journal of Inorganic Chemistry; nb. 22; (2011); p. 3284 - 3287 View in Reaxys

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S O S

Rx-ID: 32574205 View in Reaxys 300/477 Yield

Conditions & References in tert-butyl benzene, T= 59.84 °C , Chugaev reaction, Kinetics Zhou, Yanwu; He, Junpo; Li, Changxi; Hong, Linxiang; Yang, Yuliang; Macromolecules; vol. 44; nb. 21; (2011); p. 8446 - 8457 View in Reaxys S S

Rx-ID: 32574210 View in Reaxys 301/477 Yield

Conditions & References in diphenylether, T= 59.84 °C , Kinetics Zhou, Yanwu; He, Junpo; Li, Changxi; Hong, Linxiang; Yang, Yuliang; Macromolecules; vol. 44; nb. 21; (2011); p. 8446 - 8457 View in Reaxys

S S

Rx-ID: 32574215 View in Reaxys 302/477 Yield

Rx-ID: 1897663 View in Reaxys 303/477 Yield

Conditions & References With methyllithium, lithium, 1.) THF, -78deg C, 60 min, 2.) -60 deg C, 6 h, RT, Yield given. Multistep reaction Barluenga, Jose; Fernandez-Simon, Jose L.; Concellon, Jose M.; Yus, Miguel; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 3339 - 3344 View in Reaxys

Rx-ID: 2007666 View in Reaxys 304/477 Yield

Conditions & References With Lochmann-Schlosser base, Time= 24h, T= 70 °C , various quantity of Lochmann's base; various temperatures and time, Product distribution

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Ogle, Craig A.; Riley, Patrick A.; Dorchak, Joseph J.; Hubbard, John L.; Journal of Organic Chemistry; vol. 53; nb. 18; (1988); p. 4409 - 4412 View in Reaxys

Li Br

Rx-ID: 2057417 View in Reaxys 305/477 Yield

Conditions & References With 1) CoCl2, Yield given. Multistep reaction Kauffmann, Thomas; Stach, Dirk; Chemische Berichte; vol. 125; nb. 4; (1992); p. 913 - 922 View in Reaxys

N N

Rx-ID: 2827864 View in Reaxys 306/477 Yield

Conditions & References in acetonitrile, Irradiation Cookson, Richard C.; Sadler, David E.; Salisbury, Kingsley; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1981); p. 774 - 782 View in Reaxys

O N

S N

Rx-ID: 2841296 View in Reaxys 307/477 Yield

Conditions & References

6.9 %, 5.1 %

Time= 0.26h, T= 650 °C , Product distribution Abramovitch, Rudolph A.; Holcomb, William D.; Wake, Shigeo; Journal of the American Chemical Society; vol. 103; nb. 6; (1981); p. 1525 - 1533 View in Reaxys

H N

O N

S N

O S

Rx-ID: 2841298 View in Reaxys 308/477 Yield

Conditions & References

9.5 %, 3.5 %

Time= 0.35h, T= 400 °C , Product distribution Abramovitch, Rudolph A.; Holcomb, William D.; Wake, Shigeo; Journal of the American Chemical Society; vol. 103; nb. 6; (1981); p. 1525 - 1533 View in Reaxys

Rx-ID: 3112932 View in Reaxys 309/477 Yield

Conditions & References With lithium aluminium tetrahydride, methanesulfonyl chloride, triethylamine, 1) THF, 25 min, -25 deg C, 2) THF, 30 min, 65 deg C, Yield given. Multistep reaction. Yields of byproduct given

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Adam, Waldemar; Adamsky, Friedhelm; Klaerner, Frank-Gerrit; Peters, Eva-Maria; Peters, Karl; et al.; Chemische Berichte; vol. 116; nb. 5; (1983); p. 1848 - 1859 View in Reaxys

Rx-ID: 3382551 View in Reaxys 310/477 Yield

Conditions & References With methyllithium, lithium, 1.) THF, Et2O, -78 deg C to -60 deg C, 45 min, 2.) -60 deg C, 6 h; -60 deg C to 20 deg C, overnight, Yield given. Multistep reaction Barluenga, Jose; Fernandez-Simon, Jose L.; Concellon, Jose M.; Yus, Miguel; Journal of the Chemical Society, Chemical Communications; nb. 22; (1986); p. 1665 View in Reaxys

Li O

Rx-ID: 3383139 View in Reaxys 311/477 Yield

Conditions & References With [MoCl5] in tetrahydrofuran, diethyl ether, T= -70 °C , effect of use of var. solvents; effect of use of var. velocity of allowance, Product distribution Kauffmann, Thomas; Kieper, Gudrun; Angewandte Chemie; vol. 96; nb. 7; (1984); p. 502 - 503 View in Reaxys With [MoCl5], 1) THF, ether, -70 degC, Yield given. Multistep reaction. Yields of byproduct given Kauffmann, Thomas; Kieper, Gudrun; Angewandte Chemie; vol. 96; nb. 7; (1984); p. 502 - 503 View in Reaxys

E Si

Rx-ID: 3857436 View in Reaxys 312/477 Yield

Conditions & References With triethylamine, tris-(o-tolyl)phosphine, palladium diacetate in acetonitrile, var. solv., time, temp., palladium catalysts, also with AgNO3; other alkenylsilanes, Product distribution, Mechanism Karabelas, Kostas; Westerlund, Christer; Hallberg, Anders; Journal of Organic Chemistry; vol. 50; nb. 20; (1985); p. 3896 - 3900 View in Reaxys

N N

Rx-ID: 4154390 View in Reaxys 313/477 Yield 2 %, 73 %

Conditions & References in diethyl ether, Time= 1h, Ambient temperature Kashima, Choji; Kita, Isanobu; Takahashi, Katsumi; Hosomi, Akira; Journal of Heterocyclic Chemistry; vol. 32; nb. 1; (1995); p. 25 - 28

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View in Reaxys

N E N

chlorotoluene O

Rx-ID: 8449871 View in Reaxys 314/477 Yield

Conditions & References With bis(acetylacetonate)oxovanadium in chlorobenzene, Time= 96h, T= 29.9 °C , Product distribution Howard, J. A.; Tait, J. C.; Yamada, T.; Chenier, H. B.; Canadian Journal of Chemistry; vol. 59; (1981); p. 2184 2190 View in Reaxys

S S

Rx-ID: 10401396 View in Reaxys 315/477 Yield

Conditions & References With oxygen, Irradiation, Kinetics, Further Variations: Solvents, Reagents Bonesi, Sergio M.; Fagnoni, Maurizio; Monti, Sandra; Albini, Angelo; Tetrahedron; vol. 62; nb. 46; (2006); p. 10716 - 10723 View in Reaxys

23 % Chromat., 15 % Chromat., 3 % Chromat.

With oxygen, 5,15,10,20-tetraphenylporphyrin in benzene, Irradiation

20 %Chromat., 5 %Chromat., 5 %Chromat.

With 9,10-anthracenedicarbonitrile, oxygen in acetonitrile, Irradiation

Bonesi, Sergio M.; Fagnoni, Maurizio; Monti, Sandra; Albini, Angelo; Tetrahedron; vol. 62; nb. 46; (2006); p. 10716 - 10723 View in Reaxys

Bonesi, Sergio M.; Fagnoni, Maurizio; Albini, Angelo; European Journal of Organic Chemistry; nb. 15; (2008); p. 2612 - 2620 View in Reaxys

Rx-ID: 33488044 View in Reaxys 316/477 Yield

Conditions & References With water in acetone, T= 24.84 °C , Solvolysis, Kinetics Taha, Ahmed A.; International Journal of Chemical Kinetics; vol. 44; nb. 8; (2012); p. 514 - 523 View in Reaxys

E O

Rx-ID: 38012534 View in Reaxys 317/477 Yield

Conditions & References With hydrogenchloride, toluene, Time= 7h, T= 420 °C , p= 46Torr , Kinetics, Time, Temperature, Pressure Julio, Libia L.; Lezama, Jesus; Maldonado, Alexis; Mora, Jose R.; Chuchani, Gabriel; Journal of Physical Organic Chemistry; vol. 27; nb. 5; (2014); p. 450 - 455

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View in Reaxys

Rx-ID: 42024395 View in Reaxys 318/477 Yield 6%

Conditions & References With copper(l) iodide, DTBB, caesium carbonate in toluene, Time= 8h, T= 120 °C , Glovebox, Inert atmosphere, Catalytic behavior, Mechanism Chen, Hong-Jie; Tseng, Mei-Chun; Hsu, I.-Jui; Chen, Wei-Ting; Han, Chien-Chung; Shyu, Shin-Guang; Dalton Transactions; vol. 44; nb. 27; (2015); p. 12086 - 12090 View in Reaxys

Rx-ID: 42024396 View in Reaxys 319/477 Yield 24 %

Rx-ID: 1709984 View in Reaxys 320/477 Yield

Conditions & References With oxygen, 1.5E-4 zinc naphthenate, Time= 3h, T= 110 °C , activation energy; different catalyst, catalyst concentrations, reaction times and temperatures, Product distribution, Kinetics, Thermodynamic data Kozlov; Tovstokhat'ko; Potekhin; Journal of applied chemistry of the USSR; vol. 59; nb. 1 pt 2; (1986); p. 122 127 View in Reaxys With oxygen, 1,10-phenanthroline, zinc naphthenate, Time= 8h, T= 100 °C , rate constants between 100-130 deg C, Kinetics, Product distribution Kozlov; Tovstokhat'ko; Potekhin; Journal of applied chemistry of the USSR; vol. 59; nb. 6 pt 2; (1986); p. 1284 1286 View in Reaxys

H HO

Rx-ID: 1784395 View in Reaxys 321/477 Yield

Conditions & References With oxygen, in plasma generated by radiofrequency discharge, Yield given. Further byproducts given. Yields of byproduct given Tezuka, Meguru; Yajima, Tatsuhiko; Tsuchiya, Atsuhiko; Chemistry Letters; (1982); p. 1437 - 1438 View in Reaxys

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HO O

Rx-ID: 1784400 View in Reaxys 322/477 Yield

Rx-ID: 1784410 View in Reaxys 323/477 Yield

O B

Rx-ID: 1793597 View in Reaxys 324/477 Yield 48 % Chromat., 10 % Chromat.

Conditions & References With 2,3-dimethyl-naphthalene, palladium diacetate, triethylamine, triphenylphosphine in acetonitrile, Time= 25h, T= 100 °C , influence of nature of catalyst, further boronates, Product distribution Nilsson, Kristina; Hallberg, Anders; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 41; nb. 8; (1987); p. 569 - 576 View in Reaxys

O HO

Rx-ID: 2017891 View in Reaxys 325/477 Yield 68.03 % Chromat., 4.78 % Chromat.

Conditions & References With zinc bislt;OO-di-(p-tolyl)phosphorodithioategt; in decane, Time= 6h, T= 109.9 °C , Other promoters (e.g. zinc bis-<OO-dialkyl(aryl)phosphonodithioates, hexakis-<OO-dialkyl(aryl)phosphorodithioate>-μ4-tetraoxo-zincs, OOOOtetra-alkyl(aryl) thioperoxydiphosphates) were used; Ε(excit.), ΔH(excit.), ΔS(excit.)., Kinetics, Mechanism, Thermodynamic data Bridgewater, Alan J.; Dever, J. Robert; Sexton, Michael D.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1980); p. 1006 - 1016 View in Reaxys With zinc dithiocarbamates or zinc xanthates in decane, T= 109.9 °C , E (excit.); ΔH (excit.); ΔS (excit.), Product distribution, Thermodynamic data Sexton, Michael D.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1985); p. 59 - 64 View in Reaxys

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E O N

Rx-ID: 2138018 View in Reaxys 326/477 Yield

Conditions & References

11 %

With sodium hydroxide, zinc, K2[Ni(CN)4] in methanol, water, Time= 10h, T= 60 °C , variation of solvent and base, Product distribution, Mechanism Miura, Masahiro; Shimoura, Nobuhiro; Nomura, Masakatsu; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 1993 - 1996 View in Reaxys

Rx-ID: 2701559 View in Reaxys 327/477 Yield

Conditions & References With [MoCl5], acetophenone, 1) ether, -70 degC, Yield given. Multistep reaction. Yields of byproduct given Kauffmann, Thomas; Kieper, Gudrun; Angewandte Chemie; vol. 96; nb. 7; (1984); p. 502 - 503 View in Reaxys

O O

Rx-ID: 2835615 View in Reaxys 328/477 Yield

Conditions & References

69 %, 12 %

in various solvent(s), Time= 1h, T= 125 °C , effects of other solvents, temperature, reaction time; ΔG(excit.), ΔH(excit.), ΔS(excit.), E(excit.), Product distribution, Rate constant, Thermodynamic data Villenave, J. J.; Filliatre, C.; Maillard, B.; Jaouhari, R.; Bulletin des Societes Chimiques Belges; vol. 91; nb. 4; (1982); p. 301 - 310 View in Reaxys

Rx-ID: 3911567 View in Reaxys 329/477 Yield

Conditions & References With lithium diisopropyl amide, 1.) THF, -78 deg C, 20 min, 2.) THF, -78 deg C, 12 h, Yield given. Multistep reaction. Yields of byproduct given Schwan, Adrian L.; Roche, Michael R.; Gallagher, John F.; Ferguson, George; Canadian Journal of Chemistry; vol. 72; nb. 2; (1994); p. 312 - 324 View in Reaxys

O O

Rx-ID: 4159177 View in Reaxys 330/477

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Yield

Conditions & References With 9,10-dihydro-anthracene in diphenylether, T= 280 °C , Mechanism Noelke, Margot; Verevkin, Sergej P.; Beckhaus, Hans-Dieter; Ruechardt, Christoph; Liebigs Annalen; nb. 1; (1995); p. 41 - 52 View in Reaxys

N N

N O

Rx-ID: 4516211 View in Reaxys 331/477 Yield

Conditions & References With nitrogen(IV) oxide, ozone in dichloromethane, Time= 0.0166667h, T= 0 °C , var. arene/NO2 ratios, temp., reaction times, and nitrating agents, Product distribution Suzuki, Hitomi; Mori, Tadashi; Chemistry Letters; nb. 8; (1996); p. 647 - 648 View in Reaxys With oxygen, nitrogen(IV) oxide, ozone in dichloromethane, Time= 0.0833333h, T= -20 °C , further bicumene derivatives; various solvents, nitration reagents, Product distribution, Mechanism Suzuki, Hitomi; Mori, Tadashi; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 7; (1997); p. 1265 - 1274 View in Reaxys

Rx-ID: 4676584 View in Reaxys 332/477 Yield

Conditions & References With 9,10-anthracenedicarbonitrile, oxygen in acetonitrile-D3, Time= 0.666667h, T= 40 °C , Irradiation, photoinduced oxidation of benzyl phenyl sulfides promoted by 9,10-dicyanoanthracene; electron transfer reactions; reaction pathways for sulfide radical cation formed; C-S and C-H bond cleavage, S-oxidation; stability of photoproducts, Product distribution Baciocchi, Enrico; Crescenzi, Cristina; Lanzalunga, Osvaldo; Tetrahedron; vol. 53; nb. 12; (1997); p. 4469 4478 View in Reaxys

C6 hydrocarbons Rx-ID: 6726763 View in Reaxys 333/477 Yield

Conditions & References With methyl acetylene, T= 1180 - 1350 °C , p= 2280 - 5320Torr , also without propyne, and in the presence of 1,2dimethylcyclohexene, Product distribution, Rate constant, Mechanism Robaugh, David A.; Tsang, Wing; Fahr, Askar; Stein, Stephen E.; Berichte der Bunsen-Gesellschaft; vol. 90; (1986); p. 77 - 84

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View in Reaxys

Rx-ID: 42024397 View in Reaxys 334/477 Yield

Conditions & References With copper(l) iodide, DTBB, caesium carbonate, 2,4-Xylenol in toluene, Time= 8h, T= 120 °C , Glovebox, Inert atmosphere, Catalytic behavior, Mechanism Chen, Hong-Jie; Tseng, Mei-Chun; Hsu, I.-Jui; Chen, Wei-Ting; Han, Chien-Chung; Shyu, Shin-Guang; Dalton Transactions; vol. 44; nb. 27; (2015); p. 12086 - 12090 View in Reaxys

P O

Rx-ID: 716241 View in Reaxys 335/477 Yield

Conditions & References Wittig; Schoellkopf; Chemische Berichte; vol. 87; (1954); p. 1318,1327; ; vol. V; (1973); p. 751 View in Reaxys Gerst, Matthias; Ruechardt, Christoph; Tetrahedron Letters; vol. 34; nb. 48; (1993); p. 7733 - 7736 View in Reaxys

O O O O

O O

N N

N O

O O

Rx-ID: 1963344 View in Reaxys 336/477 Yield

Conditions & References

2 %, 24 %, in acetonitrile, Time= 5h, Irradiation 10 %, 5 % Bardi, Luca; Fasani, Elisa; Albini, Angelo; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 5; (1994); p. 545 - 550 View in Reaxys

Mg Cl

Rx-ID: 3364745 View in Reaxys 337/477 Yield

Conditions & References With copper(I) bromide, lithium bromide in tetrahydrofuran, Time= 2h, T= 0 °C , further reagent, further 1-alkyne, further alkyl compounds; deuterium labelling experiments, Product distribution, Mechanism Westmijze, H.; Kleijn, H.; Meijer, J.; Vermeer, P.; Recueil: Journal of the Royal Netherlands Chemical Society; vol. 100; nb. 3; (1981); p. 98 - 102 View in Reaxys

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(v2)

Zn Cl

Rx-ID: 3365621 View in Reaxys 338/477 Yield

Conditions & References With chloro-trimethyl-silane, sodium iodide, tetrakis(triphenylphosphine) palladium(0), multistep reaction; other substrates, other zinc compounds Luo, Fen-Tair; Fwu, Shiang-Long; Huang, Wen-Shu; Tetrahedron Letters; vol. 33; nb. 45; (1992); p. 6839 - 6840 View in Reaxys With chloro-trimethyl-silane, sodium iodide, tetrakis(triphenylphosphine) palladium(0), 1) CH3CN, H2O, 10 min, 2) RT, 6 h, Yield given. Multistep reaction Luo, Fen-Tair; Fwu, Shiang-Long; Huang, Wen-Shu; Tetrahedron Letters; vol. 33; nb. 45; (1992); p. 6839 - 6840 View in Reaxys

C, CO, CO2

Rx-ID: 6210792 View in Reaxys 339/477 Yield

Conditions & References

15.5 %, 25.0 %, 1.5 %, 1.0 %, 1.1 %, 1.0 %

With Cs exchanged copper doped zeolite 13X, T= 400 °C , p= 760Torr , The catalytic system was optimized vs. the catalyst preparation, basicity and promoters. Effect of nature and flow-rate of the flow gas on the yield and product ratio was also studied, Product distribution, Mechanism Lacroix, C.; Deluzarche, A.; Kiennemann, A.; Boyer, A.; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 81; nb. 7/8; (1984); p. 481 - 486 View in Reaxys

CO2, CO

Rx-ID: 6211624 View in Reaxys 340/477 Yield 18.6 %, 30.1 %, 1.8 %, 3.0 %, 0.8 %, 0.7 %

Conditions & References With Cs exchanged boron doped zeolite 13X, T= 400 - 450 °C , p= 760Torr , The catalytic system was optimized vs. the nature of the exchanged cation, the promoters and the catalyst preparation. Effect of toluene/methylal ratio, temperature, nature and flow-rate of the flow gas on the yield and product ratio was also studied, Product distribution, Kinetics Lacroix, C.; Deluzarche, A.; Kiennemann, A.; Boyer, A.; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 81; nb. 7/8; (1984); p. 473 - 480 View in Reaxys

aqueous AgNO3-solution Cl

Rx-ID: 7067047 View in Reaxys 341/477 Yield

Conditions & References Levene; Marker; Journal of Biological Chemistry; vol. 103; (1933); p. 373,376, 380 View in Reaxys Kharasch; Brown; Journal of the American Chemical Society; vol. 61; (1939); p. 2142,2146 View in Reaxys Rothstein; Saville; Journal of the Chemical Society; (1949); p. 1946,1949 View in Reaxys

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silver acetate solution Cl

Rx-ID: 7067050 View in Reaxys 342/477 Yield

H 2N

Rx-ID: 8265082 View in Reaxys 343/477 Yield

Conditions & References T= 80 - 90 °C Weston; Ruddy; Suter; Journal of the American Chemical Society; vol. 65; (1943); p. 675 View in Reaxys

Rx-ID: 8612643 View in Reaxys 344/477 Yield

Conditions & References With Fe[5,10,15,20-tetrakis(pentafluorophenyl)porphyrin]Cl, oxygen in various solvent(s), T= 100 °C , Oxidation, Product distribution, Further Variations: reaction times Evans, Steven; Smith, John R. Lindsay; Journal of the Chemical Society. Perkin Transactions 2; nb. 7; (2000); p. 1541 - 1551 View in Reaxys O

Rx-ID: 9086458 View in Reaxys 345/477 Yield

Conditions & References With γ-Al2O3 in water, T= 270 °C , atmospheric pressure, Product distribution, Further Variations: Temperatures Karalin; Busygin; Batyrshin; Cherkasova; Kharlampidi; Petroleum Chemistry; vol. 41; nb. 6; (2001); p. 419 - 421 View in Reaxys

Br Mg

Rx-ID: 34978843 View in Reaxys 346/477 Yield 79 %Chromat.

Conditions & References Stage 1: With [Co(PPh3)3Cl] Stage 2:Time= 0.333333h Guelak, Samet; Stepanek, Ondrej; Malberg, Jennifer; Rad, Babak Rezaei; Kotora, Martin; Wolf, Robert; Jacobi Von Wangelin, Axel; Chemical Science; vol. 4; nb. 2; (2013); p. 776 - 784 View in Reaxys

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Br Mg

Rx-ID: 34978856 View in Reaxys 347/477 Yield

Conditions & References

20 %Chromat.

Stage 1: With [Co(PPh3)3Cl] Stage 2:Time= 0.333333h Guelak, Samet; Stepanek, Ondrej; Malberg, Jennifer; Rad, Babak Rezaei; Kotora, Martin; Wolf, Robert; Jacobi Von Wangelin, Axel; Chemical Science; vol. 4; nb. 2; (2013); p. 776 - 784 View in Reaxys

Rx-ID: 41005949 View in Reaxys 348/477 Yield

Conditions & References With hydrogen, T= 249.84 °C , p= 760.051Torr , Catalytic behavior, Reagent/catalyst, Temperature Sazegar, Mohammad Reza; Triwahyono, Sugeng; Jalil, Aishah Abdul; Mukti, Rino R.; Mohaghegh, Seyed Mohammad Seyed; Aziz, Madzlan; New Journal of Chemistry; vol. 39; nb. 10; (2015); p. 8006 - 8016 View in Reaxys Br

Rx-ID: 1709995 View in Reaxys 349/477 Yield

Conditions & References With bromine, dibenzoyl peroxide in tetrachloromethane, Heating, other substituted arenes; var. reagents and time, Product distribution Sket, Boris; Zupan, Marko; Journal of Organic Chemistry; vol. 51; nb. 6; (1986); p. 929 - 931 View in Reaxys

Rx-ID: 2431708 View in Reaxys 350/477 Yield

Conditions & References in diethylene glycol dimethyl ether, T= 115 - 160 °C Slack, W. E.; Taylor, W.; Moseley, C. G.; Chang, K. T.; Kraska, A.; et al.; Tetrahedron Letters; vol. 35; nb. 17; (1994); p. 2647 - 2650 View in Reaxys in diethylene glycol dimethyl ether, T= 115 - 160 °C , stereochemistry of carbenic decomposition, Product distribution, Mechanism Slack, W. E.; Taylor, W.; Moseley, C. G.; Chang, K. T.; Kraska, A.; et al.; Tetrahedron Letters; vol. 35; nb. 17; (1994); p. 2647 - 2650 View in Reaxys

Rx-ID: 2701560 View in Reaxys 351/477

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Yield

Conditions & References With [MoCl5], acetophenone, 1) THF, ether, -70 degC,, Yield given. Multistep reaction. Yields of byproduct given Kauffmann, Thomas; Kieper, Gudrun; Angewandte Chemie; vol. 96; nb. 7; (1984); p. 502 - 503 View in Reaxys

HO O

Rx-ID: 4066741 View in Reaxys 352/477 Yield

Conditions & References Time= 2h, Irradiation, Yield given Consuelo Jimenez; Miranda, Miguel A.; Tormos, Rosa; Tetrahedron; vol. 51; nb. 10; (1995); p. 2953 - 2958 View in Reaxys

trimethyl-<β-phenyl-propyl>-ammonium hydroxide Rx-ID: 6712333 View in Reaxys 353/477 Yield

Conditions & References bei der Destillation v. Braun; Heider; Neumann; Chemische Berichte; vol. 49; (1916); p. 2616 View in Reaxys

poly-α-methylstyryl sodium; M(i+1), \lliving polymer\ poly-α-methylstyryl sodium; M(i), \lliving polymer\ Rx-ID: 8795861 View in Reaxys 354/477 Yield

Conditions & References in tetrahydrofuran, T= -60 - 15 °C , Equilibrium constant Kalninsh; Podolskii; Journal of Structural Chemistry; vol. 41; nb. 4; (2000); p. 572 - 578 View in Reaxys

Rx-ID: 8812556 View in Reaxys 355/477 Yield

Conditions & References With resin Amberlyst 15 (H+), T= 26.95 °C , Equilibrium constant, Further Variations: Temperatures Verevkin; Heintz; Journal of Chemical and Engineering Data; vol. 46; nb. 1; (2001); p. 41 - 46 View in Reaxys

Rx-ID: 8813746 View in Reaxys 356/477 Yield

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Rx-ID: 8813779 View in Reaxys 357/477 Yield

Rx-ID: 9017614 View in Reaxys 358/477 Yield

Conditions & References Time= 60h, T= 90 °C , Further byproducts given Maksyuta; Suprun; Opeida; Turovskii; Russian Journal of Organic Chemistry; vol. 37; nb. 6; (2001); p. 814 - 818 View in Reaxys

OH O

O O

Rx-ID: 9017617 View in Reaxys 359/477 Yield

Conditions & References Time= 29h, T= 90 °C , Further byproducts given Maksyuta; Suprun; Opeida; Turovskii; Russian Journal of Organic Chemistry; vol. 37; nb. 6; (2001); p. 814 - 818 View in Reaxys

O HO

Rx-ID: 305201 View in Reaxys 360/477 Yield

Conditions & References Johnson; Kon; Journal of the Chemical Society; (1926); p. 2755 View in Reaxys

Rx-ID: 1709992 View in Reaxys 361/477 Yield

Conditions & References With aluminum oxide, molybdenum, T= 400 °C , various oxidic and sulphided hydrorefining catalysts, Product distribution, Rate constant Lopez, Rafael; Ramos, Iran; Villalba, Victor; Garcia, Juan Jose; Collection of Czechoslovak Chemical Communications; vol. 48; nb. 8; (1983); p. 2263 - 2268 View in Reaxys With APAl-A-10-FM, T= 399.9 °C , other catalysts, other temperatures, Rate constant, Thermodynamic data

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Campelo, J. M.; Garcia, A.; Luna, D.; Marinas, J. M.; Romero, A. A.; et al.; Journal of the Chemical Society, Faraday Transactions; vol. 90; nb. 15; (1994); p. 2265 - 2276 View in Reaxys O

E E

Rx-ID: 1793049 View in Reaxys 362/477 Yield 10 % Chromat., 10 % Chromat., 20 % Chromat., 7 % Chromat., 7 % Chromat.

B O

E E

Rx-ID: 1793386 View in Reaxys 363/477 Yield 15 % Chromat., 25 % Chromat., 15 % Chromat., 4 % Chromat., 4 % Chromat.

B O

E E

Rx-ID: 1793598 View in Reaxys 364/477 Yield 12 % Chromat., 30 % Chromat., 2 % Chromat., 3 %

Conditions & References With 2,3-dimethyl-naphthalene, palladium diacetate, triethylamine, triphenylphosphine in acetonitrile, Time= 18h, T= 100 °C , influence of catalyst, further boronates, Product distribution Nilsson, Kristina; Hallberg, Anders; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 41; nb. 8; (1987); p. 569 - 576 View in Reaxys

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Chromat., 4 % Chromat.

O O

O HO

Rx-ID: 2702881 View in Reaxys 365/477 Yield

Conditions & References With [MoCl5] in tetrahydrofuran, diethyl ether, T= -70 °C , effect of use of var. solvents; effect of use of var. velocity of allowance; effect of use of Ph-CO-Me, Product distribution Kauffmann, Thomas; Kieper, Gudrun; Angewandte Chemie; vol. 96; nb. 7; (1984); p. 502 - 503 View in Reaxys

N N

Rx-ID: 4295709 View in Reaxys 366/477 Yield

Conditions & References Irradiation Fehr; Fehr, Olaf C.; Grapenthin; Grapenthin, Olaf; Kilian; Kilian, Joerg; Kirmse; Kirmse, Wolfgang; Steenken; Steenken, Steen; Tetrahedron Letters; vol. 36; nb. 33; (1995); p. 5887 - 5890 View in Reaxys

HO O HO

acetic acid

Rx-ID: 6725969 View in Reaxys 367/477 Yield

Conditions & References With tert.-butylhydroperoxide, Al tri-t-BuO- in benzene, Time= 84h, T= 20 °C , Mechanism, Product distribution Stepovik; Dodonov; Zaburdaeva; Russian Journal of General Chemistry; vol. 67; nb. 1; (1997); p. 111 - 115 View in Reaxys

alkanes, alkenes, alkylbenzenes, alkenylbenzenes Rx-ID: 6726068 View in Reaxys 368/477 Yield

Conditions & References With water, T= 535 °C , p= 187515Torr , var. of reagent, pressure, temp., time, further with D2O, Product distribution, Mechanism Kruse, Andrea; Ebert; Berichte der Bunsengesellschaft/Physical Chemistry Chemical Physics; vol. 100; nb. 1; (1996); p. 80 - 83 View in Reaxys

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HO O

acetic acid

Rx-ID: 7450706 View in Reaxys 369/477 Yield

Conditions & References With Al tri-t-BuO- in benzene, Time= 20h, T= 70 °C , Product distribution Stepovik; Dodonov; Zaburdaeva; Russian Journal of General Chemistry; vol. 67; nb. 1; (1997); p. 111 - 115 View in Reaxys

S O

Rx-ID: 10294863 View in Reaxys 370/477 Yield

Conditions & References With [NMQ][BF4] in acetonitrile, UV-irradiation, Quantum yield, Further Variations: Reagents Baciocchi, Enrico; Del Giacco, Tiziana; Giombolini, Paolo; Lanzalunga, Osvaldo; Tetrahedron; vol. 62; nb. 27; (2006); p. 6566 - 6573 View in Reaxys O

O O

Rx-ID: 22202295 View in Reaxys 371/477 Yield

Conditions & References Reaction Steps: 2 Tissier; Grignard; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 132; (1901); p. 685 View in Reaxys

Rx-ID: 31442780 View in Reaxys 372/477 Yield

Conditions & References Reaction Steps: 2 1: 12 h / 20 °C 2: 35 - 150 °C / Vacuo Haiss, Peter; Kuhn, Annette; Kuhn, Norbert; Maichle-Moessmer, Caecilia; Laufer, Stefan; Steimann, Manfred; Zeller, Klaus-Peter; European Journal of Inorganic Chemistry; nb. 22; (2011); p. 3284 - 3287 View in Reaxys O

Br–+Mg

Rx-ID: 744796 View in Reaxys 373/477 Yield

Conditions & References Tiffeneau; Annales de Chimie (Cachan, France); vol. <8>10; (1907); p. 190; Annales de Chimie (Cachan, France); vol. <8>11; (1907); p. 144

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View in Reaxys

Rx-ID: 1984358 View in Reaxys 374/477 Yield

Conditions & References With KU-23 cation exchanger, Time= 24h, T= 49.9 - 109.9 °C , var. temp., time, molar ratio, Equilibrium constant Rozhnov, A. M.; Safronov, V. V.; Alenin, V. I.; Sharonov, K. G.; Russian Journal of Physical Chemistry; vol. 62; nb. 11; (1988); p. 1511 - 1513; Zhurnal Fizicheskoi Khimii; vol. 62; (1988); p. 2902 - 2905 View in Reaxys

O HO

O O

O HO

OH O

Rx-ID: 2017863 View in Reaxys 375/477 Yield

Conditions & References With water in chlorobenzene, T= 74.9 °C , catalytically, Rate constant, Mechanism Koenig, T.; Habicher, W. D.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 331; nb. 6; (1989); p. 913 - 922 View in Reaxys

Rx-ID: 2044423 View in Reaxys 376/477 Yield

Conditions & References Irradiation, in presence of surfactants; further ketone, Mechanism Zimmt, Matthew B.; Doubleday, Charles; Turro, Nicholas J.; Journal of the American Chemical Society; vol. 106; nb. 11; (1984); p. 3363 - 3365 View in Reaxys

lithium

Rx-ID: 7920570 View in Reaxys 377/477 Yield

Conditions & References Curtin; Crump; Journal of the American Chemical Society; vol. 80; (1958); p. 1922,1925 View in Reaxys

Rx-ID: 9383464 View in Reaxys 378/477

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Yield

Conditions & References

9 %, 0.45 %, 0.6 %, 0.77 %

With γ-Al2O3, T= 500 °C , Product distribution, Further Variations: Reagents, Temperatures Kijenski; Malinowski; Kowalczyk; Osawaru; Polish Journal of Chemistry; vol. 77; nb. 6; (2003); p. 719 - 736 View in Reaxys

Rx-ID: 10205745 View in Reaxys 379/477 Yield

Conditions & References in benzene, Photolysis, Quantum yield Veerman, Marcel; Resendiz, Marino J. E.; Garcia-Garibay, Miguel A.; Organic Letters; vol. 8; nb. 12; (2006); p. 2615 - 2617 View in Reaxys

Rx-ID: 1709993 View in Reaxys 380/477 Yield

Conditions & References With sodium nitrate, magnesium oxide, T= 530 °C , various catalyst composition, temperatures, basicity of catalyst, Product distribution Matsuda, Tsuneo; Minami, Zenzaburo; Shibata, Yasumasa; Nagano, Shigeru; Miura, Hiroshi; Sugiyama, Kazuo; Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases; vol. 82; (1986); p. 1357 - 1366 View in Reaxys

Rx-ID: 2017892 View in Reaxys 381/477 Yield

Conditions & References

0.49 %, 0.041 %, 0.26 %, 0.54 %

With acetone, F-4SK, Time= 60h, Heating, varied CHP content in org. mixture; purified or technical CHP; experiments in the presence of H2SO4 or KU-23/10-60 cation-exchange resin (without F-4SK), Product distribution Etlis; Beshenova; Semenova; Shomina; Dreiman; Balaev; Journal of applied chemistry of the USSR; vol. 59; nb. 3 pt 2; (1986); p. 551 - 555 View in Reaxys

O O

Rx-ID: 2151118 View in Reaxys 382/477 Yield

Conditions & References in various solvent(s), Time= 96h, T= 50 °C , other temp., Product distribution, Kinetics, Rate constant Komai, Takeshi; Kato, Kenji; Matsuyama, Kazuo; Bulletin of the Chemical Society of Japan; vol. 61; nb. 7; (1988); p. 2641 - 2642 View in Reaxys

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Rx-ID: 5255816 View in Reaxys 383/477 Yield

Conditions & References With H-Fe-IR-28 zeolite, Time= 0.25h, T= 500 °C , Methylation, Product distribution, Further Variations: Catalysts, Temperatures, time Ponomareva; Moskovskaya; Romanovskii; Petroleum Chemistry; vol. 38; nb. 5; (1998); p. 319 - 324 View in Reaxys With H-TsVK-XI-P(2.5), Time= 0.17h, T= 510 °C , Product distribution, Further Variations: Temperatures, Catalysts, contact time Ponomareva; Moskovskaya; Romanovskii; Petroleum Chemistry; vol. 41; nb. 4; (2001); p. 257 - 261 View in Reaxys

steam Rx-ID: 6712339 View in Reaxys 384/477 Yield

Conditions & References T= 550 - 700 °C , Leiten ueber aktiviertes Magnesiumoxyd Patent; Standard Oil Devel. Co.; US2449004; (1944) View in Reaxys T= 550 - 700 °C , Leiten ueber aktiviertes Aluminiumoxyd Patent; Shell Devel Co.; US2441095; (1946) View in Reaxys T= 550 - 700 °C , Leiten ueber Zinkoxyd-Calciumoxyd auf Bleicherde Patent; I. G. Farbenind.; DE550055; (1931); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 19; p. 611 View in Reaxys T= 550 - 700 °C , Leiten ueber Aluminiumoxyd-Chrom(III)-oxyd Nickels et al.; Industrial and Engineering Chemistry; vol. 41; (1949); p. 563,565 View in Reaxys Br

Br–+Mg

cobalt (II)-chloride Rx-ID: 7067048 View in Reaxys 385/477

Yield

Conditions & References Kharasch; Fuchs; Journal of the American Chemical Society; vol. 65; (1943); p. 504; Journal of Organic Chemistry; vol. 10; (1945); p. 292,294 View in Reaxys

lithium Rx-ID: 7920571 View in Reaxys 386/477

Yield

Conditions & References Curtin; Crump; Journal of the American Chemical Society; vol. 80; (1958); p. 1922,1925 View in Reaxys

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Rx-ID: 10189989 View in Reaxys 387/477 Yield

Conditions & References With H-ZSM-5, Time= 3h, T= 349.85 °C , Product distribution, Further Variations: Reagents Thomas, Bejoy; Sugunan; Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry; vol. 45; nb. 3; (2006); p. 648 - 652 View in Reaxys H C–

O Na +

Rx-ID: 170931 View in Reaxys 388/477 Yield

Conditions & References Hoffman; Journal of the American Chemical Society; vol. 51; (1929); p. 2545 View in Reaxys

Rx-ID: 2542119 View in Reaxys 389/477 Yield

Conditions & References

63 % Chromat., 17 % Chromat.

in methanol, Time= 0.05h, Irradiation, also electrolysis, TBAP, acetonitrile, Product distribution, Quantum yield Fox, Marye Anne; Triebel, Carol A.; Journal of Organic Chemistry; vol. 48; nb. 6; (1983); p. 835 - 840 View in Reaxys

zinc dust Cl

Rx-ID: 7067051 View in Reaxys 390/477 Yield

Conditions & References T= -10 °C Brown; Mighton; Senkus; Journal of Organic Chemistry; vol. 3; (1938); p. 62,72 View in Reaxys

H O

K+

H –N

Rx-ID: 8265079 View in Reaxys 391/477 Yield

Conditions & References Hauser et al.; Journal of the American Chemical Society; vol. 69; (1947); p. 589,591 View in Reaxys

E O

Rx-ID: 11057287 View in Reaxys 392/477 Yield

Conditions & References T= 470.2 °C , p= 103.2 - 203Torr , Kinetics, Further Variations: Pressures, Temperatures, Reagents, surface-to-volume ratio

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Chaban, Omar Y.; Dominguez, Rosa M.; Herize, Armando; Tosta, Maria; Cuenca, Angela; Chuchani, Gabriel; Journal of Physical Organic Chemistry; vol. 20; nb. 5; (2007); p. 307 - 312 View in Reaxys OH (v5)

PH O S

O HO

Rx-ID: 2017877 View in Reaxys 393/477 Yield

Conditions & References in chlorobenzene, T= 74.9 °C , Rate constant Koenig, T.; Habicher, W. D.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 331; nb. 6; (1989); p. 913 - 922 View in Reaxys

S O

O S

Rx-ID: 4640482 View in Reaxys 394/477 Yield 80 % Chromat., 22 % Chromat., 4 % Chromat., 3 % Chromat.

Conditions & References in tert-butyl alcohol, Irradiation, other solvent; photolysis of alkyl aryl sulfoxides; quantum yield for disappearance of staring material; homolytic cleavage; possible reaction pathways; proposed mechanism, Product distribution, Quantum yield Guo, Yushen; Jenks, William S.; Journal of Organic Chemistry; vol. 62; nb. 4; (1997); p. 857 - 864 View in Reaxys

O O

Rx-ID: 5049332 View in Reaxys 395/477 Yield

Conditions & References in acetone, T= 42 °C , Oxidation, acetoxylation; elimination, Kinetics Kazakov; Kabal'nova; Khursan; Shereshovets; Russian Chemical Bulletin; vol. 46; nb. 4; (1997); p. 663 - 671 View in Reaxys

Rx-ID: 9783486 View in Reaxys 396/477 Yield

Conditions & References With methanol, oxygen, Irradiation, Quantum yield Van Alem, Kaj; Belder, Geerte; Lodder, Gerrit; Zuilhof, Han; Journal of Organic Chemistry; vol. 70; nb. 1; (2005); p. 179 - 190 View in Reaxys

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Rx-ID: 9783489 View in Reaxys 397/477 Yield

Rx-ID: 1709974 View in Reaxys 398/477 Yield

Conditions & References With oxygen, T= 726.9 °C , gas phase oxidation in flow reactor at various temperatures, Mechanism Litzinger, T. A.; Brezinsky, K.; Glassman, I.; Journal of Physical Chemistry; vol. 90; nb. 3; (1986); p. 508 - 513 View in Reaxys

Rx-ID: 1980169 View in Reaxys 399/477 Yield

Conditions & References With alpha,alpha-dimethylbenzyl hydroperoxide, Time= 20h, T= 120 °C , other concentrations of cumene hydroperoxide; reaction of other phenyl cycloalkanes, also with tert-butyl hydroperoxide, Product distribution Pritzkow, Wilhelm; Suprun, Vladimir Ya.; Voerckel, Volkmar; Journal fuer Praktische Chemie (Leipzig); vol. 332; nb. 3; (1990); p. 381 - 386 View in Reaxys

S P S

HO O

Rx-ID: 2017839 View in Reaxys 400/477 Yield

Conditions & References in chlorobenzene, T= 74.9 °C , catalytically, Rate constant Koenig, T.; Habicher, W. D.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 331; nb. 6; (1989); p. 913 - 922 View in Reaxys

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Al O

Rx-ID: 3383141 View in Reaxys 401/477 Yield

Conditions & References With molybdenium(VI) dioxodichloride, 1) THF, -70 degC, 2 h; 2) THF, 1 h, 66 degC; also with HMPT and WOCl3(THF)2, Product distribution Kauffmann, Thomas; Enk, Manfred; Kaschube, Wilfried; Toliopoulos, Euripides; Wingbermuehle, Dorothea; Angewandte Chemie; vol. 98; nb. 10; (1986); p. 928 - 929 View in Reaxys With N,N,N',N',N'',N''-hexamethylphosphoric triamide, molybdenium(VI) dioxodichloride, 1) THF, -70 degC, 2 h; 2) THF, 66 degC, 1 h, Yield given. Multistep reaction Kauffmann, Thomas; Enk, Manfred; Kaschube, Wilfried; Toliopoulos, Euripides; Wingbermuehle, Dorothea; Angewandte Chemie; vol. 98; nb. 10; (1986); p. 928 - 929 View in Reaxys

Rx-ID: 4489192 View in Reaxys 402/477 Yield 15 %, 17 %, 33 %

Conditions & References T= 500 °C , also 1-phenylcyclopropane-1-carbaldoxime, Mechanism Wu, Pei-Lin; Wang, Wen-Shan; Chen, Chang-Fu; Journal of the Chinese Chemical Society (Taipei, Taiwan); vol. 41; nb. 5; (1994); p. 601 - 604 View in Reaxys

infusorial earht HO

Rx-ID: 7449778 View in Reaxys 403/477 Yield

Conditions & References T= 300 - 400 °C , bei der Destillation Ramart; Amagat; Annales de Chimie (Cachan, France); vol. <10> 8; (1927); p. 295; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 182; (1926); p. 1343 View in Reaxys

copper

H20

Rx-ID: 7454258 View in Reaxys 404/477 Yield

Conditions & References T= 250 °C Tiffeneau; Annales de Chimie (Cachan, France); vol. <8>10; (1907); p. 190; Annales de Chimie (Cachan, France); vol. <8>11; (1907); p. 144 View in Reaxys O Cl

Cl O

Rx-ID: 589892 View in Reaxys 405/477

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Yield

Conditions & References T= 154 °C , Dehydrierung Dost; van Nes; Recueil des Travaux Chimiques des Pays-Bas; vol. 70; (1951); p. 403,406 View in Reaxys

C+

Rx-ID: 2181611 View in Reaxys 406/477 Yield

Conditions & References T= 34.9 °C , ΔG0, Thermodynamic data Mishima, Masaaki; Ariga, Toshifumi; Tsuno, Yuho; Ikenaga, Kazutoshi; Kikukawa, Kiyoshi; Chemistry Letters; nb. 3; (1992); p. 489 - 492 View in Reaxys

Rx-ID: 2771944 View in Reaxys 407/477 Yield

Conditions & References With silica gel, multistep reaction: 1) condensation with the surface OH-groups of silica, 2) thermolysis at 400 deg C, Mechanism, Product distribution, Rate constant Britt, Phillip F.; Buchanan, A. C.; Journal of Organic Chemistry; vol. 56; nb. 21; (1991); p. 6132 - 6140 View in Reaxys

Rx-ID: 5142925 View in Reaxys 408/477 Yield

Conditions & References T= 428.85 - 510.85 °C , Rate constant Dorrestijn, Edwin; Mulder, Peter; Journal of the Chemical Society. Perkin Transactions 2; nb. 4; (1999); p. 777 780 View in Reaxys

Rx-ID: 6712323 View in Reaxys 409/477 Yield

Conditions & References T= 625 °C , Leiten ueber V2O5-Aluminiumoxyd Balandin; Marukjan; Doklady Akademii Nauk SSSR; vol. 48; (1945); p. 482; ; (1946); p. 4686 View in Reaxys

infusorial earht HO

Rx-ID: 7449782 View in Reaxys 410/477

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Yield

Conditions & References T= 300 - 400 °C Ramart; Amagat; Annales de Chimie (Cachan, France); vol. <10> 8; (1927); p. 295; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 182; (1926); p. 1343 View in Reaxys

H20

I HO

Rx-ID: 7454254 View in Reaxys 411/477 Yield

Conditions & References T= 100 °C Klages; Chemische Berichte; vol. 35; (1902); p. 2649; Chemische Berichte; vol. 39; (1906); p. 2591 View in Reaxys

Rx-ID: 3917115 View in Reaxys 412/477 Yield

Conditions & References p= 14Torr , Ambient temperature, variation of pressure, O2 (4-10 torr), gas phase, labelled with tritium, Product distribution, Mechanism Colosimo, M.; Speranza, M.; Cacace, F.; Ciranni, G.; Tetrahedron; vol. 40; nb. 23; (1984); p. 4873 - 4884 View in Reaxys

steam Rx-ID: 6712336 View in Reaxys 413/477 Yield

Conditions & References T= 700 - 900 °C Patent; Dow Chem. Co.; US2110830; (1937) View in Reaxys

hydrogen Rx-ID: 6712337 View in Reaxys 414/477 Yield

Conditions & References T= 675 - 700 °C , Leiten durch kupferne Rohre Patent; Stanley; Minkoff; Youell; US2198185; (1937) View in Reaxys

steam Rx-ID: 6712338 View in Reaxys 415/477 Yield

Conditions & References T= 675 - 700 °C , Leiten durch kupferne Rohre Patent; Stanley; Minkoff; Youell; US2198185; (1937) View in Reaxys

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O O

OH O

H 2N 2

carbon monoxide

Rx-ID: 7451874 View in Reaxys 416/477 Yield

Conditions & References T= 550 °C , Pyrolysis Mackinnon; Ritchie; Journal of the Chemical Society; vol. k1957; p. 2564 View in Reaxys

HO O Z

O HO

Rx-ID: 8265083 View in Reaxys 417/477 Yield

Conditions & References T= 160 °C , im Einschlussrohr Thorpe; Wood; Journal of the Chemical Society; vol. 103; (1913); p. 1575; Journal of the Chemical Society; vol. 123; (1923); p. 63 View in Reaxys polypropylene BE677MO

Rx-ID: 10016616 View in Reaxys 418/477 Yield

Conditions & References T= 700 °C , Product distribution, Further Variations: Temperatures Koverzanova; Usachev; Shilkina; Lomakin; Gumargalieva; Zaikov; Russian Journal of Applied Chemistry; vol. 77; nb. 3; (2004); p. 445 - 448 View in Reaxys

Rx-ID: 2190217 View in Reaxys 419/477 Yield

Conditions & References

24 %, 9 %

Irradiation, Product distribution Shi, Min; Okamoto, Yoshiki; Takamuku, Setsuo; Chemistry Letters; nb. 7; (1990); p. 1079 - 1082 View in Reaxys

NH NH

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/PPKVB203-1550/

1-Methyl-3-phenyldihydroisoquinolines

Rx-ID: 7457401 View in Reaxys 420/477 Yield

Conditions & References

1.7 % Spectr., 2.0 % Spectr., 0.8 % Spectr., 0.5 % Spectr., 4.4 % Spectr., / PPKVB203 -1550/\3.0 % Spectr.

T= 320 - 350 °C , Sealed glass ampul, Product distribution, Mechanism Shurukhin, Yu. V.; Klyuev, N. A.; Grandberg, I. I.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 22; nb. 7; (1986); p. 723 - 732; Khimiya Geterotsiklicheskikh Soedinenii; vol. 22; nb. 7; (1986); p. 908 917 View in Reaxys

KO H

Rx-ID: 8265081 View in Reaxys 421/477 Yield

Conditions & References Sabetay; Bulletin de la Societe Chimique de France; vol. <4> 47; (1930); p. 614,617 View in Reaxys Sontag; Annales de Chimie (Cachan, France); vol. <11> 1; (1934); p. 359,404 View in Reaxys

+Mg

I–

Rx-ID: 716056 View in Reaxys 422/477 Yield

Conditions & References man erhitzt das Reaktionsprodukt auf 100grad Klages; Chemische Berichte; vol. 35; (1902); p. 2640,3506 View in Reaxys man behandelt das entstandene Doppelverbindung mit Ammoniak und dann wie gewoehnlich zersetzt Klages; Chemische Berichte; vol. 35; (1902); p. 2640,3506 View in Reaxys

+Mg

I–

Rx-ID: 716057 View in Reaxys 423/477 Yield

Conditions & References Grignard; Annales de Chimie (Cachan, France); vol. <7> 24; (1901); p. 468; Chem. Zentralbl.; vol. 72; nb. II; (1901); p. 623 View in Reaxys Klages; Chemische Berichte; vol. 35; (1902); p. 2649; Chemische Berichte; vol. 39; (1906); p. 2591 View in Reaxys Grignard; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 130; (1900); p. 1324; Annales de Chimie (Cachan, France); vol. <7>24; (1901); p. 472; Chem. Zentralbl.; vol. 72; nb. II; (1901); p. 623 View in Reaxys

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Rx-ID: 742287 View in Reaxys 424/477 Yield

Conditions & References T= 50 - 64 °C , Rate constant Sokolow; Schuschunow; ; vol. 2; (1959); p. 29,33; ; (1960); p. 6275 View in Reaxys

Rx-ID: 1709991 View in Reaxys 425/477 Yield

Conditions & References

46 % Chromat., 15 % Chromat., 35 % Chromat., 23 % Chromat.

Time= 5.55556E-05h, T= 700 °C , mechanism, other temperatures, log A, Ea, Rate constant, Thermodynamic data, Product distribution Bach, G.; Ondruschka, B.; Zychlinski, W.; Shevelkova, L. V.; Sokolovskaja, V. G.; Journal fuer Praktische Chemie (Leipzig); vol. 331; nb. 1; (1989); p. 61 - 68 View in Reaxys

Rx-ID: 1784408 View in Reaxys 426/477 Yield

Conditions & References

63 % Chromat., 27 % Chromat., 35 % Chromat., 32 % Chromat.

Rx-ID: 2009949 View in Reaxys 427/477 Yield

Conditions & References

67 % Chromat., 13 % Chromat., 34 % Chromat., 19 % Chromat.

N O

S O

Rx-ID: 3041878 View in Reaxys 428/477

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Yield

Conditions & References

32 % Chromat., 22 % Chromat., 33 % Chromat., 7 % Chromat., 5 % Chromat.

T= 200 °C , Product distribution Koikov, L. N.; Terent'ev, P. B.; Kulikov, N. S.; Journal of Organic Chemistry USSR (English Translation); vol. 17; (1981); p. 960 - 964; Zhurnal Organicheskoi Khimii; vol. 17; nb. 5; (1981); p. 1087 - 1093 View in Reaxys

alcoholic KOH-solution Cl

Rx-ID: 7067046 View in Reaxys 429/477 Yield

Conditions & References Tiffeneau; Annales de Chimie (Cachan, France); vol. <8>10; (1907); p. 190; Annales de Chimie (Cachan, France); vol. <8>11; (1907); p. 144 View in Reaxys

metal cyanide Cl

Rx-ID: 7067049 View in Reaxys 430/477 Yield

Conditions & References Rothstein; Saville; Journal of the Chemical Society; (1949); p. 1946,1949 View in Reaxys

barium hydroxide O

Rx-ID: 7449776 View in Reaxys 431/477 Yield

Conditions & References beim Destillieren Tiffeneau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 138; (1904); p. 986; Annales de Chimie (Cachan, France); vol. <8> 10; (1907); p. 172 View in Reaxys

barium hydroxide

Rx-ID: 7449777 View in Reaxys 432/477 Yield

Conditions & References beim Destillieren Tiffeneau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 138; (1904); p. 987; Annales de Chimie (Cachan, France); vol. <8> 10; (1907); p. 173 View in Reaxys

H20

acidic sulfate potassium HO

Rx-ID: 7454257 View in Reaxys 433/477 Yield

Conditions & References Matsubara; Perkin; Journal of the Chemical Society; vol. 87; (1905); p. 671 View in Reaxys

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+Mg

I–

dimethyl-phenyl-carbinol (1 mol) Rx-ID: 8265080 View in Reaxys 434/477

Yield

Conditions & References Tiffeneau; Annales de Chimie (Cachan, France); vol. <8>10; (1907); p. 190; Annales de Chimie (Cachan, France); vol. <8>11; (1907); p. 144 View in Reaxys

Rx-ID: 19775 View in Reaxys 435/477 Yield

Conditions & References Klages; Chemische Berichte; vol. 35; (1902); p. 2649; Chemische Berichte; vol. 39; (1906); p. 2591 View in Reaxys

Rx-ID: 438557 View in Reaxys 436/477 Yield

Conditions & References Erhitzen unter vermindertem Druck Faworskaja; Fridman; Zhurnal Obshchei Khimii; vol. 18; (1948); p. 2083; Chem. Zentralbl.; vol. 120; (1949); p. 3776 View in Reaxys O

Rx-ID: 818441 View in Reaxys 437/477 Yield

Conditions & References UV-Licht; Dehydrierung.Irradiation Moore; Waters; Journal of the Chemical Society; (1953); p. 3405,3408 View in Reaxys

Rx-ID: 1794115 View in Reaxys 438/477 Yield 3.6 % Chromat., 0.9 % Chromat., 5.7 % Chromat., 3.7 % Chromat.,

Conditions & References T= 710 °C , Product distribution, Mechanism Guenschel, H.; Zimmermann, G.; Lorenz, R.; Ondruschka, B.; Nowak, S.; Journal fuer Praktische Chemie (Leipzig); vol. 323; nb. 4; (1981); p. 607 - 615 View in Reaxys

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34.4 % Chromat., 15 % Chromat.

C+

Rx-ID: 1832219 View in Reaxys 439/477 Yield

Conditions & References standard free energy changes investigated, Thermodynamic data Mishima, Masaaki; Arima, Kiyoshi; Usui, Satoshi; Fujio, Mizue; Tsuno, Yuho; Chemistry Letters; (1987); p. 1047 - 1050 View in Reaxys

C+

Rx-ID: 1981293 View in Reaxys 440/477 Yield

Rx-ID: 1999324 View in Reaxys 441/477 Yield

Conditions & References Time= 80h, T= 125 °C , reaction with different catalysts, different reaction times, different initial conc. of hydroperoxide, Product distribution, Mechanism Lauterbach, Gerlinde; Pritzkow, W.; Tien, Tieu Dung; Voerckel, V.; Journal fuer Praktische Chemie (Leipzig); vol. 330; nb. 6; (1988); p. 933 - 946 View in Reaxys F

F C+

C+

Rx-ID: 2031410 View in Reaxys 442/477 Yield

Rx-ID: 2034537 View in Reaxys 443/477

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Yield

Conditions & References gas phase pyrolysis, Kinetics al-Borno, Amal; Bigley, David B.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 9; (1983); p. 1311 - 1312 View in Reaxys

C+

Rx-ID: 2056078 View in Reaxys 444/477 Yield

C+

Rx-ID: 2058332 View in Reaxys 445/477 Yield

C+

Rx-ID: 2059872 View in Reaxys 446/477 Yield

C+

Rx-ID: 2059875 View in Reaxys 447/477 Yield

Cl C+

Rx-ID: 2082694 View in Reaxys 448/477 Yield

Conditions & References standard free energy changes investigated, Thermodynamic data

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Mishima, Masaaki; Arima, Kiyoshi; Usui, Satoshi; Fujio, Mizue; Tsuno, Yuho; Chemistry Letters; (1987); p. 1047 - 1050 View in Reaxys F

F F

F C+

C+ F

Rx-ID: 2087227 View in Reaxys 449/477 Yield

C+

Rx-ID: 2113583 View in Reaxys 450/477 Yield

C+

Rx-ID: 2149966 View in Reaxys 451/477 Yield

C+

Rx-ID: 2185191 View in Reaxys 452/477 Yield

C+

F O

C+

Rx-ID: 2261585 View in Reaxys 453/477 Yield

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View in Reaxys Cl C+

Cl C+

Rx-ID: 2261586 View in Reaxys 454/477 Yield

C+

Cl C+

Rx-ID: 2261587 View in Reaxys 455/477 Yield

C+

Rx-ID: 2261588 View in Reaxys 456/477 Yield

C+

Rx-ID: 2261589 View in Reaxys 457/477 Yield

H 2N

H+

Rx-ID: 2432007 View in Reaxys 458/477 Yield

Conditions & References ΔHΓ 0, Thermodynamic data Zappey, Herman; Fokkens, Roel H.; Ingemann, Steen; Nibbering, Nico M. M.; Florencio, Helena; Organic Mass Spectrometry; vol. 26; nb. 6; (1991); p. 587 - 594

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View in Reaxys

SH P

S S

S P O

P S

Rx-ID: 3930242 View in Reaxys 459/477 Yield

Conditions & References in benzene, other dialkyl dithiophosphoric acids, other solvent; chemical polarization of nuclei, Product distribution, Mechanism Grossman, G.; Komber, G.; Kroshvitts, G.; Kirpichnikov, P. A.; Mukmeneva, N. A.; Pobedimskii, D. G.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 38; nb. 1.1; (1989); p. 26 - 32; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 1; (1989); p. 34 - 41 View in Reaxys

OH HO

S OO

Rx-ID: 7449775 View in Reaxys 460/477 Yield

Conditions & References Johnson; Kon; Journal of the Chemical Society; (1926); p. 2755 View in Reaxys Br O

magnesium Br

Rx-ID: 7449779 View in Reaxys 461/477 Yield

Conditions & References Tiffeneau; Annales de Chimie (Cachan, France); vol. <8>10; (1907); p. 190; Annales de Chimie (Cachan, France); vol. <8>11; (1907); p. 144 View in Reaxys Br O

sodium Br

Rx-ID: 7449780 View in Reaxys 462/477 Yield

Conditions & References Tiffeneau; Annales de Chimie (Cachan, France); vol. <8>10; (1907); p. 190; Annales de Chimie (Cachan, France); vol. <8>11; (1907); p. 144 View in Reaxys OH

zinc I

Rx-ID: 7449781 View in Reaxys 463/477 Yield

Conditions & References Tiffeneau; Annales de Chimie (Cachan, France); vol. <8>10; (1907); p. 190; Annales de Chimie (Cachan, France); vol. <8>11; (1907); p. 144 View in Reaxys

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H20

Rx-ID: 7454255 View in Reaxys 464/477 Yield

Conditions & References Tiffeneau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 134; (1902); p. 846; Annales de Chimie (Cachan, France); vol. <8> 10; (1907); p. 166 View in Reaxys

H20 HO

Rx-ID: 7454256 View in Reaxys 465/477 Yield

N+ I–

silver oxide

Rx-ID: 8265088 View in Reaxys 466/477 Yield

Conditions & References v. Braun; Heider; Neumann; Chemische Berichte; vol. 49; (1916); p. 2616 View in Reaxys

Rx-ID: 715526 View in Reaxys 467/477 Yield

Conditions & References Erhitzen des Reaktionsprodukts nach dem Abdestillieren des Aethers mehrere Stunden auf 100grad, Zersetzung mit Eiswasser Klages; Chemische Berichte; vol. 35; (1902); p. 2649; Chemische Berichte; vol. 39; (1906); p. 2591 View in Reaxys O

β.ε-diphenyl-β-hexylene(?)

Rx-ID: 6712335 View in Reaxys 468/477 Yield

Conditions & References Tiffeneau; Annales de Chimie (Cachan, France); vol. <8>10; (1907); p. 190; Annales de Chimie (Cachan, France); vol. <8>11; (1907); p. 144 View in Reaxys Br O

sodium-<diethyl phosphite > Br

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sodium bromide

P O

Rx-ID: 7457886 View in Reaxys 469/477 Yield

Conditions & References Arbusow; Logowlin; Zhurnal Obshchei Khimii; vol. 21; (1951); p. 99,105; ; (1951); p. 7002 View in Reaxys OH

sodium

methyl-phenyl-ethylene oxide HO

Rx-ID: 7923864 View in Reaxys 470/477 Yield

Conditions & References Tiffeneau; Annales de Chimie (Cachan, France); vol. <8>10; (1907); p. 190; Annales de Chimie (Cachan, France); vol. <8>11; (1907); p. 144 View in Reaxys HO O Z

H O HO

Rx-ID: 8265084 View in Reaxys 471/477 Yield

Conditions & References Thorpe; Wood; Journal of the Chemical Society; vol. 103; (1913); p. 1575; Journal of the Chemical Society; vol. 123; (1923); p. 63 View in Reaxys HO O

OH HO

S OO

O HO

Rx-ID: 8265085 View in Reaxys 472/477 Yield

Conditions & References Thorpe; Wood; Journal of the Chemical Society; vol. 103; (1913); p. 1575; Journal of the Chemical Society; vol. 123; (1923); p. 63 View in Reaxys

S OO

sodium hydrogencarbonate

Rx-ID: 7067053 View in Reaxys 473/477 Yield

Conditions & References Ross; Huettel; Chemische Berichte; vol. 89; (1956); p. 2641,2642, 2644 View in Reaxys

Rx-ID: 6712320 View in Reaxys 474/477

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Yield 91 %

Conditions & References 1 : Example 1 Example 1 In a 300-ml Parr pressure reactor equipped with a mechanical stirrer, acetophenone (12 g, 100 mmoles), dimethyl carbonate (13.5 g, 150 mmoles), triphenyl phosphine (23.1 g, 150 mmoles), ethyltriphenyl phosphonium iodide (0.83 g) are combined. The reactor is sealed and heating and stirring commenced. After heating at 175° C. for two hours, the reaction mixture is cooled and the reactor vented. The reactor contents are transferred to a distillation flask. The reactor is rinsed with methylene chloride and the two liquid mixtures combined for distillation. The product α-methylstyrene is recovered by distillation. Isolated yield, 91 percent, based on acetophenone. Patent; The Dow Chemical Company; US4713458; (1987); (A1) English View in Reaxys

24 %

8 : EXAMPLE 8 The major by-product was alpha-methylstyrene in 24 percent yield. Patent; Gulf Research and Development Company; US4173587; (1979); (A1) English View in Reaxys

5 : EXAMPLE 5 The major by-product was alpha-methylstyrene in 4 percent yield. The product solution was yellow and tar formation was nil. Patent; Gulf Research and Development Company; US4173587; (1979); (A1) English View in Reaxys Harney,D.W. et al.; Australian Journal of Chemistry; vol. 27; (1974); p. 1639 - 1653 View in Reaxys Jeffery,E.A. et al.; Australian Journal of Chemistry; vol. 27; (1974); p. 2569 - 2576 View in Reaxys Wittig,G.; Frommeld,H.-D.; Chemische Berichte; vol. 97; (1964); p. 3548 - 3559 View in Reaxys Nerdel,F. et al.; Chemische Berichte; vol. 101; (1968); p. 1850 - 1862 View in Reaxys Lucas,K. et al.; Chemische Berichte; vol. 104; (1971); p. 3607 - 3617 View in Reaxys Heck,R.F.; Journal of the American Chemical Society; vol. 93; (1971); p. 6896 - 6901 View in Reaxys Amaro,A.; Grohmann,K.; Journal of the American Chemical Society; vol. 97; nb. 13; (1975); p. 3830 - 3831 View in Reaxys Creary,X.; Journal of the American Chemical Society; vol. 99; nb. 23; (1977); p. 7632 - 7639 View in Reaxys Kornblum,N. et al.; Journal of the American Chemical Society; vol. 101; (1979); p. 647 - 657 View in Reaxys Collin,G. et al.; Justus Liebigs Annalen der Chemie; vol. 702; (1967); p. 55 - 67 View in Reaxys Tamao,K. et al.; Bulletin of the Chemical Society of Japan; vol. 49; (1976); p. 1958 - 1969 View in Reaxys Mastagli,P.; de Nanteuil,M.; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 268; (1969); p. 1970 - 1972 View in Reaxys Traynelis,V.J. et al.; Journal of Organic Chemistry; vol. 27; (1962); p. 2377 - 2383 View in Reaxys Brewster,J.H. et al.; Journal of Organic Chemistry; vol. 29; (1964); p. 110 - 115 View in Reaxys Gotzmer,C. et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 2964 - 2967 View in Reaxys Uijttewaal,A.P. et al.; Journal of Organic Chemistry; vol. 43; (1978); p. 3306 - 3311 View in Reaxys Uijttewaal,A.P. et al.; Journal of Organic Chemistry; vol. 44; (1979); p. 3157 - 3168

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View in Reaxys Westmijze,H. et al.; Recueil des Travaux Chimiques des Pays-Bas; vol. 95; (1976); p. 304 - 307 View in Reaxys Takai,K. et al.; Tetrahedron Letters; (1978); p. 2417 - 2420 View in Reaxys Petragnani,N. et al.; Journal of Organometallic Chemistry; vol. 124; (1977); p. 1 - 12 View in Reaxys Reisdorf,D.; Normant,H.; Organometallics in Chemical Synthesis; vol. 1; (1972); p. 375 - 391 View in Reaxys Lewina et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 31; (1961); p. 1185,1096; ; nb. 25809; (1961) View in Reaxys Smith; Wikman; Synthesis in Inorganic and Metal-Organic Chemistry; vol. 4; (1974); p. 239,246 View in Reaxys Vig et al.; Journal of the Indian Chemical Society; vol. 45; (1968); p. 1026,1031 View in Reaxys Shelton et al.; Canadian Journal of Chemistry; vol. 46; (1968); p. 1149 View in Reaxys Normant; Anales de Quimica (1968-1979); vol. 68; (1972); p. 667,674 View in Reaxys Hassner et al.; Journal of the American Chemical Society; vol. 91; (1969); p. 5046,5053 View in Reaxys Kawabata et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 3403,3406 View in Reaxys Buddrus; Chemische Berichte; vol. 107; (1974); p. 2050,2053, 2060 View in Reaxys Reisdorf; Normant; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 268; (1969); p. 959 View in Reaxys Sugi; Mitsui; Bulletin of the Chemical Society of Japan; vol. 42; (1969); p. 2984,2988 View in Reaxys Herault et al.; Bulletin de la Societe Chimique de France; (1970); p. 400,401-405 View in Reaxys Beier et al.; Journal fuer Praktische Chemie (Leipzig); vol. 26; (1964); p. 304 View in Reaxys Lapkin; Rybakowa; J. Gen. Chem. USSR (Engl. Transl.); vol. 30; (1960); p. 1227,1248; ; nb. 442; (1961) View in Reaxys Zukerwanik; Juldaschew; J. Gen. Chem. USSR (Engl. Transl.); vol. 33; (1963); p. 3497,3429 View in Reaxys Minachev et al.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 27; (1978); p. 1092,1094; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; vol. 27; (1978); p. 1256 View in Reaxys Mori et al.; Bulletin of the Chemical Society of Japan; vol. 46; (1973); p. 1505,1507 View in Reaxys Minachev et al.; Kinetics and Catalysis; vol. 18; (1977); p. 1117 View in Reaxys Tonnis et al.; Journal of the Chemical Society, Chemical Communications; (1975); p. 560 View in Reaxys Kaspar; Prochazka; Collection of Czechoslovak Chemical Communications; vol. 39; (1974); p. 3124,3125-3130 View in Reaxys Reetz; Eibach; Justus Liebigs Annalen der Chemie; (1977); p. 242,249,252,253 View in Reaxys Belomestnych et al.; Neftekhimiya; vol. 17; (1977); p. 830,833; ; vol. 88; nb. 120692; (1978) View in Reaxys Ohkatsu et al.; Bulletin of the Chemical Society of Japan; vol. 51; (1978); p. 3606 View in Reaxys Okumoto; Takeuchi; Bulletin of the Chemical Society of Japan; vol. 46; (1973); p. 1717 View in Reaxys Mukaiyama et al.; Chemistry Letters; (1972); p. 287,289 View in Reaxys Patent; BASF; DE1812098; (1968); ; vol. 73; nb. 34755 View in Reaxys

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Neumann; Seebach; Chemische Berichte; vol. 111; (1978); p. 2785,2811, 2812 View in Reaxys Alberola; Borque; Anales de Quimica (1968-1979); vol. 70; (1974); p. 882 View in Reaxys Miyaura et al.; Chemistry Letters; (1974); p. 1411 View in Reaxys Sekiguchi; Ando; Chemistry Letters; (1977); p. 1293 View in Reaxys Murry; Fleming; Journal of Organic Chemistry; vol. 40; (1975); p. 2555 View in Reaxys Nagiew et al.; Azerbaidzhanskii Khimicheskii Zhurnal; vol. 3; (1974); p. 12,14; ; vol. 82; nb. 98417; (1975) View in Reaxys Mamedaliew et al.; Azerbaidzhanskii Khimicheskii Zhurnal; vol. 3; (1962); p. 11,14; ; vol. 58; nb. 11241f; (1963) View in Reaxys Mamedaliew et al.; Doklady - Akademiya Nauk Azerbaidzhanskoi SSR; vol. 19; nb. 1; (1963); p. 13,16; ; vol. 59; nb. 6279g; (1963) View in Reaxys Morris et al.; Chemical Communications (London); (1968); p. 1134 View in Reaxys Stepovik; Khamylova; J. Gen. Chem. USSR (Engl. Transl.); vol. 45; (1975); p. 61,54 View in Reaxys McKinley; Rakshys; Journal of the Chemical Society, Chemical Communications; (1972); p. 134 View in Reaxys Kaganowa et al.; Neftekhimiya; vol. 10; (1970); p. 321,81 View in Reaxys Starowieyski et al.; Journal of Organometallic Chemistry; vol. 117; (1976); p. C1 View in Reaxys Vig et al.; Journal of the Indian Chemical Society; vol. 45; (1968); p. 734 View in Reaxys Bestmann; Klein; Tetrahedron Letters; (1966); p. 6181,6184 View in Reaxys Bahachanow et al.; Azerbaidzhanskii Khimicheskii Zhurnal; vol. 6; (1966); p. 54; ; vol. 67; nb. 73262; (1967) View in Reaxys Sekiguchi; Auclo; Chemistry Letters; (1978); p. 1385 View in Reaxys Areshidze; Chivadze; Doklady Chemistry; vol. 173; (1967); p. 297; Doklady Akademii Nauk SSSR; vol. 173; (1967); p. 821 View in Reaxys Wood et al.; Journal of the American Chemical Society; vol. 100; (1978); p. 3855,3859 View in Reaxys Mead et al.; Journal of the Chemical Society, Chemical Communications; (1972); p. 679 View in Reaxys Taschtschuk et al.; Sov. Prog. Chem. (Engl. Transl.); vol. 34; nb. 11; (1968); p. 1148,50 View in Reaxys Szwarc; Asami; Journal of the American Chemical Society; vol. 84; (1962); p. 2269 View in Reaxys Badger; Novotny; Australian Journal of Chemistry; vol. 16; (1963); p. 613,614, 621 View in Reaxys Saveant; Binh; Journal of Organic Chemistry; vol. 42; (1977); p. 1242,1243,1245 View in Reaxys Viola; Madison; Tetrahedron Letters; (1977); p. 4495,4496, 4498 View in Reaxys Okada; Hashimoto; Kogyo Kagaku Zasshi; vol. 70; (1967); p. 2152,2153, 2155 View in Reaxys Kamiya; Tetrahedron Letters; (1968); p. 4965 View in Reaxys Jullien; Minkevitch-Bonazzola; Bulletin de la Societe Chimique de France; (1967); p. 1803 View in Reaxys Caubere; Moreau; Tetrahedron; vol. 25; (1969); p. 2469 View in Reaxys Laurent et al.; Bulletin de la Societe Chimique de France; (1967); p. 1995

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View in Reaxys Bacha; Kochi; Journal of Organic Chemistry; vol. 33; (1968); p. 83 View in Reaxys Bodrikov; Okrokova; Zhurnal Organicheskoi Khimii; vol. 4; (1968); p. 1806,1742 View in Reaxys Bodrikov; Okrokova; Journal of Organic Chemistry USSR (English Translation); vol. 3; (1967); p. 1663; Zhurnal Organicheskoi Khimii; vol. 3; (1967); p. 1706 View in Reaxys Shelton et al.; Journal of the American Chemical Society; vol. 90; (1968); p. 354 View in Reaxys Mihailovic et al.; Tetrahedron; vol. 23; (1967); p. 3095 View in Reaxys Laurent et al.; Bulletin de la Societe Chimique de France; (1968); p. 3307 View in Reaxys Magerramow et al.; Uchenye Zapiski Azerbaidzhanskogo Gosudarstvennogo Universiteta, Seriya Khimicheskikh Nauk; vol. 1; (1973); p. 49,50,51; ; vol. 81; nb. 151674; Chem. Zentralbl.; Ref. Zh. Khim. 1973 Abstr. Nr. 22 Zh 95 View in Reaxys Examples of the above-described alkenes and alkynes are: ethylene, styrene, α-methylstyrene, p-methylstyrene, 2,4,6-trimethylstyrene, p-methoxystyrene, p-vinylstyrene, p-dimethylaminostyrene, p-chlorostyrene, ... Patent; Basell Polypropylen GmbH; US6492539; (2002); (B1) English View in Reaxys The olefins are illustrated by, but not limited to the following compounds. ... 2-hexene methylcyclopentene vinyl toluene ethylene α-methyl styrene styrene methyl cyclohexene 1-tetradecene ... Patent; The Goodyear Tire and Rubber Company; US4143076; (1979); (A1) English View in Reaxys VII : EXAMPLE VII EXAMPLE VII Almost complete oxidation of cumene to α-methylstyrene was obtained with the catalyst of Example I. The procedure of Example II was followed, using 250 ml (215.5 g) of cumene. Reaction temperature was 152° C. The filtrate was distilled to recover 101 g of cumene and obtain a residue of 109.2 that consisted of: Patent; Standard Oil Company (Indiana); US4151213; (1979); (A1) English View in Reaxys II : Reaction: STR22 Reaction: STR22 Into a one-liter reaction flask equipped with thermometer, addition funnel, heating mantle, reflux condenser, stirrer, Yadapter and distillation head is added 100 g of cyclohexane followed by 5 g of p-toluene sulfonic acid. The resulting mixture is heated to 50° C. and over a one-hour period, 500 g of alpha metal styrene is added to the reaction flask.

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The reaction mass is then heated to 100° C. and maintained at that temperature for a period of four hours. 529.3 g of crude product is then recovered which is then mixed with 15 g of Primol.(R). and 0.2 g of Ionox .(R).. The resulting mixture is distilled through a "Y" adapter distillation column yielding the following distillation data: Patent; International Flavors and Fragrances Inc.; US4199481; (1980); (A1) English View in Reaxys 2 : Example 2 Example 2 (according to the invention) One operated as in example 1, while adding g 2.9 of acetone to xylene. One obtained g 26.4 of a dry crystallized product having a titre (GC) of 98.9percent by weight of (alpha-phenylisopropyl)hydroquinone and 1.05percent by weight of 2.5-bis(alpha-phenylisopropyl) hydroquinone; the mother-waters coming from filtration, after having been evaporated at constant weight, gave a residue of g 12.4 having a titre (GC) = 2.9percent and 4.1percent by weight in mono and disubstituted hydroquinone respectively. Total molar yield (alpha-phenylisopropyl)hydroquinone/alpha-methylstyrene = 58percent; molar yield of alkylation = 59.13percent. Patent; HIMONT ITALIA S.r.l.; EP347835; (1989); (A2) English View in Reaxys

Rx-ID: 25283341 View in Reaxys 475/477 Yield 6%

Conditions & References 11 : EXAMPLE 11 EXAMPLE 11 A 0.009 g. portion of powdered rhenium heptasulfide was placed in a stirred glass reactor with 22 g. of a 17.4 percent solution of cumene hydroperoxide in cumene and heated to 60°-105° C. for five minutes. The catalyst did not appear to dissolve. Cumene hydroperoxide decomposition was complete and phenol yield was greater than 92 percent. The major by-product was alpha-methylstyrene in 6 percent yield with tar formation being nil. Patent; Gulf Research and Development Company; US4173587; (1979); (A1) English View in Reaxys

92 %.

13 : EXAMPLE 13 EXAMPLE 13 A 0.010 g. sample of powdered rhenium trioxide was placed in a stirred glass reactor with 22 g. of a 17.4 percent solution of cumene hydroperoxide in cumene and was heated to 60°-115° C. for five minutes. The catalyst was insoluble. Decomposition of the cumene hydroperoxide was complete and the phenol yield was greater than 92 percent. The major by-product was alpha-methylstyrene in six percent yield with tar formation being negligible. Patent; Gulf Research and Development Company; US4173587; (1979); (A1) English View in Reaxys

Rx-ID: 24904465 View in Reaxys 476/477 Yield

Conditions & References 14 : Copolymerization (suspension polymerization) of styrene, α-methylstyrene and acrylonitrile, and measurement of the physical properties of the resulting copolymer EXAMPLE 14 Copolymerization (suspension polymerization) of styrene, α-methylstyrene and acrylonitrile, and measurement of the physical properties of the resulting copolymer Patent; Nippon Oil and Fats Company, Limited; US5041624; (1991); (A1) English View in Reaxys

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Rx-ID: 32314250 View in Reaxys 477/477 Yield

Conditions & References 5; 1 Patent; AL-MASUM, Mohammad; US2012/10298; (2012); (A1) English View in Reaxys

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