1. 1-Propoxypropane [Di-n-propyl ether; n-Pr2O] by Asch

Query Query 1. Query

Results

Date

74 reactions in Reaxys

2016-09-13 02h:04m:57s (EST)

74 reactions in Reaxys

2016-09-13 02h:05m:32s (EST)

Search as: As drawn, No mixtures, No charges, No radicals 2. Query

(1. Query) AND itemno in (1)

1/22

2016-09-13 02:36:21

Rx-ID: 57785 View in Reaxys 1/74 Yield 90.8 %, 5.0 %

Conditions & References 17 :The same method was followed as described for examples 1-14, only the reaction was performed in a 300 ml capacity stainless steel autoclave at 110° C. and 4 ml of the required alcohol as indicated was used instead of hexan-1-ol. With Rh2Cl2(CO)4, tris(2,4,6-trimethylphenyl)phosphine, tetrabutylammomium bromide, hydrogen iodide in water, T= 110 °C , Inert atmosphere, Autoclave, Product distribution / selectivity Patent; Wass, Duncan Frank; Shishkov, Igor Viacheslavovich; US2010/267996; (2010); (A1) English View in Reaxys With iron(III) cation, sulphonated styrene copolymers, T= 130 °C , p= 75.006Torr , different crosslinking, various metal ions, Product distribution, Rate constant Kmostak, Svatomir; Setinek, Karel; Collection of Czechoslovak Chemical Communications; vol. 46; nb. 10; (1981); p. 2354 - 2363 View in Reaxys With aluminum oxide, T= 185 °C Mailhe; de Godon; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 170; (1920); p. 329; Bulletin de la Societe Chimique de France; vol. <4>27; (1920); p. 121 View in Reaxys With Rh2Cl2(CO)4, tris(2,4,6-trimethylphenyl)phosphine, tetrabutylammomium bromide, hydrogen iodide in water, Time= 48h, T= 110 °C Dowson, George R. M.; Shishkov, Igor V.; Wass, Duncan F.; Organometallics; vol. 29; nb. 18; (2010); p. 4001 4003 View in Reaxys General procedure: The catalysts used in this study are P25 TiO2 (Evonik) and withPd at a loading of 5 wtpercent Pd/TiO2. PdCl2 (0.1667 g, Sigma–Aldrich)was dissolved in 1.5 ml deionised water, acidified with HCl to pH1, and then added drop-wise onto 2 g of titania powder whilestirring. The samples were dried in static air at 120 C for 2 h followedby heating to 500 C (at 50 C min−1) and maintained at thistemperature for 3 h. The resulting catalysts have surface areas ofapproximately 52 m2 g−1 with TEM showing palladium particlesof sizes of∼2–4 nm (see Section 4). After calcination XPS showedthe surface Cl concentration to be <0.1percent. XP spectra were recordedwith a Kratos Axis Ultra-DLD photoelectron spectrometer using amonochromatic Al K X-ray source. The reactor consists of a stainlesssteel U-tube (6 mm o.d., 4 mm i.d.) mounted vertically in anoven that can be held at constant temperature or ramped in temperatureat a constant rate. The catalyst (0.5 g) was loaded intothe reactor tube and pre-treated in flowing helium (99.5percent purity,BOC Ltd) at 400 C for 40 min in order to remove unwanted carbonor oxygen containing species, confirmed by subsequent TPDin He, which shows no products evolving from the surface. Liquidreactants (methanol, ethanol, n-propanol and i-propanol, all99.8percent pure) were injected in 0.5 L injections through a septumassembly and they passed over the sample in well defined pulsesuntil the surface was saturated. The composition of the gas flowafter reaction with the catalyst is monitored by mass spectrometry(Hiden Analytical quadrupole (HAL 201)). Saturation of a samplewas defined as the point where no adsorption of reactant on thecatalyst could be detected from a pulse. For the temperature programmeddesorption (TPD) experiments the catalyst was exposedto the adsorbate until saturation, the temperature was then rampedat ∼1 C s−1 and the desorbing molecules monitored by mass spectrometry.Elucidation of the various products was made by use ofthe cracking patterns, and of the contribution of fragments to thevarious peaks in the TPD. For instance, a mass of 28 alone in a peakwith no mass 27 indicates CO desorption, whereas desorption ofmass 16 with coincident 15 and no higher masses is an indicationof methane desorption. With Titanium(IV) oxide, T= 400 °C Bahruji, Hasliza; Bowker, Michael; Brookes, Catherine; Davies, Philip R.; Wawata, Ibrahim; Applied Catalysis A: General; vol. 454; (2013); p. 66 - 73 View in Reaxys With SAPO-34, Time= 2h, T= 250 °C , Inert atmosphere

2/22

2016-09-13 02:36:21

Yu, Lei; Yuan, Jing; Zhang, Qi; Liu, Yong-Mei; He, He-Yong; Fan, Kang-Nian; Cao, Yong; ChemSusChem; vol. 7; nb. 3; (2014); p. 743 - 747 View in Reaxys With water, T= 159.84 °C , p= 18.7519Torr , Kinetics, Mechanism, Thermodynamic data, Temperature, Pressure, Reagent/catalyst Zhi, Yuchun; Shi, Hui; Mu, Linyu; Liu, Yue; Mei, Donghai; Camaioni, Donald M.; Lercher, Johannes A.; Journal of the American Chemical Society; vol. 137; nb. 50; (2015); p. 15781 - 15794 View in Reaxys

Rx-ID: 39117094 View in Reaxys 2/74 Yield

Conditions & References 11 : Hydrogenation of 1,2 Propanediol. Hydrogenation of 1,2 Propanediol. Using (POCOP)IrH2 and trifluoromethanesulfonic acid, 1,2-propanediol (1,2 PD) was reduced to n-propanol in up to 95percent yield in aqueous dioxane at 125° C. under 100 psi H2. The mild conditions of the reaction and the high selectivity observed are extraordinary. Even more remarkable is the stability of this catalyst to the aqueous environment. In fact, the presence of water is actually required to achieve high deoxygenation selectivity and hydrogenation efficiency, which also increased as the acid concentration in the reaction system was decreased.As shown in FIG. 1, the combined yield of 1-propanol and n-propyl ether generated in the Ir-catalyzed deoxygenation of 1,2-propanediol (1,2-PD) increased from 2percent to 95percent as the percent of water initially present in the solution was increased (from 0-20percent by volume) and as the acid concentration was reduced (from 1 to 0.05 equivalents with respect to 1,2-PD). With [C6H3-2,6-(OP(tBu)2)2]IrH2, trifluorormethanesulfonic acid, water, hydrogen in 1,4-dioxane, T= 125 °C , p= 5171.62Torr , Autoclave, Concentration, Temperature, Pressure Patent; Goldberg, Karen I.; Heinekey, Michael D.; Weliange, Nandita Malathi; Ahmed, Takiya J.; Camp, Eric R.; Wong, Gene; Lao, David; US2014/371493; (2014); (A1) English View in Reaxys

O O

Rx-ID: 57787 View in Reaxys 3/74 Yield

Conditions & References With sulfuric acid Wuyts; Lacourt; Bulletin des Societes Chimiques Belges; vol. 39; (1930); p. 161,165, 172 View in Reaxys

60 % Turn- With DELOXAN ASP in carbon dioxide, T= 150 °C , p= 200Torr ov., 8 % Gray, William K.; Smail, Fiona R.; Hitzler, Martin G.; Ross, Stephen K.; Poliakoff, Martyn; Journal of the AmeriTurnov. can Chemical Society; vol. 121; nb. 46; (1999); p. 10711 - 10718 View in Reaxys

Rx-ID: 57823 View in Reaxys 4/74 Yield 66%

Conditions & References 1 : Dehydroxylation of 1,2-Propanediol Note that the di-n-propyl ether is considered as two hydrogenation equivalents, since it requires two equivalents of npropanol to produce one equivalent of di-n-propyl ether. Therefore, the total yield of hydrogenation equivalents from this experiment indicated 66 turnovers (66percent yield). Patent; Bullock, R. Morris; Schlaf, Marcel; Fagan, Paul Joseph; US2002/77511; (2002); (A1) English View in Reaxys

3/22

2016-09-13 02:36:21

34%

9 : Dehydroxylation of 1,2-Propanediol by (CpPri4)Ru(CO)2H Note that the di-n-propyl ether is considered as two hydrogenation equivalents, since it requires two equivalents of npropanol to produce one equivalent of di-n-propyl ether. Therefore, the total yield of hydrogenation equivalents from this experiment indicated 34 catalyst turnovers (34percent yield). Patent; Bullock, R. Morris; Schlaf, Marcel; Fagan, Paul Joseph; US2002/77511; (2002); (A1) English View in Reaxys With sulfuric acid Katuno; ; vol. 41; p. 82; Chem. Zentralbl.; vol. 110; nb. I; (1939); p. 630 View in Reaxys Wuyts; Lacourt; Bulletin des Societes Chimiques Belges; vol. 39; (1930); p. 161,165, 172 View in Reaxys With acidic cations-exchanger, T= 160 °C Swistak; Mastagli; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 239; (1954); p. 709 View in Reaxys With boron trifluoride, benzene, T= 210 °C Romadan; Peltscher; Izvestiya Vysshikh Uchebnykh Zavedenii, Khimiya i Khimicheskaya Tekhnologiya; vol. 2; (1959); p. 381; ; (1960); p. 4357 View in Reaxys With sulfuric acid Senderens; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 176; (1923); p. 813; Annales de Chimie (Cachan, France); vol. <9>18; (1922); p. 122 View in Reaxys Senderens; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 181; (1925); p. 700; Annales de Chimie (Cachan, France); vol. <9>18; (1922); p. 123 View in Reaxys Wuyts; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 180; (1925); p. 673 View in Reaxys Popelier; Bulletin des Societes Chimiques Belges; vol. 32; (1923); p. 185; Chem. Zentralbl.; vol. 94; nb. III; (1923); p. 1450 View in Reaxys With aluminum oxide Ipatjew; Orlow; Petrow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 59; (1927); p. 543; Chem. Zentralbl.; vol. 99; nb. I; (1928); p. 1023 View in Reaxys Weston; Adkins; Journal of the American Chemical Society; vol. 51; (1929); p. 2589 View in Reaxys With sulfuric acid, T= 135 °C Norton; Prescott; American Chemical Journal; vol. 6; (1884); p. 243 View in Reaxys Oddo; Cusmano; Gazzetta Chimica Italiana; vol. 33 II; (1903); p. 420 View in Reaxys With benzenesulfonic Acid, T= 125 °C Krafft; Chemische Berichte; vol. 26; (1893); p. 2833 View in Reaxys Patent; Krafft; DE69115; Fortschr. Teerfarbenfabr. Verw. Industriezweige; III,11 View in Reaxys With iron(III) chloride, T= 145 - 155 °C

4/22

2016-09-13 02:36:21

Oddo; Gazzetta Chimica Italiana; vol. 31 I; (1901); p. 311 View in Reaxys Oddo; Cusmano; Gazzetta Chimica Italiana; vol. 33 II; (1903); p. 422 View in Reaxys With quinoline hydrochloride, T= 180 °C Van Hove; Chem. Zentralbl.; vol. 78; nb. I; (1907); p. 235 View in Reaxys Steady state kinetic measurements General procedure: The reactor system described in previous reports [22,23] wasused to gather steady state kinetic measurements on ether conver-sion. All experiments were performed at a reaction temperature of623 K using a mixture of liquid feeds, a He carrier gas (Grade 4.7,Minneapolis Oxygen Company) with a flowrate of 9.9 cm3s−1atambient pressure, and a mixture of 25.0percent CH4with a balance ofAr (Minneapolis Oxygen Company) fed at 0.017 cm3s−1at ambi-ent pressure to act as an internal standard for gas chromatographyanalysis. Ether conversions were kept to differential levels (<10percent)by using reactor beds containing 1.0 mg of catalyst.MPE (97percent Sigma– Aldrich with 3percent methanol as stabilizer) was fedto and vaporized in a flowing He stream to maintain a pressure of0.8 kPa for kinetic measurements of asymmetric ether conversion.Methanol (99.9percent Fisher Scientific) was also fed in these experi-ments to maintain a partial pressure of 0.2 kPa throughout thecatalyst bed. Methanol and 1PrOH dehydration kinetics were mea-sured in independent investigations by feeding 2.4–16.8 kPa ofmethanol and 1.4–9.4 kPa of 1-PrOH (99.9percent Sigma–Aldrich). Sim-ilarly, the kinetics of DEE conversion were measured by varyingthe partial pressure of ethanol-stabilized DEE (98.1percent DEE with 1.8percentethanol Fisher Scientific) between 0.4 and 8.8 kPa. Pyridine inhibi-tion measurements were carried out at 0.02–0.08 kPa of pyridine(99+percent, Sigma–Aldrich) with a co-feed of non-stabilized DEE (99.9percentSigma–Aldrich) at 1.4 kPa as well as, in an independent experiment,a co-feed of 3.5 kPa of ethanol and 1.3 kPa of water. For all exper-iments used to evaluate alcohol and ether conversion kinetics aswell as pyridine inhibition measurements, deionized water wasco-fed to establish feed partial pressures between 0.2 and 2.1 kPa. The composition of the reactor effluent was determined using anonline gas chromatograph (GC) with previously described analyti-cal protocols [22]. The 95percent confidence intervals reported in tablesand figures were evaluated from subsequent GC measurements atthe same experimental conditions. With aluminum oxide, T= 349.84 °C , p= 17.2517Torr , Inert atmosphere, Kinetics DeWilde, Joseph F.; Bhan, Aditya; Applied Catalysis A: General; vol. 502; (2015); p. 361 - 369; Art.No: 15420 View in Reaxys

Rx-ID: 1603986 View in Reaxys 5/74 Yield

Conditions & References

5 % Chromat., 94 %

With hydrogenchloride, tetrabutylphosphonium ion, silica gel, T= 170 °C , p= 760Torr Tundo, Pietro; Venturello, Paolo; Angeletti, Enrico; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1987); p. 2157 - 2158 View in Reaxys

O O

Rx-ID: 8960164 View in Reaxys 6/74 Yield

Conditions & References

41 % Turn- With DELOXAN ASP in carbon dioxide, T= 150 °C , p= 200Torr ov., 12 % Gray, William K.; Smail, Fiona R.; Hitzler, Martin G.; Ross, Stephen K.; Poliakoff, Martyn; Journal of the AmeriTurnov. can Chemical Society; vol. 121; nb. 46; (1999); p. 10711 - 10718 View in Reaxys

Rx-ID: 40843881 View in Reaxys 7/74

5/22

2016-09-13 02:36:21

Yield

Conditions & References Steady state kinetic measurements General procedure: The reactor system described in previous reports [22,23] wasused to gather steady state kinetic measurements on ether conver-sion. All experiments were performed at a reaction temperature of623 K using a mixture of liquid feeds, a He carrier gas (Grade 4.7,Minneapolis Oxygen Company) with a flowrate of 9.9 cm3s−1atambient pressure, and a mixture of 25.0percent CH4with a balance ofAr (Minneapolis Oxygen Company) fed at 0.017 cm3s−1at ambi-ent pressure to act as an internal standard for gas chromatographyanalysis. Ether conversions were kept to differential levels (<10percent)by using reactor beds containing 1.0 mg of catalyst.MPE (97percent Sigma– Aldrich with 3percent methanol as stabilizer) was fedto and vaporized in a flowing He stream to maintain a pressure of0.8 kPa for kinetic measurements of asymmetric ether conversion.Methanol (99.9percent Fisher Scientific) was also fed in these experi-ments to maintain a partial pressure of 0.2 kPa throughout thecatalyst bed. Methanol and 1PrOH dehydration kinetics were mea-sured in independent investigations by feeding 2.4–16.8 kPa ofmethanol and 1.4–9.4 kPa of 1-PrOH (99.9percent Sigma–Aldrich). Sim-ilarly, the kinetics of DEE conversion were measured by varyingthe partial pressure of ethanol-stabilized DEE (98.1percent DEE with 1.8percentethanol Fisher Scientific) between 0.4 and 8.8 kPa. Pyridine inhibi-tion measurements were carried out at 0.02–0.08 kPa of pyridine(99+percent, Sigma–Aldrich) with a co-feed of non-stabilized DEE (99.9percentSigma–Aldrich) at 1.4 kPa as well as, in an independent experiment,a co-feed of 3.5 kPa of ethanol and 1.3 kPa of water. For all exper-iments used to evaluate alcohol and ether conversion kinetics aswell as pyridine inhibition measurements, deionized water wasco-fed to establish feed partial pressures between 0.2 and 2.1 kPa. The composition of the reactor effluent was determined using anonline gas chromatograph (GC) with previously described analyti-cal protocols [22]. The 95percent confidence intervals reported in tablesand figures were evaluated from subsequent GC measurements atthe same experimental conditions. With aluminum oxide in ethanol, T= 349.84 °C , p= 17.2517Torr , Inert atmosphere, Kinetics DeWilde, Joseph F.; Bhan, Aditya; Applied Catalysis A: General; vol. 502; (2015); p. 361 - 369; Art.No: 15420 View in Reaxys

Rx-ID: 40843882 View in Reaxys 8/74 Yield

Conditions & References Steady state kinetic measurements General procedure: The reactor system described in previous reports [22,23] wasused to gather steady state kinetic measurements on ether conver-sion. All experiments were performed at a reaction temperature of623 K using a mixture of liquid feeds, a He carrier gas (Grade 4.7,Minneapolis Oxygen Company) with a flowrate of 9.9 cm3s−1atambient pressure, and a mixture of 25.0percent CH4with a balance ofAr (Minneapolis Oxygen Company) fed at 0.017 cm3s−1at ambi-ent pressure to act as an internal standard for gas chromatographyanalysis. Ether conversions were kept to differential levels (<10percent)by using reactor beds containing 1.0 mg of catalyst.MPE (97percent Sigma– Aldrich with 3percent methanol as stabilizer) was fedto and vaporized in a flowing He stream to maintain a pressure of0.8 kPa for kinetic measurements of asymmetric ether conversion.Methanol (99.9percent Fisher Scientific) was also fed in these experi-ments to maintain a partial pressure of 0.2 kPa throughout thecatalyst bed. Methanol and 1PrOH dehydration kinetics were mea-sured in independent investigations by feeding 2.4–16.8 kPa ofmethanol and 1.4–9.4 kPa of 1-PrOH (99.9percent Sigma–Aldrich). Sim-ilarly, the kinetics of DEE conversion were measured by varyingthe partial pressure of ethanol-stabilized DEE (98.1percent DEE with 1.8percentethanol Fisher Scientific) between 0.4 and 8.8 kPa. Pyridine inhibi-tion measurements were carried out at 0.02–0.08 kPa of pyridine(99+percent, Sigma–Aldrich) with a co-feed of non-stabilized DEE (99.9percentSigma–Aldrich) at 1.4 kPa as well as, in an independent experiment,a co-feed of 3.5 kPa of ethanol and 1.3 kPa of water. For all exper-iments used to evaluate alcohol and ether conversion kinetics aswell as pyridine inhibition measurements, deionized water wasco-fed to establish feed partial pressures between 0.2 and 2.1 kPa. The composition of the reactor effluent was determined using anonline gas chromatograph (GC) with previously described analyti-cal protocols [22]. The 95percent confidence intervals reported in tablesand figures were evaluated from subsequent GC measurements atthe same experimental conditions. With aluminum oxide in methanol, T= 349.84 °C , p= 17.2517Torr , Inert atmosphere, Kinetics DeWilde, Joseph F.; Bhan, Aditya; Applied Catalysis A: General; vol. 502; (2015); p. 361 - 369; Art.No: 15420 View in Reaxys

6/22

2016-09-13 02:36:21

Rx-ID: 219762 View in Reaxys 9/74 Yield

Conditions & References

100 %

With hydrogen, Super-Hydride® in tetrahydrofuran, Time= 24h, T= 23 °C , p= 30402Torr , Inert atmosphere, Schlenk technique, Catalytic behavior Manna, Kuntal; Zhang, Teng; Carboni, Michal; Abney, Carter W.; Lin, Wenbin; Journal of the American Chemical Society; vol. 136; nb. 38; (2014); p. 13182 - 13185 View in Reaxys With nickel, T= 135 - 140 °C , Hydrogenation Sabatier; Mailhe; Annales de Chimie (Cachan, France); vol. <8>16; (1909); p. 107 View in Reaxys Sabatier; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 144; (1907); p. 880 View in Reaxys

Rx-ID: 28781715 View in Reaxys 10/74 Yield

Conditions & References With {[Cp*Ru(CO)2]2(μ-H)}(+)OTf(-), trifluorormethanesulfonic acid, hydrogen in sulfolane, T= 110 °C , p= 38787.1Torr Schlaf, Marcel; Ghosh, Prasenjit; Fagan, Paul J.; Hauptman, Elisabeth; Morris Bullock; Advanced Synthesis and Catalysis; vol. 351; nb. 5; (2009); p. 789 - 800 View in Reaxys

Rx-ID: 8934623 View in Reaxys 11/74 Yield

Conditions & References

54 % Chromat., 15 % Chromat.

SiH

With trifluorormethanesulfonic acid, hydrogen, [{CpRu(CO)2}2(μ-H)](+)*OTf(-), cyclopenta-1,3-diene in sulfolane, Time= 30h, T= 110 °C , p= 39003.1Torr , Product distribution Schlaf, Marcel; Ghosh, Prasenjit; Fagan, Paul J.; Hauptman, Elisabeth; Morris Bullock; Angewandte Chemie International Edition; vol. 40; nb. 20; (2001); p. 3887 - 3890 View in Reaxys

Rx-ID: 1233178 View in Reaxys 12/74 Yield

Conditions & References With triethylsilane, nickel dichloride Bourhis,R.; Frainnet,E.; Journal of Organometallic Chemistry; vol. 86; (1975); p. 205 - 218 View in Reaxys With [Rh(C5Me5)(1-(PMe(2,6-Me2C6H3))-2,6-Me2C6H3-κ-C6,P)][BArF] in dichloromethane-d2, Time= 1h, T= 25 °C , Inert atmosphere, Glove box Rubio, Miguel; Campos, Jesuus; Carmona, Ernesto; Organic Letters; vol. 13; nb. 19; (2011); p. 5236 - 5239 View in Reaxys

7/22

2016-09-13 02:36:21

Rx-ID: 2888137 View in Reaxys 13/74 Yield

Conditions & References With triethylsilane, perchloric acid in acetonitrile, T= 24.9 °C , Rate constant Fukuzumi, Shunichi; Fujita, Morifumi; Chemistry Letters; (1991); p. 2059 - 2062 View in Reaxys With triethylsilane, perchloric acid in acetonitrile, T= 24.9 °C Fukuzumi, Shunichi; Fujita, Morifumi; Chemistry Letters; (1991); p. 2059 - 2062 View in Reaxys With {[Cp*Ru(CO)2]2(μ-H)}(+)OTf(-), hydrogen in sulfolane, T= 110 °C , p= 38787.1Torr , Kinetics Schlaf, Marcel; Ghosh, Prasenjit; Fagan, Paul J.; Hauptman, Elisabeth; Morris Bullock; Advanced Synthesis and Catalysis; vol. 351; nb. 5; (2009); p. 789 - 800 View in Reaxys

14.6 With hydrogen, T= 125 °C , p= 760.051Torr , Flow reactor %ChroPham, Trung T.; Crossley, Steven. P.; Sooknoi, Tawan; Lobban, Lance L.; Resasco, Daniel E.; Mallinson, Rimat., 6.7 %Chromat. chard G.; Applied Catalysis A: General; vol. 379; nb. 1-2; (2010); p. 135 - 140 View in Reaxys

Rx-ID: 28121871 View in Reaxys 14/74 Yield

Conditions & References 5 :A reactor system was set up as described in Example 3 above. Etherification was performed using the reactor system with n-propanol as a feedstock, instead of methanol.The reaction conditions for this example are summarized below in Table 5. Notably, the reaction was tested at two different n-propanol flow rates, 7.00 g/min, and 3.52 g/ min. TABLE 5 Reactor Inlet Temp. Outlet Temp. n-PrOH Gases Preheater Inlet Reactor of heater of heater Front Back Flow collection Temp. Temp. Outlet exchange exchanger Pressure Pressure Rate Rate (° C.) (° C.) Temp. (° C.) (° C.) (° C.) (PSI) (PSI) (g/min) (L/min) 350 350 350 225 120 2500 2500 3.522 0.085 350 350 351 269 151 2500 2500 7.000 0.100 The resulting gas was shown to be combustible by igniting the same and observing it to burn. The mass balance (liquid in versus liquid out) of chemical reactions is shown below in Table 6. TABLE 6 n-PrOH n-PrOH n-PrOH Flow Flow Cold Well Conversion nPrOH to (g/min) (g/min) at Collection Rate n-PrOH Gases at Inlet Outlet (g/min) (g/min) Recovery Conversion 3.522 3.450 0.001 0.071 98.0percent 2.0percent 7.000 6.917 0.005 0.078 98.9percent 1.1percent A sample of gas from the reactor was collected in a gas tight cell for NIR (Near Infra-Red) analysis. The NIR spectrum for gas created with an n-propanol flow rate of 3.52 g/min is shown in FIG. 8. The NIR spectrum for gas created with an n-propanol flow rate of 7.00 g/min is shown in FIG. 9. These spectra were compared with standard curve NIR spectra for pure propane and pure propene.A sample of liquid from the reactor was collected and subjected to NMR (proton nuclear magnetic resonance) analysis. The NMR spectrum for liquid created with an n-propanol flow rate of 3.52 g/min is shown in FIG. 10. The NMR spectrum for liquid created with an n-propanol flow rate of 7.00 g/min is shown in FIG. 11. These were compared with an NMR spectrum for pure n-dipropyl ether.NIR and NMR results indicated that at a flow rate of 7.00 g/min, the composition of the gas is propene, propane, methane and carbon monoxide. The NIR and NRM results further show that at a flow rate of 3.52 g/min, the composition of the gas is propene, propane, methane, and carbon monoxide. The NIR and NRM results further show that at a flow rate of 11.64 g/min, little gas is produced.The data show that an alcohol feedstock including n-propanol can be converted into an ether reaction product using a metal oxide catalyst. With Titanium(IV) oxide, T= 350 - 351 °C , p= 129290Torr , Gas phase, Conversion of starting material Patent; McNeff, Clayton V.; McNeff, Larry C.; Yan, Bingwen; US2008/319236; (2008); (A1) English View in Reaxys

–

Na +

Rx-ID: 632367 View in Reaxys 15/74

8/22

2016-09-13 02:36:21

Yield

Conditions & References With ammonia Vaughn; Vogt; Nieuwland; Journal of the American Chemical Society; vol. 57; (1935); p. 511 View in Reaxys in N,N-dimethyl acetamide, Time= 0.5h, T= -10 - 20 °C Babiak, Peter; Nemcova, Adriana; Rulisek, Lubomir; Beier, Petr; Journal of Fluorine Chemistry; vol. 129; nb. 5; (2008); p. 397 - 401 View in Reaxys

OH O

OH OH

O O

Rx-ID: 36430044 View in Reaxys 16/74 Yield

Conditions & References

86 %

With poly(p-styrenesulfonic acid)-grafted carbon nanotubes, Time= 24h, T= 120 °C , Sealed tube, Green chemistry, chemoselective reaction Liu, Ruliang; Chen, Jinzhu; Huang, Xing; Chen, Limin; Ma, Longlong; Li, Xinjun; Green Chemistry; vol. 15; nb. 10; (2013); p. 2895 - 2903 View in Reaxys

O O

OH C

Rx-ID: 25905649 View in Reaxys 17/74 Yield

Conditions & References 6; 7 :Example 6Reaction Kinetics MeasurementsThe apparatus used to conduct reaction kinetics measurements for Pt-Re/C is described elsewhere (37). Fresh catalyst was loaded into a 1/2-inch outer diameter tubular stainless steel reactor. The catalyst bed was contained between an end plug of quartz wool (Alltech) and fused SiO2 granules (-4+16 mesh; Sigma-Aldrich) which aid in vaporization of the liquid feed. The Pt-Re/C catalyst powder was mixed with equal volumes of crushed SiO2 granules to decrease the pressure drop across the catalyst bed. For combined glycerol conversion with Fischer-Tropsch synthesis experiments, a bed of 1.0 wt percent Ru/TiO2 was loaded downstream of the Pt-Re/C bed. Type-K thermocouples (Omega) were attached to the outside of the reactor to measure reactor temperature, which was controlled with a series 16A type temperature controller (Dwyer Instruments). Fresh catalyst was reduced in flowing H2, as described in the previous section. Mass-flow controllers (5850 Brooks Instruments) were used to control the flow rate of H2. An HPLC pump (Model 301, Alltech) was used to introduce the aqueous feed solution into a 6-inch needle with a point 5 style tip (Hamilton) soldered into a section of -inch stainless steel tubing. This needle introduces liquid feed solutions into the reactor. The liquid effluent from the reactor was water-cooled in a double-pipe heat exchanger and was drained periodically for gas chromatography (GC) analysis (Agilent 6890 with a flame ionization detector (FID) and HP-Innowax column or Shimadzu GC-2010 with an FID detector and Rtx-5 column) and total organic carbon analysis (Shimadzu TOC-V CSH). Each effluent was tested for the presence of glycerol and other liquid byproducts.The effluent gas stream passed through a back-pressure regulator (GO Regulator, Model BP-60) which controlled the system pressure. The effluent gas was analyzed with gas chromatography: H2 with a Carle GC (series 8700) using a thermal conductivity detector (TCD), CO and CH4 using an HP 5890 GC with TCD and washed molecular sieve 5A 80/100 column (Alltech), and CO2 and light alkanes (C2-C3) using an HP 5890 GC with TCD and a Porapak QS 100/120 column (Alltech). All feed solutions were prepared by mixing glycerol (99.5percent, ACS reagent, Sigma-Aldrich) with deionized water. The apparatus used to conduct Fischer-

9/22

2016-09-13 02:36:21

Tropsch synthesis experiments is similar to that used for reaction kinetics measurements of Pt-Re/C, except the outlet lines from the reactor were heated at 373 K. The 2.9 wt percent Ru/TiO2 catalyst was mixed with an equal volume of crushed SiO2 granules to help dissipate the heat generated by the exothermic Fischer-Tropsch reaction and loaded into a 1/2-inch outer diameter, stainless steel tubular reactor. The liquid phase products were collected in a gasliquid separator and analyzed by GC (Shimadzu GC-2010 with an FID detector and Rtx-5 column). The effluent gas stream was analyzed for C1-C10 hydrocarbons with a Varian GC-MS (Saturn 3) using an FID detector and GS-Q capillary column. CO and CO2 were analyzed with an HP 5890 GC with TCD and a Porapak QS 100/120 column (Alltech). Ultra-high purity CO and H2 (Linde) were used, and aqueous solutions of acetone, acetol, and ethanol were introduced into the reactor in a similar way as the above glycerol solutions.Example 7Carbon Distributions(a) Conversion of Glycerol Over Pt-Re/C:FIG. 6 shows the conversion to gas-phase products and the CO/CO2 and H2/CO molar ratios, and Table 10 shows the outlet carbon distribution for conversion of a 30 wt percent glycerol solution over 520 mg of 10 wt percent Pt-Re/C (atomic ratio 1:1). The total inlet flow rate of carbon (as glycerol) for this experiment was 833 μmol min-1 (feed flow rate of 0.08 cm3 min-1), and the total conversion of glycerol was 91percent (58percent to gas phase products and 33percent to liquid phase products).Tables 11-13 show the outlet carbon distributions and carbon balances for conversion of 50 and 80 wt percent glycerol solutions over 1.0 g of 10 wt percent Pt-Re/C (atomic ratio 1:1) at 548 K and total pressures between 1-11 bar. The inlet liquid flow rate was 0.04 cm3 min-1 for the 50 wt percent solution and 0.03 cm3 min-1 for the 80 wt percent solution. The total conversion of glycerol was 100percent for each condition.(b) Fischer-Tropsch Synthesis Over Ru/TiO2 Tables 14 and 15 show the carbon distributions and carbon balances for Fischer-Tropsch synthesis of 150 cm3 min-1 of an H2/CO mixture with H2:CO=2 along with co-feeds of water and aqueous solutions of oxygenated molecules at 548 K over 4 g of 2.9 wt percent Ru/TiO2. Conversion of acetol co-feed to products was 100percent, whereas less than 20percent of ethanol formed products and less than 10percent of acetone formed products.(c) Combined Glycerol Conversion and FischerTropsch Synthesis:Tables 16-18 give the carbon product distribution for conversion of an 80 wt percent glycerol solution via conversion to synthesis gas with subsequent Fischer-Tropsch synthesis in a two-bed reactor at 548 K and 5 bar. FIG. 7 shows the molecular weight distribution for these experiments. This distribution deviates from AndersonSchulz-Flory kinetics. A glycerol feed flow rate of 0.04 cm3 min-1 was used with 1.0 g of 10 wt percent Pt-Re (1:1)/C and 1.7-3.0 g 1.0 wt percent Ru/TiO2.The sum of the species in the carbon distribution tables (Tables 10-12, 14, and 16-18) may differ slightly from the total COut values in the carbon balance tables (Tables 13 and 15). This difference results from the omission of minor product species from the carbon distribution tables. With water, 5.1Pt-4.9Re/C, 1Ru/TiO2, T= 274.84 °C , p= 3750.38Torr , Product distribution / selectivity Patent; Cortright, Randy D.; Dumesic, James A.; US2007/225383; (2007); (A1) English View in Reaxys

Rx-ID: 2888145 View in Reaxys 18/74 Yield 100 % Spectr.

Conditions & References With triethylsilane, trimethylsilyl trifluoromethanesulfonate in dichloromethane, Time= 2h, Ambient temperature Sassaman, Mark B.; Kotian, Kirtivan D.; Prakash, G. K. Surya; Olah, George A.; Journal of Organic Chemistry; vol. 52; nb. 19; (1987); p. 4314 - 4319 View in Reaxys

Rx-ID: 1603710 View in Reaxys 19/74 Yield

Conditions & References

23 %, 11 % With hydrogen, CoRh, iodine, Time= 2h, T= 180 °C , p= 420Torr , other promoter, other pressure, other temperature, Product distribution Jenner, Gerard; Journal of Organometallic Chemistry; vol. 346; (1988); p. 237 - 252 View in Reaxys

10/22

2016-09-13 02:36:21

Rx-ID: 9297659 View in Reaxys 20/74 Yield

Conditions & References

84 % Chromat., 5 % Chromat., 9 % Chromat., 2 % Chromat.

With tetrachloromethane, bis(acetylacetonate)oxovanadium, Time= 1h, T= 150 °C Khusnutdinov; Shchadneva; Baiguzina; Lavrentieva; Dzhemilev; Russian Chemical Bulletin; vol. 51; nb. 11; (2002); p. 2074 - 2079 View in Reaxys

Rx-ID: 34649531 View in Reaxys 21/74 Yield

Conditions & References With hydrogen, 3-methyl-phenol, T= 200 °C , Reagent/catalyst Nie, Lei; Resasco, Daniel E.; Applied Catalysis A: General; vol. 447-448; (2012); p. 14 - 21 View in Reaxys

Rx-ID: 208800 View in Reaxys 22/74 Yield

Conditions & References With aluminum oxide, T= 800 °C , katalytischen Hydratation der entstandenen Olefine Patent; Brown; Odell; US1873538; (1927) View in Reaxys

O HO

Rx-ID: 28781714 View in Reaxys 23/74 Yield 54 %Chromat.

Conditions & References With {[Cp*Ru(CO)2]2(μ-H)}(+)OTf(-), trifluorormethanesulfonic acid, hydrogen in sulfolane, Time= 30h, T= 110 °C , p= 38787.1Torr , Mechanism, Kinetics, Solvent, Pressure, Concentration, Temperature, Time, regioselective reaction Schlaf, Marcel; Ghosh, Prasenjit; Fagan, Paul J.; Hauptman, Elisabeth; Morris Bullock; Advanced Synthesis and Catalysis; vol. 351; nb. 5; (2009); p. 789 - 800 View in Reaxys

Al3+– 2 O Cl –

Rx-ID: 57824 View in Reaxys 24/74 Yield

Conditions & References With aluminium trichloride, T= 125 °C Betse; ; vol. 6; (1931); p. 150; Chem. Zentralbl.; vol. 102; nb. II; (1931); p. 1692 View in Reaxys

11/22

2016-09-13 02:36:21

OH OH

O HO

Rx-ID: 34649536 View in Reaxys 25/74 Yield

Conditions & References With hydrogen, Time= 0.25h, T= 200 °C Nie, Lei; Resasco, Daniel E.; Applied Catalysis A: General; vol. 447-448; (2012); p. 14 - 21 View in Reaxys

Rx-ID: 1603980 View in Reaxys 26/74 Yield

Conditions & References With Al3+-montmorillonite, Time= 4h, T= 200 °C , Yield given. Yields of byproduct given Ballantine, James A.; Davies, Mary; Purnell, Howard; Rayanakorn, Mongkon; Thomas, John M.; Williams, Kevin J.; Journal of the Chemical Society, Chemical Communications; nb. 9; (1981); p. 427 - 428 View in Reaxys

Rx-ID: 9866166 View in Reaxys 27/74 Yield

Conditions & References With sulfided Ni-Mo, hydrogen, T= 180 °C , p= 51714.8Torr , Product distribution, Further Variations: Temperatures Wang, Xueqin; Saleh, Ramzi Y.; Ozkan, Umit S.; Journal of Catalysis; vol. 231; nb. 1; (2005); p. 20 - 32 View in Reaxys O

Rx-ID: 30814240 View in Reaxys 28/74 Yield

Conditions & References With NaX faujasite, T= 220 - 240 °C Selva, Maurizio; Fabris, Massimo; Perosa, Alvise; Green Chemistry; vol. 13; nb. 4; (2011); p. 863 - 872 View in Reaxys

Rx-ID: 632843 View in Reaxys 29/74 Yield

Conditions & References With silver(l) oxide Linnemann; Justus Liebigs Annalen der Chemie; vol. 161; (1872); p. 44; Chemische Berichte; vol. 10; (1877); p. 1111 View in Reaxys With mercury(II) oxide Linnemann; Justus Liebigs Annalen der Chemie; vol. 161; (1872); p. 44; Chemische Berichte; vol. 10; (1877); p. 1111 View in Reaxys

12/22

2016-09-13 02:36:21

MgCl2

Rx-ID: 6672898 View in Reaxys 30/74 Yield

Conditions & References T= 250 °C , unter Druck Ipatieff; Monroe; Journal of the American Chemical Society; vol. 66; (1944); p. 1630 View in Reaxys

MgCl2

Rx-ID: 6672903 View in Reaxys 31/74 Yield

Conditions & References T= 255 °C , unter Druck Ipatieff; Monroe; Journal of the American Chemical Society; vol. 66; (1944); p. 1630 View in Reaxys O

Rx-ID: 732470 View in Reaxys 32/74 Yield

Conditions & References T= 117 °C , unter Durchleiten von Luft Slotta; Franke; Chemische Berichte; vol. 63; (1930); p. 678,685 View in Reaxys

O+ H

E O+

Rx-ID: 1832270 View in Reaxys 33/74 Yield

Conditions & References T= 24.9 °C , ΔG0, Thermodynamic data Bromilow, J.; Abboud, J. L. M.; Lebrilla, C. B.; Taft, R. W.; Scorrano, G.; Lucchini V.; Journal of the American Chemical Society; vol. 103; nb. 18; (1981); p. 5448 - 5453 View in Reaxys

O+ H

+HO

Rx-ID: 1832276 View in Reaxys 34/74 Yield

O+ H

O+

Rx-ID: 1900415 View in Reaxys 35/74 Yield

Conditions & References T= 335 °C , -ΔGo, Thermodynamic data

13/22

2016-09-13 02:36:21

Meot-Ner (Mautner), Michael; Journal of the American Chemical Society; vol. 104; nb. 1; (1982); p. 5 - 10 View in Reaxys

O+ H

Rx-ID: 1912358 View in Reaxys 36/74 Yield

Conditions & References T= 335 °C , -ΔGo, Thermodynamic data Meot-Ner (Mautner), Michael; Journal of the American Chemical Society; vol. 104; nb. 1; (1982); p. 5 - 10 View in Reaxys OH +

O+ H

Rx-ID: 2341681 View in Reaxys 37/74 Yield

O N

O+ H

Rx-ID: 2342399 View in Reaxys 38/74 Yield

Rx-ID: 2616043 View in Reaxys 39/74 Yield

Conditions & References in cyclohexane, T= 20 °C , Equilibrium constant Bellon, Louis; Taft, Robert W.; Abboud, Jose-Luis M.; Journal of Organic Chemistry; vol. 45; nb. 6; (1980); p. 1166 - 1168 View in Reaxys

O+ H

E O+

Rx-ID: 3383328 View in Reaxys 40/74 Yield

14/22

2016-09-13 02:36:21

O+ H

+HO

Rx-ID: 3383643 View in Reaxys 41/74 Yield

O+ H

O+

Rx-ID: 3788905 View in Reaxys 42/74 Yield

O+ H

OH +

Rx-ID: 3788916 View in Reaxys 43/74 Yield

Rx-ID: 1604013 View in Reaxys 44/74 Yield

Conditions & References With hydrogen, NiOs3(η-C5H5)(μ-H)2(Cu(PPh3))(CO)9, T= 230 °C , other temp., Product distribution Castagno, Fabrizio; Castiglioni, Mario; Sappa, Enrico; Tiripicchio, Antonio; Camellini, Marisa Tiripicchio; et al.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1989); p. 1477 - 1482 View in Reaxys

O Mg

Rx-ID: 2900183 View in Reaxys 45/74 Yield

Conditions & References With acetic acid, T= 25 °C , ΔH, Thermodynamic data Freijee, F. J. M.; Wal, G. Van Der; Schat, G.; Akkerman, O. S.; Bickelhaupt, F.; Journal of Organometallic Chemistry; vol. 240; nb. 3; (1982); p. 229 - 238 View in Reaxys

OH OH

15/22

2016-09-13 02:36:21

O O

Rx-ID: 3528574 View in Reaxys 46/74 Yield 61.3 mmol, 4.9 mmol, 42.3 mmol, 6.2 mmol, 8.5 mmol, 10.2 mmol

Conditions & References With Ru(CO)4I2, hydrogen in water, Time= 8h, T= 200 °C , other conditions; var. polyols and sugars, Product distribution Braca, Giuseppe; Galletti, Anna Maria Raspolli; Sbrana, Glauco; Journal of Organometallic Chemistry; vol. 417; nb. 1/2; (1991); p. 41 - 49 View in Reaxys

aluminium oxide

Rx-ID: 6672901 View in Reaxys 47/74 Yield

Conditions & References T= 250 °C , p= 7600Torr , mit Phosphaten der Gruppe III;Gleichgewicht der Aetherbildung Newitt; Semerano; Proceedings of the Royal Society of London, Series A: Mathematical, Physical and Engineering Sciences; vol. 157; (1936); p. 354 View in Reaxys Senderens; Gazzetta Chimica Italiana; vol. 66; (1936); p. 171 View in Reaxys

O P

Cl 2Cu

ClCu

Rx-ID: 26166848 View in Reaxys 48/74 Yield

Conditions & References in acetonitrile, Kinetics, byproducts: HCl; react. in a shaken flow-typ reactor (20-40°C) Dorfman, Ya. A.; Levina, L. V.; Polimbetova, G. S.; Emel'yanova, V. S.; Kel'man, I. V.; Karinskaya, A. S.; Sov. J. Coord. Chem. (Engl. Transl.); vol. 17; (1991); p. 145 - 152; Koordinatsionnaya Khimiya; vol. 17; (1991); p. 280 287 ; (from Gmelin) View in Reaxys F

Cl F

Rx-ID: 26710492 View in Reaxys 49/74 Yield

Conditions & References 100°C for 15 min, excess of alcohol Connet, J. E.; Chemistry and Industry (London, United Kingdom); (1965); p. 1695 - 1696 ; (from Gmelin) View in Reaxys 100°C for 15 min, excess of alcohol vol. F: PerFHalOrg.2; 1.3.4, page 137 - 166 ; (from Gmelin) View in Reaxys

ClCu

Cl 2Cu

O P

Cl 2Cu( 1-)

Rx-ID: 26100361 View in Reaxys 50/74 Yield

Conditions & References in acetonitrile, Kinetics, continnous-flow apparatus, passge of PH3/Ar mixt.; gas chrommatographie anal.

16/22

2016-09-13 02:36:21

Dorfman, Ya. A.; Levina, L. V.; Petrova, T. V.; Emel'yanova, V. S.; Polimbetova, G. S.; Journal of General Chemistry USSR (English Translation); vol. 59; (1989); p. 1292 - 1293; Zhurnal Obshchei Khimii; vol. 59; (1989); p. 1454 1455 ; (from Gmelin) View in Reaxys

–

K+

Rx-ID: 632730 View in Reaxys 51/74 Yield

Conditions & References Chancel; Justus Liebigs Annalen der Chemie; vol. 151; (1869); p. 305 View in Reaxys Cl

Cl O Cl

Rx-ID: 4966209 View in Reaxys 52/74 Yield

Conditions & References in cyclohexane, T= 24.9 °C , Equilibrium constant Abraham, Michael H.; Prior, David V.; Schulz, Ronald A.; Morris, Jeffrey J.; Taylor, Peter J.; Journal of the Chemical Society - Faraday Transactions; vol. 94; nb. 7; (1998); p. 879 - 885 View in Reaxys Cl

Cl 2

O Cl

Rx-ID: 4966322 View in Reaxys 53/74 Yield

O+ C– O

O Cl

N O

Rx-ID: 32682268 View in Reaxys 54/74 Yield

Conditions & References in n-heptane, T= 21.84 °C , Kinetics Hoijemberg, Pablo A.; Moss, Robert A.; Krogh-Jespersen, Karsten; Journal of Physical Chemistry A; vol. 116; nb. 1; (2012); p. 358 - 363 View in Reaxys O

Al2O3

Rx-ID: 6672906 View in Reaxys 55/74 Yield

Conditions & References T= 253 °C , p= 38000Torr , mit Phosphaten der Gruppe III;Prod.5-7:Diaethylaether,Propylisopropylaether,Aethylalkohol

17/22

2016-09-13 02:36:21

Newitt; Semerano; Proceedings of the Royal Society of London, Series A: Mathematical, Physical and Engineering Sciences; vol. 157; (1936); p. 354 View in Reaxys T= 295 °C , p= 38000Torr , mit Phosphaten der Gruppe III;Prod.5-7:Diaethylaether,Propylisopropylaether,Aethylalkohol Newitt; Semerano; Proceedings of the Royal Society of London, Series A: Mathematical, Physical and Engineering Sciences; vol. 157; (1936); p. 354 View in Reaxys

F HO

Rx-ID: 5804654 View in Reaxys 56/74 Yield

Conditions & References Zersetzen des Reaktionsprodukts mit Na2CO3-Loesung; reagiert analog mit Butanol-(1) McKenna; Sowa; Journal of the American Chemical Society; vol. 60; (1938); p. 125 View in Reaxys O

F HO

Rx-ID: 5806311 View in Reaxys 57/74 Yield

Conditions & References Behandeln des Reaktionsgemisches mit wss. Natriumcarbonat-Loesung McKenna; Sowa; Journal of the American Chemical Society; vol. 60; (1938); p. 125 View in Reaxys

Rx-ID: 6679995 View in Reaxys 58/74 Yield

Conditions & References T= 200 - 250 °C , ueber japanischer saurer Erde Kashima; Bulletin of the Chemical Society of Japan; vol. 4; (1929); p. 187,188; Chem. Zentralbl.; vol. 101; nb. I; (1930); p. 193 View in Reaxys

nickel

Rx-ID: 6947495 View in Reaxys 59/74 Yield

Conditions & References T= 135 - 140 °C , Hydrogenation Sabatier; Mailhe; Annales de Chimie (Cachan, France); vol. <8>16; (1909); p. 107 View in Reaxys Sabatier; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 144; (1907); p. 880 View in Reaxys

Rx-ID: 840059 View in Reaxys 60/74 Yield

Conditions & References T= 218 °C

18/22

2016-09-13 02:36:21

Wolkow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 21; (1889); p. 337 View in Reaxys

O O

S O

Rx-ID: 4858842 View in Reaxys 61/74 Yield

Conditions & References T= 40 - 70 °C , Ea, ΔF(excit.), ΔH(excit.), -ΔS(excit.), Rate constant, Thermodynamic data Sendega; Makitra; Pirig; Russian Journal of Organic Chemistry; vol. 32; nb. 10; (1996); p. 1438 - 1446 View in Reaxys

dehydrated alum

Rx-ID: 6672902 View in Reaxys 62/74 Yield

Conditions & References T= 185 °C Mailhe; de Godon; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 170; (1920); p. 329; Bulletin de la Societe Chimique de France; vol. <4>27; (1920); p. 121 View in Reaxys

dehydrated alum

Rx-ID: 6672905 View in Reaxys 63/74 Yield

Conditions & References T= 180 - 185 °C , analog reagiert mit Alkohol Mailhe; de Godon; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 170; (1920); p. 329; Bulletin de la Societe Chimique de France; vol. <4>27; (1920); p. 121 View in Reaxys

CH 2

H O

Rx-ID: 1844998 View in Reaxys 64/74 Yield

Conditions & References T= 20 °C , Irradiation, Kinetics Mehta, R. K. S.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 25; (1986); p. 60 - 62 View in Reaxys T= 100 °C , Irradiation, Kinetics Mehta, R. K. S.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 25; (1986); p. 60 - 62 View in Reaxys

19/22

2016-09-13 02:36:21

OH +

O O+ H

Rx-ID: 3368837 View in Reaxys 65/74 Yield

Conditions & References Gas phase. Determ. by ICR spect., Equilibrium constant, Thermodynamic data Bouchoux, G.; Houriet, R.; Tetrahedron Letters; vol. 25; nb. 50; (1984); p. 5755 - 5758 View in Reaxys

potassium alum

Rx-ID: 6672899 View in Reaxys 66/74 Yield

Conditions & References Geschwindigkeit der Reaktion Gajendragad; Jatkar; Journal of the Indian Chemical Society; vol. 12; (1935); p. 492 View in Reaxys

HO HO

S OO

Rx-ID: 6672900 View in Reaxys 67/74 Yield

Conditions & References bei hoeherer Temperatur je nach den Reaktionsbedingungen in wechselnder Ausbeute Senderens; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 176; (1923); p. 813; Annales de Chimie (Cachan, France); vol. <9>18; (1922); p. 122 View in Reaxys Senderens; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 181; (1925); p. 700; Annales de Chimie (Cachan, France); vol. <9>18; (1922); p. 123 View in Reaxys -1

F (v4)

B FF

natrium carbonate

O+

Rx-ID: 8316908 View in Reaxys 68/74 Yield

Conditions & References Meerwein et al.; Journal fuer Praktische Chemie (Leipzig); vol. <2>154; (1940); p. 121; Journal fuer Praktische Chemie (Leipzig); vol. <2>147; (1937); p. 274 View in Reaxys

HO HO

O O

S OO

Rx-ID: 6672904 View in Reaxys 69/74 Yield

Conditions & References Geschwindigkeit der Veresterung Wuyts; Lacourt; Bulletin des Societes Chimiques Belges; vol. 39; (1930); p. 161,165, 172 View in Reaxys

Al2O3

Rx-ID: 6679996 View in Reaxys 70/74

20/22

2016-09-13 02:36:21

Yield

Conditions & References bei hohen Temperaturen und Drucken Ipatjew; Chemische Berichte; vol. 37; (1904); p. 2997; Chem. Zentralbl.; vol. 75; nb. II; (1904); p. 1021 View in Reaxys

Al3+– 3 O

Al2O3 Rx-ID: 8267812 View in Reaxys 71/74

Yield

Conditions & References beim Zersetzen in der Hitze; Produkt 5:Wasserstoff Tischtschenko; Chem. Zentralbl.; vol. 71; nb. I; (1900); p. 585 View in Reaxys

Rx-ID: 57377 View in Reaxys 72/74 Yield

Conditions & References Mailhe; de Godon; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 170; (1920); p. 329; Bulletin de la Societe Chimique de France; vol. <4>27; (1920); p. 121 View in Reaxys

–O

Na +

O O

H 2N

Rx-ID: 632824 View in Reaxys 73/74 Yield

Conditions & References Walder; Chemische Berichte; vol. 20; (1887); p. 1751 View in Reaxys

Rx-ID: 6947494 View in Reaxys 74/74 Yield

Conditions & References Kuhn,R.; Butula,I.; Justus Liebigs Annalen der Chemie; vol. 718; (1968); p. 50 - 77 View in Reaxys Bourhis,R.; Frainnet,E.; Journal of Organometallic Chemistry; vol. 86; (1975); p. 205 - 218 View in Reaxys Jacobs; Schuetz; Journal of Organic Chemistry; vol. 26; (1961); p. 3472,3475 View in Reaxys Frainnet; Bourhis; Bulletin de la Societe Chimique de France; (1966); p. 2134 View in Reaxys Nefedov et al.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 22; (1973); p. 784; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; vol. 22; (1973); p. 807 View in Reaxys Schuikin et al.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); (1964); p. 1613; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1964); p. 1705 View in Reaxys Benedict et al.; Synthesis; (1979); p. 428 View in Reaxys Bagdasaryan et al.; Armyanskii Khimicheskii Zhurnal; vol. 30; (1977); p. 661,664, 666; ; vol. 88; nb. 89029d; (1978) View in Reaxys

21/22

2016-09-13 02:36:21

Lapkin; Povarnitsyna; J. Gen. Chem. USSR (Engl. Transl.); vol. 38; (1968); p. 643,620 View in Reaxys Tsurugi et al.; Journal of the American Chemical Society; vol. 91; (1969); p. 4587 View in Reaxys Bagdasaryan et al.; Armyanskii Khimicheskii Zhurnal; vol. 30; (1977); p. 246,249; ; vol. 87; nb. 135496h; (1977) View in Reaxys Fukuda; Nippon Kagaku Zasshi; vol. 83; (1962); p. 1130,1131; ; vol. 59; nb. 11310 View in Reaxys Russell; Hoy; Journal of Organic Chemistry; vol. 36; (1971); p. 2018 View in Reaxys 158 : IA-C4,6 bis-Propyl Ether (5t"'). EXAMPLE 158 IA-C4,6 bis-Propyl Ether (5t"'). NMR (CD3 OD) δ0.82-0.96 (m, 9H), 1.56 (m, CH2 CH2 CH3), 2.11 (s, OAc), 3.49, 3.64, 3.82 and 4.02 (4 m, CH2 O), 4.03 (d, J=2.0 Hz H-7), 4.98 (s, 1H), 5.02 (s, 1H), 5.0 (d, J=2.0 Hz, H-6), 5.08 (d, J=5 0 Hz, CHOAc), 5.12 (s, H-3), 7.10-7.37 (m, ArH); MS (FAB-) m/z 621. Patent; Merck and Co., Inc.; US5506262; (1996); (A1) English View in Reaxys

22/22

2016-09-13 02:36:21