o-Xylene (1,2-Dimethylbenzene) to Benzene

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13 reactions in Reaxys

2018-04-23 18h:23m:03s (UTC)

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Rx-ID: 46175562 View in Reaxys 1/13 Yield

Conditions & References With TNU-9 in neat (no solvent), Time= 0.25h, T= 250 °C , Catalytic behavior, Reagent/catalyst Gołbek, Kinga; Tarach, Karolina A.; Góra-Marek, Kinga; Dalton Transactions; vol. 46; nb. 30; (2017); p. 9934 - 9950 View in Reaxys

Rx-ID: 46175564 View in Reaxys 2/13 Yield

Conditions & References With ZSM-5_hs in neat (no solvent), Time= 0.25h, T= 250 °C , Catalytic behavior Gołbek, Kinga; Tarach, Karolina A.; Góra-Marek, Kinga; Dalton Transactions; vol. 46; nb. 30; (2017); p. 9934 - 9950 View in Reaxys

F

N

Ag+ O N

F

– 4 O

4 Ag+

F

1.62

O

F

N

O–

0.38

4 N

Rx-ID: 47422160 View in Reaxys 3/13 Yield 40 %

Conditions & References in methanol Wright, James S.; Vitórica-Yrezábal, Iñigo J.; Thompson, Stephen P.; Brammer, Lee; Chemistry - A European Journal; vol. 22; nb. 37; (2016); p. 13120 - 13126 View in Reaxys

Rx-ID: 25670711 View in Reaxys 4/13 Yield

Conditions & References III :Catalysts are prepared using similar procedures and components as in Example I and are evaluated in a similar manner to that described in Example II. The following table sets forth the catalyst compositions and performance. The benzene purity (BZ purity) is the mass percent benzene based upon total benzene and naphthenes and paraffins of 6 and 7 carbon atoms. The table also sets forth the temperature of the impregnation of each catalyst. The evaluation is at 75 percent conversion of ethylbenzene. With hydrogen, Al-phosphate-bound MFI zeolite, 220 ppm-m Pt, 0.19 mass-percent Sn; impregnated at 130 deg C, T= 391 °C , p= 9000.9Torr , Product distribution / selectivity Patent; Bogdan, Paula L.; Whitchurch, Patrick C.; Larson, Robert B.; Rekoske, James E.; Trufanov, Dimitri A.; US2007/60779; (2007); (A1) English View in Reaxys III :Catalysts are prepared using similar procedures and components as in Example I and are evaluated in a similar manner to that described in Example II. The following table sets forth the catalyst compositions and performance. The benzene purity (BZ

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purity) is the mass percent benzene based upon total benzene and naphthenes and paraffins of 6 and 7 carbon atoms. The table also sets forth the temperature of the impregnation of each catalyst. The evaluation is at 75 percent conversion of ethylbenzene. With hydrogen, Al-phosphate-bound MFI zeolite, 280 ppm-m Pt, 0.22 mass-percent Sn; impregnated at 100 deg C, T= 393 °C , p= 9000.9Torr , Product distribution / selectivity Patent; Bogdan, Paula L.; Whitchurch, Patrick C.; Larson, Robert B.; Rekoske, James E.; Trufanov, Dimitri A.; US2007/60779; (2007); (A1) English View in Reaxys III :Catalysts are prepared using similar procedures and components as in Example I and are evaluated in a similar manner to that described in Example II. The following table sets forth the catalyst compositions and performance. The benzene purity (BZ purity) is the mass percent benzene based upon total benzene and naphthenes and paraffins of 6 and 7 carbon atoms. The table also sets forth the temperature of the impregnation of each catalyst. The evaluation is at 75 percent conversion of ethylbenzene. With hydrogen, Al-phosphate-bound MFI zeolite, 280 ppm-m Pt, 0.22 mass-percent Sn; impregnated at 130 deg C, T= 396 °C , p= 9000.9Torr , Product distribution / selectivity Patent; Bogdan, Paula L.; Whitchurch, Patrick C.; Larson, Robert B.; Rekoske, James E.; Trufanov, Dimitri A.; US2007/60779; (2007); (A1) English View in Reaxys III :Catalysts are prepared using similar procedures and components as in Example I and are evaluated in a similar manner to that described in Example II. The following table sets forth the catalyst compositions and performance. The benzene purity (BZ purity) is the mass percent benzene based upon total benzene and naphthenes and paraffins of 6 and 7 carbon atoms. The table also sets forth the temperature of the impregnation of each catalyst. The evaluation is at 75 percent conversion of ethylbenzene. With hydrogen, Al-phosphate-bound MFI zeolite, 350 ppm-m Pt, 0.04 mass-percent Sn; impregnated at 130 deg C, T= 387 °C , p= 9000.9Torr , Product distribution / selectivity Patent; Bogdan, Paula L.; Whitchurch, Patrick C.; Larson, Robert B.; Rekoske, James E.; Trufanov, Dimitri A.; US2007/60779; (2007); (A1) English View in Reaxys III :Catalysts are prepared using similar procedures and components as in Example I and are evaluated in a similar manner to that described in Example II. The following table sets forth the catalyst compositions and performance. The benzene purity (BZ purity) is the mass percent benzene based upon total benzene and naphthenes and paraffins of 6 and 7 carbon atoms. The table also sets forth the temperature of the impregnation of each catalyst. The evaluation is at 75 percent conversion of ethylbenzene. With hydrogen, Al-phosphate-bound MFI zeolite, 370 ppm-m Pt, 0.04 mass-percent Sn; impregnated at 130 deg C, T= 387 °C , p= 9000.9Torr , Product distribution / selectivity Patent; Bogdan, Paula L.; Whitchurch, Patrick C.; Larson, Robert B.; Rekoske, James E.; Trufanov, Dimitri A.; US2007/60779; (2007); (A1) English View in Reaxys III :Catalysts are prepared using similar procedures and components as in Example I and are evaluated in a similar manner to that described in Example II. The following table sets forth the catalyst compositions and performance. The benzene purity (BZ purity) is the mass percent benzene based upon total benzene and naphthenes and paraffins of 6 and 7 carbon atoms. The table also sets forth the temperature of the impregnation of each catalyst. The evaluation is at 75 percent conversion of ethylbenzene. With hydrogen, Al-phosphate-bound MFI zeolite, 380 ppm-m Pt, 0.07 mass-percent Sn; impregnated at 130 deg C, T= 384 °C , p= 9000.9Torr , Product distribution / selectivity Patent; Bogdan, Paula L.; Whitchurch, Patrick C.; Larson, Robert B.; Rekoske, James E.; Trufanov, Dimitri A.; US2007/60779; (2007); (A1) English View in Reaxys III :Catalysts are prepared using similar procedures and components as in Example I and are evaluated in a similar manner to that described in Example II. The following table sets forth the catalyst compositions and performance. The benzene purity (BZ purity) is the mass percent benzene based upon total benzene and naphthenes and paraffins of 6 and 7 carbon atoms. The table also sets forth the temperature of the impregnation of each catalyst. The evaluation is at 75 percent conversion of ethylbenzene. With hydrogen, Al-phosphate-bound MFI zeolite, 430 ppm-m Pt, 0.096 mass-percent Sn; impregnated at 130 deg C, T= 388 °C , p= 9000.9Torr , Product distribution / selectivity

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Patent; Bogdan, Paula L.; Whitchurch, Patrick C.; Larson, Robert B.; Rekoske, James E.; Trufanov, Dimitri A.; US2007/60779; (2007); (A1) English View in Reaxys III :Catalysts are prepared using similar procedures and components as in Example I and are evaluated in a similar manner to that described in Example II. The following table sets forth the catalyst compositions and performance. The benzene purity (BZ purity) is the mass percent benzene based upon total benzene and naphthenes and paraffins of 6 and 7 carbon atoms. The table also sets forth the temperature of the impregnation of each catalyst. The evaluation is at 75 percent conversion of ethylbenzene. With hydrogen, Al-phosphate-bound MFI zeolite, 450 ppm-m Pt, 0.052 mass-percent Sn; impregnated at 130 deg C, T= 388 °C , p= 9000.9Torr , Product distribution / selectivity Patent; Bogdan, Paula L.; Whitchurch, Patrick C.; Larson, Robert B.; Rekoske, James E.; Trufanov, Dimitri A.; US2007/60779; (2007); (A1) English View in Reaxys III :Catalysts are prepared using similar procedures and components as in Example I and are evaluated in a similar manner to that described in Example II. The following table sets forth the catalyst compositions and performance. The benzene purity (BZ purity) is the mass percent benzene based upon total benzene and naphthenes and paraffins of 6 and 7 carbon atoms. The table also sets forth the temperature of the impregnation of each catalyst. The evaluation is at 75 percent conversion of ethylbenzene. With hydrogen, Al-phosphate-bound MFI zeolite, ~230 ppm-m Pt, 0.07 mass-percent Sn; impregnated at 130 deg C, T= 387 °C , p= 9000.9Torr , Product distribution / selectivity Patent; Bogdan, Paula L.; Whitchurch, Patrick C.; Larson, Robert B.; Rekoske, James E.; Trufanov, Dimitri A.; US2007/60779; (2007); (A1) English View in Reaxys II.7 :EXAMPLE Il[0064] In this example, a catalyst of the type described in Example I is used in a pilot plant. A feed of substantially the same C8 aromatic composition as in Example <n="20"/>I is used for a number of runs with out added benzene or toluene and with additional benzene or toluene as set forth below in Table 2. The pilot plant is operated at a pressure of 1200 kPa gauge, a hydrogen to hydrocarbon mole ratio of 4:1 , and a weight hourly space velocity of 10 hrλ[0065] A summary of the runs is provided in Table 2. A number of analyses are conducted at each temperature and composition over a several hour period after the pilot plant has arrived at steady state conditions for each temperature and additive level. The analyses reported below are means. With hydrogen, reduced 0.037wtpercentt platinum on aluminum-phosphate-bound MFI zeolite, T= 396 °C , Product distribution / selectivity Patent; UOP LLC; WO2009/117000; (2009); (A1) English View in Reaxys 11 :Example 11Catalyst samples prepared in Example 9 and Example 10 were tested according to the procedure and test conditions described in Example 4. The key performance parameters are listed in Table 4, and compared at 75 wt percent ethylbenzene conversion level. TABLE 4 Temperature Required for 75 wt percent Ethylbenzene Conversion, Benzene Selectivity, Benzene Purity, and Xylene Losses at 75 wt percent Ethylbenzene Conversion (EBC) Treq. for Benzene Benzene Xylene 75 wt percent EBC selectivity purity losses ° C. mol percent wt percent wt percent Catalyst 7 396 91.4 99.9 6.0 Catalyst 8 405 97.7 99.7 3.2 In each run p-xylene was produced in an amount which was a minimum of 98percent of its equilibrium value.It is clear that the surface modification dramatically alters the benzene selectivity and the xylene losses. The temperature required for 75 wt percent ethylbenzene conversion is however also increased slightly. The selectivity pattern of the treated catalyst is very attractive: the xylene losses are almost halved, while the benzene purity is retained. The benzene selectivity is increased to close to 100 mol percent. With hydrogen, zeolite/silica/alumina/Pt/Sn/ammonium hexafluorosilicate catalyst, T= 405 °C , p= 9750.98Torr , Product distribution / selectivity Patent; Berg-Slot, Johanna Jacoba; Domokos, Laszlo; Van Vegghel, Ingrid Maria; US2010/249479; (2010); (A1) English View in Reaxys

Rx-ID: 28272351 View in Reaxys 5/13

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Yield

Conditions & References 1; 2 :Example 1In Accordance with the Prior ArtThe facility in the process of Example 1 corresponds to that indicated in FIG. 1, and comprises a SMB unit with a single raffinate and a dealkylation isomerization. However, the lines shown as dotted lines in said figure (line 7 and the first portion of line 11) are not included in this facility.The flow chart remains the same, between the start and end of the cycle, but with a flow rate of the first feed which reduces and a PX production leaving the SMB which substantially reduces at the end of the cycle to be able to maintain the required minimum purity (99.7percent) for para-xylene. The yield of SMB also falls, along with the benzene production.Table 1 shows a material balance (in tonnes per hour) for the various streams referred to in FIG. 1 at the start of the cycle (fresh absorbent) and Table 2 shows the same material balance, bat at the end of the cycle (used absorbent, just before its replacement). The following abbreviations are used: PX=para-xylene; OX=ortho-xylene; MX=meta-xylene; EB=ethylbenzene; T=toluene; BZ=benzene; LPG=C4/C3, and possibly small quantities of C2 and C1. TABLE 1 Start of Feed SMB Feed Outlet Inlet Outlet cycle 1 inlet R E Ea 2 DISP CRYST PX1 ML HPPX ISOM EB 17 22.4 22.4 - - - - - - - - 5.4 PX 19.6 90.8 2.7 88.1 - - 17 17 11.9 5.1 100 66.1 MX 40 177 177 - - - 2 2 - 2 - 135 OX 20.4 90.2 90.2 - - - 1 1 - 1 - 68.8 T - - - - - 42 -(*) - - - - - BZ - - - - - - 20 - - - - 12.4 LPG and - - - - - - 2 - - - - 4.6 losses Total 97 380.4 292.3 88.1 0 42 42 20 11.9 8.1 100 292.3 (*)After recycling unconverted toluene. The conversion per pass is typically 30percent. The purity of the distilled extract E is 99.85percent at the start of the cycle, with a high yield (at the SMB) of 97percent. TABLE 2 End of Feed SMB Feed Outlet Inlet Outlet cycle 1 inlet R E Ea 2 DISP CRYST PX1 ML HPPX ISOM EB 13.6 17.89 17.89 - - - - - - - 4.29 PX 15.68 78.37 6.27 72.1 - - 17 17 11.9 5.1 84 57.59 MX 32 151.53 151.53 - - - 2 2 - 2 - 117.53 OX 16.32 77.26 77.26 - - - 1 1 - 1 - 59.94 T - - - - - 42 -(*) - - - - - BZ - - - - - - 20 - - - - 9.88 LPG and - - - - - - 2 - - - - 3.72 losses Total 77.6 325.05 252.95 72.1 0 42 42 20 11.9 8.1 84 292.3 It can be seen that at the end of the cycle, due to ageing of the absorbent, the rate of supply of the first feed (and thus the overhead cut from column D) has had to be reduced by about 20percent to maintain a minimum purity of the extract of 99.7percent. In parallel, the PX yield from the SMB has dropped, moving from 97percent to 92percent. This results in a drop in overall production (HPPX) of 16percent, which is a big drop. Further, the reduction in feed causes a drop in the overall production of benzene by about 8percent. , Product distribution / selectivity Patent; Hotier, Gerard; Seo Il, Kim; US2009/69612; (2009); (A1) English View in Reaxys

Rx-ID: 11104697 View in Reaxys 6/13 Yield

Conditions & References With oxygen, T= 1172.84 °C , p= 5890.4Torr , Product distribution, Further Variations: Temperatures, Pressures Battin-Leclerc; Bounaceur; Belmekki; Glaude; International Journal of Chemical Kinetics; vol. 38; nb. 4; (2006); p. 284 302 View in Reaxys

aliphatics and others aromatics Rx-ID: 7068572 View in Reaxys 7/13 Yield

Conditions & References With MnAPO-36, T= 399.9 °C , others molecular sieves as catalysts, Product distribution Akolekar, Deepak B.; Journal of the Chemical Society, Faraday Transactions; vol. 90; nb. 7; (1994); p. 1041 - 1046 View in Reaxys

HO

Rx-ID: 3924836 View in Reaxys 8/13

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Yield

Conditions & References With H-mordenite, iron, T= 430 °C , p= 11250.9Torr , other xylenes; var. zeolites as catalyst; var. temp. and pressures, Product distribution Agaev, A. A.; Tagiev, D. B.; J. Appl. Chem. USSR (Engl. Transl.); vol. 64; nb. 8.2; (1991); p. 1781 - 1785,1639 - 1642 View in Reaxys

O 2

S

O–

(v4)

0.5

Pd2+

N (v4) Pd SP-4 N (v4) Cl

Rx-ID: 26886121 View in Reaxys 9/13 Yield

Conditions & References

11 %

With [2,2]bipyridinyl, sodium chloride in o-xylene=o-xylol, byproducts: {PdCl2(C10H8N2)}; (N2); heated at 90-95°C for 1 h; removed in vacuo; extd. (acetone); added NaCl in water; at room temp. for 1 day; evapd. to dryness; extd. (CHCl3); chromd. (CHCl3); added (C5H4N)2 in benzene; at room temp.for 1 day; chromd. (CHCl3); collected; recrystd. (CHCl3-hexane); elem. anal. Fuchita, Yoshio; Kawakami, Mina; Shimoke, Kohji; Polyhedron; vol. 10; (1991); p. 2037 - 2044 ; (from Gmelin) View in Reaxys

Rx-ID: 1969084 View in Reaxys 10/13 Yield

Conditions & References With aluminum oxide, silica gel, DM-14, T= 250 °C , other temperatures and catalysts, Product distribution Minachev, Kh. M.; Kondrat'ev, D. A.; Klyachko, A. L.; Borodkin, A. Yu.; Glonti, G. O.; et. al.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; (1984); p. 232 - 239; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1984); p. 266 - 274 View in Reaxys

(v3)

Cl O

(v6)

W

Cl

(v4)

C 2-

Cl Cl

(v3)

0.5

W (v6)

O Mg2+

Rx-ID: 27028259 View in Reaxys 11/13 Yield

Conditions & References in tetrahydrofuran, to stirred soln. of WCl4O in THF at -78°C was slowly added a THFsoln. of Mg-reagent, after slowly warmed to ca. 50°C for 1 h solvent was removed in vac., residue was extd. with Et2O; concd., cooled to -30°C, recrystd. from C6H6, crystd. in vac. Lappert, Michael F.; Raston, Colin L.; Rowbottom, Graham L.; Skelton, Brian W.; White, Allan H.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1984); p. 883 - 892 ; (from Gmelin) View in Reaxys

hydrogen

nickel silicon dioxide

C

Rx-ID: 7066964 View in Reaxys 12/13

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Yield

Conditions & References T= 420 °C , Kinetics Melander; Arkiv foer Kemi; vol. 21 A; nb. 18; (1946); p. 1,7 View in Reaxys

hydrogen

C

Rx-ID: 7066962 View in Reaxys 13/13 Yield

Conditions & References T= 480 °C , p= 73550.8Torr Hall; Journal of the Society of Chemical Industry, London; vol. 54; (1935); p. 208 T, 212 T View in Reaxys

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