CA1270000A - Conversion de composes aromatiques - Google Patents

Conversion de composes aromatiques

Info

Publication number: CA1270000A
Authority: CA; Canada
Prior art keywords: conversion; feedstock; zsm; benzene; toluene
Prior art date: 1985-06-27
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000500726A

Other languages

English (en)

Inventor

David Harold Olson

Ernest William Valyocsik

Paul Gerhard Rodewald

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Mobil Oil AS

Original Assignee

Mobil Oil AS

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1985-06-27

Filing date

1986-01-30

Publication date

1990-06-05

1986-01-30 Application filed by Mobil Oil AS filed Critical Mobil Oil AS

1990-06-05 Application granted granted Critical

1990-06-05 Publication of CA1270000A publication Critical patent/CA1270000A/fr

Status Expired legal-status Critical Current

Links

238000006243 chemical reaction Methods 0.000 title claims abstract description 39
238000000034 method Methods 0.000 title claims abstract description 25
230000008569 process Effects 0.000 title claims abstract description 21
125000003118 aryl group Chemical group 0.000 title description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 30
239000003054 catalyst Substances 0.000 claims abstract description 24
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 22
239000000203 mixture Substances 0.000 claims abstract description 22
239000010457 zeolite Substances 0.000 claims abstract description 22
-1 monocyclic alkyl-substituted benzene Chemical class 0.000 claims abstract description 20
229910021536 Zeolite Inorganic materials 0.000 claims abstract description 19
150000001491 aromatic compounds Chemical class 0.000 claims abstract description 12
238000002441 X-ray diffraction Methods 0.000 claims abstract description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 4
239000012084 conversion product Substances 0.000 claims abstract description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 33
239000008096 xylene Substances 0.000 claims description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
238000007323 disproportionation reaction Methods 0.000 claims description 6
230000029936 alkylation Effects 0.000 claims description 5
238000005804 alkylation reaction Methods 0.000 claims description 5
230000001747 exhibiting effect Effects 0.000 claims description 4
238000006317 isomerization reaction Methods 0.000 claims description 4
238000010555 transalkylation reaction Methods 0.000 claims description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
239000013078 crystal Substances 0.000 description 16
239000000047 product Substances 0.000 description 16
239000000463 material Substances 0.000 description 15
239000000377 silicon dioxide Substances 0.000 description 15
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 12
150000001768 cations Chemical class 0.000 description 12
235000012239 silicon dioxide Nutrition 0.000 description 12
229910052681 coesite Inorganic materials 0.000 description 11
229910052906 cristobalite Inorganic materials 0.000 description 11
229910052682 stishovite Inorganic materials 0.000 description 11
229910052905 tridymite Inorganic materials 0.000 description 11
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
238000001179 sorption measurement Methods 0.000 description 9
150000003738 xylenes Chemical class 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 8
150000003839 salts Chemical class 0.000 description 8
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 7
229910052782 aluminium Inorganic materials 0.000 description 7
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
150000002430 hydrocarbons Chemical class 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
229930195733 hydrocarbon Natural products 0.000 description 6
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
238000007669 thermal treatment Methods 0.000 description 6
239000004215 Carbon black (E152) Substances 0.000 description 5
239000002156 adsorbate Substances 0.000 description 5
229940100198 alkylating agent Drugs 0.000 description 5
239000002168 alkylating agent Substances 0.000 description 5
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
229910000323 aluminium silicate Inorganic materials 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
239000003513 alkali Substances 0.000 description 4
229910052784 alkaline earth metal Inorganic materials 0.000 description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 4
238000012360 testing method Methods 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 3
150000001336 alkenes Chemical class 0.000 description 3
235000012211 aluminium silicate Nutrition 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
238000006555 catalytic reaction Methods 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
238000005342 ion exchange Methods 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000002245 particle Substances 0.000 description 3
229910052697 platinum Inorganic materials 0.000 description 3
239000011148 porous material Substances 0.000 description 3
239000000376 reactant Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
239000005995 Aluminium silicate Substances 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000001354 calcination Methods 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
125000002091 cationic group Chemical group 0.000 description 2
230000008859 change Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000002131 composite material Substances 0.000 description 2
239000000470 constituent Substances 0.000 description 2
239000002178 crystalline material Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
229910052809 inorganic oxide Inorganic materials 0.000 description 2
239000007788 liquid Substances 0.000 description 2
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
239000011159 matrix material Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
229910044991 metal oxide Inorganic materials 0.000 description 2
150000004706 metal oxides Chemical class 0.000 description 2
239000002808 molecular sieve Substances 0.000 description 2
150000002892 organic cations Chemical group 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
229910052710 silicon Inorganic materials 0.000 description 2
239000010703 silicon Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
WGSMMQXDEYYZTB-UHFFFAOYSA-N 1,2,4,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C=C1C.CC1=CC(C)=C(C)C=C1C WGSMMQXDEYYZTB-UHFFFAOYSA-N 0.000 description 1
WZEYZMKZKQPXSX-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1.CC1=CC(C)=CC(C)=C1 WZEYZMKZKQPXSX-UHFFFAOYSA-N 0.000 description 1
CYHOMWAPJJPNMW-UHFFFAOYSA-N 8-methyl-8-azabicyclo[3.2.1]octan-3-ol Chemical compound C1C(O)CC2CCC1N2C CYHOMWAPJJPNMW-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
SKXYCTMELBVCFQ-UHFFFAOYSA-N CO.CC1=CC=CC=C1.C(C)C1=CC=CC=C1.C=C.C1=CC=CC=C1 Chemical compound CO.CC1=CC=CC=C1.C(C)C1=CC=CC=C1.C=C.C1=CC=CC=C1 SKXYCTMELBVCFQ-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
239000004115 Sodium Silicate Substances 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
239000002253 acid Substances 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001260 acyclic compounds Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001342 alkaline earth metals Chemical group 0.000 description 1
150000004996 alkyl benzenes Chemical class 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
HPTYUNKZVDYXLP-UHFFFAOYSA-N aluminum;trihydroxy(trihydroxysilyloxy)silane;hydrate Chemical group O.[Al].[Al].O[Si](O)(O)O[Si](O)(O)O HPTYUNKZVDYXLP-UHFFFAOYSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000001450 anions Chemical group 0.000 description 1
229940045985 antineoplastic platinum compound Drugs 0.000 description 1
238000010420 art technique Methods 0.000 description 1
239000011324 bead Substances 0.000 description 1
230000008901 benefit Effects 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
PURMVPJVXRMEDP-UHFFFAOYSA-N benzene;cumene;prop-1-ene Chemical compound CC=C.C1=CC=CC=C1.CC(C)C1=CC=CC=C1 PURMVPJVXRMEDP-UHFFFAOYSA-N 0.000 description 1
DALDUXIBIKGWTK-UHFFFAOYSA-N benzene;toluene Chemical compound C1=CC=CC=C1.CC1=CC=CC=C1 DALDUXIBIKGWTK-UHFFFAOYSA-N 0.000 description 1
LTPBRCUWZOMYOC-UHFFFAOYSA-N beryllium oxide Inorganic materials O=[Be] LTPBRCUWZOMYOC-UHFFFAOYSA-N 0.000 description 1
238000004523 catalytic cracking Methods 0.000 description 1
238000005341 cation exchange Methods 0.000 description 1
238000007385 chemical modification Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
238000005336 cracking Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
229910001649 dickite Inorganic materials 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
229910052621 halloysite Inorganic materials 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
239000012535 impurity Substances 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052909 inorganic silicate Inorganic materials 0.000 description 1
229910052622 kaolinite Inorganic materials 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
239000011707 mineral Substances 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
229940078552 o-xylene Drugs 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
125000000352 p-cymenyl group Chemical class C1(=C(C=C(C=C1)C)*)C(C)C 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
150000003058 platinum compounds Chemical class 0.000 description 1
CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000005855 radiation Effects 0.000 description 1
229910052761 rare earth metal Inorganic materials 0.000 description 1
150000002910 rare earth metals Chemical class 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
229910052702 rhenium Inorganic materials 0.000 description 1
WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
238000011935 selective methylation Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
229910052911 sodium silicate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
230000003068 static effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)

CA000500726A 1985-06-27 1986-01-30 Conversion de composes aromatiques Expired CA1270000A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US74924085A	1985-06-27	1985-06-27
US749,240		1985-06-27

Publications (1)

Publication Number	Publication Date
CA1270000A true CA1270000A (fr)	1990-06-05

Family

ID=25012882

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000500726A Expired CA1270000A (fr)	1985-06-27	1986-01-30	Conversion de composes aromatiques

Country Status (1)

Country	Link
CA (1)	CA1270000A (fr)

1986
- 1986-01-30 CA CA000500726A patent/CA1270000A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1993-12-06	MKLA	Lapsed

Publication	Publication Date	Title
US4698217A (en)	1987-10-06	Crystalline silicate ZSM-58 and process for its preparation using a methyltropinium cation
US4873067A (en)	1989-10-10	Zeolite ZSM-57
US4973781A (en)	1990-11-27	Zeolite ZSM-57 and catalysis therewith
US5001296A (en)	1991-03-19	Catalytic hydrodealkylation of aromatics
EP0147034B1 (fr)	1989-08-02	Procédé pour préparer la zéolithe ZSM-45 avec l'agent dirigeant diméthyldiéthylammonium
US5534656A (en)	1996-07-09	Organic compound conversion with MCM-58
EP0174121B1 (fr)	1992-02-05	Zéolite, son procédé de synthèse et conversion organique l'utilisant
US5030787A (en)	1991-07-09	Catalytic disproportionation/transalkylation utilizing a C9+ aromatics feed
US4954325A (en)	1990-09-04	Composition of synthetic porous crystalline material, its synthesis and use
US5236575A (en)	1993-08-17	Synthetic porous crystalline mcm-49, its synthesis and use
EP0001695B1 (fr)	1980-12-10	Aluminosilicate zéolitique cristallin, sa préparation et son utilisation
US5437855A (en)	1995-08-01	Synthetic porous crystalline MCM-58, its synthesis and use
US4982040A (en)	1991-01-01	Process for the catalytic disproportionation of methylnaphthalenes
US4973784A (en)	1990-11-27	Process for reducing the durene content of effluent resulting from the catalytic conversion of C1 -C4 oxygenates to gasoline
US5043512A (en)	1991-08-27	Alkylaromatic isomerization process
US5173281A (en)	1992-12-22	Synthesis of a synthetic porous crystalline material
EP0193282B1 (fr)	1990-12-05	Silicate cristallin et son procédé de préparation
US4637923A (en)	1987-01-20	Synthetic crystalline silicate
US4717780A (en)	1988-01-05	Catalytic aromatics conversion
US4665264A (en)	1987-05-12	Catalytic conversion
US5043513A (en)	1991-08-27	Catalytic hydrodealkylation of aromatics
US5670131A (en)	1997-09-23	Synthetic porous crystalline MCM-61, its synthesis and use
CA1270000A (fr)	1990-06-05	Conversion de composes aromatiques
US4752378A (en)	1988-06-21	Catalysis over crystalline silicate ZSM-58
US4670615A (en)	1987-06-02	Hydrocarbon compound conversion