CA1185267A - Conversion de xylenes renfermant de l'ethylbenzene - Google Patents

Conversion de xylenes renfermant de l'ethylbenzene

Info

Publication number: CA1185267A
Authority: CA; Canada
Prior art keywords: catalyst; conversion process; process according; zeolite; weight
Prior art date: 1982-11-26
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

CA000416502A

Other languages

English (en)

Inventor

Atsushi Ebitani

Kazuyoshi Iwayama

Takehisa Inoue

Atsuo Kanai

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.)

Toray Industries Inc

Original Assignee

Toray Industries Inc

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.)

1982-11-26

Filing date

1982-11-26

Publication date

1985-04-09

1982-11-26 Application filed by Toray Industries Inc filed Critical Toray Industries Inc

1982-11-26 Priority to CA000416502A priority Critical patent/CA1185267A/fr

1985-04-09 Application granted granted Critical

1985-04-09 Publication of CA1185267A publication Critical patent/CA1185267A/fr

Status Expired legal-status Critical Current

Links

YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 title claims abstract description 58
239000008096 xylene Substances 0.000 title claims abstract description 30
150000003738 xylenes Chemical class 0.000 title claims abstract description 26
238000006243 chemical reaction Methods 0.000 title claims description 39
239000003054 catalyst Substances 0.000 claims abstract description 75
239000010457 zeolite Substances 0.000 claims abstract description 57
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 33
229910021536 Zeolite Inorganic materials 0.000 claims abstract description 32
239000002253 acid Substances 0.000 claims abstract description 23
-1 for example Chemical compound 0.000 claims abstract description 20
229910052680 mordenite Inorganic materials 0.000 claims abstract description 20
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
239000001257 hydrogen Substances 0.000 claims abstract description 19
238000006317 isomerization reaction Methods 0.000 claims abstract description 7
230000006204 deethylation Effects 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 38
WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 12
229910052702 rhenium Inorganic materials 0.000 claims description 11
150000001768 cations Chemical class 0.000 claims description 9
150000001875 compounds Chemical class 0.000 claims description 9
238000002441 X-ray diffraction Methods 0.000 claims description 8
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 7
150000002500 ions Chemical class 0.000 claims description 7
229910052750 molybdenum Inorganic materials 0.000 claims description 7
239000011733 molybdenum Substances 0.000 claims description 7
229910052721 tungsten Inorganic materials 0.000 claims description 7
239000010937 tungsten Substances 0.000 claims description 7
229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 3
229910052720 vanadium Inorganic materials 0.000 claims description 3
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
150000002894 organic compounds Chemical class 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 1
125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
239000012808 vapor phase Substances 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
239000000047 product Substances 0.000 description 25
239000000843 powder Substances 0.000 description 24
229940058172 ethylbenzene Drugs 0.000 description 22
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
238000005342 ion exchange Methods 0.000 description 17
239000000203 mixture Substances 0.000 description 17
239000000243 solution Substances 0.000 description 17
238000011282 treatment Methods 0.000 description 17
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 14
239000012153 distilled water Substances 0.000 description 14
238000003756 stirring Methods 0.000 description 14
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 13
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 12
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 12
238000001354 calcination Methods 0.000 description 10
235000012239 silicon dioxide Nutrition 0.000 description 10
239000011230 binding agent Substances 0.000 description 9
229910052681 coesite Inorganic materials 0.000 description 9
229910052906 cristobalite Inorganic materials 0.000 description 9
239000000377 silicon dioxide Substances 0.000 description 9
229910052682 stishovite Inorganic materials 0.000 description 9
229910052905 tridymite Inorganic materials 0.000 description 9
ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical group [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 8
229910052751 metal Inorganic materials 0.000 description 8
239000002184 metal Substances 0.000 description 8
239000002245 particle Substances 0.000 description 8
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
235000019270 ammonium chloride Nutrition 0.000 description 7
238000004458 analytical method Methods 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
238000001035 drying Methods 0.000 description 7
238000004898 kneading Methods 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
150000003863 ammonium salts Chemical class 0.000 description 6
230000000694 effects Effects 0.000 description 6
GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 6
YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 6
238000005406 washing Methods 0.000 description 6
QSHYGLAZPRJAEZ-UHFFFAOYSA-N 4-(chloromethyl)-2-(2-methylphenyl)-1,3-thiazole Chemical compound CC1=CC=CC=C1C1=NC(CCl)=CS1 QSHYGLAZPRJAEZ-UHFFFAOYSA-N 0.000 description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 5
229910052784 alkaline earth metal Inorganic materials 0.000 description 5
150000001342 alkaline earth metals Chemical class 0.000 description 5
239000011575 calcium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
229910052791 calcium Inorganic materials 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
150000007522 mineralic acids Chemical class 0.000 description 4
229910052697 platinum Inorganic materials 0.000 description 4
239000002243 precursor Substances 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
238000000465 moulding Methods 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
QUBBAXISAHIDNM-UHFFFAOYSA-N 1-ethyl-2,3-dimethylbenzene Chemical group CCC1=CC=CC(C)=C1C QUBBAXISAHIDNM-UHFFFAOYSA-N 0.000 description 2
HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 2
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical group [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 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
ANBBXQWFNXMHLD-UHFFFAOYSA-N aluminum;sodium;oxygen(2-) Chemical compound [O-2].[O-2].[Na+].[Al+3] ANBBXQWFNXMHLD-UHFFFAOYSA-N 0.000 description 2
APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 2
239000011609 ammonium molybdate Substances 0.000 description 2
229940010552 ammonium molybdate Drugs 0.000 description 2
235000018660 ammonium molybdate Nutrition 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229910001424 calcium ion Chemical group 0.000 description 2
238000004821 distillation Methods 0.000 description 2
230000001747 exhibiting effect Effects 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
238000005470 impregnation Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000011259 mixed solution Substances 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
125000001477 organic nitrogen group Chemical group 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
239000012266 salt solution Substances 0.000 description 2
238000000926 separation method Methods 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
239000002002 slurry Substances 0.000 description 2
229910001388 sodium aluminate Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000011973 solid acid Substances 0.000 description 2
DHEQXMRUPNDRPG-UHFFFAOYSA-N strontium nitrate Chemical compound [Sr+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O DHEQXMRUPNDRPG-UHFFFAOYSA-N 0.000 description 2
NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical group [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
241000765309 Vanadis Species 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910001413 alkali metal ion Inorganic materials 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
229910000323 aluminium silicate Inorganic materials 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
239000001099 ammonium carbonate Substances 0.000 description 1
235000012501 ammonium carbonate Nutrition 0.000 description 1
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
YVBOZGOAVJZITM-UHFFFAOYSA-P ammonium phosphomolybdate Chemical compound [NH4+].[NH4+].[NH4+].[NH4+].[O-]P([O-])=O.[O-][Mo]([O-])(=O)=O YVBOZGOAVJZITM-UHFFFAOYSA-P 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
238000010923 batch production Methods 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
230000001588 bifunctional effect Effects 0.000 description 1
150000004653 carbonic acids Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000004517 catalytic hydrocracking Methods 0.000 description 1
239000007795 chemical reaction product 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
238000010276 construction Methods 0.000 description 1
238000005336 cracking Methods 0.000 description 1
230000006378 damage Effects 0.000 description 1
238000006900 dealkylation reaction Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000006866 deterioration Effects 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
238000007323 disproportionation reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
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 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910001425 magnesium ion Chemical group 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
229910000476 molybdenum oxide Inorganic materials 0.000 description 1
VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000002407 reforming Methods 0.000 description 1
229910003449 rhenium oxide Inorganic materials 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
UONOETXJSWQNOL-UHFFFAOYSA-N tungsten carbide Chemical compound [W+]#[C-] UONOETXJSWQNOL-UHFFFAOYSA-N 0.000 description 1
ITRNXVSDJBHYNJ-UHFFFAOYSA-N tungsten disulfide Chemical compound S=[W]=S ITRNXVSDJBHYNJ-UHFFFAOYSA-N 0.000 description 1
229910001930 tungsten oxide Inorganic materials 0.000 description 1

Landscapes

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

CA000416502A 1982-11-26 1982-11-26 Conversion de xylenes renfermant de l'ethylbenzene Expired CA1185267A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000416502A CA1185267A (fr)	1982-11-26	1982-11-26	Conversion de xylenes renfermant de l'ethylbenzene

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000416502A CA1185267A (fr)	1982-11-26	1982-11-26	Conversion de xylenes renfermant de l'ethylbenzene

Publications (1)

Publication Number	Publication Date
CA1185267A true CA1185267A (fr)	1985-04-09

Family

ID=4124031

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000416502A Expired CA1185267A (fr)	1982-11-26	1982-11-26	Conversion de xylenes renfermant de l'ethylbenzene

Country Status (1)

Country	Link
CA (1)	CA1185267A (fr)

1982
- 1982-11-26 CA CA000416502A patent/CA1185267A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2002-04-10	MKEC	Expiry (correction)
2002-11-26	MKEX	Expiry

Publication	Publication Date	Title
US4467129A (en)	1984-08-21	Conversion of xylenes containing ethylbenzene
US5243116A (en)	1993-09-07	Alkylation of aromatic compounds
CA1173017A (fr)	1984-08-21	Zeolites nu-5
JP4348651B2 (ja)	2009-10-21	ゼオライトｉｍ―５、その調製方法およびその触媒的適用
US5952536A (en)	1999-09-14	Aromatics and toluene/trimethylbenzene gas phase transalkylation processes
RU2141934C1 (ru)	1999-11-27	Способ получения кумола
EP0307113B1 (fr)	1991-12-04	Procédé pour la conversion d'éthylbenzène contenu dans un mélange d'hydrocarbures aromatiques en C8
EP0109962B1 (fr)	1986-07-16	Procédé de conversion de xylènes en présence d'éthylbenzène
JP2020524072A (ja)	2020-08-13	重質改質油をキシレンに変換するためのゼオライト複合触媒
EP0306181B1 (fr)	1992-09-16	Synthèse de zéolite en deux étapes
EP0042754B1 (fr)	1984-05-30	Procédé de conversion de xylènes contenant de l'éthylbenzène
EP0589876B1 (fr)	1995-11-29	Alkylation de composes aromatiques
EP0433932B1 (fr)	1996-05-01	Procédé pour l'alkylation de benzène ou de benzène substitué ou pour la transalkylation de benzène alkylé
JPH0576453B2 (fr)	1993-10-22
US4670617A (en)	1987-06-02	Propylation of toluene with a high surface area, zinc-modified, crystalline silica molecular sieve
CA1185267A (fr)	1985-04-09	Conversion de xylenes renfermant de l'ethylbenzene
Wu et al.	1997	Synthesis of ferrisilicate with the MCM-22 structure
JPH0230299B2 (fr)	1990-07-05
EP0065364B1 (fr)	1984-12-27	Procédé pour l'isomérisation d'alkylbenzènes
JPS6245849B2 (fr)	1987-09-29
JPH11253809A (ja)	1999-09-21	芳香族アルキル化用のＧａ−βゼオライト触媒
JPH1071334A (ja)	1998-03-17	アルキル芳香族炭化水素のトランスアルキル化反応用触媒組成物及びキシレンの製造方法
Pavia et al.	1997	Perego et a
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