DE2441516C3 - Verwendung von wenigstens teilweise durch Wasserstoffionen ausgetauschten Zeolithen zum Isomerisieren von Xylolen - Google Patents
Verwendung von wenigstens teilweise durch Wasserstoffionen ausgetauschten Zeolithen zum Isomerisieren von XylolenInfo
- Publication number
- DE2441516C3 DE2441516C3 DE2441516A DE2441516A DE2441516C3 DE 2441516 C3 DE2441516 C3 DE 2441516C3 DE 2441516 A DE2441516 A DE 2441516A DE 2441516 A DE2441516 A DE 2441516A DE 2441516 C3 DE2441516 C3 DE 2441516C3
- Authority
- DE
- Germany
- Prior art keywords
- xylene
- ethylbenzene
- zsm
- xylenes
- catalyst
- Prior art date
- 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
Links
- 150000003738 xylenes Chemical class 0.000 title claims description 33
- 239000010457 zeolite Substances 0.000 title claims description 31
- 239000001257 hydrogen Substances 0.000 title claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 title claims description 15
- -1 hydrogen ions Chemical class 0.000 title claims description 6
- 239000008096 xylene Substances 0.000 title description 58
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 149
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 239000007791 liquid phase Substances 0.000 claims description 10
- 239000011230 binding agent Substances 0.000 claims description 8
- 238000000638 solvent extraction Methods 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 67
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 52
- 239000003054 catalyst Substances 0.000 description 47
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 41
- 238000006317 isomerization reaction Methods 0.000 description 30
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 28
- 238000000034 method Methods 0.000 description 27
- 230000008569 process Effects 0.000 description 22
- 229940078552 o-xylene Drugs 0.000 description 19
- 229910021536 Zeolite Inorganic materials 0.000 description 18
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 17
- 238000007323 disproportionation reaction Methods 0.000 description 13
- 125000003118 aryl group Chemical group 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 238000010555 transalkylation reaction Methods 0.000 description 8
- 238000004821 distillation Methods 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000004508 fractional distillation Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 230000032683 aging Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000004517 catalytic hydrocracking Methods 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000001640 fractional crystallisation Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 230000003679 aging effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000000571 coke Substances 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical group O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GEAHSFIOZABQIK-UHFFFAOYSA-N 1,2-xylene;1,3-xylene Chemical group CC1=CC=CC(C)=C1.CC1=CC=CC=C1C GEAHSFIOZABQIK-UHFFFAOYSA-N 0.000 description 1
- QUBBAXISAHIDNM-UHFFFAOYSA-N 1-ethyl-2,3-dimethylbenzene Chemical group CCC1=CC=CC(C)=C1C QUBBAXISAHIDNM-UHFFFAOYSA-N 0.000 description 1
- HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 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 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- SYWDWCWQXBUCOP-UHFFFAOYSA-N benzene;ethene Chemical compound C=C.C1=CC=CC=C1 SYWDWCWQXBUCOP-UHFFFAOYSA-N 0.000 description 1
- NHVNKPKDUATJOK-UHFFFAOYSA-N benzene;ethylbenzene Chemical compound C1=CC=CC=C1.CCC1=CC=CC=C1 NHVNKPKDUATJOK-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
- 238000001354 calcination Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- HBGFKRXFJPVYFB-UHFFFAOYSA-N ethylbenzene;1,4-xylene Chemical group CCC1=CC=CC=C1.CC1=CC=C(C)C=C1 HBGFKRXFJPVYFB-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002884 o-xylenes Chemical class 0.000 description 1
- 150000002938 p-xylenes Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical class CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/7034—MTW-type, e.g. ZSM-12, NU-13, TPZ-12 or Theta-3
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/2702—Catalytic processes not covered by C07C5/2732 - C07C5/31; Catalytic processes covered by both C07C5/2732 and C07C5/277 simultaneously
- C07C5/2708—Catalytic processes not covered by C07C5/2732 - C07C5/31; Catalytic processes covered by both C07C5/2732 and C07C5/277 simultaneously with crystalline alumino-silicates, e.g. molecular sieves
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/2729—Changing the branching point of an open chain or the point of substitution on a ring
- C07C5/2732—Catalytic processes
- C07C5/2737—Catalytic processes with crystalline alumino-silicates, e.g. molecular sieves
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/10—After treatment, characterised by the effect to be obtained
- B01J2229/26—After treatment, characterised by the effect to be obtained to stabilize the total catalyst structure
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/30—After treatment, characterised by the means used
- B01J2229/42—Addition of matrix or binder particles
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00397038A US3856871A (en) | 1973-09-13 | 1973-09-13 | Xylene isomerization |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2441516A1 DE2441516A1 (de) | 1975-03-20 |
| DE2441516B2 DE2441516B2 (de) | 1979-04-26 |
| DE2441516C3 true DE2441516C3 (de) | 1979-12-13 |
Family
ID=23569629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2441516A Expired DE2441516C3 (de) | 1973-09-13 | 1974-08-30 | Verwendung von wenigstens teilweise durch Wasserstoffionen ausgetauschten Zeolithen zum Isomerisieren von Xylolen |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US3856871A (enExample) |
| JP (1) | JPS5341657B2 (enExample) |
| AR (1) | AR224491A1 (enExample) |
| BE (1) | BE819848A (enExample) |
| CA (1) | CA1026384A (enExample) |
| CS (1) | CS189668B2 (enExample) |
| DD (1) | DD113741B3 (enExample) |
| DE (1) | DE2441516C3 (enExample) |
| ES (1) | ES428167A1 (enExample) |
| FR (1) | FR2243919B1 (enExample) |
| GB (1) | GB1444702A (enExample) |
| IN (1) | IN142292B (enExample) |
| IT (1) | IT1021337B (enExample) |
| NL (1) | NL173846C (enExample) |
| PL (1) | PL94144B1 (enExample) |
| RO (1) | RO71348A (enExample) |
| SU (1) | SU890971A3 (enExample) |
| ZA (1) | ZA743917B (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4101596A (en) * | 1977-01-10 | 1978-07-18 | Mobil Oil Company | Low pressure xylene isomerization |
| US4101595A (en) * | 1977-05-02 | 1978-07-18 | Mobil Oil Corporation | Conversion of ethyl benzene to para xylene |
| US4163028A (en) * | 1977-07-22 | 1979-07-31 | Mobil Oil Corporation | Xylene isomerization |
| US4159283A (en) * | 1978-04-07 | 1979-06-26 | Mobil Oil Corporation | Isomerization process |
| US4245130A (en) * | 1978-06-02 | 1981-01-13 | The British Petroleum Company Limited | Isomerization of alkyl aromatics using a gallium containing aluminosilicate catalyst |
| USRE31782E (en) * | 1978-06-09 | 1984-12-25 | Mobil Oil Corporation | Xylene isomerization |
| US4159282A (en) * | 1978-06-09 | 1979-06-26 | Mobil Oil Corporation | Xylene isomerization |
| US4188282A (en) * | 1978-06-12 | 1980-02-12 | Mobile Oil Corporation | Manufacture of benzene, toluene and xylene |
| US4218573A (en) * | 1978-06-12 | 1980-08-19 | Mobil Oil Corporation | Xylene isomerization |
| US4224141A (en) * | 1979-05-21 | 1980-09-23 | Mobil Oil Corporation | Manufacture of aromatic compounds |
| US4236996A (en) * | 1979-05-25 | 1980-12-02 | Mobil Oil Corporation | Xylene isomerization |
| US4283584A (en) * | 1980-04-14 | 1981-08-11 | Mobil Oil Corporation | Manufacture of aromatic compounds |
| US4409413A (en) * | 1980-06-23 | 1983-10-11 | Toray Industries, Incorporated | Conversion of xylenes containing ethyl benzene |
| US4427577A (en) * | 1980-12-12 | 1984-01-24 | Exxon Research & Engineering Co. | Composite zeolite |
| EP0054385B1 (en) | 1980-12-12 | 1985-08-14 | Exxon Research And Engineering Company | Xylene isomerization |
| NZ199280A (en) * | 1980-12-17 | 1985-05-31 | Ici Plc | Isomerisation of hydrocarbons using catalytic zeolite designated nu-5 |
| DE3261680D1 (en) * | 1981-05-20 | 1985-02-07 | Ici Plc | Process for the isomerization of alkylbenzenes |
| JPS63196528A (ja) * | 1985-09-13 | 1988-08-15 | ユ−オ−ピ− インコ−ポレイテツド | 異性化／トランスアルキル化兼用帯域を用いたキシレンの製造法 |
| US5043512A (en) * | 1988-10-06 | 1991-08-27 | Mobil Oil Corp. | Alkylaromatic isomerization process |
| US6518472B1 (en) | 1996-08-05 | 2003-02-11 | Bp Corporation North America Inc. | Stabilized dual bed xylene isomerization catalyst system |
| US5763714A (en) * | 1997-01-08 | 1998-06-09 | Catalytic Distillation Technologies | Process and apparatus for the production and recovery of p-xylene |
| US5866736A (en) * | 1997-10-14 | 1999-02-02 | Catalytic Distillation Technologies | Process for the production of alkyl benzene |
| TWI263630B (en) * | 2003-07-08 | 2006-10-11 | Toray Industries | Conversion catalyst for ethylbenzene containing xylenes and process for converting ethylbenzene containing xylenes by using catalyst |
| US6872866B1 (en) * | 2003-12-15 | 2005-03-29 | Uop Llc | Liquid phase process for C8 alkylaromatic isomerization |
| US20050143615A1 (en) * | 2003-12-30 | 2005-06-30 | Bogdan Paula L. | Process and bimetallic catalyst for C8 alkylaromatic isomerization |
| US20050143614A1 (en) * | 2003-12-30 | 2005-06-30 | Leon-Escamilla E. A. | Process and catalyst for C8 alkylaromatic isomerization |
| EP1699556A2 (en) * | 2003-12-30 | 2006-09-13 | Uop Llc | Process and catalyst for c8 alkylaromatic isomerization |
| RU2360736C1 (ru) * | 2007-12-12 | 2009-07-10 | Общество с ограниченной ответственностью "Еврохим-СПб-Трейдинг" | Катализатор изомеризации ксилолов и способ его приготовления |
| MY162584A (en) | 2010-04-21 | 2017-06-30 | Exxonmobil Chemical Patents Inc | Xylene isomerization process and catalyst therefor |
| US8569559B2 (en) * | 2010-06-25 | 2013-10-29 | Exxonmobil Chemical Patents Inc. | Paraxylene production process and apparatus |
| WO2013159081A2 (en) | 2012-04-20 | 2013-10-24 | The Coca-Cola Company | Methods of preparing para-xylene from biomass |
| ES2809484T3 (es) | 2015-08-18 | 2021-03-04 | Bp Corp North America Inc | Procedimiento para la fabricación de catalizadores ZSM-5 desilicatados para la isomerización de xileno |
| WO2018118208A1 (en) | 2016-12-21 | 2018-06-28 | Uop Llc | Composition of matter and structure of zeolite uzm-55 and use in isomerization of aromatic molecules |
| WO2020018871A1 (en) | 2018-07-20 | 2020-01-23 | Scg Chemicals Co., Ltd. | Process for the separation of ethylbenzene from other c8 aromatic compounds |
| TWI736941B (zh) | 2018-07-20 | 2021-08-21 | 泰商Ｓｃｇ化學股份有限公司 | 用於製造對-二甲苯之整合方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2795630A (en) * | 1954-08-26 | 1957-06-11 | Standard Oil Co | Preparation of trialkylbenzenes |
| US3281483A (en) * | 1963-08-15 | 1966-10-25 | Shell Oil Co | Disproportionation of alkyl aromatic hydrocarbons in the presence of hydrogen mordenite |
| US3790471A (en) * | 1969-10-10 | 1974-02-05 | Mobil Oil Corp | Conversion with zsm-5 family of crystalline aluminosilicate zeolites |
| US3646236A (en) * | 1970-03-27 | 1972-02-29 | Engelhard Min & Chem | Disproportionation of toluene with a platinum-rhenium-solid oxide catalyst |
| US3691247A (en) * | 1970-09-28 | 1972-09-12 | Phillips Petroleum Co | Selectively removing monoalkylbenzenes from mixtures thereof with dialkylbenzenes |
| US3751504A (en) * | 1972-05-12 | 1973-08-07 | Mobil Oil Corp | Vapor-phase alkylation in presence of crystalline aluminosilicate catalyst with separate transalkylation |
| US3756942A (en) * | 1972-05-17 | 1973-09-04 | Mobil Oil Corp | Process for the production of aromatic compounds |
| US3761389A (en) * | 1972-08-28 | 1973-09-25 | Mobil Oil Corp | Process of converting aliphatics to aromatics |
-
1973
- 1973-09-13 US US00397038A patent/US3856871A/en not_active Expired - Lifetime
-
1974
- 1974-05-23 CA CA200,640A patent/CA1026384A/en not_active Expired
- 1974-06-10 IN IN1261/CAL/74A patent/IN142292B/en unknown
- 1974-06-18 ZA ZA00743917A patent/ZA743917B/xx unknown
- 1974-06-19 FR FR7421256A patent/FR2243919B1/fr not_active Expired
- 1974-06-20 JP JP6972974A patent/JPS5341657B2/ja not_active Expired
- 1974-07-11 ES ES428167A patent/ES428167A1/es not_active Expired
- 1974-07-17 GB GB3166374A patent/GB1444702A/en not_active Expired
- 1974-07-24 SU SU742049507A patent/SU890971A3/ru active
- 1974-08-13 RO RO7479759A patent/RO71348A/ro unknown
- 1974-08-30 DE DE2441516A patent/DE2441516C3/de not_active Expired
- 1974-09-11 NL NLAANVRAGE7412093,A patent/NL173846C/xx not_active IP Right Cessation
- 1974-09-12 IT IT27243/74A patent/IT1021337B/it active
- 1974-09-12 CS CS746283A patent/CS189668B2/cs unknown
- 1974-09-12 BE BE148467A patent/BE819848A/xx not_active IP Right Cessation
- 1974-09-12 DD DD74181056A patent/DD113741B3/de unknown
- 1974-09-13 AR AR255604A patent/AR224491A1/es active
- 1974-09-13 PL PL1974174095A patent/PL94144B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2243919B1 (enExample) | 1979-08-03 |
| DD113741A5 (de) | 1975-06-20 |
| CS189668B2 (en) | 1979-04-30 |
| FR2243919A1 (enExample) | 1975-04-11 |
| ES428167A1 (es) | 1976-07-16 |
| BE819848A (fr) | 1975-03-12 |
| DE2441516A1 (de) | 1975-03-20 |
| SU890971A3 (ru) | 1981-12-15 |
| NL173846C (nl) | 1984-03-16 |
| DD113741B3 (de) | 1986-06-11 |
| AR224491A1 (es) | 1981-12-15 |
| PL94144B1 (enExample) | 1977-07-30 |
| NL7412093A (nl) | 1975-03-17 |
| IT1021337B (it) | 1978-01-30 |
| DE2441516B2 (de) | 1979-04-26 |
| ZA743917B (en) | 1976-01-28 |
| NL173846B (nl) | 1983-10-17 |
| CA1026384A (en) | 1978-02-14 |
| RO71348A (ro) | 1982-02-01 |
| US3856871A (en) | 1974-12-24 |
| JPS5053335A (enExample) | 1975-05-12 |
| GB1444702A (en) | 1976-08-04 |
| JPS5341657B2 (enExample) | 1978-11-06 |
| IN142292B (enExample) | 1977-06-18 |
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