CA2341603A1 - Para-xylene production process - Google Patents
Para-xylene production process Download PDFInfo
- Publication number
- CA2341603A1 CA2341603A1 CA002341603A CA2341603A CA2341603A1 CA 2341603 A1 CA2341603 A1 CA 2341603A1 CA 002341603 A CA002341603 A CA 002341603A CA 2341603 A CA2341603 A CA 2341603A CA 2341603 A1 CA2341603 A1 CA 2341603A1
- Authority
- CA
- Canada
- Prior art keywords
- xylene
- feedstock
- stream
- isomerization
- para
- 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.)
- Abandoned
Links
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 title claims abstract description 58
- 238000004519 manufacturing process Methods 0.000 title abstract description 8
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims abstract description 136
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 129
- 239000008096 xylene Substances 0.000 claims abstract description 93
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 81
- 238000006317 isomerization reaction Methods 0.000 claims abstract description 64
- 238000006243 chemical reaction Methods 0.000 claims abstract description 50
- 238000000034 method Methods 0.000 claims abstract description 43
- 230000008569 process Effects 0.000 claims abstract description 41
- 150000003738 xylenes Chemical class 0.000 claims abstract description 25
- 238000011084 recovery Methods 0.000 claims description 19
- 238000000926 separation method Methods 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- 238000004064 recycling Methods 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
- 239000003054 catalyst Substances 0.000 description 14
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 238000011144 upstream manufacturing Methods 0.000 description 8
- 238000001179 sorption measurement Methods 0.000 description 5
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 4
- 208000007542 Paresis Diseases 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 208000012318 pareses Diseases 0.000 description 4
- 230000008901 benefit Effects 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- -1 ZSM-S Chemical compound 0.000 description 2
- 239000000571 coke Substances 0.000 description 2
- 238000010960 commercial process Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 238000004517 catalytic hydrocracking Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000020335 dealkylation Effects 0.000 description 1
- 238000006900 dealkylation reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000002715 modification method Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000010555 transalkylation reaction Methods 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/02—Monocyclic hydrocarbons
- C07C15/067—C8H10 hydrocarbons
- C07C15/08—Xylenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C4/00—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
- C07C4/08—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule
- C07C4/12—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule from hydrocarbons containing a six-membered aromatic ring, e.g. propyltoluene to vinyltoluene
- C07C4/14—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule from hydrocarbons containing a six-membered aromatic ring, e.g. propyltoluene to vinyltoluene splitting taking place at an aromatic-aliphatic bond
- C07C4/18—Catalytic processes
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C2523/32—Manganese, technetium or rhenium
- C07C2523/36—Rhenium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C07C2523/42—Platinum
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C07C2523/44—Palladium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C07C2523/46—Ruthenium, rhodium, osmium or iridium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/80—Mixtures of different zeolites
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/139,463 US5977420A (en) | 1998-08-25 | 1998-08-25 | Dual-loop xylene isomerization process |
| US09/139,465 | 1998-08-25 | ||
| US09/139,463 | 1998-08-25 | ||
| US09/139,465 US5998688A (en) | 1998-08-25 | 1998-08-25 | Xylene isomerization process using toluene co-feed |
| PCT/US1999/018353 WO2000010944A1 (en) | 1998-08-25 | 1999-08-12 | Para-xylene production process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2341603A1 true CA2341603A1 (en) | 2000-03-02 |
Family
ID=26837245
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002341603A Abandoned CA2341603A1 (en) | 1998-08-25 | 1999-08-12 | Para-xylene production process |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP1109761B1 (enExample) |
| JP (1) | JP4808313B2 (enExample) |
| KR (1) | KR100637963B1 (enExample) |
| CN (1) | CN1177783C (enExample) |
| AR (1) | AR020266A1 (enExample) |
| AT (1) | ATE239683T1 (enExample) |
| AU (1) | AU5558699A (enExample) |
| BR (1) | BR9913240A (enExample) |
| CA (1) | CA2341603A1 (enExample) |
| DE (1) | DE69907694T2 (enExample) |
| ES (1) | ES2198945T3 (enExample) |
| TW (1) | TW518316B (enExample) |
| WO (1) | WO2000010944A1 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007127049A2 (en) * | 2006-04-25 | 2007-11-08 | Exxonmobil Chemical Patents Inc. | Process for producing para-xylene |
| US7553998B2 (en) * | 2006-06-21 | 2009-06-30 | Uop Llc | Energy-efficient process for para-xylene production |
| CN102199066B (zh) * | 2010-03-25 | 2014-05-28 | 中国石油化工股份有限公司 | 一种烷基芳烃异构化方法 |
| KR101947247B1 (ko) * | 2010-10-29 | 2019-02-12 | 엑손모빌 케미칼 패턴츠 인코포레이티드 | 파라자일렌의 제조 방법 |
| SG189199A1 (en) * | 2010-10-29 | 2013-05-31 | Exxonmobil Chem Patents Inc | Process for the production of purified xylene isomers |
| US9309170B2 (en) * | 2011-11-14 | 2016-04-12 | Uop Llc | Aromatics isomerization using a dual-catalyst system |
| JP6290180B2 (ja) | 2012-04-19 | 2018-03-07 | サウジ アラビアン オイル カンパニー | キシレン生成を最大化するための複合重質リフォメートの脱アルキル化−トランスアルキル化法 |
| US20150251973A1 (en) * | 2012-10-09 | 2015-09-10 | Exxonmobil Chemical Patents Inc. | Purge Streams in Paraxylene Production |
| EP2925710A4 (en) | 2012-11-30 | 2016-05-11 | Exxonmobil Chem Patents Inc | ENERGY-EFFICIENT METHOD OF XYLENE MANUFACTURE |
| US9309169B2 (en) | 2012-11-30 | 2016-04-12 | Exxonmobil Chemical Patents Inc. | Process for the production of purified xylene isomers |
| US9809509B2 (en) | 2015-12-15 | 2017-11-07 | Exxonmobil Chemical Patents Inc. | Process for xylenes isomerization |
| WO2017105617A1 (en) * | 2015-12-15 | 2017-06-22 | Exxonmobil Chemical Patents Inc. | Process for xylenes isomerization |
| US10173950B2 (en) * | 2017-01-04 | 2019-01-08 | Saudi Arabian Oil Company | Integrated process for the production of benzene and xylenes from heavy aromatics |
| US10252958B2 (en) | 2017-05-26 | 2019-04-09 | Saudi Arabian Oil Company | Process for xylene production with energy optimization |
| US10464868B2 (en) | 2017-05-26 | 2019-11-05 | Saudi Arabian Oil Company | Process for maximizing production of xylenes from heavy reformate without purge |
| US10035742B1 (en) | 2017-05-26 | 2018-07-31 | Saudi Arabian Oil Company | Process for maximizing xylenes production from heavy aromatics for use therein |
| US10894755B2 (en) | 2018-10-15 | 2021-01-19 | Saudi Arabian Oil Company | Integrated process for optimum production of para-xylene |
| US10696609B2 (en) | 2018-10-15 | 2020-06-30 | Saudi Arabian Oil Company | Integrated process for maximizing production of para-xylene from full reformate |
| US10501389B1 (en) | 2018-10-25 | 2019-12-10 | Saudi Arabian Oil Company | Process and system for the production of para-xylene and benzene from streams rich in C6 to C12+ aromatics |
| KR20210126101A (ko) | 2019-03-29 | 2021-10-19 | 엑손모빌 케미칼 패턴츠 인코포레이티드 | 방향족 탄화수소 전환용 mel형 제올라이트, 상기 제올라이트의 제조 방법, 및 상기 제올라이트를 포함하는 촉매 조성물 |
| CN113646287B (zh) | 2019-03-29 | 2025-04-25 | 埃克森美孚化学专利公司 | 新型沸石、所述沸石的制备方法及所述沸石用于转化芳族烃的用途 |
| WO2021015900A1 (en) * | 2019-07-19 | 2021-01-28 | Exxonmobil Chemical Patents Inc. | Isomerization processes for converting aromatic hydrocarbons comprising alkyl-demethylation |
| EP3978461A1 (en) * | 2020-09-30 | 2022-04-06 | Sulzer Management AG | A process and apparatus for preparing a purified styrene composition using a divided-wall column and a crystallization unit |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3948758A (en) * | 1974-06-17 | 1976-04-06 | Mobil Oil Corporation | Production of alkyl aromatic hydrocarbons |
| US4101595A (en) * | 1977-05-02 | 1978-07-18 | Mobil Oil Corporation | Conversion of ethyl benzene to para xylene |
| KR810000478B1 (ko) * | 1978-01-11 | 1981-05-20 | 에드워드 에이취. 밸랜스 | P-크실렌의 제조방법 |
| US4159282A (en) * | 1978-06-09 | 1979-06-26 | Mobil Oil Corporation | Xylene isomerization |
| 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 |
| JPS6456628A (en) * | 1987-08-25 | 1989-03-03 | Toray Industries | Production of p-xylene |
| JPH08245436A (ja) * | 1995-03-09 | 1996-09-24 | Toray Ind Inc | ｐ−キシレンの製造方法 |
-
1999
- 1999-08-12 DE DE69907694T patent/DE69907694T2/de not_active Expired - Fee Related
- 1999-08-12 BR BR9913240-0A patent/BR9913240A/pt not_active IP Right Cessation
- 1999-08-12 CA CA002341603A patent/CA2341603A1/en not_active Abandoned
- 1999-08-12 ES ES99942143T patent/ES2198945T3/es not_active Expired - Lifetime
- 1999-08-12 AT AT99942143T patent/ATE239683T1/de not_active IP Right Cessation
- 1999-08-12 KR KR1020017002362A patent/KR100637963B1/ko not_active Expired - Fee Related
- 1999-08-12 WO PCT/US1999/018353 patent/WO2000010944A1/en not_active Ceased
- 1999-08-12 JP JP2000566220A patent/JP4808313B2/ja not_active Expired - Fee Related
- 1999-08-12 CN CNB998111333A patent/CN1177783C/zh not_active Expired - Lifetime
- 1999-08-12 AU AU55586/99A patent/AU5558699A/en not_active Abandoned
- 1999-08-12 EP EP99942143A patent/EP1109761B1/en not_active Expired - Lifetime
- 1999-08-25 AR ARP990104258A patent/AR020266A1/es active IP Right Grant
- 1999-10-05 TW TW088114558A patent/TW518316B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP4808313B2 (ja) | 2011-11-02 |
| CN1177783C (zh) | 2004-12-01 |
| WO2000010944A1 (en) | 2000-03-02 |
| AU5558699A (en) | 2000-03-14 |
| KR20010072935A (ko) | 2001-07-31 |
| CN1319078A (zh) | 2001-10-24 |
| ATE239683T1 (de) | 2003-05-15 |
| DE69907694T2 (de) | 2004-01-29 |
| KR100637963B1 (ko) | 2006-10-23 |
| ES2198945T3 (es) | 2004-02-01 |
| BR9913240A (pt) | 2001-05-15 |
| DE69907694D1 (de) | 2003-06-12 |
| AR020266A1 (es) | 2002-05-02 |
| TW518316B (en) | 2003-01-21 |
| EP1109761A1 (en) | 2001-06-27 |
| JP2002523385A (ja) | 2002-07-30 |
| EP1109761A4 (en) | 2001-11-07 |
| EP1109761B1 (en) | 2003-05-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |