CA2869550A1 - Process for production of xylenes through integration of methylation and transalkylation - Google Patents
Process for production of xylenes through integration of methylation and transalkylation Download PDFInfo
- Publication number
- CA2869550A1 CA2869550A1 CA2869550A CA2869550A CA2869550A1 CA 2869550 A1 CA2869550 A1 CA 2869550A1 CA 2869550 A CA2869550 A CA 2869550A CA 2869550 A CA2869550 A CA 2869550A CA 2869550 A1 CA2869550 A1 CA 2869550A1
- Authority
- CA
- Canada
- Prior art keywords
- transalkylation
- methylation
- benzene
- toluene
- production
- 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
- 238000010555 transalkylation reaction Methods 0.000 title claims abstract description 67
- 230000011987 methylation Effects 0.000 title claims abstract description 50
- 238000007069 methylation reaction Methods 0.000 title claims abstract description 50
- 238000000034 method Methods 0.000 title claims abstract description 41
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 26
- 239000008096 xylene Substances 0.000 title claims abstract description 22
- 150000003738 xylenes Chemical class 0.000 title claims abstract description 20
- 230000010354 integration Effects 0.000 title abstract description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 96
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 72
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 10
- 238000000926 separation method Methods 0.000 claims description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 30
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 7
- 150000001491 aromatic compounds Chemical class 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 5
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 4
- 239000010457 zeolite Substances 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical class CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 238000002407 reforming Methods 0.000 description 3
- 101100074836 Caenorhabditis elegans lin-22 gene Proteins 0.000 description 2
- 229910019142 PO4 Inorganic materials 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
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000001833 catalytic reforming Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- 229910052680 mordenite Inorganic materials 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 description 2
- 229920002215 polytrimethylene terephthalate Polymers 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 238000005899 aromatization reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
- C07C6/02—Metathesis reactions at an unsaturated carbon-to-carbon bond
- C07C6/04—Metathesis reactions at an unsaturated carbon-to-carbon bond at a carbon-to-carbon double bond
- C07C6/06—Metathesis reactions at an unsaturated carbon-to-carbon bond at a carbon-to-carbon double bond at a cyclic carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/862—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms
- C07C2/864—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms the non-hydrocarbon is an alcohol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
- C07C6/08—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond
- C07C6/12—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring
- C07C6/126—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring of more than one hydrocarbon
-
- 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
- Y02P20/10—Process efficiency
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261620830P | 2012-04-05 | 2012-04-05 | |
| US61/620,830 | 2012-04-05 | ||
| PCT/US2013/031148 WO2013151710A1 (en) | 2012-04-05 | 2013-03-14 | Process for production of xylenes through integration of methylation and transalkylation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2869550A1 true CA2869550A1 (en) | 2013-10-10 |
Family
ID=49292829
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2869550A Abandoned CA2869550A1 (en) | 2012-04-05 | 2013-03-14 | Process for production of xylenes through integration of methylation and transalkylation |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US10131595B2 (enExample) |
| EP (1) | EP2834209B1 (enExample) |
| JP (1) | JP2015512444A (enExample) |
| KR (1) | KR102027994B1 (enExample) |
| CN (2) | CN104395267A (enExample) |
| AR (1) | AR090609A1 (enExample) |
| AU (1) | AU2013243901A1 (enExample) |
| CA (1) | CA2869550A1 (enExample) |
| ES (1) | ES2910355T3 (enExample) |
| IL (1) | IL234940A0 (enExample) |
| IN (1) | IN2014DN09038A (enExample) |
| MX (1) | MX2014011889A (enExample) |
| PL (1) | PL2834209T3 (enExample) |
| RU (1) | RU2663839C2 (enExample) |
| TW (1) | TWI622571B (enExample) |
| WO (1) | WO2013151710A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9783462B2 (en) * | 2013-09-10 | 2017-10-10 | Saudi Basic Industries Corporation | Toluene methylation with transalkylation of heavy aromatics |
| JP6254882B2 (ja) * | 2014-03-26 | 2017-12-27 | コスモ石油株式会社 | キシレンの製造方法 |
| US10196329B2 (en) * | 2014-11-21 | 2019-02-05 | Exxonmobil Chemical Patents Inc. | Process for making para-xylene |
| WO2017131862A1 (en) * | 2016-01-29 | 2017-08-03 | Exxonmobil Chemical Patents Inc. | Process for converting alkanes to para-xylene |
| CN106083512B (zh) * | 2016-07-31 | 2018-10-02 | 宁波中金石化有限公司 | 一种由甲苯和重芳烃制备苯和二甲苯的装置和方法 |
| US10392316B2 (en) * | 2017-10-11 | 2019-08-27 | Uop Llc | Process for minimizing benzene, toluene, and a recycle loop in a zero benzene aromatics complex |
| US10308571B2 (en) * | 2017-10-11 | 2019-06-04 | Uop Llc | Process for minimizing benzene, toluene, and a recycle loop in a zero benzene aromatics complex |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3551510A (en) * | 1968-08-15 | 1970-12-29 | Universal Oil Prod Co | Alkylation-transalkylation process |
| FR2245588B1 (enExample) * | 1973-09-27 | 1977-10-14 | Inst Francais Du Petrole | |
| US4053388A (en) * | 1976-12-06 | 1977-10-11 | Moore-Mccormack Energy, Inc. | Process for preparing aromatics from naphtha |
| US5321183A (en) | 1992-03-12 | 1994-06-14 | Mobil Oil Corp. | Process for the regioselective conversion of aromatics to para-disubstituted benzenes |
| US6459006B1 (en) * | 1999-05-14 | 2002-10-01 | Exxonmobil Chemical Patents Inc. | Selective methylation to para-xylene using fuel syngas |
| US20040097769A1 (en) * | 2002-11-14 | 2004-05-20 | Ou John D. Y. | Para-xylene production process employing in-situ catalyst selectivation |
| US20040138511A1 (en) * | 2003-01-10 | 2004-07-15 | James Butler | Aromatic alkylation process with direct recycle |
| GB0303659D0 (en) * | 2003-02-18 | 2003-03-19 | Johnson Matthey Plc | Process |
| US7060644B2 (en) * | 2004-01-08 | 2006-06-13 | Saudi Basic Industries Corporation | Aromatic alkylation catalyst and method |
| US7834227B2 (en) * | 2006-12-29 | 2010-11-16 | Uop Llc | Aromatics co-production in a methanol-to-propylene unit |
| US7629498B2 (en) * | 2007-06-28 | 2009-12-08 | Exxonmobil Chemical Patents, Inc. | Process of manufacturing para-xylene |
| US8598395B2 (en) * | 2010-01-19 | 2013-12-03 | Uop Llc | Process for increasing a mole ratio of methyl to phenyl |
| US8563795B2 (en) * | 2010-01-19 | 2013-10-22 | Uop Llc | Aromatic aklylating agent and an aromatic production apparatus |
| WO2012078373A2 (en) * | 2010-12-10 | 2012-06-14 | Exxonmobil Chemical Patents Inc. | Method and apparatus for obtaining aromatics from diverse feedstock |
| US20130190546A1 (en) * | 2012-01-24 | 2013-07-25 | Uop Llc | Benzene alkylation with staged alkane injection |
| KR20150003253A (ko) * | 2012-04-02 | 2015-01-08 | 사우디 아라비안 오일 컴퍼니 | 크실렌 및 석유화학 공급원료를 생산하기 위한 중질 개질유의 알킬교환반응을 위한 다중금속 제올라이트계 촉매 |
-
2013
- 2013-03-14 RU RU2014144325A patent/RU2663839C2/ru active
- 2013-03-14 JP JP2015504583A patent/JP2015512444A/ja active Pending
- 2013-03-14 AU AU2013243901A patent/AU2013243901A1/en not_active Abandoned
- 2013-03-14 KR KR1020147031091A patent/KR102027994B1/ko active Active
- 2013-03-14 EP EP13772120.5A patent/EP2834209B1/en active Active
- 2013-03-14 CN CN201380018739.9A patent/CN104395267A/zh active Pending
- 2013-03-14 WO PCT/US2013/031148 patent/WO2013151710A1/en not_active Ceased
- 2013-03-14 ES ES13772120T patent/ES2910355T3/es active Active
- 2013-03-14 MX MX2014011889A patent/MX2014011889A/es unknown
- 2013-03-14 PL PL13772120T patent/PL2834209T3/pl unknown
- 2013-03-14 US US13/830,112 patent/US10131595B2/en active Active
- 2013-03-14 IN IN9038DEN2014 patent/IN2014DN09038A/en unknown
- 2013-03-14 CA CA2869550A patent/CA2869550A1/en not_active Abandoned
- 2013-03-14 CN CN201910720904.4A patent/CN110452084A/zh active Pending
- 2013-04-02 TW TW102111883A patent/TWI622571B/zh active
- 2013-04-04 AR ARP130101109A patent/AR090609A1/es unknown
-
2014
- 2014-10-02 IL IL234940A patent/IL234940A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US10131595B2 (en) | 2018-11-20 |
| CN110452084A (zh) | 2019-11-15 |
| RU2014144325A (ru) | 2016-05-27 |
| TW201345875A (zh) | 2013-11-16 |
| EP2834209B1 (en) | 2022-03-09 |
| TWI622571B (zh) | 2018-05-01 |
| MX2014011889A (es) | 2014-11-25 |
| EP2834209A1 (en) | 2015-02-11 |
| IN2014DN09038A (enExample) | 2015-05-22 |
| RU2663839C2 (ru) | 2018-08-10 |
| EP2834209A4 (en) | 2015-12-02 |
| KR20150003792A (ko) | 2015-01-09 |
| KR102027994B1 (ko) | 2019-10-02 |
| ES2910355T3 (es) | 2022-05-12 |
| PL2834209T3 (pl) | 2022-06-20 |
| US20130267746A1 (en) | 2013-10-10 |
| CN104395267A (zh) | 2015-03-04 |
| AR090609A1 (es) | 2014-11-26 |
| AU2013243901A1 (en) | 2014-11-20 |
| IL234940A0 (en) | 2014-12-31 |
| JP2015512444A (ja) | 2015-04-27 |
| WO2013151710A1 (en) | 2013-10-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20170314 |