CA2346431C - Fluid-bed aromatics alkylation - Google Patents
Fluid-bed aromatics alkylation Download PDFInfo
- Publication number
- CA2346431C CA2346431C CA002346431A CA2346431A CA2346431C CA 2346431 C CA2346431 C CA 2346431C CA 002346431 A CA002346431 A CA 002346431A CA 2346431 A CA2346431 A CA 2346431A CA 2346431 C CA2346431 C CA 2346431C
- Authority
- CA
- Canada
- Prior art keywords
- fluidized bed
- methanol
- toluene
- reaction zone
- reactor
- 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 - Fee Related
Links
- 238000005804 alkylation reaction Methods 0.000 title claims abstract description 23
- 230000029936 alkylation Effects 0.000 title claims abstract description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 205
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 164
- 238000006243 chemical reaction Methods 0.000 claims abstract description 71
- 230000002152 alkylating effect Effects 0.000 claims abstract description 47
- 239000000376 reactant Substances 0.000 claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 44
- 125000003118 aryl group Chemical group 0.000 claims abstract description 43
- 239000008096 xylene Substances 0.000 claims abstract description 20
- 239000003153 chemical reaction reagent Substances 0.000 claims description 45
- 239000003054 catalyst Substances 0.000 claims description 23
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 21
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 150000002430 hydrocarbons Chemical class 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000012808 vapor phase Substances 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 150000003738 xylenes Chemical class 0.000 abstract description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 18
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 230000011987 methylation Effects 0.000 description 8
- 238000007069 methylation reaction Methods 0.000 description 8
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 6
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 238000007086 side reaction Methods 0.000 description 6
- 239000002245 particle Substances 0.000 description 5
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 4
- JRLPEMVDPFPYPJ-UHFFFAOYSA-N 1-ethyl-4-methylbenzene Chemical compound CCC1=CC=C(C)C=C1 JRLPEMVDPFPYPJ-UHFFFAOYSA-N 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000011144 upstream manufacturing Methods 0.000 description 4
- 230000002411 adverse Effects 0.000 description 3
- 230000006203 ethylation Effects 0.000 description 3
- 238000006200 ethylation reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000006207 propylation Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-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
- 229910021536 Zeolite Inorganic materials 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
- 239000000446 fuel Substances 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- MARCAKLHFUYDJE-UHFFFAOYSA-N 1,2-xylene;hydrate Chemical compound O.CC1=CC=CC=C1C MARCAKLHFUYDJE-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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 150000001336 alkenes Chemical class 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
- 239000011230 binding agent Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
Classifications
-
- 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
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/166,188 US6642426B1 (en) | 1998-10-05 | 1998-10-05 | Fluid-bed aromatics alkylation with staged injection of alkylating agents |
| US09/166,188 | 1998-10-05 | ||
| PCT/US1999/022414 WO2000020360A1 (en) | 1998-10-05 | 1999-09-27 | Fluid-bed aromatics alkylation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2346431A1 CA2346431A1 (en) | 2000-04-13 |
| CA2346431C true CA2346431C (en) | 2009-02-03 |
Family
ID=22602174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002346431A Expired - Fee Related CA2346431C (en) | 1998-10-05 | 1999-09-27 | Fluid-bed aromatics alkylation |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6642426B1 (enExample) |
| EP (1) | EP1119532B1 (enExample) |
| JP (1) | JP4607326B2 (enExample) |
| KR (1) | KR100637964B1 (enExample) |
| CN (1) | CN1218913C (enExample) |
| AT (1) | ATE247613T1 (enExample) |
| AU (1) | AU6165499A (enExample) |
| BR (1) | BR9915913B1 (enExample) |
| CA (1) | CA2346431C (enExample) |
| DE (1) | DE69910598T2 (enExample) |
| ES (1) | ES2205882T3 (enExample) |
| ID (1) | ID29191A (enExample) |
| TW (1) | TW505620B (enExample) |
| WO (1) | WO2000020360A1 (enExample) |
Families Citing this family (74)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7232936B1 (en) | 2000-02-22 | 2007-06-19 | Exxonmobil Chemical Patents Inc. | Conversion of oxygenate to olefins with staged injection of oxygenate |
| US7226771B2 (en) | 2002-04-19 | 2007-06-05 | Diversa Corporation | Phospholipases, nucleic acids encoding them and methods for making and using them |
| WO2004000974A1 (en) * | 2002-06-19 | 2003-12-31 | Exxonmobil Chemical Patents Inc. | Manufacture of xylenes from reformate |
| CA2538520C (en) | 2003-07-24 | 2015-02-10 | The Queen's Medical Center | Preparation and use of alkylating agents |
| US7084318B2 (en) | 2003-08-01 | 2006-08-01 | Saudi Basic Industries Corporation | Toluene methylation process |
| US7060864B2 (en) | 2003-09-30 | 2006-06-13 | Saudi Basic Industries Corporation | Toluene methylation process |
| US7060644B2 (en) | 2004-01-08 | 2006-06-13 | Saudi Basic Industries Corporation | Aromatic alkylation catalyst and method |
| US6943131B1 (en) | 2004-03-02 | 2005-09-13 | Saudi Basic Industries Corporation | Selective zeolite catalyst modification |
| US7285511B2 (en) | 2004-04-23 | 2007-10-23 | Saudi Basic Industries Corporation | Method of modifying zeolite catalyst |
| US7399727B2 (en) | 2004-04-23 | 2008-07-15 | Saudi Basic Industries Corporation | Zeolite catalyst and method |
| US7304198B2 (en) * | 2004-05-14 | 2007-12-04 | Battelle Memorial Institute | Staged alkylation in microchannels |
| US7105713B2 (en) | 2004-06-09 | 2006-09-12 | Saudi Basic Industries Corporation | Preparation of alkyl-aromatic products |
| DE102004041011A1 (de) | 2004-08-24 | 2006-03-02 | Martin Schleske | Resonanzplatte in Faserverbund-Bauweise für akustische Musikinstrumente |
| US7304194B2 (en) | 2005-05-05 | 2007-12-04 | Saudi Basic Industries Corporation | Hydrothermal treatment of phosphorus-modified zeolite catalysts |
| KR100598988B1 (ko) * | 2005-05-18 | 2006-07-12 | 주식회사 하이닉스반도체 | 오버레이 버니어 및 이를 이용한 반도체소자의 제조방법 |
| US7368410B2 (en) | 2005-08-03 | 2008-05-06 | Saudi Basic Industries Corporation | Zeolite catalyst and method of preparing and use of zeolite catalyst |
| EP2297310A2 (en) | 2008-05-23 | 2011-03-23 | E. I. du Pont de Nemours and Company | Novel dgat genes for increased seed storage lipid production and altered fatty acid profiles in oilseed plants |
| US8846559B2 (en) | 2008-11-03 | 2014-09-30 | Saudi Basic Industries Corporation | Stable shape-selective catalyst for aromatic alkylation and methods of using and preparing |
| US8252967B2 (en) * | 2009-04-14 | 2012-08-28 | Exxonmobil Chemical Patents Inc. | Process for the purification of paraxylene |
| US8558046B2 (en) * | 2009-05-28 | 2013-10-15 | Saudi Basic Industries Corporation | Aromatic alkylation process |
| US8062987B2 (en) | 2009-10-05 | 2011-11-22 | Saudi Basic Industries Corporation | Phosphorus-containing zeolite catalysts and their method of preparation |
| US8399727B2 (en) * | 2009-10-21 | 2013-03-19 | Exxonmobil Chemical Patents Inc. | Production of para-xylene by the methylation of benzene and/or toluene |
| US8344197B2 (en) * | 2009-10-21 | 2013-01-01 | Exxonmobil Chemical Patents Inc. | Production of para-xylene by the methylation of benzene and/or toluene |
| CN102372582A (zh) * | 2010-08-23 | 2012-03-14 | 中国石油化工股份有限公司 | 甲苯甲基化的流化催化方法 |
| CN102372587A (zh) * | 2010-08-23 | 2012-03-14 | 中国石油化工股份有限公司 | 芳烃甲基化的流化床方法 |
| CN102372585B (zh) * | 2010-08-23 | 2015-12-09 | 中国石油化工股份有限公司 | 芳烃烷基化制对二甲苯的流化床方法 |
| CN102464559A (zh) * | 2010-11-17 | 2012-05-23 | 中国石油化工股份有限公司 | 用于生产烷基化芳烃的方法 |
| CN102464557B (zh) * | 2010-11-17 | 2014-03-26 | 中国石油化工股份有限公司 | 由含氧化合物和甲苯制备二甲苯的方法 |
| CN103596907B (zh) * | 2011-06-10 | 2016-04-27 | 埃克森美孚化学专利公司 | 对二甲苯的生产 |
| CN103619786B (zh) * | 2011-07-11 | 2016-06-01 | 埃克森美孚化学专利公司 | 苯和/或甲苯与甲醇的烷基化 |
| TWI495511B (zh) * | 2011-07-27 | 2015-08-11 | Exxonmobil Chem Patents Inc | 具有分階擋板的流體床反應器 |
| TWI623511B (zh) * | 2011-12-08 | 2018-05-11 | Ｇｔｃ科技美國有限責任公司 | 藉由將芳香族化合物甲基化以製造二甲苯的方法 |
| US9278342B2 (en) | 2012-07-02 | 2016-03-08 | Saudi Basic Industries Corporation | Method of modifying a phosphorus-containing zeolite catalyst |
| US9802876B2 (en) | 2012-07-12 | 2017-10-31 | China Petroleum & Chemical Corporation | Alkylating process for alkyl benzenes |
| CN103664485B (zh) * | 2012-09-05 | 2016-05-18 | 中国石油化工股份有限公司 | 甲苯、甲醇侧链烷基化生产乙苯、苯乙烯的方法 |
| CN103772129A (zh) * | 2012-10-25 | 2014-05-07 | 中国石油化工股份有限公司 | 甲苯甲基化生产混合二甲苯的方法 |
| US9353024B2 (en) | 2013-02-06 | 2016-05-31 | Exxonmobil Chemical Patents Inc. | Selective hydrogenation of styrene to ethylbenzene |
| WO2015094698A1 (en) | 2013-12-20 | 2015-06-25 | Exxonmobil Chemical Patents Inc. | Process for converting oxygenates to aromatic hydrocarbons |
| US9469579B2 (en) | 2014-06-30 | 2016-10-18 | Exxonmobil Chemical Patents Inc. | Process for the production of xylenes |
| WO2016003613A2 (en) | 2014-06-30 | 2016-01-07 | Exxonmobil Chemical Patents Inc. | Process for the production of xylenes |
| CN106458788B (zh) | 2014-06-30 | 2019-11-26 | 埃克森美孚化学专利公司 | 制备二甲苯的方法 |
| WO2016003612A1 (en) | 2014-06-30 | 2016-01-07 | Exxonmobil Chemical Patents Inc. | Processes for the production of para-xylene |
| US9802877B2 (en) | 2014-08-29 | 2017-10-31 | Exxonmobil Chemical Patents Inc. | Process of producing para-xylene by alkylation of benzene and/or toluene including treatment of an alkylating agent to remove metal salts |
| CN106433761B (zh) * | 2015-08-06 | 2018-07-13 | 中国石油天然气股份有限公司 | 异丁烷与丁烯烷基化合成烷基化油的多级沸腾床催化工艺 |
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| WO2017146914A1 (en) | 2016-02-26 | 2017-08-31 | Exxonmobil Chemical Patents Inc. | Process for recovering para-xylene |
| KR102231925B1 (ko) | 2016-03-25 | 2021-03-25 | 엑손모빌 케미칼 패턴츠 인코포레이티드 | 파라-크실렌의 제조 방법 및 촉매 |
| WO2018057125A2 (en) | 2016-09-22 | 2018-03-29 | Exxonmobil Chemical Patents Inc. | Use of light gas by-products in the production of paraxylene by the methylation of toluene and/or benzene |
| US10961168B2 (en) * | 2016-09-22 | 2021-03-30 | Exxonmobil Chemical Patents Inc. | Use of light gas by-products in the production of paraxylene by the methylation of toluene and or benzene |
| KR102235872B1 (ko) | 2016-10-06 | 2021-04-06 | 엑손모빌 케미칼 패턴츠 인코포레이티드 | 방향족 탄화수소의 메틸화 방법 |
| KR102235874B1 (ko) | 2016-10-06 | 2021-04-06 | 엑손모빌 케미칼 패턴츠 인코포레이티드 | 벤젠 및/또는 톨루엔의 메틸화에 의해 파라크실렌을 생성시키기 위한 촉매의 선택화 방법 |
| KR20190040081A (ko) | 2016-10-06 | 2019-04-16 | 엑손모빌 케미칼 패턴츠 인코포레이티드 | 벤젠 및/또는 톨루엔의 메틸화에 의한 파라크실렌의 제조 방법 |
| US11208365B2 (en) | 2016-12-20 | 2021-12-28 | Uop Llc | Processes and apparatuses for methylation of aromatics in an aromatics complex |
| US11673849B2 (en) | 2016-12-21 | 2023-06-13 | Exxonmobil Chemical Patents Inc. | Process for selectivating catalyst for producing paraxylene by methylation of benzene and/or toluene |
| CN108786672B (zh) * | 2017-04-27 | 2021-01-26 | 中国科学院大连化学物理研究所 | 甲醇和/或二甲醚与苯制对二甲苯联产低碳烯烃的方法 |
| CN108794291B (zh) * | 2017-04-27 | 2020-11-27 | 中国科学院大连化学物理研究所 | 甲醇和/或二甲醚与甲苯制对二甲苯联产低碳烯烃的流化床装置及方法 |
| CN108786671B (zh) | 2017-04-27 | 2021-04-23 | 中国科学院大连化学物理研究所 | 甲醇和/或二甲醚与苯制对二甲苯联产低碳烯烃的流化床装置及方法 |
| CN108794294B (zh) * | 2017-04-27 | 2020-12-11 | 中国科学院大连化学物理研究所 | 流化床气体分布器、应用其的反应器及生产对二甲苯联产低碳烯烃的方法 |
| CN108786670B (zh) * | 2017-04-27 | 2021-01-26 | 中国科学院大连化学物理研究所 | 甲醇和/或二甲醚与甲苯制对二甲苯联产低碳烯烃的方法 |
| CN108786669B (zh) * | 2017-04-27 | 2021-01-12 | 中国科学院大连化学物理研究所 | 流化床气体分布器、应用其的反应器及生产对二甲苯联产低碳烯烃的方法 |
| WO2019108361A1 (en) | 2017-11-30 | 2019-06-06 | Exxonmobil Chemical Patents Inc | Systems and methods for aromatic alkylation |
| US11377399B2 (en) | 2017-12-05 | 2022-07-05 | Exxonmobil Chemical Patents Inc. | Xylene production processes and systems |
| US11130719B2 (en) * | 2017-12-05 | 2021-09-28 | Uop Llc | Processes and apparatuses for methylation of aromatics in an aromatics complex |
| US10556214B2 (en) | 2017-12-20 | 2020-02-11 | Uop Llc | Apparatuses for mixing of staged methanol injection |
| CN111511705A (zh) | 2017-12-22 | 2020-08-07 | 埃克森美孚化学专利公司 | 通过苯和/或甲苯的甲基化制备对二甲苯的催化剂 |
| CN108441257B (zh) * | 2018-03-20 | 2020-10-13 | 中国石油大学(华东) | 一种重油裂解轻质石油烃原位烷基化的方法 |
| US11130720B2 (en) | 2018-03-23 | 2021-09-28 | Uop Llc | Processes for methylation of aromatics in an aromatics complex |
| US11078133B2 (en) * | 2019-12-06 | 2021-08-03 | Uop Llc | Aromatic alkylation process |
| CA3184956A1 (en) | 2020-07-31 | 2022-02-03 | Robert G. Tinger | Processes for producing high-octane-number fuel component |
| WO2023044278A1 (en) | 2021-09-16 | 2023-03-23 | Exxonmobil Chemical Patents Inc. | Xylene isomer separation processes |
| WO2023204947A1 (en) | 2022-04-19 | 2023-10-26 | Exxonmobil Chemical Patents Inc. | Processes for oxidizing p-xylene or p-xylene-containing mixtures |
| WO2023244394A1 (en) | 2022-06-14 | 2023-12-21 | Exxonmobil Chemical Patents Inc. | Production of p-xylene by liquid-phase isomerization and separation thereof |
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| JPS4924921B1 (enExample) * | 1970-06-27 | 1974-06-26 | ||
| US3751504A (en) | 1972-05-12 | 1973-08-07 | Mobil Oil Corp | Vapor-phase alkylation in presence of crystalline aluminosilicate catalyst with separate transalkylation |
| US4049738A (en) * | 1976-07-12 | 1977-09-20 | Mobil Oil Corporation | Selective production of para-xylene |
| JPS5726627A (en) | 1980-07-25 | 1982-02-12 | Teijin Yuka Kk | Preparation of p-xylene |
| JPS5835128A (ja) * | 1981-08-27 | 1983-03-01 | Teijin Yuka Kk | ｐ−キシレンの改良製造法 |
| US4761513A (en) | 1987-07-01 | 1988-08-02 | Uop Inc. | Temperature control for aromatic alkylation process |
| DE3868194D1 (de) * | 1987-09-02 | 1992-03-12 | Mobil Oil Corp | Verfahren zur transalkylierung von (polyalkyl)aromatischen kohlenwasserstoffen. |
| US5198595A (en) * | 1987-11-23 | 1993-03-30 | The Dow Chemical Company | Alkylation of aromatic compounds |
| US4891458A (en) * | 1987-12-17 | 1990-01-02 | Innes Robert A | Liquid phase alkylation or transalkylation process using zeolite beta |
| US4992607A (en) * | 1989-03-20 | 1991-02-12 | Mobil Oil Corporation | Petroleum refinery process and apparatus for the production of alkyl aromatic hydrocarbons from fuel gas and catalytic reformate |
| US5120890A (en) | 1990-12-31 | 1992-06-09 | Uop | Process for reducing benzene content in gasoline |
| DE69115056T2 (de) * | 1991-06-21 | 1996-04-18 | Dow Benelux | Verfahren zur Alkylierung von aromatischen Verbindungen. |
| EP0760025B1 (en) * | 1994-05-16 | 2002-08-28 | Honeywell International, Inc. | Filled cut-resistant fiber |
| CN1043036C (zh) * | 1994-05-24 | 1999-04-21 | 中国石油化工总公司 | 芳烃烷基化方法及其所用液固循环流化床设备 |
| US5600048A (en) * | 1994-12-27 | 1997-02-04 | Mobil Oil Corporation | Continuous process for preparing ethylbenzene using liquid phase alkylation and vapor phase transalkylation |
| US5660048A (en) * | 1996-02-16 | 1997-08-26 | Laroche Industries, Inc. | Air conditioning system for cooling warm moisture-laden air |
| JPH10298117A (ja) * | 1997-04-23 | 1998-11-10 | Mitsubishi Heavy Ind Ltd | 芳香族炭化水素の選択的アルキル化法 |
-
1998
- 1998-10-05 US US09/166,188 patent/US6642426B1/en not_active Expired - Lifetime
-
1999
- 1999-09-27 ES ES99948489T patent/ES2205882T3/es not_active Expired - Lifetime
- 1999-09-27 KR KR1020017004337A patent/KR100637964B1/ko not_active Expired - Lifetime
- 1999-09-27 EP EP99948489A patent/EP1119532B1/en not_active Expired - Lifetime
- 1999-09-27 WO PCT/US1999/022414 patent/WO2000020360A1/en not_active Ceased
- 1999-09-27 AU AU61654/99A patent/AU6165499A/en not_active Abandoned
- 1999-09-27 AT AT99948489T patent/ATE247613T1/de not_active IP Right Cessation
- 1999-09-27 JP JP2000574481A patent/JP4607326B2/ja not_active Expired - Lifetime
- 1999-09-27 DE DE69910598T patent/DE69910598T2/de not_active Expired - Lifetime
- 1999-09-27 ID IDW00200101004D patent/ID29191A/id unknown
- 1999-09-27 CA CA002346431A patent/CA2346431C/en not_active Expired - Fee Related
- 1999-09-27 CN CNB998131873A patent/CN1218913C/zh not_active Expired - Lifetime
- 1999-09-27 BR BRPI9915913-9A patent/BR9915913B1/pt not_active IP Right Cessation
- 1999-10-05 TW TW088117148A patent/TW505620B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BR9915913A (pt) | 2001-10-16 |
| KR20010083889A (ko) | 2001-09-03 |
| ATE247613T1 (de) | 2003-09-15 |
| US6642426B1 (en) | 2003-11-04 |
| KR100637964B1 (ko) | 2006-10-23 |
| EP1119532A4 (en) | 2002-08-14 |
| CN1326430A (zh) | 2001-12-12 |
| EP1119532A1 (en) | 2001-08-01 |
| EP1119532B1 (en) | 2003-08-20 |
| DE69910598D1 (de) | 2003-09-25 |
| JP2002526513A (ja) | 2002-08-20 |
| CN1218913C (zh) | 2005-09-14 |
| ES2205882T3 (es) | 2004-05-01 |
| JP4607326B2 (ja) | 2011-01-05 |
| DE69910598T2 (de) | 2004-06-24 |
| CA2346431A1 (en) | 2000-04-13 |
| BR9915913B1 (pt) | 2011-01-25 |
| TW505620B (en) | 2002-10-11 |
| AU6165499A (en) | 2000-04-26 |
| WO2000020360A1 (en) | 2000-04-13 |
| ID29191A (id) | 2001-08-09 |
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