TW505620B - Fluid-bed aromatics alkylation - Google Patents
Fluid-bed aromatics alkylation Download PDFInfo
- Publication number
- TW505620B TW505620B TW088117148A TW88117148A TW505620B TW 505620 B TW505620 B TW 505620B TW 088117148 A TW088117148 A TW 088117148A TW 88117148 A TW88117148 A TW 88117148A TW 505620 B TW505620 B TW 505620B
- Authority
- TW
- Taiwan
- Prior art keywords
- methanol
- aromatic
- toluene
- bed
- reaction
- Prior art date
Links
- 238000005804 alkylation reaction Methods 0.000 title abstract description 18
- 230000029936 alkylation Effects 0.000 title abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 61
- 238000000034 method Methods 0.000 claims abstract description 41
- 125000003118 aryl group Chemical group 0.000 claims abstract description 32
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 27
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
- -1 aromatic aromatic alcohols Chemical class 0.000 claims description 3
- 238000010025 steaming Methods 0.000 claims 2
- 238000005899 aromatization reaction Methods 0.000 claims 1
- 230000003115 biocidal effect Effects 0.000 claims 1
- 239000008393 encapsulating agent Substances 0.000 claims 1
- 239000002304 perfume Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 183
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 141
- 239000000376 reactant Substances 0.000 abstract description 33
- 239000008096 xylene Substances 0.000 abstract description 20
- 230000002152 alkylating effect Effects 0.000 abstract description 7
- 150000003738 xylenes Chemical class 0.000 abstract 1
- 239000002168 alkylating agent Substances 0.000 description 22
- 229940100198 alkylating agent Drugs 0.000 description 22
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 21
- 239000003054 catalyst Substances 0.000 description 20
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 19
- 239000000047 product Substances 0.000 description 14
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 9
- 150000001491 aromatic compounds Chemical class 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 239000002994 raw material Substances 0.000 description 7
- 239000004215 Carbon black (E152) Substances 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
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 238000007069 methylation reaction Methods 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 4
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000001354 calcination Methods 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- 238000011144 upstream manufacturing Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000005243 fluidization Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- JRLPEMVDPFPYPJ-UHFFFAOYSA-N 1-ethyl-4-methylbenzene Chemical compound CCC1=CC=C(C)C=C1 JRLPEMVDPFPYPJ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 239000013043 chemical agent Substances 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
- 230000000694 effects Effects 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 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
- 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 1
- AMBHHSBRXZAGDZ-UHFFFAOYSA-N 1-phenyl-2,3-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(C=2C=CC=CC=2)=C1C(C)C AMBHHSBRXZAGDZ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 1
- 238000006640 acetylation reaction Methods 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
- 125000000320 amidine group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 238000007796 conventional method 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
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler 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
- 230000008676 import Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- BKBMACKZOSMMGT-UHFFFAOYSA-N methanol;toluene Chemical compound OC.CC1=CC=CC=C1 BKBMACKZOSMMGT-UHFFFAOYSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000010422 painting 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
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000006207 propylation Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 230000003313 weakening effect Effects 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 (1)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW505620B true TW505620B (en) | 2002-10-11 |
Family
ID=22602174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW088117148A TW505620B (en) | 1998-10-05 | 1999-10-05 | 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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
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| CA2538520C (en) | 2003-07-24 | 2015-02-10 | The Queen's Medical Center | Preparation and use of alkylating agents |
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| 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 |
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| 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 |
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| 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 |
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- 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
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
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 |
| AU6165499A (en) | 2000-04-26 |
| CA2346431C (en) | 2009-02-03 |
| WO2000020360A1 (en) | 2000-04-13 |
| ID29191A (id) | 2001-08-09 |
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