CA2022982C - Procede de transalkylation - Google Patents

Procede de transalkylation Download PDF

Info

Publication number: CA2022982C
Authority: CA; Canada
Prior art keywords: benzene; transalkylation; zone; reaction zone; supplying
Prior art date: 1990-08-09
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 - Lifetime

Application number

CA002022982A

Other languages

English (en)

Other versions

CA2022982A1 (fr

Inventor

James R. Butler

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Fina Technology Inc

Original Assignee

Fina Technology Inc

Priority date (The priority date 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 date listed.)

1990-08-09

Filing date

1990-08-09

Publication date

2001-07-17

1990-08-09 Application filed by Fina Technology Inc filed Critical Fina Technology Inc

1990-08-09 Priority to CA002022982A priority Critical patent/CA2022982C/fr

1992-02-10 Publication of CA2022982A1 publication Critical patent/CA2022982A1/fr

2001-07-17 Application granted granted Critical

2001-07-17 Publication of CA2022982C publication Critical patent/CA2022982C/fr

2010-08-09 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000010555 transalkylation reaction Methods 0.000 title claims abstract description 141
238000000034 method Methods 0.000 title claims abstract description 55
230000008569 process Effects 0.000 title claims abstract description 51
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 397
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims abstract description 174
238000005804 alkylation reaction Methods 0.000 claims abstract description 106
239000003054 catalyst Substances 0.000 claims abstract description 95
238000000926 separation method Methods 0.000 claims abstract description 87
230000029936 alkylation Effects 0.000 claims abstract description 78
238000009835 boiling Methods 0.000 claims abstract description 53
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 49
239000010457 zeolite Substances 0.000 claims abstract description 49
229910021536 Zeolite Inorganic materials 0.000 claims abstract description 46
125000003118 aryl group Chemical group 0.000 claims abstract description 42
239000007791 liquid phase Substances 0.000 claims abstract description 40
239000002168 alkylating agent Substances 0.000 claims abstract description 28
229940100198 alkylating agent Drugs 0.000 claims abstract description 28
238000007323 disproportionation reaction Methods 0.000 claims abstract description 25
239000000203 mixture Substances 0.000 claims abstract description 23
239000002808 molecular sieve Substances 0.000 claims abstract description 21
238000004519 manufacturing process Methods 0.000 claims abstract description 19
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 17
239000000758 substrate Substances 0.000 claims abstract description 16
239000012808 vapor phase Substances 0.000 claims abstract description 13
150000001555 benzenes Chemical class 0.000 claims abstract description 8
KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 claims description 60
238000006243 chemical reaction Methods 0.000 claims description 60
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 10
239000005977 Ethylene Substances 0.000 claims description 10
VIDOPANCAUPXNH-UHFFFAOYSA-N 1,2,3-triethylbenzene Chemical compound CCC1=CC=CC(CC)=C1CC VIDOPANCAUPXNH-UHFFFAOYSA-N 0.000 claims description 7
230000000694 effects Effects 0.000 claims description 7
230000006203 ethylation Effects 0.000 claims description 7
238000006200 ethylation reaction Methods 0.000 claims description 7
229930195733 hydrocarbon Natural products 0.000 claims description 7
150000002430 hydrocarbons Chemical class 0.000 claims description 7
150000001336 alkenes Chemical group 0.000 claims description 5
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 4
150000004996 alkyl benzenes Chemical class 0.000 claims description 2
238000004064 recycling Methods 0.000 claims description 2
239000012021 ethylating agents‎ Substances 0.000 claims 5
239000003795 chemical substances by application Substances 0.000 claims 4
YTAHJIFKAKIKAV-XNMGPUDCSA-N [(1R)-3-morpholin-4-yl-1-phenylpropyl] N-[(3S)-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl]carbamate Chemical compound O=C1[C@H](N=C(C2=C(N1)C=CC=C2)C1=CC=CC=C1)NC(O[C@H](CCN1CCOCC1)C1=CC=CC=C1)=O YTAHJIFKAKIKAV-XNMGPUDCSA-N 0.000 claims 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 28
239000000047 product Substances 0.000 description 23
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 22
239000008096 xylene Substances 0.000 description 15
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
238000012360 testing method Methods 0.000 description 10
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 5
230000004048 modification Effects 0.000 description 5
238000012986 modification Methods 0.000 description 5
229940078552 o-xylene Drugs 0.000 description 5
150000003738 xylenes Chemical class 0.000 description 5
DSNHSQKRULAAEI-UHFFFAOYSA-N 1,4-Diethylbenzene Chemical compound CCC1=CC=C(CC)C=C1 DSNHSQKRULAAEI-UHFFFAOYSA-N 0.000 description 4
229910000147 aluminium phosphate Inorganic materials 0.000 description 4
229910000323 aluminium silicate Inorganic materials 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
230000018044 dehydration Effects 0.000 description 4
238000006297 dehydration reaction Methods 0.000 description 4
238000004821 distillation Methods 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000007787 solid Substances 0.000 description 4
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 3
OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical class CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 3
238000010586 diagram Methods 0.000 description 3
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 3
239000000463 material Substances 0.000 description 3
229910052680 mordenite Inorganic materials 0.000 description 3
238000010926 purge Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
LGXAANYJEHLUEM-UHFFFAOYSA-N 1,2,3-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1C(C)C LGXAANYJEHLUEM-UHFFFAOYSA-N 0.000 description 2
GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 2
AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
AFZZYIJIWUTJFO-UHFFFAOYSA-N 1,3-diethylbenzene Chemical compound CCC1=CC=CC(CC)=C1 AFZZYIJIWUTJFO-UHFFFAOYSA-N 0.000 description 2
JRLPEMVDPFPYPJ-UHFFFAOYSA-N 1-ethyl-4-methylbenzene Chemical compound CCC1=CC=C(C)C=C1 JRLPEMVDPFPYPJ-UHFFFAOYSA-N 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical compound CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001350 alkyl halides Chemical class 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000009849 deactivation Effects 0.000 description 2
238000006356 dehydrogenation reaction Methods 0.000 description 2
-1 e.g. Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
229910052761 rare earth metal Inorganic materials 0.000 description 2
150000002910 rare earth metals Chemical class 0.000 description 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) 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
239000006057 Non-nutritive feed additive Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001345 alkine derivatives Chemical class 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003729 cation exchange resin Substances 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
238000005336 cracking Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000006204 deethylation Effects 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
150000005195 diethylbenzenes Chemical class 0.000 description 1
230000003292 diminished effect Effects 0.000 description 1
238000011143 downstream manufacturing Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
150000005673 monoalkenes Chemical class 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
239000012071 phase Substances 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
239000001294 propane Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
230000000630 rising effect Effects 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
238000003860 storage Methods 0.000 description 1
238000011144 upstream manufacturing Methods 0.000 description 1

Classifications

- 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
- Y02P20/582—Recycling of unreacted starting or intermediate materials

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA002022982A 1990-08-09 1990-08-09 Procede de transalkylation Expired - Lifetime CA2022982C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA002022982A CA2022982C (fr)	1990-08-09	1990-08-09	Procede de transalkylation

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA002022982A CA2022982C (fr)	1990-08-09	1990-08-09	Procede de transalkylation

Publications (2)

Publication Number	Publication Date
CA2022982A1 CA2022982A1 (fr)	1992-02-10
CA2022982C true CA2022982C (fr)	2001-07-17

Family

ID=4145687

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002022982A Expired - Lifetime CA2022982C (fr)	1990-08-09	1990-08-09	Procede de transalkylation

Country Status (1)

Country	Link
CA (1)	CA2022982C (fr)

1990
- 1990-08-09 CA CA002022982A patent/CA2022982C/fr not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CA2022982A1 (fr)	1992-02-10

Legal Events

Date	Code	Title	Description
1996-10-15	EEER	Examination request
2010-08-09	MKEX	Expiry

Publication	Publication Date	Title
EP0467007B1 (fr)	1996-04-17	Procédé de transalkylation
EP1062191B1 (fr)	2003-07-23	Production de composes alkylaromatiques
US5003119A (en)	1991-03-26	Manufacture of alkylbenzenes
US6376729B1 (en)	2002-04-23	Multi-phase alkylation process
EP1002778B1 (fr)	2003-04-02	Procédé d'alkylation en phase gazeuse avec charge repartie de catalyseur
US5847255A (en)	1998-12-08	Gas phase alkylation-liquid phase transalkylation process
EP0485683B1 (fr)	2001-01-10	Préparation d'aromatiques alkylées
US6222084B1 (en)	2001-04-24	Gas phase alkylation-liquid phase transalkylation process
EP0424393B1 (fr)	1995-08-09	Fabrication d'alkylbenzenes
EP0839783B1 (fr)	2001-08-16	Procédé d'alkylation en phase gazeuse et de transalkylation en phase liquide
EP0839784B1 (fr)	2002-06-12	Procédé d'alkylation et de transalkylation avec échange de chaleur intégré
US6897346B1 (en)	2005-05-24	Aromatic conversion process employing low surface area zeolite Y
US6268542B1 (en)	2001-07-31	Multi-phase alkylation-transalkylation process
CA2022982C (fr)	2001-07-17	Procede de transalkylation
EP1188734A1 (fr)	2002-03-20	Procédé pour la préparation de l'éthylbenzène par alkylation et transalkylation
JP2882542B2 (ja)	1999-04-12	トランスアルキル化法