CA2516648A1 - Process for the production of alkylbenzene - Google Patents
Process for the production of alkylbenzene Download PDFInfo
- Publication number
- CA2516648A1 CA2516648A1 CA002516648A CA2516648A CA2516648A1 CA 2516648 A1 CA2516648 A1 CA 2516648A1 CA 002516648 A CA002516648 A CA 002516648A CA 2516648 A CA2516648 A CA 2516648A CA 2516648 A1 CA2516648 A1 CA 2516648A1
- Authority
- CA
- Canada
- Prior art keywords
- stream
- benzene
- overhead
- alkylation
- alkylbenzene
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract 16
- 150000004996 alkyl benzenes Chemical class 0.000 title claims abstract 15
- 238000004519 manufacturing process Methods 0.000 title claims abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract 51
- 238000005804 alkylation reaction Methods 0.000 claims abstract 24
- 150000001336 alkenes Chemical class 0.000 claims abstract 13
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract 13
- 230000029936 alkylation Effects 0.000 claims abstract 12
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims abstract 10
- 239000003054 catalyst Substances 0.000 claims abstract 10
- 125000003118 aryl group Chemical group 0.000 claims abstract 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract 3
- 239000005977 Ethylene Substances 0.000 claims abstract 3
- 238000004821 distillation Methods 0.000 claims 15
- 229910021536 Zeolite Inorganic materials 0.000 claims 10
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims 10
- 239000010457 zeolite Substances 0.000 claims 10
- 239000006096 absorbing agent Substances 0.000 claims 6
- 238000010521 absorption reaction Methods 0.000 claims 6
- 239000007788 liquid Substances 0.000 claims 4
- 238000010555 transalkylation reaction Methods 0.000 claims 4
- 238000005201 scrubbing Methods 0.000 claims 3
- 230000003197 catalytic effect Effects 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- 229910052680 mordenite Inorganic materials 0.000 claims 2
- 230000002152 alkylating effect Effects 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract 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
- C07C2/66—Catalytic processes
-
- 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
- C07C15/073—Ethylbenzene
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/12—Silica and alumina
-
- 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
- C07C2529/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
-
- 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
- C07C2529/18—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the mordenite type
-
- 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
- C07C2529/60—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the type L
-
- 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
- C07C2529/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65
-
- 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
-
- 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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Abstract
A process for the production of alkylbenzene includes the steps of introducing benzene and an olefin feed into a first alkylation reaction zone in the presence of a first alkylation catalyst under first alkylation reaction conditions to produce alkylbenzene and a vapor containing unconverted olefin;
absorbing the unconverted olefin into an aromatic stream containing benzene and alkylbenzene; and, introducing the aromatic stream containing absorbed olefin into a second alkylation reaction zone containing a second alkylation catalyst under second alkylation reaction conditions to convert the absorbed olefin and at least some of the benzene of the aromatic stream to alkylbenzene. The process is particularly advantageous for the alkylation of benzene with ethylene to produce ethylbenzene. About 99.9 % conversion of ethylene is achieved overall, with a substantial reduction in the required catalyst.
absorbing the unconverted olefin into an aromatic stream containing benzene and alkylbenzene; and, introducing the aromatic stream containing absorbed olefin into a second alkylation reaction zone containing a second alkylation catalyst under second alkylation reaction conditions to convert the absorbed olefin and at least some of the benzene of the aromatic stream to alkylbenzene. The process is particularly advantageous for the alkylation of benzene with ethylene to produce ethylbenzene. About 99.9 % conversion of ethylene is achieved overall, with a substantial reduction in the required catalyst.
Claims (20)
1. A process for the production of alkylbenzene comprising the steps of:
a) introducing benzene and an olefin feed into a first alkylation reaction zone in the presence of a first alkylation catalyst under first alkylation reaction conditions to produce a first alkylation effluent containing alkylbenzene and a first alkylation overhead stream;
b) separating the first alkylation overhead stream into a liquid portion containing benzene and a vapor portion containing unconverted olefin;
c) absorbing a major portion of the unconverted olefin in the vapor portion of the first alkylation overhead stream into an aromatic lean oil stream containing benzene and alkylbenzene in an absorption zone to produce an olefin-containing rich oil stream; and, d) introducing said rich oil stream into a second alkylation reaction zone containing a second alkylation catalyst under second alkylation reaction conditions to produce the aromatic lean oil stream, at least a portion of the aromatic lean oil stream being cycled back to the absorption zone.
a) introducing benzene and an olefin feed into a first alkylation reaction zone in the presence of a first alkylation catalyst under first alkylation reaction conditions to produce a first alkylation effluent containing alkylbenzene and a first alkylation overhead stream;
b) separating the first alkylation overhead stream into a liquid portion containing benzene and a vapor portion containing unconverted olefin;
c) absorbing a major portion of the unconverted olefin in the vapor portion of the first alkylation overhead stream into an aromatic lean oil stream containing benzene and alkylbenzene in an absorption zone to produce an olefin-containing rich oil stream; and, d) introducing said rich oil stream into a second alkylation reaction zone containing a second alkylation catalyst under second alkylation reaction conditions to produce the aromatic lean oil stream, at least a portion of the aromatic lean oil stream being cycled back to the absorption zone.
2. The process of claim 1 further including the step of introducing the liquid portion of the first alkylation overhead stream and a stream of polyalkylbenzene into a transalkylation zone in the presence of a transalkylation catalyst under transalkylation reaction conditions to convert at least some benzene and polyalkylbenzene to alkylbenzene.
3. The process of claim 1 wherein the olefin is ethylene, the alkylbenzene is ethylbenzene, and the polyalkylbenzene is polyethylbenzene.
4. The process of claim 3 wherein the first alkylation reaction conditions include a pressure of from about 300 psig to about 550 psig and a temperature of from about 185°C
to about 240°C, and a phenyl:ethyl ratio ranging from about 2.0 to about 3.5.
to about 240°C, and a phenyl:ethyl ratio ranging from about 2.0 to about 3.5.
5. The process of claim 4 wherein the first alkylation reaction zone comprises a catalytic distillation unit operating in a mixed phase liquid-vapor mode.
6. The process of claim 3 wherein the absorption zone produces an absorber overhead vapor stream containing unreacted gases and benzene, the absorber overhead vapor stream being transferred to a scrubbing unit wherein the absorber overhead vapor stream is contacted with a down flow stream containing polyethylbenzene, the scrubbing unit producing a scrubber bottom effluent containing polyethylbenzene which is cycled to the transalkylation zone.
7. The process of claim 6 wherein the ethylbenzene-containing effluent from the first alkylation reaction zone is transferred to a first distillation unit which produces a first distillation overhead stream containing benzene and a first distillation bottom stream containing ethylbenzene, at least a first portion of the first distillation overhead stream being cycled to the aromatic lean oil stream from the second alkylation reaction zone.
8. The process of claim 7 wherein the first distillation bottom stream is transferred to a second distillation unit which produces a second distillation overhead stream containing ethylbenzene and a second distillation bottom stream containing polyethylbenzene.
9. The process of claim 8 wherein the second distillation bottom stream is transferred to a third distillation unit which produces a third distillation overhead stream containing polyethylbenzene, said third distillation overhead being cycled back to the scrubbing unit.
10. The process of claim 1 wherein the absorption zone comprises a packed column.
11. The process of claim 1 wherein the absorption zone comprises a tray column.
12. The process of claim 3 wherein the first alkylation catalyst comprises a material selected from the group consisting of zeolite X, zeolite Y, zeolite L, TMA
offretite, mordenite, amorphous silica-aliumina, zeolite BEA, zeolite MWW and MFI catalyst.
offretite, mordenite, amorphous silica-aliumina, zeolite BEA, zeolite MWW and MFI catalyst.
13. The process of claim 3 wherein the second alkylation catalyst comprises a material selected from the group consisting of zeolite X, zeolite Y, zeolite L, TMA
offretite, mordenite, amorphous silica-aliumina, zeolite BEA, zeolite MWW and MFI catalyst.
offretite, mordenite, amorphous silica-aliumina, zeolite BEA, zeolite MWW and MFI catalyst.
14. A system for the production of alkylbenzene comprising:
a) first alkylator means for alkylating benzene with an olefin, wherein the first alkylator means produces an effluent containing alkylbenzene and benzene, and an overhead stream;
b) condensing means for separating the overhead stream from the first alkylator means into a vapor stream and a liquid stream;
c) transalkylator means for contacting the liquid stream from the first alkylator means overhead with a stream containing polyalkylbenzene to produce a transalkylator effluent containing alkylbenzene and benzene;
d) absorber means for contacting the vapor stream from the first alkylator means overhead with a lean oil stream containing benzene and alkylbenzene to produce a rich oil stream containing benzene, alkylbenzene and unconverted olefin; and e) second alkylator means for converting the unconverted olefin and at least some of the benzene in the rich oil stream to produce the lean oil stream.
a) first alkylator means for alkylating benzene with an olefin, wherein the first alkylator means produces an effluent containing alkylbenzene and benzene, and an overhead stream;
b) condensing means for separating the overhead stream from the first alkylator means into a vapor stream and a liquid stream;
c) transalkylator means for contacting the liquid stream from the first alkylator means overhead with a stream containing polyalkylbenzene to produce a transalkylator effluent containing alkylbenzene and benzene;
d) absorber means for contacting the vapor stream from the first alkylator means overhead with a lean oil stream containing benzene and alkylbenzene to produce a rich oil stream containing benzene, alkylbenzene and unconverted olefin; and e) second alkylator means for converting the unconverted olefin and at least some of the benzene in the rich oil stream to produce the lean oil stream.
15. The system of claim 14 wherein the first alkylator means comprises a catalytic distillation unit.
16. The system of claim 14 wherein the absorber means comprises a packed column.
17. The system of claim 14 wherein the absorber means comprises a tray column.
18. The system of claim 14 further comprising a scrubber unit for contacting a vapor overhead from the absorption means with a downflow of stream containing polyalkylbenzene.
19. The system of claim 14 further comprising distillation means for separating out benzene and alhylbenzene from the alkylator means effluent.
20. The system of claim 14 further comprising heat transfer means for transferring heat between the lean oil stream and the rich oil stream.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/372,449 | 2003-02-25 | ||
| US10/372,449 US7074978B2 (en) | 2003-02-25 | 2003-02-25 | Process for the production of alkylbenzene |
| PCT/US2004/005540 WO2004076387A2 (en) | 2003-02-25 | 2004-02-24 | Process for the production of alkylbenzene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2516648A1 true CA2516648A1 (en) | 2004-09-10 |
| CA2516648C CA2516648C (en) | 2012-05-01 |
Family
ID=32868528
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2516648A Expired - Fee Related CA2516648C (en) | 2003-02-25 | 2004-02-24 | Process for the production of alkylbenzene |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US7074978B2 (en) |
| EP (1) | EP1606234B1 (en) |
| JP (1) | JP4667365B2 (en) |
| KR (1) | KR101016880B1 (en) |
| CN (1) | CN100465141C (en) |
| AU (2) | AU2004215343B2 (en) |
| BR (1) | BRPI0407706B1 (en) |
| CA (1) | CA2516648C (en) |
| MX (1) | MXPA05008417A (en) |
| RU (1) | RU2298541C2 (en) |
| WO (1) | WO2004076387A2 (en) |
| ZA (1) | ZA200506798B (en) |
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| US7074978B2 (en) * | 2003-02-25 | 2006-07-11 | Abb Lummus Global Inc. | Process for the production of alkylbenzene |
| US7071369B2 (en) * | 2003-06-10 | 2006-07-04 | Abb Lummus Global Inc. | Process for the production of alkylbenzene with ethane stripping |
| US7259282B2 (en) * | 2003-09-08 | 2007-08-21 | Abb Lummus Global Inc. | Process for production of ethylbenzene from dilute ethylene streams |
| US6977319B2 (en) * | 2004-03-12 | 2005-12-20 | Chevron Oronite Company Llc | Alkylated aromatic compositions, zeolite catalyst compositions and processes for making the same |
| US7622622B1 (en) | 2004-06-21 | 2009-11-24 | Uop Llc | Process for the high yield production of monoalkylaromatics |
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| CN103664484B (en) * | 2012-09-05 | 2016-04-06 | 中国石油化工股份有限公司 | The method of benzene and ethene gas phase hydrocarbonylation ethylbenzene |
| RU2514948C1 (en) * | 2013-05-16 | 2014-05-10 | ФЕДЕРАЛЬНОЕ ГОСУДАРСТВЕННОЕ БЮДЖЕТНОЕ УЧРЕЖДЕНИЕ НАУКИ ИНСТИТУТ ОРГАНИЧЕСКОЙ ХИМИИ им. Н.Д. ЗЕЛИНСКОГО РОССИЙСКОЙ АКАДЕМИИ НАУК (ИОХ РАН) | Catalyst for producing ethylbenzene from benzene and ethane and method of producing ethylbenzene with use thereof |
| CN104860790B (en) * | 2015-05-26 | 2016-08-24 | 天津大学 | Utilize the device and method of the ethylbenzene manufactured from ethylene that oil refinery dry gas pressure-variable adsorption reclaims |
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-
2003
- 2003-02-25 US US10/372,449 patent/US7074978B2/en active Active
-
2004
- 2004-02-24 KR KR1020057015697A patent/KR101016880B1/en active IP Right Grant
- 2004-02-24 MX MXPA05008417A patent/MXPA05008417A/en active IP Right Grant
- 2004-02-24 CA CA2516648A patent/CA2516648C/en not_active Expired - Fee Related
- 2004-02-24 CN CNB2004800051421A patent/CN100465141C/en not_active Expired - Lifetime
- 2004-02-24 RU RU2005129711/04A patent/RU2298541C2/en not_active IP Right Cessation
- 2004-02-24 AU AU2004215343A patent/AU2004215343B2/en not_active Ceased
- 2004-02-24 JP JP2006503850A patent/JP4667365B2/en not_active Expired - Fee Related
- 2004-02-24 WO PCT/US2004/005540 patent/WO2004076387A2/en active Application Filing
- 2004-02-24 BR BRPI0407706-7A patent/BRPI0407706B1/en not_active IP Right Cessation
- 2004-02-24 EP EP04714203A patent/EP1606234B1/en not_active Expired - Fee Related
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2005
- 2005-08-24 ZA ZA200506798A patent/ZA200506798B/en unknown
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2006
- 2006-06-08 US US11/449,548 patent/US7524467B2/en not_active Expired - Lifetime
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- 2009-12-11 AU AU2009248464A patent/AU2009248464B2/en not_active Ceased
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| BRPI0407706A (en) | 2006-02-14 |
| JP2006518762A (en) | 2006-08-17 |
| EP1606234A2 (en) | 2005-12-21 |
| BRPI0407706B1 (en) | 2014-04-15 |
| US7524467B2 (en) | 2009-04-28 |
| US7074978B2 (en) | 2006-07-11 |
| KR20050106042A (en) | 2005-11-08 |
| WO2004076387A3 (en) | 2004-10-14 |
| EP1606234B1 (en) | 2012-04-11 |
| AU2004215343B2 (en) | 2010-01-07 |
| AU2009248464A1 (en) | 2010-01-07 |
| JP4667365B2 (en) | 2011-04-13 |
| AU2009248464B2 (en) | 2011-08-25 |
| KR101016880B1 (en) | 2011-02-22 |
| RU2005129711A (en) | 2006-03-20 |
| WO2004076387A2 (en) | 2004-09-10 |
| US20040167371A1 (en) | 2004-08-26 |
| AU2004215343A1 (en) | 2004-09-10 |
| ZA200506798B (en) | 2006-05-31 |
| CN100465141C (en) | 2009-03-04 |
| CA2516648C (en) | 2012-05-01 |
| CN1753851A (en) | 2006-03-29 |
| MXPA05008417A (en) | 2005-10-19 |
| US20060229479A1 (en) | 2006-10-12 |
| RU2298541C2 (en) | 2007-05-10 |
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