CA2516898A1 - Process for the production of alkylaromatics - Google Patents
Process for the production of alkylaromatics Download PDFInfo
- Publication number
- CA2516898A1 CA2516898A1 CA002516898A CA2516898A CA2516898A1 CA 2516898 A1 CA2516898 A1 CA 2516898A1 CA 002516898 A CA002516898 A CA 002516898A CA 2516898 A CA2516898 A CA 2516898A CA 2516898 A1 CA2516898 A1 CA 2516898A1
- Authority
- CA
- Canada
- Prior art keywords
- olefin
- stream
- alkylaromatic
- alkylation
- compound
- 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
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
- C07C6/08—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
- 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
Abstract
A process for producing an alkylaromatic compound includes contacting a dilute olefin feed with a lean oil stream containing aromatic compound and alkylaromatic compound in an absorption zone to provide an alkylation reaction stream containing aromatic compound, alkylaromatic compound and olefin. The alkylation reaction stream is reacted under alkylation reaction conditions in an alkylation reaction zone to provide an effluent containing the aromatic compound and alkylaromatic compound. The effluent of step is separated into the Jean oil stream which is recycled to the absorption zone and a product portion from which an alkylaromatic product is recovered.
Claims (30)
1. A process for producing an alkylaromatic compound, comprising:
a) contacting a dilute olefin feed with a lean oil stream containing aromatic compound and alkylaromatic compound in an absorption zone to provide an alkylation reaction stream containing aromatic compound, alkylaromatic compound and olefin;
b) reacting the alkylation reaction stream of step (a) under alkylation reaction conditions in an alkylation reaction zone to provide an effluent containing the aromatic compound and alkylaromatic compound;
c) separating the effluent of step (b) into the lean oil stream which is recycled to the absorption zone of step (a) and a product portion; and, d) recovering an alkylaromatic product from the product portion of step (c).
a) contacting a dilute olefin feed with a lean oil stream containing aromatic compound and alkylaromatic compound in an absorption zone to provide an alkylation reaction stream containing aromatic compound, alkylaromatic compound and olefin;
b) reacting the alkylation reaction stream of step (a) under alkylation reaction conditions in an alkylation reaction zone to provide an effluent containing the aromatic compound and alkylaromatic compound;
c) separating the effluent of step (b) into the lean oil stream which is recycled to the absorption zone of step (a) and a product portion; and, d) recovering an alkylaromatic product from the product portion of step (c).
2. The process of claim 1, wherein the aromatic compound is selected from the group consisting of benzene, naphthalene, anthracene, phenanthrene, and derivatives thereof.
3. The process of claim 1, wherein the olefin alkylation agent is selected from the group consisting of ethylene, propylene, and other branched or linear olefins containing 2 to at least 20 carbon atoms.
4. The process of claim 1, wherein the alkylaromatic compound is selected from the group consisting of alkylbenzene, polyalkylbenzene and mixtures thereof.
5. The process of claim 4, wherein the alkylbenzene is selected from the group consisting of ethylbenzene and cumene.
6. The process of claim 4, wherein the polyalkylbenzene is selected from the group consisting of diethylbenzene, triethylbenzene, higher ethylated benzenes and mixtures thereof.
7. The process of claim 1, wherein the dilute olefin feed has an olefin concentration in the range of about 3 mol% to about 95 mol%.
8. The process of claim 7, wherein the dilute olefin feed has an olefin concentration in the range of about 3mol%
to about 70mol%.
to about 70mol%.
9. The process of claim 1, wherein the dilute olefin feed includes one or more inert low molecular weight impurities selected from the group consisting of hydrogen, methane, ethane, nitrogen, carbon dioxide, carbon monoxide, butane and pentane.
10. The process of claim 9, wherein the dilute olefin feed has an inert low molecular weight impurities concentration of at least about 5 mol%.
11. The process of claim 10, wherein the dilute olefin alkylation agent feed has an olefin concentration in the range of about 3 mol% to about 70 mol%.
12. The process of claim 1, wherein the absorption zone comprises an absorber selected from the group consisting of a packed column absorber, tray absorber and combined tray and packed column absorber.
13. The process of claim 12, wherein gaseous overheads from the absorber are transferred to a vent scrubber.
14. The process of claim 12, wherein the absorber operates in the gas phase.
15. The process of claim 1, wherein the alkylation reaction zone comprises an alkylator.
16. The process of claim 15, wherein the alkylator is a fixed bed reactor.
17. The process of claim 16 wherein the alkylator comprises multiple beds and multiple olefin inlets respectively positioned between the beds.
18. The process of claim 15, wherein the alkylator operates in the liquid phase.
19. The process of claim 15, wherein the alkylator contains a catalyst selected from the group consisting of zeolite BEA, zeolite MWW, zeolite Y, Mordenite catalyst, MFI
catalyst and Faujasite catalyst, or combinations thereof.
catalyst and Faujasite catalyst, or combinations thereof.
20. The process of claim 1, wherein the lean oil stream in step (c) comprises about 5 wt% to about 99 wt% of the effluent of step (b).
21. The process of claim 20, wherein the lean oil stream in step (c) comprises about 75 wt% to about 95 wt% of the effluent of step (b).
22. The process, of claim 1, wherein the recovery step (d) includes one or more distillation operations.
23. The process of claim 22, wherein unreacted aromatic compound is recovered in a first distillation operation and the alkylaromatic product is recovered in a second distillation operation.
24. The process of claim 23, wherein at least a portion of the unreacted aromatic compound is recycled to the lean oil stream.
25. The process of claim 1, wherein the effluent of step (b) also contains polyalkylaromatic byproduct which is recovered in a distillation operation.
26. The process of claim 25, wherein at least a portion of the recovered polyalkylaromatic byproduct is directed to a vent scrubber to provide a transalkylation reaction stream for transfer to a transalkylator.
27. The process of claim 26, wherein the transalkylation reaction stream is subjected to catalytic transalkylation reaction conditions to form a transalkylation reaction product stream having a higher aromatic to polyalkylaromatic ratio than that of the transalkylation reaction stream.
28. The process of claim 26, wherein the transalkylation reaction product stream is directed to the operations to separately recover unreacted aromatic compound and alkylaromatic compound.
28. The process of claim 1, wherein additional olefin alkylation agent is added to the alkylation reaction zone of step (b).
28. The process of claim 1, wherein additional olefin alkylation agent is added to the alkylation reaction zone of step (b).
29. The process of claim 28, wherein the additional olefin alkylation agent is high purity ethylene.
30. The process of claim 1, wherein step (c) includes the additional step of subjecting the first portion of the alkylation product stream of step (b) to an operation to recover ethane before recycling the first portion of the alkylation product stream to the contact zone of step (a).
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/376,683 US7238843B2 (en) | 2003-02-28 | 2003-02-28 | Process for the production of alkylaromatics |
| US10/376,683 | 2003-02-28 | ||
| PCT/US2004/005548 WO2004078681A2 (en) | 2003-02-28 | 2004-02-25 | Process for the production of alkylaromatics |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2516898A1 true CA2516898A1 (en) | 2004-09-16 |
| CA2516898C CA2516898C (en) | 2011-10-11 |
Family
ID=32907973
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2516898A Expired - Fee Related CA2516898C (en) | 2003-02-28 | 2004-02-25 | Process for the production of alkylaromatics |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7238843B2 (en) |
| EP (1) | EP1597217B1 (en) |
| JP (1) | JP4915733B2 (en) |
| KR (1) | KR101149717B1 (en) |
| CN (1) | CN1756727B (en) |
| AU (1) | AU2004218011B2 (en) |
| BR (1) | BRPI0407792B1 (en) |
| CA (1) | CA2516898C (en) |
| MX (1) | MXPA05008716A (en) |
| RU (1) | RU2322430C2 (en) |
| WO (1) | WO2004078681A2 (en) |
| ZA (1) | ZA200506862B (en) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040254414A1 (en) * | 2003-06-11 | 2004-12-16 | Hildreth James M. | Process for production of propylene and ethylbenzene from dilute ethylene streams |
| US7259282B2 (en) | 2003-09-08 | 2007-08-21 | Abb Lummus Global Inc. | Process for production of ethylbenzene from dilute ethylene streams |
| US7525002B2 (en) | 2005-02-28 | 2009-04-28 | Exxonmobil Research And Engineering Company | Gasoline production by olefin polymerization with aromatics alkylation |
| RU2404949C2 (en) * | 2005-02-28 | 2010-11-27 | ЭкссонМобил Рисерч энд Энджиниринг Компани | Method of alkylating aromatic compounds in vapour phase |
| EP1866268B1 (en) * | 2005-02-28 | 2024-04-03 | ExxonMobil Technology and Engineering Company | Gasoline production by olefin polymerization with aromatics alkylation |
| US7476774B2 (en) * | 2005-02-28 | 2009-01-13 | Exxonmobil Research And Engineering Company | Liquid phase aromatics alkylation process |
| KR100922032B1 (en) * | 2005-03-31 | 2009-10-19 | 엑손모빌 케미칼 패턴츠 인코포레이티드 | Process and catalyst for the transalkylation of aromatics |
| JP2008537939A (en) * | 2005-03-31 | 2008-10-02 | エクソンモービル・ケミカル・パテンツ・インク | Production of multi-phase alkyl aromatics |
| EP1866267B1 (en) * | 2005-03-31 | 2014-11-05 | Badger Licensing LLC | Alkylaromatics production using dilute alkene |
| WO2007081781A2 (en) * | 2006-01-07 | 2007-07-19 | Fina Technology, Inc. | Dilute liquid phase alkylation |
| US7501547B2 (en) * | 2006-05-10 | 2009-03-10 | Exxonmobil Chemical Patents Inc. | Alkylaromatics production |
| US8395006B2 (en) * | 2009-03-13 | 2013-03-12 | Exxonmobil Research And Engineering Company | Process for making high octane gasoline with reduced benzene content by benzene alkylation at high benzene conversion |
| US8889937B2 (en) | 2011-06-09 | 2014-11-18 | Uop Llc | Process for producing one or more alkylated aromatics |
| CN103664474B (en) * | 2012-09-05 | 2016-01-13 | 中国石油化工股份有限公司 | The method of ethylbenzene and ethanol alkylation Reactive Synthesis p-Diethylbenzene |
| CN103664473A (en) * | 2012-09-05 | 2014-03-26 | 中国石油化工股份有限公司 | Method for synthesizing p-diethylbenzene by ethylbenzene and ethylene |
| US9732014B2 (en) * | 2014-03-07 | 2017-08-15 | Uop Llc | Method of producing alkylaromatic compounds using aromatic compound from catalyst regeneration |
| WO2016030447A1 (en) * | 2014-08-28 | 2016-03-03 | Sabic Global Technologies B.V. | Process for producing alkylated aromatic hydrocarbons from a mixed hydrocarbon feedstream |
| CN110997875A (en) * | 2017-08-15 | 2020-04-10 | 沙特基础工业全球技术有限公司 | Method and system for cracking hydrocarbon feed |
| CN110498725B (en) * | 2018-05-16 | 2022-03-11 | 中国石油化工股份有限公司 | Solid acid catalyzed alkylation method |
| EP4063468A1 (en) | 2021-03-25 | 2022-09-28 | Indian Oil Corporation Limited | A process for enhancement of ron of fcc gasoline with simultaneous reduction in benzene |
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| US2909574A (en) * | 1958-01-29 | 1959-10-20 | Texaco Inc | Manufacture of alkylated aromatic hydrocarbons |
| US2902574A (en) * | 1958-02-03 | 1959-09-01 | Hughes Aircraft Co | Source for vapor deposition |
| US2998684A (en) * | 1959-09-22 | 1961-09-05 | Kenneth S Corey | Method and means for conditioning shaving lather |
| US3205277A (en) | 1962-12-21 | 1965-09-07 | Universal Oil Prod Co | Alkylation-transalkylation process |
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| US3843739A (en) | 1971-04-09 | 1974-10-22 | Gulf Research Development Co | Process for transalkylating diethyl benzene |
| US4008290A (en) | 1975-03-10 | 1977-02-15 | Uop Inc. | Cumene production |
| DE2511674C3 (en) | 1975-03-18 | 1978-12-21 | Chemische Werke Huels Ag, 4370 Marl | Process for the production of ethylbenzene by dehydrogenative aromatization |
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| US4083886A (en) | 1976-03-29 | 1978-04-11 | Uop Inc. | Transalkylation of alkylaromatic hydrocarbons |
| US4051191A (en) | 1977-01-03 | 1977-09-27 | Uop Inc. | Solid phosphoric acid catalyzed alkylation of aromatic hydrocarbons |
| US4107224A (en) * | 1977-02-11 | 1978-08-15 | Mobil Oil Corporation | Manufacture of ethyl benzene |
| US4169111A (en) | 1978-02-02 | 1979-09-25 | Union Oil Company Of California | Manufacture of ethylbenzene |
| US4215011A (en) | 1979-02-21 | 1980-07-29 | Chemical Research And Licensing Company | Catalyst system for separating isobutene from C4 streams |
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-
2003
- 2003-02-28 US US10/376,683 patent/US7238843B2/en active Active
-
2004
- 2004-02-25 CN CN2004800055085A patent/CN1756727B/en not_active Expired - Lifetime
- 2004-02-25 MX MXPA05008716A patent/MXPA05008716A/en active IP Right Grant
- 2004-02-25 KR KR1020057015702A patent/KR101149717B1/en active IP Right Grant
- 2004-02-25 RU RU2005130259/04A patent/RU2322430C2/en not_active IP Right Cessation
- 2004-02-25 CA CA2516898A patent/CA2516898C/en not_active Expired - Fee Related
- 2004-02-25 BR BRPI0407792-0A patent/BRPI0407792B1/en not_active IP Right Cessation
- 2004-02-25 EP EP04714609.7A patent/EP1597217B1/en not_active Expired - Fee Related
- 2004-02-25 AU AU2004218011A patent/AU2004218011B2/en not_active Ceased
- 2004-02-25 WO PCT/US2004/005548 patent/WO2004078681A2/en active Application Filing
- 2004-02-25 JP JP2006508824A patent/JP4915733B2/en not_active Expired - Fee Related
-
2005
- 2005-08-26 ZA ZA200506862A patent/ZA200506862B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2004078681A2 (en) | 2004-09-16 |
| ZA200506862B (en) | 2006-04-26 |
| KR20050106043A (en) | 2005-11-08 |
| US7238843B2 (en) | 2007-07-03 |
| US20040171899A1 (en) | 2004-09-02 |
| AU2004218011B2 (en) | 2010-02-25 |
| CN1756727A (en) | 2006-04-05 |
| JP4915733B2 (en) | 2012-04-11 |
| EP1597217A2 (en) | 2005-11-23 |
| AU2004218011A1 (en) | 2004-09-16 |
| BRPI0407792B1 (en) | 2014-01-28 |
| KR101149717B1 (en) | 2012-06-11 |
| MXPA05008716A (en) | 2005-09-20 |
| EP1597217B1 (en) | 2014-08-06 |
| CA2516898C (en) | 2011-10-11 |
| RU2005130259A (en) | 2006-02-10 |
| CN1756727B (en) | 2010-07-14 |
| JP2006519857A (en) | 2006-08-31 |
| RU2322430C2 (en) | 2008-04-20 |
| WO2004078681A3 (en) | 2004-12-09 |
| BRPI0407792A (en) | 2006-02-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20200225 |
|
| MKLA | Lapsed |
Effective date: 20200225 |