CA2528283A1 - Process for the production of alkylbenzene with ethane stripping - Google Patents

Process for the production of alkylbenzene with ethane stripping Download PDF

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Publication number
CA2528283A1
CA2528283A1 CA002528283A CA2528283A CA2528283A1 CA 2528283 A1 CA2528283 A1 CA 2528283A1 CA 002528283 A CA002528283 A CA 002528283A CA 2528283 A CA2528283 A CA 2528283A CA 2528283 A1 CA2528283 A1 CA 2528283A1
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Prior art keywords
stream
alkylation
overhead
alkylbenzene
benzene
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CA002528283A
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French (fr)
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CA2528283C (en
Inventor
Stephen L. Pohl
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CB&I Technology Inc
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Individual
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    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
    • B01D3/009—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping in combination with chemical reactions
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
    • B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
    • B01J29/084—Y-type faujasite
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
    • B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
    • B01J29/7007—Zeolite Beta
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00002—Chemical plants
    • B01J2219/00004—Scale aspects
    • B01J2219/00006—Large-scale industrial plants
    • 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 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. The first alkylation overhead stream is separated into a liquid portion containing benzene and a vapor portion containing unconverted olefin and ethane. A major portion of the unconverted olefin in the vapor portion of the first alkylation overhead stream is absorbed into a de-ethanized aromatic lean oil stream containing benzene and alkylbenzene in an absorption zone to produce a rich oil stream containing olefins and at least some of the ethane. The rich oil stream is sent to a second alkylation reaction zone containing a second alkylation catalyst under second alkylation reaction conditions to produce a first aromatic lean oil stream, which is fractionated in a de-ethanizer to produces a de-ethanizer vapor overhead containing a major portion of the ethane and a, liquid bottoms containing the de-ethanized aromatic lean oil.

Claims (21)

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 and ethane;
c) absorbing a major portion of the unconverted olefin in the vapor portion of the first alkylation overhead stream into a de-ethanized aromatic substantially olefin-free lean oil stream containing benzene and alkylbenzene in an absorption zone to produce a rich oil stream containing olefins and at least some of the ethane;
d) introducing said rich oil stream into a second alkylation reaction zone containing a second alkylation catalyst under second alkylation.reaction conditions to produce a first aromatic lean oil stream; and, e) fractionating the first aromatic lean oil stream in a de-ethanizer to produces a de-ethanizer vapor overhead containing a major portion of the ethane and a liquid bottoms stream containing the de-ethanized aromatic lean oil.
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.
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 absorber overhead vapor stream is combined with the de-ethanizer vapor overhead to produce a combined vapor stream which is transferred to a scrubbing unit wherein the combined 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 de-ethanized aromatic lean oil stream from the de-ethanizer.
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 zeolite Beta.
13. The process of claim 3 wherein the second alkylation catalyst comprises zeolite Y.
14. The process of claim 1 wherein the vapor portion separated from the first alkylation overhead stream further contains one or more component selected from. the group consisting of hydrogen, methane, carbon monoxide, carbon dioxide, propane and nitrogen.
15. 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 de-ethanized lean oil stream containing benzene and alkylbenzene to produce a rich oil stream containing benzene, alkylbenzene and unconverted olefin;

e) second alkylator means for converting the unconverted olefin and at least some of the benzene in the rich oil stream to produce a first lean oil stream; and, f). a fractionator for de-ethanizing the first lean oil stream to produce the de-ethanized lean oil stream.
16. The system of claim 15 wherein the first alkylator means comprises a catalytic distillation unit.
17. The system of claim 15 wherein the absorber means comprises a packed column.
18. The system of claim 15 wherein the absorber means comprises a tray column.
19. The system of claim 15 further comprising a scrubber unit for contacting a vapor overhead from the absorption means with a downflow of stream containing polyalkylbenzene.
20. The system. of claim 15 further comprising distillation means for separating out benzene and alkylbenzene from the alkylator means effluent.
21. The system of claim 15 further comprising heat transfer means for transferring heat between the de-ethanized lean oil stream and the rich oil stream.
CA2528283A 2003-06-10 2004-06-08 Process for the production of alkylbenzene with ethane stripping Expired - Fee Related CA2528283C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US10/457,863 US7071369B2 (en) 2003-06-10 2003-06-10 Process for the production of alkylbenzene with ethane stripping
US10/457,863 2003-06-10
PCT/US2004/018086 WO2004110965A1 (en) 2003-06-10 2004-06-08 Process for the production of alkzbenzene with ethane stripping

Publications (2)

Publication Number Publication Date
CA2528283A1 true CA2528283A1 (en) 2004-12-23
CA2528283C CA2528283C (en) 2011-08-30

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Family Applications (1)

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CA2528283A Expired - Fee Related CA2528283C (en) 2003-06-10 2004-06-08 Process for the production of alkylbenzene with ethane stripping

Country Status (12)

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US (2) US7071369B2 (en)
EP (1) EP1636153A1 (en)
JP (1) JP4455597B2 (en)
KR (1) KR100969742B1 (en)
CN (1) CN100376517C (en)
AU (1) AU2004247693B2 (en)
BR (1) BRPI0411238B1 (en)
CA (1) CA2528283C (en)
MX (1) MXPA05013248A (en)
RU (1) RU2320629C2 (en)
WO (1) WO2004110965A1 (en)
ZA (1) ZA200510006B (en)

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ZA200510006B (en) 2006-11-29
KR100969742B1 (en) 2010-07-13
US7071369B2 (en) 2006-07-04
KR20060059895A (en) 2006-06-02
US20060204410A1 (en) 2006-09-14
RU2005138508A (en) 2006-06-10
JP2007537987A (en) 2007-12-27
MXPA05013248A (en) 2006-03-09
CA2528283C (en) 2011-08-30
WO2004110965A1 (en) 2004-12-23
JP4455597B2 (en) 2010-04-21
US20040254412A1 (en) 2004-12-16
AU2004247693B2 (en) 2009-11-26
RU2320629C2 (en) 2008-03-27
US7517506B2 (en) 2009-04-14
CN100376517C (en) 2008-03-26
EP1636153A1 (en) 2006-03-22
AU2004247693A1 (en) 2004-12-23
BRPI0411238A (en) 2006-07-11
CN1802336A (en) 2006-07-12
BRPI0411238B1 (en) 2015-07-21

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