WO2011112189A8 - Alkylated aromatics production - Google Patents

Alkylated aromatics production Download PDF

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Publication number
WO2011112189A8
WO2011112189A8 PCT/US2010/026844 US2010026844W WO2011112189A8 WO 2011112189 A8 WO2011112189 A8 WO 2011112189A8 US 2010026844 W US2010026844 W US 2010026844W WO 2011112189 A8 WO2011112189 A8 WO 2011112189A8
Authority
WO
WIPO (PCT)
Prior art keywords
impurities
alkylation
water
alkylatable aromatic
zone
Prior art date
Application number
PCT/US2010/026844
Other languages
French (fr)
Other versions
WO2011112189A1 (en
Inventor
Matthew J. Vincent
Vijay Nanda
Maruti Bhandarkar
Brian Maerz
Terry E. Helton
Original Assignee
Exxonmobil Chemical Patents Inc.
Stone & Webster, 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.)
Filing date
Publication date
Priority to CN201080065284.2A priority Critical patent/CN102906054B/en
Priority to EP10847601.1A priority patent/EP2545018A4/en
Priority to BR112012022691A priority patent/BR112012022691A2/en
Priority to KR1020127023242A priority patent/KR101533875B1/en
Priority to SG2012060281A priority patent/SG183322A1/en
Priority to RU2012141942/04A priority patent/RU2528825C2/en
Application filed by Exxonmobil Chemical Patents Inc., Stone & Webster, Inc. filed Critical Exxonmobil Chemical Patents Inc.
Priority to JP2012557019A priority patent/JP5659247B2/en
Priority to PCT/US2010/026844 priority patent/WO2011112189A1/en
Priority to TW099144498A priority patent/TWI523831B/en
Publication of WO2011112189A1 publication Critical patent/WO2011112189A1/en
Publication of WO2011112189A8 publication Critical patent/WO2011112189A8/en
Priority to US14/075,218 priority patent/US8877996B2/en

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    • 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
    • B01J29/60—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the type L, as exemplified by patent document US3216789
    • 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
    • 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
    • B01J29/18—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the mordenite type
    • 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
    • B01J29/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively
    • 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
    • B01J29/50—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the erionite or offretite type, e.g. zeolite T, as exemplified by patent document US2950952
    • 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
    • B01J29/65—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the ferrierite type, e.g. types ZSM-21, ZSM-35 or ZSM-38, as exemplified by patent documents US4046859, US4016245 and US4046859, respectively
    • 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
    • B01J29/7038—MWW-type, e.g. MCM-22, ERB-1, ITQ-1, PSH-3 or SSZ-25
    • 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
    • B01J29/80—Mixtures of different zeolites
    • 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
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/02—Monocyclic hydrocarbons
    • C07C15/085—Isopropylbenzene
    • 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
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/12—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers
    • C07C7/13—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers by molecular-sieve technique
    • 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
    • C07C2529/70—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
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Materials Engineering (AREA)
  • Analytical Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Water Supply & Treatment (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

Disclosed is a process for the production of alkylated aromatics by contacting a feed stream comprising an alkylatable aromatic, an alkylating agent and trace amounts of water and impurities in the presence of first and second alkylation catalysts wherein the water and impurities are removed in order to improve the cycle length of such alkylation catalysts. Water and a portion of impurities are removed in a dehydration zone. A first alkylation zone having a first alkylation catalyst which, in some embodiments is a large pore molecular sieve, acts to remove a larger portion of impurities, such as nitrogenous and other species, and to alkylate a smaller portion of the alkylatable aromatic compound. A second alkylation zone, which in some embodiments is a medium pore molecular sieve, acts to remove a smaller portion of impurities, and to alkylate a larger portion of the alkylatable aromatic compound.
PCT/US2010/026844 2010-03-10 2010-03-10 Alkylated aromatics production WO2011112189A1 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
EP10847601.1A EP2545018A4 (en) 2010-03-10 2010-03-10 Alkylated aromatics production
BR112012022691A BR112012022691A2 (en) 2010-03-10 2010-03-10 production of alkylated aromatics
KR1020127023242A KR101533875B1 (en) 2010-03-10 2010-03-10 Alkylated aromatics production
SG2012060281A SG183322A1 (en) 2010-03-10 2010-03-10 Alkylated aromatics production
RU2012141942/04A RU2528825C2 (en) 2010-03-10 2010-03-10 Production of alkylated aromatic compounds
CN201080065284.2A CN102906054B (en) 2010-03-10 2010-03-10 Alkylating aromatic substance is produced
JP2012557019A JP5659247B2 (en) 2010-03-10 2010-03-10 Production of alkylated aromatics
PCT/US2010/026844 WO2011112189A1 (en) 2010-03-10 2010-03-10 Alkylated aromatics production
TW099144498A TWI523831B (en) 2010-03-10 2010-12-17 Alkylated aromatics production
US14/075,218 US8877996B2 (en) 2010-03-10 2013-11-08 Alkylated aromatics production

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2010/026844 WO2011112189A1 (en) 2010-03-10 2010-03-10 Alkylated aromatics production

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US12/721,326 Continuation US8629311B2 (en) 2010-03-10 2010-03-10 Alkylated aromatics production

Publications (2)

Publication Number Publication Date
WO2011112189A1 WO2011112189A1 (en) 2011-09-15
WO2011112189A8 true WO2011112189A8 (en) 2012-03-08

Family

ID=44563758

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2010/026844 WO2011112189A1 (en) 2010-03-10 2010-03-10 Alkylated aromatics production

Country Status (8)

Country Link
EP (1) EP2545018A4 (en)
JP (1) JP5659247B2 (en)
KR (1) KR101533875B1 (en)
CN (1) CN102906054B (en)
BR (1) BR112012022691A2 (en)
RU (1) RU2528825C2 (en)
SG (1) SG183322A1 (en)
WO (1) WO2011112189A1 (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9249067B2 (en) 2010-05-20 2016-02-02 Exxonmobil Chemical Patents Inc. Alkylation process
KR20150002714A (en) 2012-04-03 2015-01-07 릴라이언스 인더스트리즈 리미티드 An oxygenates-free c8-c12 aromatic hydrocarbon stream and a process for preparing the same
RU2640595C2 (en) * 2013-05-08 2018-01-10 БЭДЖЕР ЛАЙСЕНСИНГ ЭлЭлСи Method for alkylation of aromatic compounds
US20160130196A1 (en) * 2014-11-07 2016-05-12 Uop Llc Highly selective alkylation process with low zeolite catalyst composition
WO2018160327A1 (en) * 2017-02-28 2018-09-07 Exxonmobil Chemical Patents Inc. Catalyst compositions and their use in aromatic alkylation processes
US11654423B2 (en) 2017-02-28 2023-05-23 Exxonmobil Chemical Patents Inc. Catalyst compositions and their use in aromatic alkylation processes
KR102343528B1 (en) * 2017-03-29 2021-12-29 엑손모빌 케미칼 패턴츠 인코포레이티드 Catalyst compositions and their use in aromatic alkylation processes
CN111574318B (en) * 2020-06-04 2022-09-30 常州瑞华化工工程技术股份有限公司 Energy-saving reaction process for producing ethylbenzene from pure ethylene
RU2756954C1 (en) * 2020-12-09 2021-10-07 Акционерное общество "Газпромнефть - Омский НПЗ" (АО "Газпромнефть-ОНПЗ") Method for obtaining alkyl derivatives of arenes
CN113333014A (en) * 2021-06-02 2021-09-03 辽宁师范大学 Solid catalyst for preparing diethylbenzene by ethyl benzene ethanol/ethylene alkylation and preparation method thereof

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8028A (en) * 1851-04-08 Hokse-poweb
US5030786A (en) * 1989-06-23 1991-07-09 Fina Technology, Inc. Liquid phase aromatic conversion process
JPH04346939A (en) * 1991-05-24 1992-12-02 Asahi Chem Ind Co Ltd Production of alkyl aromatic compound
US5777187A (en) * 1996-02-08 1998-07-07 Huntsman Petrochemical Corporation Two-step process for alkylation of benzene to form linear alkylbenzenes
JP2000516248A (en) * 1996-08-20 2000-12-05 ザ ダウ ケミカル カンパニー Method for producing alkylated benzene
US6617482B1 (en) * 2000-08-16 2003-09-09 Exxonmobil Chemical Patents Inc. Removable of polar contaminants from aromatic feedstocks
WO2003074452A1 (en) * 2002-02-28 2003-09-12 Stone & Webster, Inc. Production of alkyl aromatic compounds
US6995295B2 (en) * 2002-09-23 2006-02-07 Exxonmobil Chemical Patents Inc. Alkylaromatics production
US7425659B2 (en) * 2006-01-31 2008-09-16 Exxonmobil Chemical Patents Inc. Alkylaromatics production
US7645913B2 (en) * 2007-01-19 2010-01-12 Exxonmobil Chemical Patents Inc. Liquid phase alkylation with multiple catalysts

Also Published As

Publication number Publication date
BR112012022691A2 (en) 2016-08-23
RU2528825C2 (en) 2014-09-20
CN102906054B (en) 2015-11-25
RU2012141942A (en) 2014-04-10
SG183322A1 (en) 2012-09-27
CN102906054A (en) 2013-01-30
KR20120136357A (en) 2012-12-18
JP5659247B2 (en) 2015-01-28
EP2545018A4 (en) 2014-10-08
JP2013521336A (en) 2013-06-10
EP2545018A1 (en) 2013-01-16
KR101533875B1 (en) 2015-07-03
WO2011112189A1 (en) 2011-09-15

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