CA2661021C - Processes for the reduction of alkylation catalyst deactivation utilizing low silica to alumina ratio catalyst - Google Patents

Processes for the reduction of alkylation catalyst deactivation utilizing low silica to alumina ratio catalyst Download PDF

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Publication number
CA2661021C
CA2661021C CA2661021A CA2661021A CA2661021C CA 2661021 C CA2661021 C CA 2661021C CA 2661021 A CA2661021 A CA 2661021A CA 2661021 A CA2661021 A CA 2661021A CA 2661021 C CA2661021 C CA 2661021C
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CA
Canada
Prior art keywords
catalyst
alkylation
preliminary
alkylation catalyst
sio2
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.)
Active
Application number
CA2661021A
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English (en)
French (fr)
Other versions
CA2661021A1 (en
Inventor
James Butler
Xin Xiao
Jim Merrill
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Fina Technology Inc
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Fina Technology Inc
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Publication of CA2661021A1 publication Critical patent/CA2661021A1/en
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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
    • 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
    • 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
    • B01J29/7049—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65 containing rare earth elements, titanium, zirconium, hafnium, zinc, cadmium, mercury, gallium, indium, thallium, tin or lead
    • B01J29/7057—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
    • 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
    • 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
    • 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
    • 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
    • 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
    • Y02P20/584—Recycling of catalysts

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (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)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CA2661021A 2006-09-05 2007-08-27 Processes for the reduction of alkylation catalyst deactivation utilizing low silica to alumina ratio catalyst Active CA2661021C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US11/515,679 US20080058566A1 (en) 2006-09-05 2006-09-05 Processes for reduction of alkylation catalyst deactivation utilizing low silica to alumina ratio catalyst
US11/515,679 2006-09-05
PCT/US2007/076872 WO2008030722A2 (en) 2006-09-05 2007-08-27 Processes for the reduction of alkylation catalyst deactivation utilizing low silica to alumina ratio catalyst

Publications (2)

Publication Number Publication Date
CA2661021A1 CA2661021A1 (en) 2008-03-13
CA2661021C true CA2661021C (en) 2015-11-24

Family

ID=39152703

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2661021A Active CA2661021C (en) 2006-09-05 2007-08-27 Processes for the reduction of alkylation catalyst deactivation utilizing low silica to alumina ratio catalyst

Country Status (8)

Country Link
US (5) US20080058566A1 (https=)
EP (1) EP2064168A4 (https=)
JP (1) JP5486306B2 (https=)
KR (3) KR101586629B1 (https=)
CN (2) CN102153435A (https=)
CA (1) CA2661021C (https=)
MX (2) MX2009002350A (https=)
WO (1) WO2008030722A2 (https=)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101119814B1 (ko) * 2004-06-07 2012-03-06 가부시키가이샤 니콘 스테이지 장치, 노광 장치 및 노광 방법
US7645913B2 (en) * 2007-01-19 2010-01-12 Exxonmobil Chemical Patents Inc. Liquid phase alkylation with multiple catalysts
US8134036B2 (en) * 2008-03-13 2012-03-13 Fina Technology Inc Process for liquid phase alkylation
US8865958B2 (en) * 2008-09-30 2014-10-21 Fina Technology, Inc. Process for ethylbenzene production
US8697208B2 (en) * 2009-07-24 2014-04-15 Fina Technology, Inc. Polystyrene nanocomposites for blow molding applications
US8455383B2 (en) 2009-09-28 2013-06-04 Fina Technology, Inc. Process for catalyst regeneration and extended use
RU2577317C2 (ru) * 2010-05-20 2016-03-20 Эксонмобил Кемикэл Пейтентс Инк. Улучшенный способ алкилирования
US8785706B2 (en) * 2011-05-22 2014-07-22 Fina Technology, Inc. Addition of a base to enhance product yield in alkylation reactions
US20120296142A1 (en) * 2011-05-22 2012-11-22 Fina Technology, Inc. Addition of basic nitrogen to alkylation reactions
CN105709815B (zh) * 2014-12-02 2018-06-19 中国石油化工股份有限公司 一种甲苯与乙烯选择性烷基化催化剂及其制备方法
EP3416933B1 (en) * 2016-02-17 2020-06-03 Badger Licensing LLC Process for producing ethylbenzene
BR112019006868A2 (pt) 2016-10-06 2019-06-25 Exxonmobil Chemical Patents Inc processo para seletivar catalisador para produzir paraxileno por metilação de benzeno e/ou tolueno
WO2018067280A1 (en) * 2016-10-06 2018-04-12 Exxonmobil Chemical Patents Inc. Process for producing paraxylene by methylation of benzene and/or toluene
KR102235872B1 (ko) 2016-10-06 2021-04-06 엑손모빌 케미칼 패턴츠 인코포레이티드 방향족 탄화수소의 메틸화 방법
US11673849B2 (en) 2016-12-21 2023-06-13 Exxonmobil Chemical Patents Inc. Process for selectivating catalyst for producing paraxylene by methylation of benzene and/or toluene

Family Cites Families (28)

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US3308069A (en) 1964-05-01 1967-03-07 Mobil Oil Corp Catalytic composition of a crystalline zeolite
US4185040A (en) 1977-12-16 1980-01-22 Union Oil Company Of California Alkylation of aromatic hydrocarbons
US4358362A (en) * 1981-01-15 1982-11-09 Mobil Oil Corporation Method for enhancing catalytic activity
US4642226A (en) 1984-04-16 1987-02-10 Mobil Oil Corporation Process for the preparation of zeolite Beta using dibenzyldimethylammonium ions and the product produced
US5081323A (en) * 1987-12-17 1992-01-14 Chevron Research And Technology Company Liquid phase alkylation or transalkylation process using zeolite beta
US4992606A (en) 1988-10-06 1991-02-12 Mobil Oil Corp. Process for preparing short chain alkyl aromatic compounds
US5535817A (en) * 1989-07-28 1996-07-16 Uop Sorption cooling process and apparatus
US5334795A (en) * 1990-06-28 1994-08-02 Mobil Oil Corp. Production of ethylbenzene
US5258565A (en) 1992-05-04 1993-11-02 Mobil Oil Corp. Process for preparing short chain alkylaromatic compounds
US5362697A (en) 1993-04-26 1994-11-08 Mobil Oil Corp. Synthetic layered MCM-56, its synthesis and use
AU674427B2 (en) 1993-06-16 1996-12-19 Mobil Oil Corporation Liquid phase ethylbenzene synthesis
KR100601744B1 (ko) * 1996-08-20 2006-07-19 다우 글로벌 테크놀로지스 인크. 알킬화 벤젠의 제조방법
JP4275739B2 (ja) * 1996-09-06 2009-06-10 エクソンモービル・ケミカル・パテンツ・インク ゼオライトβを用いるアルキル化方法
US5998687A (en) * 1997-07-29 1999-12-07 Uop Llc Ethylbenzene process using stacked reactor loading of beta and Y zeolites
US6057485A (en) * 1998-11-17 2000-05-02 Fina Technology, Inc. Gas phase alkylation with split load of catalyst
US6617482B1 (en) * 2000-08-16 2003-09-09 Exxonmobil Chemical Patents Inc. Removable of polar contaminants from aromatic feedstocks
US20020042548A1 (en) * 2001-07-11 2002-04-11 Dandekar Ajit B. Process for producing cumene
FR2832144B1 (fr) * 2001-11-15 2004-09-24 Inst Francais Du Petrole Procede de production de phenylalcanes utilisant une combinaison de deux catalyseurs
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US6933418B2 (en) * 2002-10-04 2005-08-23 Fina Technology, Inc. Critical phase alkylation process
US20040138511A1 (en) * 2003-01-10 2004-07-15 James Butler Aromatic alkylation process with direct recycle
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US6894201B1 (en) * 2003-12-19 2005-05-17 Uop Llc Process and apparatus for the removal of nitrogen compounds from a fluid stream
US20060194991A1 (en) * 2005-02-25 2006-08-31 Fina Technology, Inc. Treatment of alkylation catalyst poisons
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US7476774B2 (en) * 2005-02-28 2009-01-13 Exxonmobil Research And Engineering Company Liquid phase aromatics alkylation process
US7501547B2 (en) * 2006-05-10 2009-03-10 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
KR101586629B1 (ko) 2016-01-19
JP5486306B2 (ja) 2014-05-07
JP2010502636A (ja) 2010-01-28
KR20140051390A (ko) 2014-04-30
KR101587786B1 (ko) 2016-01-25
US20080058566A1 (en) 2008-03-06
US8552238B2 (en) 2013-10-08
US9556083B2 (en) 2017-01-31
KR20090059139A (ko) 2009-06-10
CN102153435A (zh) 2011-08-17
US20140128651A1 (en) 2014-05-08
US20130225888A1 (en) 2013-08-29
US20110301396A1 (en) 2011-12-08
WO2008030722A3 (en) 2008-04-24
KR20140051389A (ko) 2014-04-30
MX374947B (es) 2025-03-06
US9556084B2 (en) 2017-01-31
KR101542785B1 (ko) 2015-08-07
CN101511753A (zh) 2009-08-19
EP2064168A4 (en) 2010-12-15
CA2661021A1 (en) 2008-03-13
MX2009002350A (es) 2009-03-23
US8680354B2 (en) 2014-03-25
US20140005454A1 (en) 2014-01-02
WO2008030722A2 (en) 2008-03-13
EP2064168A2 (en) 2009-06-03

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Effective date: 20250228