US20070043181A1 - Methods of preparation of an olefin oligomerization catalyst - Google Patents

Methods of preparation of an olefin oligomerization catalyst Download PDF

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Publication number
US20070043181A1
US20070043181A1 US11/207,232 US20723205A US2007043181A1 US 20070043181 A1 US20070043181 A1 US 20070043181A1 US 20723205 A US20723205 A US 20723205A US 2007043181 A1 US2007043181 A1 US 2007043181A1
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United States
Prior art keywords
chromium
catalyst
containing compound
composition
halide
Prior art date
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Abandoned
Application number
US11/207,232
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English (en)
Inventor
Ronald Knudsen
Ronald Abbott
Bruce Kreischer
Eduardo Baralt
Brooke Small
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Chevron Phillips Chemical Co LP
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Chevron Phillips Chemical Co LP
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.)
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Application filed by Chevron Phillips Chemical Co LP filed Critical Chevron Phillips Chemical Co LP
Priority to US11/207,232 priority Critical patent/US20070043181A1/en
Assigned to CHEVRON PHILLIPS CHEMICAL COMPANY LP reassignment CHEVRON PHILLIPS CHEMICAL COMPANY LP ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KNUDSEN, RONALD D., BARALT, EDUARDO J., KREISCHER, BRUCE E., SMALL, BROOKE L, ABBOTT, RONALD G.
Priority to PCT/US2006/031303 priority patent/WO2007024504A1/en
Priority to AU2006283779A priority patent/AU2006283779A1/en
Priority to CN2006800388951A priority patent/CN101291733B/zh
Priority to CA002619226A priority patent/CA2619226A1/en
Priority to EP06801210A priority patent/EP1931469A1/en
Priority to ARP060103611A priority patent/AR057506A1/es
Publication of US20070043181A1 publication Critical patent/US20070043181A1/en
Priority to US12/534,536 priority patent/US7910670B2/en
Priority to US12/897,296 priority patent/US8993822B2/en
Priority to US14/633,461 priority patent/US9550841B2/en
Abandoned legal-status Critical Current

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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
    • C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
    • C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
    • C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
    • C07C2/08—Catalytic processes
    • C07C2/26—Catalytic processes with hydrides or organic compounds
    • C07C2/32—Catalytic processes with hydrides or organic compounds as complexes, e.g. acetyl-acetonates
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
    • B01J31/128—Mixtures of organometallic compounds
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
    • B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
    • B01J31/143—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron of aluminium
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/40—Regeneration or reactivation
    • B01J31/4015—Regeneration or reactivation of catalysts containing metals
    • B01J31/4092—Regeneration or reactivation of catalysts containing metals involving a stripping step, with stripping gas or solvent
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • 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
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/20—Olefin oligomerisation or telomerisation
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/60—Complexes comprising metals of Group VI (VIA or VIB) as the central metal
    • B01J2531/62—Chromium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/06—Halogens; Compounds thereof
    • C07C2527/125—Compounds comprising a halogen and scandium, yttrium, aluminium, gallium, indium or thallium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • C07C2531/22—Organic complexes
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
US11/207,232 2004-02-20 2005-08-19 Methods of preparation of an olefin oligomerization catalyst Abandoned US20070043181A1 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
US11/207,232 US20070043181A1 (en) 2005-08-19 2005-08-19 Methods of preparation of an olefin oligomerization catalyst
EP06801210A EP1931469A1 (en) 2005-08-19 2006-08-08 Methods of preparation of an olefin oligomerization catalyst
CA002619226A CA2619226A1 (en) 2005-08-19 2006-08-08 Methods of preparation of an olefin oligomerization catalyst
AU2006283779A AU2006283779A1 (en) 2005-08-19 2006-08-08 Methods of preparation of an olefin oligomerization catalyst
CN2006800388951A CN101291733B (zh) 2005-08-19 2006-08-08 烯烃低聚催化剂的制备方法
PCT/US2006/031303 WO2007024504A1 (en) 2005-08-19 2006-08-08 Methods of preparation of an olefin oligomerization catalyst
ARP060103611A AR057506A1 (es) 2005-08-19 2006-08-18 METODOS DE PREPARACION DE UN CATALIZADOR DE OLEGOMERIZACIoN DE OLEFINAS
US12/534,536 US7910670B2 (en) 2005-08-19 2009-08-03 Methods of preparation of an olefin oligomerization catalyst
US12/897,296 US8993822B2 (en) 2004-02-20 2010-10-04 Methods of preparation of an olefin oligomerization catalyst
US14/633,461 US9550841B2 (en) 2004-02-20 2015-02-27 Methods of preparation of an olefin oligomerization catalyst

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US11/207,232 US20070043181A1 (en) 2005-08-19 2005-08-19 Methods of preparation of an olefin oligomerization catalyst

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US12/534,536 Continuation US7910670B2 (en) 2004-02-20 2009-08-03 Methods of preparation of an olefin oligomerization catalyst

Publications (1)

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US20070043181A1 true US20070043181A1 (en) 2007-02-22

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US11/207,232 Abandoned US20070043181A1 (en) 2004-02-20 2005-08-19 Methods of preparation of an olefin oligomerization catalyst
US12/534,536 Active US7910670B2 (en) 2004-02-20 2009-08-03 Methods of preparation of an olefin oligomerization catalyst

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US (2) US20070043181A1 (US07910670-20110322-C00010.png)
EP (1) EP1931469A1 (US07910670-20110322-C00010.png)
CN (1) CN101291733B (US07910670-20110322-C00010.png)
AR (1) AR057506A1 (US07910670-20110322-C00010.png)
AU (1) AU2006283779A1 (US07910670-20110322-C00010.png)
CA (1) CA2619226A1 (US07910670-20110322-C00010.png)
WO (1) WO2007024504A1 (US07910670-20110322-C00010.png)

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050187418A1 (en) * 2004-02-19 2005-08-25 Small Brooke L. Olefin oligomerization
US20050187391A1 (en) * 2004-02-20 2005-08-25 Knudsen Ronald D. Methods of preparation of an olefin oligomerization catalyst
WO2008004986A1 (en) * 2006-07-05 2008-01-10 National University Of Singapore Catalyst system for oligomerization of olefins
US20080207857A1 (en) * 2006-07-25 2008-08-28 Chevron Phillips Chemical Company Lp Olefin Oligomerization Catalysts and Methods of Using Same
US7902415B2 (en) 2007-12-21 2011-03-08 Chevron Phillips Chemical Company Lp Processes for dimerizing or isomerizing olefins
US7910670B2 (en) 2005-08-19 2011-03-22 Chevron Phillips Chemical Company Lp Methods of preparation of an olefin oligomerization catalyst
WO2011130822A1 (en) * 2010-04-20 2011-10-27 Nova Chemicals (International) S.A. By-product mitigation in an ethylene oligomerisation process
US8329608B2 (en) 2004-02-20 2012-12-11 Chevron Phillips Chemical Company Lp Methods of preparation of an olefin oligomerization catalyst
US20130150642A1 (en) * 2011-12-12 2013-06-13 Chevron Phillips Chemical Company Lp Preparation of an Olefin Oligomerization Catalyst
WO2013089963A1 (en) * 2011-12-12 2013-06-20 Chevron Phillips Chemical Company Lp Preparation of transition metal carboxylates
NL1039868C2 (en) * 2012-11-01 2014-05-06 Stichting Dutch Polymer Inst Process for producing an oligo(alpha-olefin) and the use of a particular form of methylaluminoxane in such process.
US8865610B2 (en) 2012-06-06 2014-10-21 Chevron Phillips Chemical Company Lp Phosphinyl guanidine compounds, metal salt complexes, catalyst systems, and their use to oligomerize or polymerize olefins
EP2853521A1 (en) * 2010-05-24 2015-04-01 Siluria Technologies, Inc. Method for the oxidative coupling of methane in the presence of a nanowire catalyst
US9283555B2 (en) 2009-12-31 2016-03-15 Chevron Phillips Chemical Company Lp Phosphinyl amidine compounds, metal complexes, catalyst systems, and their use to oligomerize or polymerize olefins
US9446397B2 (en) 2012-02-03 2016-09-20 Siluria Technologies, Inc. Method for isolation of nanomaterials
US9446387B2 (en) 2011-05-24 2016-09-20 Siluria Technologies, Inc. Catalysts for petrochemical catalysis
US9550841B2 (en) 2004-02-20 2017-01-24 Chevron Phillips Chemical Company Lp Methods of preparation of an olefin oligomerization catalyst
US9586872B2 (en) 2011-12-30 2017-03-07 Chevron Phillips Chemical Company Lp Olefin oligomerization methods
US9738571B2 (en) 2013-03-15 2017-08-22 Siluria Technologies, Inc. Catalysts for petrochemical catalysis
US9751079B2 (en) 2014-09-17 2017-09-05 Silura Technologies, Inc. Catalysts for natural gas processes
US9751818B2 (en) 2011-11-29 2017-09-05 Siluria Technologies, Inc. Nanowire catalysts and methods for their use and preparation
US9956544B2 (en) 2014-05-02 2018-05-01 Siluria Technologies, Inc. Heterogeneous catalysts
CN112517080A (zh) * 2020-12-25 2021-03-19 中化泉州石化有限公司 一种乙烯选择性四聚催化剂组合物及其应用
EP3717890A4 (en) * 2017-12-01 2021-07-21 Public Joint Stock Company "Sibur Holding" OLEFIN OLIGOMERIZATION PROCESS USING ONLINE MEASUREMENT OF CHROME CONCENTRATION IN A CATALYTIC SYSTEM
US11148126B2 (en) * 2017-10-11 2021-10-19 Lotte Chemical Corporation Catalyst system for olefin oligomerization and method for preparing olefin oligomer by using same
US11370724B2 (en) 2012-05-24 2022-06-28 Lummus Technology Llc Catalytic forms and formulations

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AU2009308801B2 (en) 2008-10-31 2015-05-07 Chevron Phillips Chemical Company Lp Oligomerization catalyst system and process for oligomerizing olefins
US20120172645A1 (en) * 2010-12-29 2012-07-05 Chevron Phillips Chemical Company Lp Olefin Oligomerization catalysts and Methods of Making and Using Same
US9175109B1 (en) 2014-05-20 2015-11-03 Chevron Phillips Chemical Company Lp Oligomerization processes and polymer compositions produced therefrom
US9505675B2 (en) 2015-02-09 2016-11-29 Chevron Phillips Chemical Company Lp Deactivation of a process by-product
WO2017010998A1 (en) 2015-07-14 2017-01-19 Chevron Phillips Chemical Company Lp Olefin compositions
US9732300B2 (en) 2015-07-23 2017-08-15 Chevron Phillipa Chemical Company LP Liquid propylene oligomers and methods of making same
KR102058142B1 (ko) 2015-09-02 2019-12-20 주식회사 엘지화학 리간드 화합물, 올레핀 올리고머화용 촉매계, 및 이를 이용한 올레핀 올리고머화 방법
US10513473B2 (en) 2015-09-18 2019-12-24 Chevron Phillips Chemical Company Lp Ethylene oligomerization/trimerization/tetramerization reactor
US10519077B2 (en) 2015-09-18 2019-12-31 Chevron Phillips Chemical Company Lp Ethylene oligomerization/trimerization/tetramerization reactor
KR101982789B1 (ko) 2015-12-04 2019-05-27 주식회사 엘지화학 리간드 화합물, 유기 크롬 화합물, 올레핀 올리고머화용 촉매 시스템, 및 이를 이용한 올레핀의 올리고머화 방법
US20170267605A1 (en) 2016-03-16 2017-09-21 Siluria Technologies, Inc. Catalysts and methods for natural gas processes
US11859041B2 (en) 2021-08-16 2024-01-02 Chevron Phillips Chemical Company Lp Modulating co-monomer selectivity using non-covalent dispersion interactions in group 4 olefin polymerization catalysts

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