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WO2012166259A3 - Nouvelle classe de catalyseurs de métathèse d'oléfine, procédés de préparation et procédés pour l'utilisation de celle-ci - Google Patents

Nouvelle classe de catalyseurs de métathèse d'oléfine, procédés de préparation et procédés pour l'utilisation de celle-ci Download PDF

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Publication number
WO2012166259A3
WO2012166259A3 PCT/US2012/034044 US2012034044W WO2012166259A3 WO 2012166259 A3 WO2012166259 A3 WO 2012166259A3 US 2012034044 W US2012034044 W US 2012034044W WO 2012166259 A3 WO2012166259 A3 WO 2012166259A3
Authority
WO
WIPO (PCT)
Prior art keywords
group
processes
preparation
methods
olefin metathesis
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.)
Ceased
Application number
PCT/US2012/034044
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English (en)
Other versions
WO2012166259A2 (fr
Inventor
Matthew W. Holtcamp
Matthew S. Bedoya
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ExxonMobil Chemical Patents Inc
Original Assignee
ExxonMobil Chemical Patents 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 claimed from US13/149,012 external-priority patent/US8524930B2/en
Application filed by ExxonMobil Chemical Patents Inc filed Critical ExxonMobil Chemical Patents Inc
Priority to EP20120792029 priority Critical patent/EP2714272A4/fr
Priority to CN201280026256.9A priority patent/CN103596685B/zh
Priority to BR112013030429A priority patent/BR112013030429A2/pt
Publication of WO2012166259A2 publication Critical patent/WO2012166259A2/fr
Publication of WO2012166259A3 publication Critical patent/WO2012166259A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • B01J31/1845—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 phosphorus
    • 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
    • B01J31/2265—Carbenes or carbynes, i.e.(image)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0046—Ruthenium 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
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
    • B01J2231/54—Metathesis reactions, e.g. olefin metathesis
    • B01J2231/543—Metathesis reactions, e.g. olefin metathesis alkene metathesis
    • 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
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/821—Ruthenium
    • 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
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/825—Osmium
    • 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
    • C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
    • C08G2261/332—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms
    • C08G2261/3324—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms derived from norbornene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
    • C08G2261/332—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms
    • C08G2261/3325—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms derived from other polycyclic systems
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/40—Polymerisation processes
    • C08G2261/41—Organometallic coupling reactions
    • C08G2261/418—Ring opening metathesis polymerisation [ROMP]
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/40—Polymerisation processes
    • C08G2261/41—Organometallic coupling reactions
    • C08G2261/419—Acyclic diene metathesis [ADMET]
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
    • C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
    • C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Catalysts (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Cette invention porte sur un catalyseur de métathèse comprenant un complexe de métal du Groupe 8 représenté par la formule : (I) dans laquelle : M représente un métal du Groupe 8 ; chaque X représente indépendamment un ligand anionique ; R1 et R2 sont indépendamment choisis dans le groupe consistent en hydrogène, un hydrocarbyle en C1 à C30 et un hydrocarbyle substitué en C1 à C30 ; R3 et R4 sont indépendamment choisis dans le groupe consistant en hydrogène, les groupes hydrocarbyle en C1 à C12, les groupes hydrocarbyle en C1 à C12 substitués et les halogénures ; et L représente un ligand donneur neutre. Cette invention porte également sur des procédés pour effectuer une réaction de métathèse, en particulier des réactions de métathèse croisée par ouverture de cycle et des réactions de polymérisation par métathèse par ouverture de cycle, à l'aide des complexes de métal du Groupe 8.
PCT/US2012/034044 2011-05-31 2012-04-18 Nouvelle classe de catalyseurs de métathèse d'oléfine, procédés de préparation et procédés pour l'utilisation de celle-ci Ceased WO2012166259A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP20120792029 EP2714272A4 (fr) 2011-05-31 2012-04-18 Nouvelle classe de catalyseurs de métathèse d'oléfine, procédés de préparation et procédés pour l'utilisation de celle-ci
CN201280026256.9A CN103596685B (zh) 2011-05-31 2012-04-18 新的一类烯烃复分解催化剂、制备方法和使用其的方法
BR112013030429A BR112013030429A2 (pt) 2011-05-31 2012-04-18 classe nova de catalisadores de metátese de olefina, métodos de preparação e processos para o uso da mesma

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US13/149,012 2011-05-31
US13/149,012 US8524930B2 (en) 2011-05-31 2011-05-31 Class of olefin metathesis catalysts, methods of preparation, and processes for the use thereof
EP11174172 2011-07-15
EP11174172.4 2011-07-15

Publications (2)

Publication Number Publication Date
WO2012166259A2 WO2012166259A2 (fr) 2012-12-06
WO2012166259A3 true WO2012166259A3 (fr) 2013-01-24

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2012/034044 Ceased WO2012166259A2 (fr) 2011-05-31 2012-04-18 Nouvelle classe de catalyseurs de métathèse d'oléfine, procédés de préparation et procédés pour l'utilisation de celle-ci

Country Status (4)

Country Link
EP (1) EP2714272A4 (fr)
CN (1) CN103596685B (fr)
BR (1) BR112013030429A2 (fr)
WO (1) WO2012166259A2 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11673130B2 (en) * 2018-12-12 2023-06-13 Arlanxeo Deutschland Gmbh Catalyst system containing a metathesis catalyst and at least one phenolic compound and a process for metathesis of nitrile-butadiene rubber (NBR) using the catalyst system

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6306988B1 (en) * 1999-01-26 2001-10-23 California Institute Of Technology Methods for cross-metathesis of terminal olefins
US6323296B1 (en) * 1997-09-05 2001-11-27 Mark Warner Metathesis polymerized olefin composites including sized reinforcement material
US20020015519A1 (en) * 1998-12-11 2002-02-07 Lord Corporation Fiber substrate adhesion and coatings by contact metathesis polymerization
WO2002026857A1 (fr) * 2000-09-25 2002-04-04 Lord Corporation Polymerisation par metathese pour contact
US20040225073A1 (en) * 2003-05-06 2004-11-11 Kerr Corporation Metathesis-curable composition with a reaction control agent
US7294717B2 (en) * 1998-04-06 2007-11-13 Degussa Ag Alkylidene complexes of ruthenium containing N-heterocyclic carbene ligands; use as highly active, selective catalysts for olefin metathesis

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996004289A1 (fr) 1992-04-03 1996-02-15 California Institute Of Technology Complexes carbeniques de ruthenium et d'osmium a haute activite pour reactions de metathese des olefines, et leur procede de synthese
US5710298A (en) 1992-04-03 1998-01-20 California Institute Of Technology Method of preparing ruthenium and osmium carbene complexes
US5312940A (en) 1992-04-03 1994-05-17 California Institute Of Technology Ruthenium and osmium metal carbene complexes for olefin metathesis polymerization
US5831108A (en) 1995-08-03 1998-11-03 California Institute Of Technology High metathesis activity ruthenium and osmium metal carbene complexes
US5939504A (en) 1995-12-07 1999-08-17 Advanced Polymer Technologies Method for extending the pot life of an olefin metathesis polymerization reaction
US6020443A (en) 1996-02-08 2000-02-01 Advanced Polymer Technologies, Inc. Polymerization of low grade DCPD monomers using an olefin metathesis catalyst
US7329758B1 (en) 1999-05-24 2008-02-12 California Institute Of Technology Imidazolidine-based metal carbene metathesis catalysts
US7312331B2 (en) 2005-06-17 2007-12-25 The Regents Of The University Of California Stable cyclic (alkyl)(amino) carbenes as ligands for transition metal catalysts
JP5361715B2 (ja) * 2006-07-12 2013-12-04 エレバンス リニューアブル サイエンシーズ， インク． 環状オレフィンと種子油および類似物との開環交差メタセシス反応
WO2008010961A2 (fr) 2006-07-13 2008-01-24 Elevance Renewable Sciences, Inc. Synthèse d'alcènes à double liaison terminale à partir d'alcènes à double liaison interne et d'éthylène via la métathèse d'oléfines
US9024034B2 (en) * 2009-11-09 2015-05-05 Exxonmobil Chemical Patents Inc. Metathesis catalysts and processes for use thereof

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6323296B1 (en) * 1997-09-05 2001-11-27 Mark Warner Metathesis polymerized olefin composites including sized reinforcement material
US7294717B2 (en) * 1998-04-06 2007-11-13 Degussa Ag Alkylidene complexes of ruthenium containing N-heterocyclic carbene ligands; use as highly active, selective catalysts for olefin metathesis
US20020015519A1 (en) * 1998-12-11 2002-02-07 Lord Corporation Fiber substrate adhesion and coatings by contact metathesis polymerization
US6306988B1 (en) * 1999-01-26 2001-10-23 California Institute Of Technology Methods for cross-metathesis of terminal olefins
WO2002026857A1 (fr) * 2000-09-25 2002-04-04 Lord Corporation Polymerisation par metathese pour contact
US20040225073A1 (en) * 2003-05-06 2004-11-11 Kerr Corporation Metathesis-curable composition with a reaction control agent

Also Published As

Publication number Publication date
CN103596685B (zh) 2016-08-24
EP2714272A2 (fr) 2014-04-09
WO2012166259A2 (fr) 2012-12-06
EP2714272A4 (fr) 2015-03-04
CN103596685A (zh) 2014-02-19
BR112013030429A2 (pt) 2016-12-13

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