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WO2012166259A3 - A novel class of olefin metathesis catalysts, methods of preparation, and processes for the use thereof - Google Patents

A novel class of olefin metathesis catalysts, methods of preparation, and processes for the use thereof 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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French (fr)
Other versions
WO2012166259A2 (en
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/en
Priority to CN201280026256.9A priority patent/CN103596685B/en
Priority to BR112013030429A priority patent/BR112013030429A2/en
Publication of WO2012166259A2 publication Critical patent/WO2012166259A2/en
Publication of WO2012166259A3 publication Critical patent/WO2012166259A3/en
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

This invention relates to a metathesis catalyst comprising a Group 8 metal complex represented by the formula: (I) wherein: M is a Group 8 metal; each X is independently an anionic ligand; R1 and R2 are independently selected from the group consisting of hydrogen, a C1 to C30 hydrocarbyl, and a C1 to C30 substituted hydrocarbyl; R3 and R4 are independently selected from the group consisting of hydrogen, C1 to C12 hydrocarbyl groups, substituted C1 to C12 hydrocarbyl groups, and halides; and L is a neutral donor ligand. This invention also relates to processes for performing a metathesis reaction, in particular ring opening cross metathesis reactions and ring opening metathesis polymerization reactions, using the Group 8 metal complexes.
PCT/US2012/034044 2011-05-31 2012-04-18 A novel class of olefin metathesis catalysts, methods of preparation, and processes for the use thereof Ceased WO2012166259A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP20120792029 EP2714272A4 (en) 2011-05-31 2012-04-18 NOVEL CLASS OF OLEFIN METATHESIS CATALYSTS, PREPARATION METHODS AND METHODS FOR THE USE THEREOF
CN201280026256.9A CN103596685B (en) 2011-05-31 2012-04-18 A new class of olefin metathesis catalysts, methods of making and methods of using them
BR112013030429A BR112013030429A2 (en) 2011-05-31 2012-04-18 new class of olefin metathesis catalysts, preparation methods and processes for use thereof

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 (en) 2012-12-06
WO2012166259A3 true WO2012166259A3 (en) 2013-01-24

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PCT/US2012/034044 Ceased WO2012166259A2 (en) 2011-05-31 2012-04-18 A novel class of olefin metathesis catalysts, methods of preparation, and processes for the use thereof

Country Status (4)

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EP (1) EP2714272A4 (en)
CN (1) CN103596685B (en)
BR (1) BR112013030429A2 (en)
WO (1) WO2012166259A2 (en)

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 (en) * 2000-09-25 2002-04-04 Lord Corporation Contact metathesis polymerization
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 (en) 1992-04-03 1996-02-15 California Institute Of Technology High activity ruthenium or osmium metal carbene complexes for olefin metathesis reactions and synthesis thereof
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 (en) * 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． Ring-opening cross-metathesis reaction of cyclic olefins with seed oil and the like
WO2008010961A2 (en) 2006-07-13 2008-01-24 Elevance Renewable Sciences, Inc. Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis
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 (en) * 2000-09-25 2002-04-04 Lord Corporation Contact metathesis polymerization
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 (en) 2016-08-24
EP2714272A2 (en) 2014-04-09
WO2012166259A2 (en) 2012-12-06
EP2714272A4 (en) 2015-03-04
CN103596685A (en) 2014-02-19
BR112013030429A2 (en) 2016-12-13

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