EP2714272A4 - 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

Info

Publication number
EP2714272A4
EP2714272A4 EP20120792029 EP12792029A EP2714272A4 EP 2714272 A4 EP2714272 A4 EP 2714272A4 EP 20120792029 EP20120792029 EP 20120792029 EP 12792029 A EP12792029 A EP 12792029A EP 2714272 A4 EP2714272 A4 EP 2714272A4
Authority
EP
European Patent Office
Prior art keywords
processes
preparation
methods
olefin metathesis
novel class
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.)
Withdrawn
Application number
EP20120792029
Other languages
German (de)
French (fr)
Other versions
EP2714272A2 (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
Publication of EP2714272A2 publication Critical patent/EP2714272A2/en
Publication of EP2714272A4 publication Critical patent/EP2714272A4/en
Withdrawn legal-status Critical Current

Links

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 System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System 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
EP20120792029 2011-05-31 2012-04-18 A novel class of olefin metathesis catalysts, methods of preparation, and processes for the use thereof Withdrawn EP2714272A4 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP20120792029 EP2714272A4 (en) 2011-05-31 2012-04-18 A novel class of olefin metathesis catalysts, methods of preparation, and processes for the use thereof

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
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
EP20120792029 EP2714272A4 (en) 2011-05-31 2012-04-18 A novel class of olefin metathesis catalysts, methods of preparation, and processes for the use thereof
PCT/US2012/034044 WO2012166259A2 (en) 2011-05-31 2012-04-18 A novel class of olefin metathesis catalysts, methods of preparation, and processes for the use thereof

Publications (2)

Publication Number Publication Date
EP2714272A2 EP2714272A2 (en) 2014-04-09
EP2714272A4 true EP2714272A4 (en) 2015-03-04

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP20120792029 Withdrawn EP2714272A4 (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)

Country Link
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

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2196061C (en) 1992-04-03 2000-06-13 Robert H. Grubbs High activity ruthenium or osmium metal carbene complexes for olefin metathesis reactions and synthesis thereof
US5312940A (en) 1992-04-03 1994-05-17 California Institute Of Technology Ruthenium and osmium metal carbene complexes for olefin metathesis polymerization
US5710298A (en) 1992-04-03 1998-01-20 California Institute Of Technology Method of preparing ruthenium and osmium carbene complexes
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
AU9303798A (en) * 1997-09-05 1999-03-22 A.O. Smith Corporation Metathesis polymerized olefin composites including sized reinforcement material
DE19815275B4 (en) * 1998-04-06 2009-06-25 Evonik Degussa Gmbh Alkylidene complexes of ruthenium with N-heterocyclic carbene ligands and their 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
EP1248764B1 (en) * 1999-01-26 2012-08-01 California Institute Of Technology Novel method for cross-metathesis of terminal olefins
US7329758B1 (en) 1999-05-24 2008-02-12 California Institute Of Technology Imidazolidine-based metal carbene metathesis catalysts
JP2004511359A (en) * 2000-09-25 2004-04-15 ロード　コーポレーション Catalytic metathesis polymerization
US7060770B2 (en) * 2003-05-06 2006-06-13 Kerr Corporation Metathesis-curable composition with a reaction control agent
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
WO2008008440A2 (en) * 2006-07-12 2008-01-17 Elevance Renewable Sciences, Inc. Ring opening cross-metathesis reaction of cyclic olefins with seed oils and the like
US8067610B2 (en) 2006-07-13 2011-11-29 Yann Schrodi 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

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; PEREIRA DA SILVA, CARLOS ET AL: "Investigation of the catalysis mechanism of ROMP of norbornene using density functional theory", XP002658781, retrieved from STN Database accession no. 2010:1265734 *
JACOBSEN, HEIKO: "P-Heterocyclic carbenes as potential ligands in the design of new metathesis catalysts. A computational study", DALTON TRANSACTIONS , (18), 2214-2224 CODEN: DTARAF; ISSN: 1477-9226, 2006, XP002658782 *
MATHEW, JOMON ET AL: "Assessment of Stereoelectronic Effects in Grubbs First-Generation Olefin Metathesis Catalysis Using Molecular Electrostatic Potential", ORGANOMETALLICS , 30(6), 1438-1444 CODEN: ORGND7; ISSN: 0276-7333, 24 February 2011 (2011-02-24), XP002658780 *
RANDALL M L ET AL: "SELECTIVE RING-OPENING CROSS METATHESIS. SHORT SYNTHESES OF MULTIFIDENE AND VIRIDIENE", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC; US, vol. 117, no. 37, 20 September 1995 (1995-09-20), XP002066314, ISSN: 0002-7863, DOI: 10.1021/JA00142A048 *
See also references of WO2012166259A2 *
SLIWA, PAWEL ET AL: "Assessment of density functional methods for the study of olefin metathesis catalyzed by ruthenium alkylidene complexes", CHEMICAL PHYSICS LETTERS , 493(4-6), 273-278 CODEN: CHPLBC; ISSN: 0009-2614, 2010, XP002658783 *

Also Published As

Publication number Publication date
CN103596685B (en) 2016-08-24
EP2714272A2 (en) 2014-04-09
BR112013030429A2 (en) 2016-12-13
WO2012166259A3 (en) 2013-01-24
CN103596685A (en) 2014-02-19
WO2012166259A2 (en) 2012-12-06

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