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EP2498908A4 - METATHESIS CATALYSTS AND METHODS OF USE - Google Patents

METATHESIS CATALYSTS AND METHODS OF USE

Info

Publication number
EP2498908A4
EP2498908A4 EP10829029.7A EP10829029A EP2498908A4 EP 2498908 A4 EP2498908 A4 EP 2498908A4 EP 10829029 A EP10829029 A EP 10829029A EP 2498908 A4 EP2498908 A4 EP 2498908A4
Authority
EP
European Patent Office
Prior art keywords
methods
metathesis catalysts
metathesis
catalysts
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Withdrawn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
EP10829029.7A
Other languages
German (de)
French (fr)
Other versions
EP2498908A2 (en
Inventor
Matthew W Holtcamp
Matthew S Bedoya
Catherine A Faler
Caol P Huff
John R Hagadorn
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 US12/705,136 external-priority patent/US8237003B2/en
Application filed by ExxonMobil Chemical Patents Inc filed Critical ExxonMobil Chemical Patents Inc
Publication of EP2498908A2 publication Critical patent/EP2498908A2/en
Publication of EP2498908A4 publication Critical patent/EP2498908A4/en
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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)
    • B01J31/2269—Heterocyclic carbenes
    • B01J31/2273—Heterocyclic carbenes with only nitrogen as heteroatomic ring members, e.g. 1,3-diarylimidazoline-2-ylidenes
    • 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)
    • B01J31/2278—Complexes comprising two carbene ligands differing from each other, e.g. Grubbs second generation catalysts
    • 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
    • C07C6/02—Metathesis reactions at an unsaturated carbon-to-carbon bond
    • C07C6/04—Metathesis reactions at an unsaturated carbon-to-carbon bond at a carbon-to-carbon double bond
    • 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
    • C07F15/002—Osmium 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
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0261—Complexes comprising ligands with non-tetrahedral chirality
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP10829029.7A 2009-11-09 2010-11-03 METATHESIS CATALYSTS AND METHODS OF USE Withdrawn EP2498908A4 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US25925109P 2009-11-09 2009-11-09
US12/705,136 US8237003B2 (en) 2009-11-09 2010-02-12 Metathesis catalyst and process for use thereof
US31438810P 2010-03-16 2010-03-16
PCT/US2010/055302 WO2011056874A2 (en) 2009-11-09 2010-11-03 Metathesis catalysts and processes for use thereof

Publications (2)

Publication Number Publication Date
EP2498908A2 EP2498908A2 (en) 2012-09-19
EP2498908A4 true EP2498908A4 (en) 2013-08-14

Family

ID=46208932

Family Applications (1)

Application Number Title Priority Date Filing Date
EP10829029.7A Withdrawn EP2498908A4 (en) 2009-11-09 2010-11-03 METATHESIS CATALYSTS AND METHODS OF USE

Country Status (3)

Country Link
EP (1) EP2498908A4 (en)
BR (1) BR112012010894A2 (en)
WO (1) WO2011056874A2 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9024034B2 (en) 2009-11-09 2015-05-05 Exxonmobil Chemical Patents Inc. Metathesis catalysts and processes for use thereof
FR2983475B1 (en) 2011-12-02 2014-01-17 IFP Energies Nouvelles PROCESS FOR THE METATHESIS OF ALPHA LINEAR OLEFINS USING AN RUTHENIUM COMPLEX COMPRISING A DISSYMETRIC N-HETEROCYCLIC CARBENE
KR20150034679A (en) 2012-06-29 2015-04-03 아페이론 신세시스 에스.아. Metal complexes, their application and methods of carrying out a metathesis reaction
GB2522640B (en) 2014-01-30 2018-04-25 Univ Court Univ St Andrews Method of alkene metathesis
CN112779100B (en) * 2021-01-25 2023-04-25 南京工业大学 A kind of vegetable oil polyol with suspended chain removed and its preparation method and application
CN112898160B (en) * 2021-01-25 2021-09-24 南京工业大学 A kind of vegetable oil polyol and preparation method and its application in polyurethane material

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000071554A2 (en) * 1999-05-24 2000-11-30 California Institute Of Technology Imidazolidine-based metal carbene metathesis catalysts
WO2003097234A1 (en) * 2002-05-15 2003-11-27 The Trustees Of Boston College Recyclable chiral metathesis catalysts
US20060287450A1 (en) * 2003-08-11 2006-12-21 Katrin Kohler Immobilizable ruthenium catalysts having n-heterocyclic carbene ligands
US20080027194A1 (en) * 2006-07-13 2008-01-31 Yann Schrodi Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis
WO2009009597A1 (en) * 2007-07-09 2009-01-15 The Regents Of The University Of California Water soluble olefin metathesis
WO2009126831A1 (en) * 2008-04-09 2009-10-15 Materia, Inc. Ruthenium olefin metathesis catalysts bearing n-heterocyclic carbene ligands with substituted backbone
EP2151446A1 (en) * 2008-08-01 2010-02-10 Telene SAS Process for the preparation of bidentate schiff base ruthenium catalysts containing a salicylaldimine-type ligand

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6900347B2 (en) * 1998-09-01 2005-05-31 Tilliechem, Inc. Impurity inhibition in olefin metathesis reactions
CA2512815A1 (en) * 2003-01-13 2004-07-29 Cargill, Incorporated Method for making industrial chemicals
WO2007081987A2 (en) * 2006-01-10 2007-07-19 Elevance Renewable Sciences, Inc. Method of making hydrogenated metathesis products
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
WO2008048520A2 (en) * 2006-10-13 2008-04-24 Elevance Renewable Sciences, Inc. Methods of making organic compounds by metathesis and hydrocyanation

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000071554A2 (en) * 1999-05-24 2000-11-30 California Institute Of Technology Imidazolidine-based metal carbene metathesis catalysts
WO2003097234A1 (en) * 2002-05-15 2003-11-27 The Trustees Of Boston College Recyclable chiral metathesis catalysts
US20060287450A1 (en) * 2003-08-11 2006-12-21 Katrin Kohler Immobilizable ruthenium catalysts having n-heterocyclic carbene ligands
US20080027194A1 (en) * 2006-07-13 2008-01-31 Yann Schrodi Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis
WO2009009597A1 (en) * 2007-07-09 2009-01-15 The Regents Of The University Of California Water soluble olefin metathesis
WO2009126831A1 (en) * 2008-04-09 2009-10-15 Materia, Inc. Ruthenium olefin metathesis catalysts bearing n-heterocyclic carbene ligands with substituted backbone
EP2151446A1 (en) * 2008-08-01 2010-02-10 Telene SAS Process for the preparation of bidentate schiff base ruthenium catalysts containing a salicylaldimine-type ligand

Non-Patent Citations (19)

* Cited by examiner, † Cited by third party
Title
ALBERT POATER ET AL: "The activation mechanism of Fe-based olefin metathesis catalysts", CHEMICAL PHYSICS LETTERS, vol. 610-611, 8 July 2014 (2014-07-08), NL, pages 29 - 32, XP055648436, ISSN: 0009-2614, DOI: 10.1016/j.cplett.2014.06.063 *
ALLEN DARYL P ET AL: "Well-defined silica-supported olefin metathesis catalysts", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 11, no. 6, 19 March 2009 (2009-03-19), pages 1261 - 1264, XP009142583, ISSN: 1523-7060, [retrieved on 20090224], DOI: 10.1021/OL9000153 *
BLUM A P ET AL: "Synthesis of N-heterocylic carbene-containing metal complexes from 2-(pentafluorophenyl)imidazolidines", ORGANOMETALLICS, ACS, WASHINGTON, DC, US, vol. 26, no. 8, 9 April 2007 (2007-04-09), pages 2122 - 2124, XP009142588, ISSN: 0276-7333, [retrieved on 20070306], DOI: 10.1021/OM060949F *
BURDETT K A ET AL: "Renewable monomer feedstocks via olefin metathesis: Fundamental mechanistic studies of methyl oleate ethenolysis with the first-generation grubbs catalyst", ORGANOMETALLICS, ACS, WASHINGTON, DC, US, vol. 23, no. 9, 26 April 2004 (2004-04-26), pages 2027 - 2047, XP009142547, ISSN: 0276-7333, [retrieved on 20040326], DOI: 10.1021/OM0341799 *
CHUNG CHEOL K ET AL: "Olefin metathesis catalyst: stabilization effect of backbone substitutions of N-heterocyclic carbene", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 10, no. 13, 3 July 2008 (2008-07-03), pages 2693 - 2696, XP009142582, ISSN: 1523-7060, [retrieved on 20080530], DOI: 10.1021/OL800824H *
DINGER M B ET AL: "Adamantyl-Substituted N-Heterocyclic Carbene Ligands in Second-Generation Grubbs-Type Metathesis Catalysts", ORGANOMETALLICS, ACS, WASHINGTON, DC, US, vol. 22, no. 25, 8 December 2003 (2003-12-08), pages 5291 - 5296, XP009142587, ISSN: 0276-7333, [retrieved on 20031111], DOI: 10.1021/OM034062K *
KUMAR P SANTHOSH ET AL: "Factors Relevant for the Regioselective Cyclopolymerization of 1,6-Heptadiynes, N,N-Dipropargylamines, N,N-Dipropargylammonium Salts, and Dipropargyl Ethers by RuIV-Alkylidene-Based Metathesis Initiators", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, ACS PUBLICATIONS, US, vol. 131, no. 1, 14 January 2009 (2009-01-14), pages 387 - 395, XP009142603, ISSN: 0002-7863, [retrieved on 20081212], DOI: 10.1021/JA804563T *
LEDOUX N ET AL: "N,N'-dialkyl- and N-aIkyl-N-mesityl-substituted N-heterocyclic carbenes as ligands in Grubbs catalysts", CHEMISTRY - A EUROPEAN JOURNAL, WILEY - V C H VERLAG GMBH & CO. KGAA, WEINHEIM, DE, vol. 12, no. 17, 2 June 2006 (2006-06-02), pages 4654 - 4661, XP009142586, ISSN: 0947-6539, [retrieved on 20060315], DOI: 10.1002/CHEM.200600064 *
LEDOUX NELE ET AL: "Comparative investigation of Hoveyda-Grubbs catalysts bearing modified N-heterocyclic carbene ligands", ADVANCED SYNTHESIS & CATALYSIS, WILEY VCH VERLAG, WEINHEIM, DE, vol. 349, no. 10, 2 July 2007 (2007-07-02), pages 1692 - 1700, XP009142602, ISSN: 1615-4150, [retrieved on 20070717], DOI: 10.1002/ADSC.200700042 *
LEUTHÄUBER STEFFEN ET AL: "pi-Face donor properties of N-heterocyclic carbenes in Grubbs II complexes", CHEMISTRY - A EUROPEAN JOURNAL, WILEY - V C H VERLAG GMBH & CO. KGAA, WEINHEIM, DE, vol. 14, no. 18, 20 June 2008 (2008-06-20), pages 5465 - 5481, XP009142581, ISSN: 0947-6539, [retrieved on 20080506], DOI: 10.1002/CHEM.200800139 *
LICHTENHELDT M ET AL: "Alternating ring-opening metathesis copolymerization by grubbs-type initiators with unsymmetrical N-heterocyclic carbenes", CHEMISTRY - A EUROPEAN JOURNAL, WILEY - V C H VERLAG GMBH & CO. KGAA, WEINHEIM, DE, vol. 15, no. 37, 21 September 2009 (2009-09-21), pages 9451 - 9457, XP009142590, ISSN: 0947-6539, [retrieved on 20090807], DOI: 10.1002/CHEM.200900384 *
SÜSSNER MARCUS ET AL: "pi-Face donor properties of N-heterocyclic carbenes", CHEMICAL COMMUNICATIONS - CHEMCOM; [6015D], ROYAL SOCIETY OF CHEMISTRY, GB, no. 43, 21 November 2005 (2005-11-21), pages 5417 - 5419, XP009142579, ISSN: 1359-7345, DOI: 10.1039/B512008J *
TIEDE S ET AL: "Highly active chiral ruthenium-based metathesis catalysts through a monosubstitution in the N-heterocyclic carbene", ANGEWANDTE CHEMIE. INTERNATIONAL EDITION, WILEY VCH VERLAG, WEINHEIM, vol. 49, no. 23, 25 May 2010 (2010-05-25), pages 3972 - 3975, XP009142594, ISSN: 1433-7851, [retrieved on 20100505], DOI: 10.1002/ANIE.201000940 *
VEHLOW K ET AL: "Alternating copolymerizations using a grubbs-type initiator with an unsymmetrical, chiral n-heterocyclic carbene ligand", ANGEWANDTE CHEMIE. INTERNATIONAL EDITION, WILEY VCH VERLAG, WEINHEIM, vol. 47, no. 14, 25 March 2008 (2008-03-25), pages 2615 - 2618, XP009142593, ISSN: 1433-7851, [retrieved on 20080215], DOI: 10.1002/ANIE.200704822 *
VEHLOW K ET AL: "Deactivation of ruthenium olefin metathesis catalysts through intramolecular carbene-arene bond formation", ANGEWANDTE CHEMIE. INTERNATIONAL EDITION, WILEY VCH VERLAG, WEINHEIM, vol. 46, no. 42, 22 October 2007 (2007-10-22), pages 8082 - 8085, XP009142592, ISSN: 1433-7851, [retrieved on 20070913], DOI: 10.1002/ANIE.200702560 *
VEHLOW K ET AL: "Ruthenium metathesis catalysts with saturated unsymmetrical N-heterocyclic carbene ligands", ORGANOMETALLICS, ACS, WASHINGTON, DC, US, vol. 25, no. 1, 2 January 2006 (2006-01-02), pages 25 - 28, XP009142546, ISSN: 0276-7333, [retrieved on 20051125], DOI: 10.1021/OM0508233 *
VOUGIOUKALAKIS G C ET AL: "Ruthenium olefin metathesis catalysts bearing an N-fluorophenyl-N-mesityl- substituted unsymmetrical N-heterocyclic carbene", ORGANOMETALLICS, ACS, WASHINGTON, DC, US, vol. 26, no. 9, 23 April 2007 (2007-04-23), pages 2469 - 2472, XP009142589, ISSN: 0276-7333, [retrieved on 20070329], DOI: 10.1021/OM0610593 *
VOUGIOUKALAKIS G C ET AL: "Ruthenium-based olefin metathesis catalysts coordinated with unsymmetrical N-heterocyclic carbene ligands: Synthesis, structure, and catalytic activity", CHEMISTRY - A EUROPEAN JOURNAL, WILEY - V C H VERLAG GMBH & CO. KGAA, WEINHEIM, DE, vol. 14, no. 25, 28 August 2008 (2008-08-28), pages 7545 - 7556, XP009142591, ISSN: 0947-6539, [retrieved on 20080721], DOI: 10.1002/CHEM.200800470 *
XU GUOPIN ET AL: "Development of building blocks for the synthesis of N-heterocyclic carbene ligands", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 7, no. 21, 13 October 2005 (2005-10-13), pages 4605 - 4608, XP009142580, ISSN: 1523-7060, [retrieved on 20050917], DOI: 10.1021/OL0516521 *

Also Published As

Publication number Publication date
WO2011056874A2 (en) 2011-05-12
WO2011056874A3 (en) 2011-10-06
BR112012010894A2 (en) 2020-12-15
EP2498908A2 (en) 2012-09-19

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