CA2905209C - Metathesis catalysts and reactions using the catalysts - Google Patents

Metathesis catalysts and reactions using the catalysts Download PDF

Info

Publication number
CA2905209C
CA2905209C CA2905209A CA2905209A CA2905209C CA 2905209 C CA2905209 C CA 2905209C CA 2905209 A CA2905209 A CA 2905209A CA 2905209 A CA2905209 A CA 2905209A CA 2905209 C CA2905209 C CA 2905209C
Authority
CA
Canada
Prior art keywords
ipr
optionally substituted
phenyl
alkyl
compound
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.)
Active
Application number
CA2905209A
Other languages
English (en)
French (fr)
Other versions
CA2905209A1 (en
Inventor
Levente Ondi
Jeno VARGA
Agota Bucsai
Florian Toth
Krisztian LORINCZ
Csaba Hegedus
Emmanuel Robe
Geog FRATER
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.)
Verbio Vereinigte Bioenergie AG
Original Assignee
Verbio Vereinigte Bioenergie AG
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
Application filed by Verbio Vereinigte Bioenergie AG filed Critical Verbio Vereinigte Bioenergie AG
Publication of CA2905209A1 publication Critical patent/CA2905209A1/en
Application granted granted Critical
Publication of CA2905209C publication Critical patent/CA2905209C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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
    • B01J31/22—Organic complexes
    • B01J31/2265—Carbenes or carbynes, i.e.(image)
    • 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
    • B01J31/1608—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes the ligands containing silicon
    • 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
    • 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
    • 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
    • B01J31/16—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
    • B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
    • 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
    • C07F11/00—Compounds containing elements of Groups 6 or 16 of the Periodic Table
    • 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
    • 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
    • B01J2531/0266—Axially chiral or atropisomeric ligands, e.g. bulky biaryls such as donor-substituted binaphthalenes, e.g. "BINAP" or "BINOL"
    • 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
    • B01J2531/0286—Complexes comprising ligands or other components characterized by their function
    • B01J2531/0288—Sterically demanding or shielding ligands
    • 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
    • B01J2531/64—Molybdenum
    • 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
    • B01J2531/66—Tungsten
    • 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
    • B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
    • B01J2540/20—Non-coordinating groups comprising halogens
    • 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
    • B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
    • B01J2540/20—Non-coordinating groups comprising halogens
    • B01J2540/22—Non-coordinating groups comprising halogens comprising fluorine, e.g. trifluoroacetate
    • 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
    • B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
    • B01J2540/20—Non-coordinating groups comprising halogens
    • B01J2540/22—Non-coordinating groups comprising halogens comprising fluorine, e.g. trifluoroacetate
    • B01J2540/225—Non-coordinating groups comprising halogens comprising fluorine, e.g. trifluoroacetate comprising perfluoroalkyl groups or moieties
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
    • 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]

Landscapes

  • 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)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CA2905209A 2013-03-14 2014-03-13 Metathesis catalysts and reactions using the catalysts Active CA2905209C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201361781120P 2013-03-14 2013-03-14
US61/781,120 2013-03-14
EP13001297 2013-03-14
EP13001297.4 2013-03-14
PCT/EP2014/000671 WO2014139679A2 (en) 2013-03-14 2014-03-13 Metathesis catalysts and reactions using the catalysts

Publications (2)

Publication Number Publication Date
CA2905209A1 CA2905209A1 (en) 2014-09-18
CA2905209C true CA2905209C (en) 2021-11-09

Family

ID=47912849

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2905209A Active CA2905209C (en) 2013-03-14 2014-03-13 Metathesis catalysts and reactions using the catalysts

Country Status (7)

Country Link
US (3) US10343153B2 (enExample)
EP (2) EP2969204A2 (enExample)
JP (2) JP6636804B2 (enExample)
CN (1) CN105555402B (enExample)
BR (1) BR112015023269B8 (enExample)
CA (1) CA2905209C (enExample)
WO (1) WO2014139679A2 (enExample)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8362311B2 (en) 2009-09-30 2013-01-29 Massachusetts Institute Of Technology Highly Z-selective olefins metathesis
EP2969204A2 (en) 2013-03-14 2016-01-20 XiMo AG Molybdenum and tungsten complexes as olefin metathesis catalysts and reactions using the catalysts
US20140330018A1 (en) * 2013-05-01 2014-11-06 Massachusetts Institute Of Technology Metathesis catalysts and methods thereof
US10071950B2 (en) 2013-07-12 2018-09-11 Ximo Ag Use of immobilized molybdenum- and tungsten-containing catalysts in olefin cross metathesis
US10427146B2 (en) 2013-10-01 2019-10-01 Ximo Ag Immobilized metathesis tungsten oxo alkylidene catalysts and use thereof in olefin metathesis
EP3215516B1 (en) * 2014-11-05 2020-01-08 Massachusetts Institute Of Technology Metathesis catalysts and methods thereof
JP6696435B2 (ja) * 2014-12-26 2020-05-20 Ａｇｃ株式会社 オレフィンの製造方法
JP6583289B2 (ja) * 2014-12-26 2019-10-02 Ａｇｃ株式会社 含塩素含フッ素オレフィンの製造方法
US10351664B2 (en) * 2015-03-09 2019-07-16 Zeon Corporation Resin molded body, resin film, and injection molded article
US10519288B2 (en) * 2015-03-09 2019-12-31 Zeon Corporation Resin molded body manufacturing method, resin film manufacturing method, and injection molded article manufacturing method
CN108697072A (zh) 2015-11-18 2018-10-23 普罗维维股份有限公司 用于产生昆虫信息素及相关化合物的微生物
US9776179B2 (en) 2015-11-18 2017-10-03 Provivi, Inc. Production of fatty olefin derivatives via olefin metathesis
US10744494B2 (en) 2015-12-23 2020-08-18 Ximo Ag Immobilized metal alkylidene catalysts and use thereof in olefin metathesis
GB201604110D0 (en) * 2016-03-10 2016-04-20 Givaudan Sa Preparation of macrocyclic lactones
EP3464311A4 (en) 2016-06-06 2020-03-18 Provivi, Inc. SEMI-BIOSYNTHETIC PRODUCTION OF FATTY ALCOHOLS AND FATTY ALDEHYDES
US11020730B2 (en) 2016-07-15 2021-06-01 Massachusetts Institute Of Technology Halogen-containing metathesis catalysts and methods thereof
JP7153937B2 (ja) 2017-02-17 2022-10-17 プロビビ インコーポレイテッド オレフィンメタセシスによるフェロモンおよび関連材料の合成方法
WO2018213554A1 (en) 2017-05-17 2018-11-22 Provivi, Inc. Microorganisms for the production of insect pheromones and related compounds
US11332426B2 (en) 2017-09-22 2022-05-17 Trustees Of Boston College Method of preparing trisubstituted ethylene compounds
EP3768691A1 (en) 2018-03-22 2021-01-27 Verbio Vereinigte BioEnergie AG Tetraphenylphenoxy tungsten oxo alkylidene complexes, methods of making same and use thereof
US20220227797A1 (en) * 2019-05-27 2022-07-21 Verbio Vereinigte Bioenergie Ag Tungsten imido alkylidene o-bitet and o-binol complexes and use thereof in olefin metathesis reactions
US10995049B2 (en) 2019-07-19 2021-05-04 California Institute Of Technology Total synthesis of prostaglandin J natural products and their intermediates
WO2021188337A1 (en) 2020-03-19 2021-09-23 Exxonmobil Chemical Patents Inc. Pentavalent dimeric group 6 transition metal complexes and methods for use thereof
US20230203072A1 (en) * 2020-05-27 2023-06-29 Verbio Vereinigte Bioenergie Ag Air-stable imido alkylidene complexes and use thereof in olefin metathesis reactions
CN113980097B (zh) * 2021-12-29 2022-03-29 浙江湃肽生物有限公司南京分公司 棕榈酰三肽-5的纯化方法
CN114230702B (zh) * 2022-01-17 2023-10-13 万华化学集团股份有限公司 一种萘氧基骨架的烯烃聚合催化剂、制备方法与应用

Family Cites Families (59)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1037866A (en) * 1962-05-28 1966-08-03 Ethyl Corp Improved process for preparing alpha olefins of high vinyl olefin content
BE755794A (fr) * 1969-09-08 1971-03-08 Polymer Corp Procede de purification d'hydrocarbures olefiniques
US3689584A (en) * 1970-08-24 1972-09-05 Ethyl Corp A chemical process of separating olefins from aluminum alkyls by forming complexes of the aluminum alkyls which are insoluble in the olefins
US3696161A (en) * 1970-09-30 1972-10-03 Ethyl Corp A chemical process of separating hydrocarbyl aluminum from olefins by the use of 2:1 complexes of aluminum alkyls and an alkali metal salt
DE2845974A1 (de) * 1978-10-21 1980-04-30 Basf Ag Verfahren zur herstellung von carbonsaeureestern vicinaler glykole
IN160358B (enExample) 1983-01-10 1987-07-11 Thiokol Corp
US4637197A (en) * 1984-10-15 1987-01-20 Epoxy Technology, Inc. Method and compositions for removal of moisture
JPH0428714A (ja) 1990-05-23 1992-01-31 Nippon Zeon Co Ltd 高重合活性ジシクロペンタジエンの製造法およびその重合法
US5210365A (en) 1990-08-27 1993-05-11 Shell Oil Company Olefin disproportionation catalyst and process
US5194534A (en) * 1991-09-24 1993-03-16 Hercules Incorporated Tungsten-imido catalysts for ring-opening metathesis polymerization of cycloolefins
EP0864595B1 (en) * 1997-03-13 2001-08-16 Borealis Technology Oy Supported catalysts for the ringopening metathesis polymerization of cycloolefins
DE19744102A1 (de) * 1997-10-06 1999-04-15 Targor Gmbh Katalysatorsystem
US6121473A (en) 1998-02-19 2000-09-19 Massachusetts Institute Of Technology Asymmetric ring-closing metathesis reactions
WO2001046096A1 (en) 1999-12-21 2001-06-28 Sasol Technology (Pty) Ltd Metathesis process for converting short chain olefins to longer chain olefins
US6720468B2 (en) * 2000-06-30 2004-04-13 Chevron Phillips Chemical Company Lp Process for the removal of conjugated olefins from a monoolefin stream
US7411108B2 (en) * 2000-06-30 2008-08-12 Chevron Phillips Chemical Company Lp Process for the removal of conjugated olefins from a monoolefin stream
US20050124839A1 (en) 2001-06-13 2005-06-09 Gartside Robert J. Catalyst and process for the metathesis of ethylene and butene to produce propylene
CN102936536B (zh) 2002-04-29 2014-01-29 陶氏环球技术有限责任公司 关于种子油工业应用的综合化学方法
US7605217B2 (en) * 2003-11-14 2009-10-20 Exxonmobil Chemical Patents Inc. High strength propylene-based elastomers and uses thereof
US7813511B2 (en) 2005-07-01 2010-10-12 Cisco Technology, Inc. Facilitating mobility for a mobile station
US7932397B2 (en) 2006-11-22 2011-04-26 Massachusetts Institute Of Technology Olefin metathesis catalysts and related methods
CN101821218A (zh) 2007-08-09 2010-09-01 埃莱文斯可更新科学公司 用于处理复分解原料的热方法
EP2183205A4 (en) * 2007-08-09 2013-10-02 Elevance Renewable Sciences CHEMICAL PROCESSES FOR TREATING METATHESIS RAW MATERIAL
US9284515B2 (en) 2007-08-09 2016-03-15 Elevance Renewable Sciences, Inc. Thermal methods for treating a metathesis feedstock
BRPI0906685A2 (pt) 2008-01-25 2016-10-11 Massachusetts Inst Technology catalisadores para reações de metátese incluindo metátese de olefina enantiosseletiva, e métodos relacionados
JP5483940B2 (ja) 2009-07-13 2014-05-07 ユニ・チャーム株式会社 吸収体及び吸収性物品
US8222469B2 (en) * 2009-07-15 2012-07-17 Massachusetts Institute Of Technology Catalysts and processes for the formation of terminal olefins by ethenolysis
US8362311B2 (en) * 2009-09-30 2013-01-29 Massachusetts Institute Of Technology Highly Z-selective olefins metathesis
RU2565057C2 (ru) 2009-10-12 2015-10-20 Елевансе Реневабле Сайенсез, Инк. Способы очистки и производства топлива из натурального масляного исходного сырья
US8735640B2 (en) 2009-10-12 2014-05-27 Elevance Renewable Sciences, Inc. Methods of refining and producing fuel and specialty chemicals from natural oil feedstocks
US9051519B2 (en) * 2009-10-12 2015-06-09 Elevance Renewable Sciences, Inc. Diene-selective hydrogenation of metathesis derived olefins and unsaturated esters
US9222056B2 (en) 2009-10-12 2015-12-29 Elevance Renewable Sciences, Inc. Methods of refining natural oils, and methods of producing fuel compositions
JP5557536B2 (ja) 2010-01-26 2014-07-23 シンポ株式会社 油脂回収フィルター
US8598400B2 (en) * 2010-02-08 2013-12-03 Massachusetts Institute Of Technology Efficient methods for Z- or cis-selective cross-metathesis
US8704029B2 (en) 2010-03-30 2014-04-22 Uop Llc Conversion of butylene to propylene under olefin metathesis conditions
EP2556078B1 (de) 2010-04-03 2014-09-24 Studiengesellschaft Kohle MbH Katalysatoren für die alkinmetathese
US8722950B2 (en) 2010-04-26 2014-05-13 Saudi Basic Industries Corporation Process for producing propylene and aromatics from butenes by metathesis and aromatization
US8935891B2 (en) 2011-06-09 2015-01-20 Uop Llc Olefin metathesis catalyst containing tungsten fluorine bonds
DE102011012629A1 (de) 2011-02-28 2012-08-30 Studiengesellschaft Kohle Mbh Metallkomplexe des Molybdäns und Wolframs und ihre Verwendung als Präkatalysatoren für die Olefinmetathese
JP2013014562A (ja) 2011-07-06 2013-01-24 Nippon Zeon Co Ltd タングステン錯体、メタセシス反応用触媒および環状オレフィン開環重合体の製造方法
WO2013192384A1 (en) 2012-06-20 2013-12-27 Elevance Renewable Sciences, Inc. Natural oil metathesis compositions
EP2690838A1 (en) 2012-07-23 2014-01-29 Alcatel Lucent Authentification system preserving secret data confidentiality
EP2703081B1 (en) * 2012-09-04 2019-08-07 XiMo AG Molybdenum and tungsten complexes as olefin metathesis catalysts and reactions using the catalysts
KR102202927B1 (ko) 2013-03-14 2021-01-14 윌마르 트레이딩 피티이 엘티디 처리된 복분해 기질 물질 및 이의 제조 및 사용 방법
EP2969204A2 (en) 2013-03-14 2016-01-20 XiMo AG Molybdenum and tungsten complexes as olefin metathesis catalysts and reactions using the catalysts
MY172162A (en) 2013-03-14 2019-11-15 Wilmar Trading Pte Ltd Methods for treating a metathesis feedstock with metal alkoxides
US10071950B2 (en) 2013-07-12 2018-09-11 Ximo Ag Use of immobilized molybdenum- and tungsten-containing catalysts in olefin cross metathesis
EP3019511B1 (en) 2013-07-12 2019-01-02 XiMo AG Immobilized metathesis tungsten catalysts and use thereof in olefin metathesis
US10427146B2 (en) 2013-10-01 2019-10-01 Ximo Ag Immobilized metathesis tungsten oxo alkylidene catalysts and use thereof in olefin metathesis
US10858573B2 (en) 2014-01-16 2020-12-08 Wilmar Trading Pte Ltd Olefinic ester compositions and their use as cleaning agents
EP3119738B1 (en) 2014-03-19 2019-01-30 Elevance Renewable Sciences, Inc. Systems and methods of refining natural oil feedstocks and derivatives thereof
GB201406591D0 (en) 2014-04-11 2014-05-28 Ximo Ag Compounds
DE102014105885A1 (de) 2014-04-25 2015-10-29 Universität Stuttgart N-Heterozyklische Carbenkomplexe von Metallimidoalkylidenen und Metalloxoalkylidenen und deren Verwendung
WO2016095061A1 (en) 2014-12-17 2016-06-23 Eth Zurich Activation of supported olefin metathesis catalysts by organic reductants
US20170011038A1 (en) 2015-07-06 2017-01-12 David Revelle System and method for multiple factor sorting and user interface thereof
US9776179B2 (en) 2015-11-18 2017-10-03 Provivi, Inc. Production of fatty olefin derivatives via olefin metathesis
DE102016122096A1 (de) 2016-11-17 2018-05-17 Universität Stuttgart Latente Katalysatoren zur vernetzenden Polymerisation von Dicyclopentadien (DCPD)
DE102017101431A1 (de) 2017-01-25 2018-07-26 Universität Stuttgart Molybdän- und Wolfram-Alkylidin-N-heterozyklische Carben-Komplexe
JP7153937B2 (ja) 2017-02-17 2022-10-17 プロビビ インコーポレイテッド オレフィンメタセシスによるフェロモンおよび関連材料の合成方法

Also Published As

Publication number Publication date
US20140309466A1 (en) 2014-10-16
US10343153B2 (en) 2019-07-09
US11285466B2 (en) 2022-03-29
US9919299B2 (en) 2018-03-20
BR112015023269A2 (pt) 2017-07-18
WO2014139679A3 (en) 2015-02-19
JP2016510070A (ja) 2016-04-04
EP2969204A2 (en) 2016-01-20
US20190366318A1 (en) 2019-12-05
WO2014139679A2 (en) 2014-09-18
JP6636804B2 (ja) 2020-01-29
WO2014139679A8 (en) 2014-12-11
CA2905209A1 (en) 2014-09-18
BR112015023269B8 (pt) 2022-08-16
JP2018193379A (ja) 2018-12-06
BR112015023269B1 (pt) 2021-05-04
US20160030936A1 (en) 2016-02-04
CN105555402A (zh) 2016-05-04
EP3662996A3 (en) 2020-12-16
CN105555402B (zh) 2019-03-22
EP3662996A2 (en) 2020-06-10

Similar Documents

Publication Publication Date Title
CA2905209C (en) Metathesis catalysts and reactions using the catalysts
AU2013294909B2 (en) Novel ruthenium complexes, their use in the metathesis reactions, and a process for carrying out the metathesis reaction
Schrock et al. Recent advances in the syntheses and applications of molybdenum and tungsten alkylidene and alkylidyne catalysts for the metathesis of alkenes and alkynes
CN106103403A (zh) 包括烯烃的交叉复分解反应的方法
WO2015003814A1 (en) Use of immobilized molybden- und tungsten-containing catalysts in olefin cross metathesis
EP2703081A1 (en) Molybdenum and tungsten complexes as olefin metathesis catalysts and reactions using the catalysts
EP3814363B1 (en) Organoruthenium complexes as precatalysts for olefin metathesis
Tkach et al. Palladium carboxylate/boron trifluoride etherate catalyst system for the selective dimerization of styrene
KR101540487B1 (ko) 알릴 화합물의 이성화 방법
Drăguţan et al. Immobilized ruthenium complexes bearing N, O-bidentate ligands
tom Dieck et al. Diazadiene-Controlled CC Coupling Reactions on Palladium and Iron
La Enantioselective synthesis through catalytic metathesis
Myagmarsuren et al. Novel palladium acetate based protocols for transformations of unsaturated hydrocarbons
Ge Reactivity of rare earth metal organometallics bearing ancillary ligands derived the 1, 4-Diazepan-6-amine framework
Marciniec et al. Metathesis of vinylsubstituted silanes in the presence of ruthenium complexes
Gregory Block Copolymer Formation by Transformation Reactions
CA2973092A1 (en) Process for dehydrogenation of alkyl-containing compounds using molybdenum and tungsten nitrosyl complexes

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20181220

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 11TH ANNIV.) - STANDARD

Year of fee payment: 11

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20250226

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT DETERMINED COMPLIANT

Effective date: 20250226

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20250226

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 12TH ANNIV.) - STANDARD

Year of fee payment: 12

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20260302

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20260302