CN103402628B - Z-选择性烯烃复分解催化剂及其合成步骤 - Google Patents

Z-选择性烯烃复分解催化剂及其合成步骤 Download PDF

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CN103402628B
CN103402628B CN201280010878.2A CN201280010878A CN103402628B CN 103402628 B CN103402628 B CN 103402628B CN 201280010878 A CN201280010878 A CN 201280010878A CN 103402628 B CN103402628 B CN 103402628B
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heteroatom
group
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hydrocarbyl
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CN103402628A (zh
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远藤浩司
本杰明·基思·凯茨
迈尔斯·本顿·赫伯特
佩尔斯玛·拉西科拉尔·帕特尔
罗伯特·霍华德·格拉布斯
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California Institute of Technology
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    • 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
    • B01J31/2282—Unsaturated compounds used as ligands
    • B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
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    • 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
    • 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
    • B01J31/02—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
    • 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
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    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
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    • 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
    • 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
    • C07C67/30—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
    • 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
    • B01J2531/02—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
    • 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
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CN201280010878.2A 2011-01-14 2012-01-17 Z-选择性烯烃复分解催化剂及其合成步骤 Active CN103402628B (zh)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US201161432849P 2011-01-14 2011-01-14
US61/432,849 2011-01-14
US201161433949P 2011-01-18 2011-01-18
US61/433,949 2011-01-18
US201161515262P 2011-08-04 2011-08-04
US61/515,262 2011-08-04
PCT/US2012/021609 WO2012097379A2 (en) 2011-01-14 2012-01-17 Z-selective olefin metathesis catalysts and their synthetic procedure

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CN103402628A CN103402628A (zh) 2013-11-20
CN103402628B true CN103402628B (zh) 2015-12-23

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US (1) US9597674B2 (https=)
EP (1) EP2663398B1 (https=)
JP (1) JP5893646B2 (https=)
KR (1) KR101835170B1 (https=)
CN (1) CN103402628B (https=)
AU (1) AU2012206966B2 (https=)
BR (1) BR112013017938B1 (https=)
CA (1) CA2824518C (https=)
IL (1) IL227432A (https=)
PL (1) PL2663398T3 (https=)
SG (1) SG191980A1 (https=)
WO (1) WO2012097379A2 (https=)
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EP2838359A4 (en) 2012-03-05 2015-12-09 California Inst Of Techn SYNTHESIS OF Z-OLEFIN-CONTAINING PHEROMONES OF LEPIDOPTERA INSECTS
JP6092379B2 (ja) 2012-06-29 2017-03-08 アペイロン シンセシス エス アー 金属錯体、その適用、及びメタセシス反応の実施方法
US9147844B2 (en) 2012-08-01 2015-09-29 California Institute Of Technology Solvent-free enyne metathesis polymerization
US9234985B2 (en) 2012-08-01 2016-01-12 California Institute Of Technology Birefringent polymer brush structures formed by surface initiated ring-opening metathesis polymerization
BR112015013580A2 (pt) 2012-12-12 2017-07-11 California Inst Of Techn catalisador de metátese z-seletiva
US9758445B2 (en) 2013-04-09 2017-09-12 Materia, Inc. Preparation of surfactants via cross-metathesis
US9663440B2 (en) 2013-04-09 2017-05-30 Materia, Inc. Cross metathesis of poly-branched poly-olefins
ES2699416T3 (es) 2013-04-09 2019-02-11 Materia Inc Preparación de tensioactivos mediante metátesis cruzada
US20160101414A1 (en) * 2013-05-15 2016-04-14 California Institute Of Technology Highly z-selective and enantioselective ring opening/cross metathesis catalyzed by a resolved stereogenic-at-ru complex
EP3008078B1 (en) 2013-06-12 2018-12-19 Trustees of Boston College Catalysts for efficient z-selective metathesis
WO2016014954A1 (en) * 2014-07-25 2016-01-28 California Institute Of Technology Tandem z-selective metathesis / dihydroxylation
PL3353187T3 (pl) * 2015-09-24 2021-11-22 Umicore Ag & Co. Kg Katalizatory metatezy olefin na bazie karbenu metalu
KR20180116238A (ko) 2015-12-10 2018-10-24 우미코레 아게 운트 코 카게 올레핀 복분해 촉매
CN114106057B (zh) * 2016-10-19 2023-06-23 优美科股份公司及两合公司 Ru亚烷基络合物的合成与表征
US10320390B1 (en) 2016-11-17 2019-06-11 X Development Llc Field programmable gate array including coupled lookup tables
WO2018220088A1 (en) 2017-05-30 2018-12-06 Ximo Ag Methods of making olefinic e- and z-isomers
EP3762143A1 (en) * 2018-03-09 2021-01-13 PPG Industries Ohio Inc. Compounds for coordinating with a metal, compositions containing such compounds, and methods of catalyzing reactions
CN112119055A (zh) * 2018-05-15 2020-12-22 加利福尼亚技术学院 通过立体保留性复分解全合成前列腺素j天然产物
US11939410B2 (en) * 2018-06-29 2024-03-26 Apeiron Synthesis S.A. Organoruthenium complexes as precatalysts for olefin metathesis
CN114206889A (zh) * 2019-07-17 2022-03-18 加利福尼亚技术学院 Z选择性烯烃复分解催化剂的新合成
EP4069667A1 (en) * 2020-03-05 2022-10-12 Firmenich SA Process for preparing perfuming intermediate
CN115298191A (zh) * 2020-03-13 2022-11-04 伊利诺伊大学评议会 催化氢化硅烷化的方法
CN114478166B (zh) * 2020-10-26 2024-09-27 中国石油天然气股份有限公司 一种制备端烯烃的方法
CN118056617A (zh) * 2022-11-15 2024-05-21 中国石油天然气股份有限公司 一种用于1-己烯自歧化的负载型催化剂及其制备方法

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CN101243098A (zh) * 2004-06-09 2008-08-13 Uti有限合伙公司 作为烯烃易位反应催化剂的含阳离子取代基的过渡金属卡宾配合物

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US20140106960A1 (en) 2014-04-17
IL227432A0 (en) 2013-09-30
JP2014503356A (ja) 2014-02-13
EP2663398A4 (en) 2014-07-23
CA2824518A1 (en) 2012-07-19
BR112013017938A2 (pt) 2018-11-27
BR112013017938B1 (pt) 2019-10-15
ZA201408071B (en) 2019-06-26
EP2663398B1 (en) 2018-07-18
US9597674B2 (en) 2017-03-21
WO2012097379A2 (en) 2012-07-19
KR101835170B1 (ko) 2018-03-06
JP5893646B2 (ja) 2016-03-23
WO2012097379A3 (en) 2012-10-11
ZA201305726B (en) 2018-12-19
CA2824518C (en) 2019-03-26
PL2663398T3 (pl) 2019-01-31
AU2012206966B2 (en) 2016-11-17
KR20140021995A (ko) 2014-02-21
IL227432A (en) 2017-12-31
CN103402628A (zh) 2013-11-20
SG191980A1 (en) 2013-08-30
EP2663398A2 (en) 2013-11-20

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