DE69819501T2 - Ruthenium und osmiumcarbenkatalysatoren - Google Patents

Ruthenium und osmiumcarbenkatalysatoren Download PDF

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Publication number
DE69819501T2
DE69819501T2 DE69819501T DE69819501T DE69819501T2 DE 69819501 T2 DE69819501 T2 DE 69819501T2 DE 69819501 T DE69819501 T DE 69819501T DE 69819501 T DE69819501 T DE 69819501T DE 69819501 T2 DE69819501 T2 DE 69819501T2
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DE
Germany
Prior art keywords
tert
butyl
bis
alkyl
group
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.)
Expired - Fee Related
Application number
DE69819501T
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German (de)
English (en)
Other versions
DE69819501D1 (de
Inventor
Adriaan Paul VAN DER SCHAAF
Andreas Hafner
Andreas MÜHLEBACH
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.)
BASF Schweiz AG
Original Assignee
Ciba Spezialitaetenchemie Holding AG
Ciba SC Holding AG
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Publication of DE69819501D1 publication Critical patent/DE69819501D1/de
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Publication of DE69819501T2 publication Critical patent/DE69819501T2/de
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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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
    • B01J31/18—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
    • 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
    • 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
    • B01J31/1825—Ligands comprising condensed ring systems, e.g. acridine, carbazole
    • 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
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2282—Unsaturated compounds used as 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • 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
    • C07F15/0013—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group without a metal-carbon linkage
    • 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
    • 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
    • B01J2231/10—Polymerisation reactions involving at least dual use catalysts, e.g. for both oligomerisation and polymerisation
    • B01J2231/14—Other (co) polymerisation, e.g. of lactides or epoxides
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
DE69819501T 1997-06-27 1998-06-20 Ruthenium und osmiumcarbenkatalysatoren Expired - Fee Related DE69819501T2 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH156297 1997-06-27
CH156297 1997-06-27
PCT/EP1998/003781 WO1999000397A1 (en) 1997-06-27 1998-06-20 Ruthenium and osmium catalysts

Publications (2)

Publication Number Publication Date
DE69819501D1 DE69819501D1 (de) 2003-12-11
DE69819501T2 true DE69819501T2 (de) 2004-09-23

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
DE69819501T Expired - Fee Related DE69819501T2 (de) 1997-06-27 1998-06-20 Ruthenium und osmiumcarbenkatalysatoren

Country Status (11)

Country Link
US (1) US6306987B1 (https=)
EP (1) EP0993466B1 (https=)
JP (1) JP2002506455A (https=)
KR (1) KR100569620B1 (https=)
AU (1) AU8800498A (https=)
BR (1) BR9810488A (https=)
CA (1) CA2289709A1 (https=)
DE (1) DE69819501T2 (https=)
ES (1) ES2209185T3 (https=)
MX (1) MX210210B (https=)
WO (1) WO1999000397A1 (https=)

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US7507854B2 (en) 1998-09-01 2009-03-24 Materia, Inc. Impurity reduction in Olefin metathesis reactions
US6696597B2 (en) 1998-09-01 2004-02-24 Tilliechem, Inc. Metathesis syntheses of pheromones or their components
US6900347B2 (en) 1998-09-01 2005-05-31 Tilliechem, Inc. Impurity inhibition in olefin metathesis reactions
DE19840107A1 (de) * 1998-09-03 2000-03-09 Bayer Ag Verfahren zur Synthese alpha-substituierter Ringsysteme
IT1314204B1 (it) * 1999-10-28 2002-12-06 Sigea Srl Complessi di rutenio con elevata attivita' antitumorale
WO2002076920A1 (en) 2001-03-26 2002-10-03 Dow Global Technologies Inc. Metathesis of unsaturated fatty acid esters or unsaturated fatty acids with lower olefins
DE60229158D1 (de) * 2001-08-30 2008-11-13 Materia Inc Infusion von zyklischen olefinharzen in poröse materialien
JP4138417B2 (ja) * 2001-09-28 2008-08-27 積水化学工業株式会社 有機金属化合物の合成方法
US6620955B1 (en) 2001-11-15 2003-09-16 Richard L. Pederson Chelating carbene ligand precursors and their use in the synthesis of metathesis catalysts
RU2352549C2 (ru) 2002-04-29 2009-04-20 Дау Глобал Текнолоджиз Инк. Интегрированные химические способы промышленного применения растительных масел из семян
AU2003232067A1 (en) 2002-05-06 2003-11-17 Kerr Corporation Composition curable by metathesis reaction
US7683148B2 (en) 2003-05-06 2010-03-23 Kerr Corporation Metathesis-curable composition with a reaction control agent
US7060769B2 (en) * 2003-05-06 2006-06-13 Kerr Corporation Method of curing composition by metathesis reaction using reaction control agent
US7173097B2 (en) 2003-05-06 2007-02-06 Kerr Corporation Metathesis-curable composition with a reaction control agent
US7060770B2 (en) * 2003-05-06 2006-06-13 Kerr Corporation Metathesis-curable composition with a reaction control agent
CN100588638C (zh) 2003-10-09 2010-02-10 陶氏环球技术公司 合成不饱和醇的改进方法
US7109344B2 (en) * 2003-12-04 2006-09-19 Boehringer Ingelheim International Gmbh Ruthenium catalyst
ES2320776T3 (es) * 2003-12-08 2009-05-28 Boehringer Ingelheim International Gmbh Eliminacion de subproductos de rutenio por tratamiento con fluidos supercriticos.
DE102004002178A1 (de) 2004-01-15 2005-08-11 Ivoclar Vivadent Ag Dentalmeterialien auf der Basis von RÖMP-Kompositen
AU2011205218B2 (en) * 2004-03-29 2015-12-17 California Institute Of Technology Latent, high-activity olefin metathesis catalysts containing an N-heterocyclic carbene ligand
MXPA06011302A (es) * 2004-03-29 2007-01-16 Materia Inc Catalizadores de metatesis de olefinas de alta actividad, latentes que contienen un ligando de carbeno n-heterociclico.
US7001590B1 (en) 2004-11-15 2006-02-21 Kerr Corporation Metathesis-curable composition
US7645443B2 (en) 2004-11-15 2010-01-12 Kerr Corporation Polyether-based composition curable by metathesis reaction
US7625551B2 (en) 2004-11-15 2009-12-01 Kerr Corporation Polyether-based dental impression material curable by metathesis reaction
AU2006220708B9 (en) 2005-03-08 2013-01-17 Boehringer Ingelheim International Gmbh Process for preparing macrocyclic compounds
EP1934243B1 (en) 2005-09-09 2011-05-25 Boehringer Ingelheim International GmbH Ring-closing metathesis process for the preparation of macrocyclic peptides
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NZ568325A (en) 2005-11-16 2011-05-27 S Bio Pte Ltd Macrocyclic oxygen linked pyrimidine derivatives
EP1847245A1 (en) 2006-02-21 2007-10-24 Kerr Corporation Method for making alkoxy-siloxane polyether carboxylates terminated with functional olefin groups
PL379879A1 (pl) 2006-06-07 2007-12-10 Umicore Ag & Co.Kg. Kompleksy rutenu i osmu, sposób ich wytwarzania oraz ich zastosowanie jako (pre)katalizatorów reakcji metatezy
EP2044095B1 (en) * 2006-06-30 2009-08-26 F. Hoffmann-Roche AG New ruthenium complexes as catalysts for metathesis reactions
DE102007020694A1 (de) 2007-05-03 2008-11-06 Evonik Degussa Gmbh Schwefelhaltige Metathesekatalysatoren
US8241575B2 (en) 2008-01-28 2012-08-14 The Johns Hopkins University Molecularly imprinted polymer sensor device
JP5365625B2 (ja) * 2008-03-31 2013-12-11 日本ゼオン株式会社 重合性組成物、樹脂成形体、及び架橋樹脂成形体
WO2010051268A1 (en) 2008-10-31 2010-05-06 Dow Global Technologies Inc. Olefin metathesis process employing bimetallic ruthenium complex with bridging hydrido ligands
BRPI1008853A2 (pt) * 2009-02-18 2016-03-15 Henkel Corp iniciadores de rutênio termicamente comutáveis
ES2391340B1 (es) 2010-05-11 2013-09-30 Melchor Daumal Castellón Conjunto soporte multifuncion para columna de direccion
KR101297431B1 (ko) * 2011-04-18 2013-08-19 주식회사 폴리사이언텍 폴리프로필렌계 수지조성물 및 이로부터 제조된 스크래치 자기재생성 성형품
PL220408B1 (pl) * 2011-09-26 2015-10-30 Inst Chemii Organicznej Polskiej Akademii Nauk Kompleks rutentu, sposób jego wytwarzania oraz zastosowanie
US10933409B2 (en) * 2016-02-01 2021-03-02 Seoul National University R&Db Foundation Transition metal complex containing sulfonamide or amide group for olefin metathesis reaction and application thereof
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
CN116157262A (zh) * 2020-08-28 2023-05-23 Rimtec株式会社 阻氧性环烯烃系树脂固化物
JP2024534168A (ja) * 2021-08-31 2024-09-18 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング 組成物

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Also Published As

Publication number Publication date
DE69819501D1 (de) 2003-12-11
MX9911931A (es) 2000-03-31
BR9810488A (pt) 2000-09-12
JP2002506455A (ja) 2002-02-26
KR100569620B1 (ko) 2006-04-11
US6306987B1 (en) 2001-10-23
EP0993466B1 (en) 2003-11-05
ES2209185T3 (es) 2004-06-16
WO1999000397A1 (en) 1999-01-07
AU8800498A (en) 1999-01-19
EP0993466A1 (en) 2000-04-19
CA2289709A1 (en) 1999-01-07
MX210210B (es) 2002-09-06
KR20010014234A (ko) 2001-02-26

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Owner name: CIBA HOLDING INC., BASEL, CH

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