CA2079211A1 - Use of organic derivatives of rhenium oxides as catalysts for ethenolytic metathesis of olefinic compounds and process for ethenolytic metathesis of olefinic compounds using thesecatalysts - Google Patents

Use of organic derivatives of rhenium oxides as catalysts for ethenolytic metathesis of olefinic compounds and process for ethenolytic metathesis of olefinic compounds using thesecatalysts

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Publication number
CA2079211A1
CA2079211A1 CA2079211A CA2079211A CA2079211A1 CA 2079211 A1 CA2079211 A1 CA 2079211A1 CA 2079211 A CA2079211 A CA 2079211A CA 2079211 A CA2079211 A CA 2079211A CA 2079211 A1 CA2079211 A1 CA 2079211A1
Authority
CA
Canada
Prior art keywords
olefinic compounds
ethenolytic
metathesis
catalysts
carbon atoms
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.)
Granted
Application number
CA2079211A
Other languages
French (fr)
Other versions
CA2079211C (en
Inventor
Wolfgang Anton Herrmann
Werner Wagner
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.)
Hoechst AG
Original Assignee
Wolfgang Anton Herrmann
Werner Wagner
Hoechst Aktiengesellschaft
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 DE4009910A external-priority patent/DE4009910A1/en
Application filed by Wolfgang Anton Herrmann, Werner Wagner, Hoechst Aktiengesellschaft filed Critical Wolfgang Anton Herrmann
Publication of CA2079211A1 publication Critical patent/CA2079211A1/en
Application granted granted Critical
Publication of CA2079211C publication Critical patent/CA2079211C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • 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
    • 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
    • C07C6/06—Metathesis reactions at an unsaturated carbon-to-carbon bond at a carbon-to-carbon double bond at a cyclic carbon-to-carbon double bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
    • C07C2521/04—Alumina
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • C07C2521/08—Silica
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • C07C2523/20—Vanadium, niobium or tantalum
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • C07C2523/24—Chromium, molybdenum or tungsten
    • C07C2523/26—Chromium
    • 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
    • C07C2531/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups C07C2531/02 - C07C2531/24
    • C07C2531/34—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups C07C2531/02 - C07C2531/24 of chromium, molybdenum or tungsten
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups C07C2531/02 - C07C2531/24
    • C07C2531/36—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups C07C2531/02 - C07C2531/24 of vanadium, niobium or tantalum
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups C07C2531/02 - C07C2531/24
    • C07C2531/38—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups C07C2531/02 - C07C2531/24 of titanium, zirconium or hafnium

Abstract

Use of compounds of formula R1aRebOc (I), in which a is 1 to 6, b is 1 to 4 and c is 1 to 14 and the sum of a, b and c is such that it satisfied rhenium in its 5- or 7- valency states, with the proviso that c is not greater than 3b, and in which R1 is an alkyl radical with 1 to 9 carbon atoms, a cycloalkyl radical with 5 to 10 carbon atoms or an aralkyl radical with 7 to 9 carbon atoms, where R1 may be at least partially fluorinated, the compounds do not contain more than three groups with more than 6 carbon atoms per rhenium atom and at least one hydrogen atom is bonded to the carbon atom in the .alpha.-position, which are applied to oxidic support materials, as catalysts for the ethenolytic metathesis of olefinic compounds.
CA002079211A 1990-03-28 1991-03-20 Use of organic derivatives of rhenium oxides as catalysts for ethenolytic metathesis of olefinic compounds and process for ethenolytic metathesis of olefinic compounds using thesecatalysts Expired - Fee Related CA2079211C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4009910A DE4009910A1 (en) 1988-12-10 1990-03-28 Ethenolytic metathesis of olefin(s) - using organo-rhenium oxide catalyst on oxidic carrier
DEP4009910.5 1990-03-28

Publications (2)

Publication Number Publication Date
CA2079211A1 true CA2079211A1 (en) 1991-09-29
CA2079211C CA2079211C (en) 1998-09-22

Family

ID=6403216

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002079211A Expired - Fee Related CA2079211C (en) 1990-03-28 1991-03-20 Use of organic derivatives of rhenium oxides as catalysts for ethenolytic metathesis of olefinic compounds and process for ethenolytic metathesis of olefinic compounds using thesecatalysts

Country Status (5)

Country Link
EP (1) EP0522067B1 (en)
JP (1) JPH0776184B2 (en)
CA (1) CA2079211C (en)
DE (1) DE59105881D1 (en)
WO (1) WO1991014665A1 (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2726488B1 (en) 1994-11-04 1996-12-13 Inst Francais Du Petrole NOVEL SUPPORTED CATALYSTS CONTAINING RHENIUM AND ALUMINUM, THEIR PREPARATION AND THEIR USE FOR OLEFIN METATHESIS
EP0975622B1 (en) * 1997-04-18 2002-10-09 Studiengesellschaft Kohle mbH Selective olefin metathesis of bifunctional or polyfunctional substrates in compressed carbon dioxide as reaction medium
KR100869981B1 (en) 2001-03-26 2008-11-24 다우 글로벌 테크놀로지스 인크. Metathesis of unsaturated fatty acid esters or unsaturated fatty acids with lower olefins
US7576227B2 (en) 2002-04-29 2009-08-18 Union Carbide Chemicals & Plastics Technology Corporation Integrate chemical processes for industrial utilization of seed oils
US7002049B2 (en) 2002-08-19 2006-02-21 Eastman Chemical Company Process for α,β-dihydroxyalkenes and derivatives
BRPI0415176B1 (en) 2003-10-09 2014-04-15 Dow Global Technologies Llc Process of preparation of an unsaturated alcohol and composition
DE502005002564D1 (en) * 2005-02-22 2008-03-06 Miltitz Aromatics Gmbh Method and apparatus for conducting a ring-opening cross-metathesis reaction between cyclic and acyclic olefins
EP1896385B1 (en) * 2005-06-06 2013-08-28 Dow Global Technologies LLC Metathesis process for preparing an alpha, omega -functionalized olefin

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3776973A (en) * 1967-05-03 1973-12-04 Phillips Petroleum Co Olefin conversion using complexes of mn,tc,and re with organoaluminum
US4180524A (en) * 1978-02-16 1979-12-25 Phillips Petroleum Company Disproportionation/double-bond isomerization of olefins
FR2499083B1 (en) * 1981-02-04 1986-02-21 Rhone Poulenc Chim Base NOVEL OXO COMPLEXES OF TRANSITIONAL METALS COORDINATED WITH LEWIS ACID - PROCESS FOR THE PREPARATION OF SUCH COMPLEXES - USE OF THESE COMPLEXES AS CATALYSTS IN THE REACTION OF METATHESIS OF OLEFINS
CA1330566C (en) * 1988-12-10 1994-07-05 Wolfgang Anton Herrmann Organic derivatives of rhenium oxides and their preparation and use for the metathesis of olefins

Also Published As

Publication number Publication date
JPH0776184B2 (en) 1995-08-16
JPH05506219A (en) 1993-09-16
WO1991014665A1 (en) 1991-10-03
EP0522067A1 (en) 1993-01-13
DE59105881D1 (en) 1995-08-03
EP0522067B1 (en) 1995-06-28
CA2079211C (en) 1998-09-22

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