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Title: Methods of making organic compounds by metathesis

Patent ·
OSTI ID:1213457
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Described are methods of making organic compounds by metathesis chemistry. The methods of the invention are particularly useful for making industrially-important organic compounds beginning with starting compositions derived from renewable feedstocks, such as natural oils. The methods make use of a cross-metathesis step with an olefin compound to produce functionalized alkene intermediates having a pre-determined double bond position. Once isolated, the functionalized alkene intermediate can be self-metathesized or cross-metathesized (e.g., with a second functionalized alkene) to produce the desired organic compound or a precursor thereto. The method may be used to make bifunctional organic compounds, such as diacids, diesters, dicarboxylate salts, acid/esters, acid/amines, acid/alcohols, acid/aldehydes, acid/ketones, acid/halides, acid/nitriles, ester/amines, ester/alcohols, ester/aldehydes, ester/ketones, ester/halides, ester/nitriles, and the like.

Research Organization:
Elevance Renewable Sciences, Inc., Woodridge, IL (United States)
Sponsoring Organization:
USDOE
DOE Contract Number:
FG36-04GO14016
Assignee:
Elevance Renewable Sciences, Inc. (Woodridge, IL)
Patent Number(s):
9,120,742
Application Number:
12/422,096
OSTI ID:
1213457
Resource Relation:
Patent File Date: 2009 Apr 10
Country of Publication:
United States
Language:
English

References (114)

Selective esterification of long chain fatty acid monoglycerides with medium chain fatty acid anhydrides patent August 1992
Ruthenium and osmium metal carbene complexes for olefin metathesis polymerization patent May 1994
Method of preparing ruthenium and osmium carbene complexes patent January 1998
Romp polymerization in the presence of peroxide crosslinking agents to form high-density crosslinked polymers patent March 1998
Polymer depolymerization using ruthenium and osmium carbene complexes patent March 1998
Olefin metathesis coupling using ruthenium and osmium carbene complexes patent May 1998
Synthesis of conformationally restricted amino acids, peptides, and peptidomimetics by catalytic ring closing metathesis patent September 1998
High metathesis activity ruthenium and osmium metal carbene complexes patent November 1998
Romp of functionalized cyclic olefins using ruthenium and osmium carbene complexes patent December 1998
Synthesis of telechelic polymers using ruthenium and osmium carbene complexes patent March 1999
Synthesis of ruthenium or osmium metathesis catalysts patent June 1999
Diene cyclization using ruthenium and osmium carbene complexes patent July 1999
Method for extending the pot life of an olefin metathesis polymerization reaction patent August 1999
High activity ruthenium and osmium metal carbene complexes for olefin metathesis reactions patent October 1999
Schiff base derivatives of ruthenium and osmium olefin metathesis catalysts patent November 1999
Polymerization of low grade DCPD monomers using an olefin metathesis catalyst patent February 2000
Metathesis polymerizered olefin composites including sized reinforcement material patent March 2000
Template-directed ring-closing metathesis and ring-opening metathesis polymerization of functionalized dienes patent June 2000
Thermally initiated polymerization of olefins using Ruthenium or osmium vinylidene complexes patent August 2000
Method for producing mixtures of monoolefinic C5-mononitriles by catalytic hydrocyanation patent January 2001
Preparation of hydrogenated product of cyclic olefin ring-opening metathesis polymer patent March 2001
Lewis acid-catalyzed polymerization of biological oils and resulting polymeric materials patent April 2001
Synthesis of 5-decenyl acetate and other pheromone components patent April 2001
Acid activation of ruthenium metathesis catalysts and living ROMP metathesis polymerization in water patent September 2001
Methods for cross-metathesis of terminal olefins patent October 2001
Polymeric composites including dicyclopentadiene and related monomers patent October 2001
Catalyst system comprising transition metal and imidazoline-2-ylidene or imidazolidine-2-ylidene patent November 2001
Metathesis polymerized olefin composites including sized reinforcement material patent November 2001
Method of removing transition metals patent April 2002
Metathesis-active adhesion agents and methods for enhancing polymer adhesion to surfaces patent June 2002
Pipe made from metathesis polymerized olefins patent June 2002
ABA triblock and diblock copolymers and methods of preparing the same patent June 2002
Ruthenium metal alkylidene complexes coordinated with triazolylidene ligands that exhibit high olefin metathesis activity patent July 2002
Fluorinated polymers and methods for their preparation patent August 2002
Telechelic alkadiene polymers with crosslinkable end groups and methods for making the same patent October 2002
Process for producing hydrogenated ring-opening polymerization polymer of cycloolefin patent November 2002
Polyolefin compositions having variable density and methods for their production and use patent February 2003
Polyolefin compositions having enhanced ultraviolet and oxidative resistance and methods for their production and use patent June 2003
Highly active metathesis catalysts generated in situ from inexpensive and air stable precursors patent August 2003
One-pot synthesis of group 8 transition metal carbene complexes useful as olefin metathesis catalysts patent September 2003
Chelating carbene ligand precursors and their use in the synthesis of metathesis catalysts patent September 2003
Metathesis syntheses of pheromones or their components patent February 2004
Hexacoordinated ruthenium or osmium metal carbene metathesis catalysts patent July 2004
Synthesis of functionalized and unfunctionalized olefins via cross and ring-closing metathesis patent September 2004
Selective ring-opening cross-metathesis of cycloolefins patent October 2004
Hexacoordinated ruthenium or osmium metal carbene metathesis catalysts patent November 2004
High activity metal carbene metathesis catalysts generated using a thermally activated N-heterocyclic carbene precursor patent January 2005
Ring-opening metathesis polymerization of bridged bicyclic and polycyclic olefins containing two or more heteroatoms patent April 2005
Impurity inhibition in olefin metathesis reactions patent May 2005
Recyclable metathesis catalysts patent July 2005
Simply assembled and recyclable polymer-supported olefin metathesis catalysts patent July 2005
Synthesis of macrocyclic polymers by ring insertion polymerization of cyclic olefin monomers patent September 2005
Contact metathesis polymerization patent November 2005
Synthesis of A,B-alternating copolymers by olefin metathesis reactions of cyclic olefins or olefinic polymers with an acyclic diene patent January 2006
Chelating carbene ligand precursors and their use in the synthesis of metathesis catalysts patent April 2006
Ring-expansion of cyclic olefins metathesis reactions with an acyclic diene patent April 2006
Synthesis of 1,3 distributed imidazolium salts patent September 2006
Metathesis of unsaturated fatty acid esters or unsaturated fatty acids with lower olefins patent October 2006
Process for the synthesis of unsaturated alcohols patent February 2007
Preparation of ruthenium-based olefin metathesis catalysts patent April 2007
Polyolefin compositions optionally having variable toughness and/or hardness patent October 2007
Functionalized polyalphaolefins patent January 2008
Imidazolidine-based metal carbene metathesis catalysts patent February 2008
Transition metal carbene complexes containing a cationic substituent as catalysts of olefin metathesis reactions patent April 2008
Impurity reduction in Olefin metathesis reactions patent March 2009
Integrate chemical processes for industrial utilization of seed oils patent August 2009
Low trans-fatty acid fat compositions; low-temperature hydrogenation, e.g., of edible oils patent September 2009
Cross-metathesis of olefins directly substituted with an electron-withdrawing group using transition metal carbene catalysts patent October 2009
Catalyst complex with carbene ligand patent November 2009
Process for co-producing olefins and esters by ethenolysis of unsaturated fats in non-aqueous ionic liquids patent March 2010
Metathesis process for preparing an alpha, omega-functionalized olefin patent October 2010
Lewis acid-catalyzed polymerization of biological oils and resulting polymeric materials patent-application July 2002
Group 8 transition metal carbene complexes as enantioselective olefin metathesis catalysts patent-application March 2003
Cross-metathesis reaction of functionalized and substituted olefins using group 8 transition metal carbene complexes as metathesis catalysts patent-application May 2003
Catalytic osmium-assisted oxidative cleavage of olefins patent-application August 2003
Infusion of cyclic olefin resins into porous materials patent-application October 2003
Metathesis of unsaturated fatty acid esters or unsaturated fatty acids with lower olefins patent-application March 2005
Latent, high-activity olefin metathesis catalysts containing an N-heterocyclic carbene ligand patent-application November 2005
Process for co-producing olefins and esters by ethenolysis of unsaturated fats in non-aqueous ionic liquids patent-application April 2006
Novel wax emulsion coating applications patent-application December 2006
Process for Co-Producing Olefins and Diesters or Diacids Starting from Unsaturated Fts patent-application August 2007
Method for Making Industrial Chemicals patent-application November 2007
Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis patent-application January 2008
Ring opening cross-metathesis reaction of cyclic olefins with seed oils and the like patent-application March 2008
Method of Making Hydrogenated Metathesis Products patent-application February 2009
Colorant Compositions Comprising Metathesized Unsaturated Polyol Esters patent-application May 2009
Candle and candle wax containing metathesis and metathesis-like products patent-application September 2009
Compositions Comprising Metathesized Unsaturated Polyol Esters patent-application September 2009
Methods of Making Organic Compounds by Metathesis and Hydrocyanation patent-application October 2009
Hot Melt Adhesive Compositions Comprising Metathesized Unsaturated Polyol Ester Wax patent-application February 2010
Metathesis Methods Involving Hydrogenation and Compositions Relating to Same patent-application April 2010
Synthesis of Terminal Alkenes From Internal Alkenes Via Olefin Metathesis patent-application June 2010
Metathesis of unsaturated fatty acids: Synthesis of long-chain unsaturated-α,ω-dicarboxylic acids journal July 2006
Synthesis and Reactivity of Olefin Metathesis Catalysts Bearing Cyclic (Alkyl)(Amino)Carbenes journal September 2007
Natural Fats and Oils—Renewable Raw Materials for the Chemical Industry journal January 1988
New Syntheses with Oils and Fats as Renewable Raw Materials for the Chemical Industry journal July 2000
Metathesis reactions of fatty acid esters journal January 1985
Olefin Metathesis Involving Ruthenium Enoic Carbene Complexes journal October 2001
A solid-Supported phosphine-Free ruthenium alkylidene for olefin metathesis in methanol and water journal July 2002
A highly efficient olefin metathesis initiator: improved synthesis and reactivity studies journal March 2003
Drying properties of metathesized soybean oil journal June 1997
Stable Cyclic (Alkyl)(Amino)Carbenes as Rigid or Flexible, Bulky, Electron-Rich Ligands for Transition-Metal Catalysts: A Quaternary Carbon Atom Makes the Difference journal September 2005
Purification technique for the removal of ruthenium from olefin metathesis reaction products journal May 1999
Metathesis of unsaturated fatty acid esters and fatty oils journal May 1994
Metathesis in Oleochemistry journal January 1998
Catalytic Metathesis of Unsaturated Fatty Acid Esters and Oils journal February 2004
Ruthenium-catalyzed metathesis of vegetable oils journal January 1999
Synthesis of Highly Substituted Cyclopentane and Tetrahydrofuran Derivatives by Crossed Olefin Metathesis journal March 1996
Model studies and the ADMET polymerization of soybean oil journal May 2002
Metathese ungesättigter Fettsäureester – ein einfacher Zugang zu langkettigen Dicarbonsäuren journal January 1992
Polymers and surfactants on the basis of renewable resources journal April 2001
The chemistry of metathesized soybean oil journal January 1999
Synthesis of dicarboxylic acids by transition-metal catalyzed oxidative cleavage of terminal-unsaturated fatty acids book January 1993
Synthesis of Trisubstituted Alkenes via Olefin Cross-Metathesis journal December 1999

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