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Title: Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis

Patent ·
OSTI ID:1241345

This invention relates generally to olefin metathesis, and more particularly relates to the synthesis of terminal alkenes from internal alkenes using a cross-metathesis reaction catalyzed by a selected olefin metathesis catalyst. In one embodiment of the invention, for example, a method is provided for synthesizing a terminal olefin, the method comprising contacting an olefinic substrate comprised of at least one internal olefin with ethylene, in the presence of a metathesis catalyst, wherein the catalyst is present in an amount that is less than about 1000 ppm relative to the olefinic substrate, and wherein the metathesis catalyst has the structure of formula (II) ##STR00001## wherein the various substituents are as defined herein. The invention has utility, for example, in the fields of catalysis, organic synthesis, and industrial chemistry.

Research Organization:
MATERIA, INC., Pasadena, CA (United States)
Sponsoring Organization:
USDOE
DOE Contract Number:
FG36-04GO14016
Assignee:
MATERIA, INC. (Pasadena, CA)
Patent Number(s):
9,255,117
Application Number:
08/13/2013
OSTI ID:
1241345
Resource Relation:
Patent File Date: 2013 Aug 13
Country of Publication:
United States
Language:
English

References (175)

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Synthesis of conformationally restricted amino acids, peptides, and peptidomimetics by catalytic ring closing metathesis patent September 1998
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Romp of functionalized cyclic olefins using ruthenium and osmium carbene complexes patent December 1998
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Schiff base derivatives of ruthenium and osmium olefin metathesis catalysts patent November 1999
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Non-paraffin candle composition patent May 2000
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Synthesis of 5-decenyl acetate and other pheromone components patent April 2001
Process for producing a paraffin-based object and such an object patent May 2001
Repulpable hot melt paper coating and coated product patent July 2001
Colored wax articles patent July 2001
Hydrogenation catalyst particles patent August 2001
Vegetable lipid-based composition and candle patent September 2001
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Metathesis polymerized olefin composites including sized reinforcement material patent November 2001
Method of removing transition metals patent April 2002
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Pipe made from metathesis polymerized olefins patent June 2002
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Triacylglycerol based candle wax patent January 2003
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Colored wax articles patent July 2003
Soybean wax candles patent July 2003
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One-pot synthesis of group 8 transition metal carbene complexes useful as olefin metathesis catalysts patent September 2003
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Vegetable oil candle patent May 2004
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Triacylglycerol based wax for use in container candles patent September 2004
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Hexacoordinated ruthenium or osmium metal carbene metathesis catalysts patent November 2004
Vegetable oil based wax compositions patent November 2004
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Moisture resistant, repulpable paper products and method of making same patent January 2005
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Impurity inhibition in olefin metathesis reactions patent May 2005
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Chelating carbene ligand precursors and their use in the synthesis of metathesis catalysts patent April 2006
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Triacylglycerol based wax compositions patent October 2006
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Imidazolidine-based metal carbene metathesis catalysts patent February 2008
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Triacylglycerol based candle wax patent December 2008
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Catalyst complex with carbene ligand patent November 2009
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Metathesis process for preparing an alpha, omega-functionalized olefin patent October 2010
Colored wax articles patent-application December 2001
Lewis acid-catalyzed polymerization of biological oils and resulting polymeric materials patent-application July 2002
Triacylglycerol-based alternative to paraffin wax patent-application October 2002
Vegetable oil based wax compositions patent-application January 2003
Vegetable fat-based candles patent-application March 2003
Group 8 transition metal carbene complexes as enantioselective olefin metathesis catalysts patent-application March 2003
Triacylglycerol based wax compositions patent-application March 2003
Vegetable lipid-based composition and candle patent-application April 2003
Vegetable oil candle patent-application May 2003
Cross-metathesis reaction of functionalized and substituted olefins using group 8 transition metal carbene complexes as metathesis catalysts patent-application May 2003
Triacylglycerol based candle wax patent-application June 2003
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Moisture resistant, repulpable paper products and method of making same patent-application October 2003
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Synthesis of A,B-alternating copolymers by olefin metathesis reactions of cyclic olefins or olefinic polymers with an acyclic diene patent-application December 2003
Triacylglycerol-based alternative to paraffin wax patent-application March 2004
Triacylglycerol based wax for use in container candles patent-application May 2004
Triacylglycerol based wax for use in candles patent-application May 2004
Vegetable lipid-based composition and candle patent-application October 2004
Wax and wax-based products patent-application November 2004
Triacylglycerol based candle wax patent-application November 2004
Functionalized polyalphaolefins patent-application January 2005
Low trans-fatty acid fat compositions; low-temperature hydrogenation, e.g., of edible oils patent-application February 2005
Triacylglycerol based wax for use in container candles patent-application March 2005
Metathesis of unsaturated fatty acid esters or unsaturated fatty acids with lower olefins patent-application March 2005
Process for the synthesis of unsaturated alcohols patent-application April 2005
Moisture resistant, repulpable paper products and method of making same patent-application June 2005
Integrate chemical processes for industrial utilization of seed oils patent-application July 2005
Compression-molded vegetable wax-based candle patent-application July 2005
Latent, high-activity olefin metathesis catalysts containing an N-heterocyclic carbene ligand patent-application November 2005
Triglyceride/wax replacement for conventional slack and emulsified waxes used in forest products based composites patent-application December 2005
Process for co-producing olefins and esters by ethenolysis of unsaturated fats in non-aqueous ionic liquids patent-application April 2006
Transition metal carbene complexes containing a cationic substituent as catalysts of olefin metathesis reactions patent-application June 2006
Candle refill kit and method of use patent-application October 2006
Aqueous gel candle for use with a warming device patent-application December 2006
Wax and wax-based products patent-application December 2006
Novel wax emulsion coating applications patent-application December 2006
Vegetable lipid-based composition and candle patent-application January 2007
Triacylglycerol based wax composition patent-application February 2007
Compression-molded vegetable wax-based candle patent-application June 2007
Hydrogenated and partially hydrogenated heat-bodied oils and uses thereof patent-application July 2007
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
Triacylglycerol-based alternative to paraffin wax patent-application December 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
Methods of Making Organic Compounds by Metathesis 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

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