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Methods of making organic compounds by metathesis

Patent ·
OSTI ID:1213457
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
Country of Publication:
United States
Language:
English

References (25)

Drying properties of metathesized soybean oil journal June 1997
Metathesis in Oleochemistry journal January 1998
Polymers and surfactants on the basis of renewable resources journal April 2001
Natural Fats and Oils—Renewable Raw Materials for the Chemical Industry journal January 1988
Metathesis of unsaturated fatty acid esters and fatty oils journal May 1994
Synthesis of dicarboxylic acids by transition-metal catalyzed oxidative cleavage of terminal-unsaturated fatty acids book January 1993
Model studies and the ADMET polymerization of soybean oil journal May 2002
Synthesis of Highly Substituted Cyclopentane and Tetrahydrofuran Derivatives by Crossed Olefin Metathesis journal March 1996
New Syntheses with Oils and Fats as Renewable Raw Materials for the Chemical Industry journal July 2000
Application of olefin metathesis in oleochemistry: an example of green chemistry journal February 2002
Metathesis of unsaturated fatty acids: Synthesis of long-chain unsaturated-α,ω-dicarboxylic acids journal July 2006
Synthesis of Trisubstituted Alkenes via Olefin Cross-Metathesis journal December 1999
The chemistry of metathesized soybean oil journal January 1999
Catalytic Metathesis of Unsaturated Fatty Acid Esters and Oils journal February 2004
A solid-Supported phosphine-Free ruthenium alkylidene for olefin metathesis in methanol and water journal July 2002
Ruthenium-catalyzed metathesis of vegetable oils journal January 1999
High conversion and productive catalyst turnovers in cross-metathesis reactions of natural oils with 2-butene journal January 2006
A highly efficient olefin metathesis initiator: improved synthesis and reactivity studies journal March 2003
Synthesis and Reactivity of Olefin Metathesis Catalysts Bearing Cyclic (Alkyl)(Amino)Carbenes journal September 2007
Metathese ungesättigter Fettsäureester – ein einfacher Zugang zu langkettigen Dicarbonsäuren journal January 1992
Purification technique for the removal of ruthenium from olefin metathesis reaction products journal May 1999
Olefin Metathesis Involving Ruthenium Enoic Carbene Complexes journal October 2001
Metathesis reactions of fatty acid esters journal January 1985
Cross-metathesis of unsaturated natural oils with 2-butene. High conversion and productive catalyst turnovers journal January 2005
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

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