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Title: Methods of making organic compounds by metathesis

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.
Inventors:
; ; ; ; ;
Issue Date:
OSTI Identifier:
1213457
Assignee:
Elevance Renewable Sciences, Inc. (Woodridge, IL) GFO
Patent Number(s):
9,120,742
Application Number:
12/422,096
Contract Number:
FG36-04GO14016
Resource Relation:
Patent File Date: 2009 Apr 10
Research Org:
Elevance Renewable Sciences, Inc., Woodridge, IL (United States)
Sponsoring Org:
USDOE
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Other works cited in this record:

Synthesis and Reactivity of Olefin Metathesis Catalysts Bearing Cyclic (Alkyl)(Amino)Carbenes
journal, September 2007
  • Anderson, Donde R.; Lavallo, Vincent; O'Leary, Daniel J.
  • Angewandte Chemie International Edition, Vol. 46, Issue 38, p. 7262-7265
  • DOI: 10.1002/anie.200702085

Natural Fats and Oils—Renewable Raw Materials for the Chemical Industry
journal, January 1988
  • Baumann, Horst; Bühler, Matthias; Fochem, Heinz
  • Angewandte Chemie International Edition in English, Vol. 27, Issue 1, p. 41-62
  • DOI: 10.1002/anie.198800411

Metathesis reactions of fatty acid esters
journal, January 1985

Olefin Metathesis Involving Ruthenium Enoic Carbene Complexes
journal, October 2001
  • Choi, Tae-Lim; Lee, Choon Woo; Chatterjee, Arnab K.
  • Journal of the American Chemical Society, Vol. 123, Issue 42, p. 10417-10418
  • DOI: 10.1021/ja016386a

A solid-Supported phosphine-Free ruthenium alkylidene for olefin metathesis in methanol and water
journal, July 2002
  • Connon, Stephen J.; Blechert, Siegfried
  • Bioorganic & Medicinal Chemistry Letters, Vol. 12, Issue 14, p. 1873-1876
  • DOI: 10.1016/S0960-894X(02)00260-3

A highly efficient olefin metathesis initiator: improved synthesis and reactivity studies
journal, March 2003

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
  • Lavallo, Vincent; Canac, Yves; Präsang, Carsten
  • Angewandte Chemie International Edition, Vol. 44, Issue 35, p. 5705-5709
  • DOI: 10.1002/anie.200501841

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

Synthesis of Highly Substituted Cyclopentane and Tetrahydrofuran Derivatives by Crossed Olefin Metathesis
journal, March 1996
  • Schneider, Matthias F.; Blechert, Siegfried
  • Angewandte Chemie International Edition in English, Vol. 35, Issue 4, p. 411-412
  • DOI: 10.1002/anie.199604111

Polymers and surfactants on the basis of renewable resources
journal, April 2001

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