Methods of making organic compounds by metathesis
Abstract
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:
- Research Org.:
- Elevance Renewable Sciences, Inc., Woodridge, IL (United States)
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1213457
- Patent Number(s):
- 9120742
- Application Number:
- 12/422,096
- Assignee:
- Elevance Renewable Sciences, Inc. (Woodridge, IL)
- Patent Classifications (CPCs):
-
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
B - PERFORMING OPERATIONS B01 - PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL B01J - CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY
- DOE Contract Number:
- FG36-04GO14016
- Resource Type:
- Patent
- Resource Relation:
- Patent File Date: 2009 Apr 10
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Abraham, Timothy W., Kaido, Hiroki, Lee, Choon Woo, Pederson, Richard L., Schrodi, Yann, and Tupy, Michael John. Methods of making organic compounds by metathesis. United States: N. p., 2015.
Web.
Abraham, Timothy W., Kaido, Hiroki, Lee, Choon Woo, Pederson, Richard L., Schrodi, Yann, & Tupy, Michael John. Methods of making organic compounds by metathesis. United States.
Abraham, Timothy W., Kaido, Hiroki, Lee, Choon Woo, Pederson, Richard L., Schrodi, Yann, and Tupy, Michael John. Tue .
"Methods of making organic compounds by metathesis". United States. https://www.osti.gov/servlets/purl/1213457.
@article{osti_1213457,
title = {Methods of making organic compounds by metathesis},
author = {Abraham, Timothy W. and Kaido, Hiroki and Lee, Choon Woo and Pederson, Richard L. and Schrodi, Yann and Tupy, Michael John},
abstractNote = {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.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2015},
month = {9}
}
Works referenced in this record:
Metathesis of unsaturated fatty acids: Synthesis of long-chain unsaturated-α,ω-dicarboxylic acids
journal, July 2006
- Ngo, Helen L.; Jones, Kerby; Foglia, Thomas A.
- Journal of the American Oil Chemists' Society, Vol. 83, Issue 7
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
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
New Syntheses with Oils and Fats as Renewable Raw Materials for the Chemical Industry
journal, July 2000
- Biermann, Ursula; Friedt, Wolfgang; Lang, Siegmund
- Angewandte Chemie International Edition, Vol. 39, Issue 13
Metathesis reactions of fatty acid esters
journal, January 1985
- Boelhouwer, C.; Mol, J. C.
- Progress in Lipid Research, Vol. 24, Issue 3, p. 243-267
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
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
A highly efficient olefin metathesis initiator: improved synthesis and reactivity studies
journal, March 2003
- Dunne, Aideen M.; Mix, Stefan; Blechert, Siegfried
- Tetrahedron Letters, Vol. 44, Issue 13, p. 2733-2736
Drying properties of metathesized soybean oil
journal, June 1997
- Erhan, Sevim Z.; Bagby, Marvin O.; Nelsen, T. C.
- Journal of the American Oil Chemists' Society, Vol. 74, Issue 6
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
Purification technique for the removal of ruthenium from olefin metathesis reaction products
journal, May 1999
- Maynard, Heather D.; Grubbs, Robert H.
- Tetrahedron Letters, Vol. 40, Issue 22, p. 4137-4140
Metathesis of unsaturated fatty acid esters and fatty oils
journal, May 1994
- Mol, J. C.
- Journal of Molecular Catalysis, Vol. 90, Issue 1-2, p. 185-199
Application of olefin metathesis in oleochemistry: an example of green chemistry
journal, February 2002
- Mol, J. C.
- Green Chemistry, Vol. 4, Issue 1
Metathesis in Oleochemistry
journal, January 1998
- Mol, Johannes C.; Buffon, Regina
- Journal of the Brazilian Chemical Society, Vol. 9, Issue 1
Catalytic Metathesis of Unsaturated Fatty Acid Esters and Oils
journal, February 2004
- Mol, J. C.
- Topics in Catalysis, Vol. 27, Issue 1-4
Ruthenium-catalyzed metathesis of vegetable oils
journal, January 1999
- Refvik, M. D.; Larock, R. C.; Tian, Q.
- Journal of the American Oil Chemists' Society, Vol. 76, Issue 1
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
Model studies and the ADMET polymerization of soybean oil
journal, May 2002
- Tian, Qingping; Larock, Richard C.
- Journal of the American Oil Chemists' Society, Vol. 79, Issue 5
Metathese ungesättigter Fettsäureester – ein einfacher Zugang zu langkettigen Dicarbonsäuren
journal, January 1992
- Warwel, S.; Jägers, H. -G; Thomas, S.
- Fett Wissenschaft Technologie/Fat Science Technology, Vol. 94, Issue 9
Polymers and surfactants on the basis of renewable resources
journal, April 2001
- Warwel, Siegfried; Brüse, Falk; Demes, Christoph
- Chemosphere, Vol. 43, Issue 1, p. 39-48
The chemistry of metathesized soybean oil
journal, January 1999
- Refvik, M. D.; Larock, R. C.
- Journal of the American Oil Chemists' Society, Vol. 76, Issue 1
Synthesis of Trisubstituted Alkenes via Olefin Cross-Metathesis
journal, December 1999
- Chatterjee, Arnab K.; Grubbs, Robert H.
- Organic Letters, Vol. 1, Issue 11