Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis
Abstract
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.
- Inventors:
- Issue Date:
- Research Org.:
- MATERIA, INC., Pasadena, CA (United States)
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1241345
- Patent Number(s):
- 9255117
- Application Number:
- 08/13/2013
- Assignee:
- MATERIA, INC. (Pasadena, CA)
- Patent Classifications (CPCs):
-
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07F - ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- DOE Contract Number:
- FG36-04GO14016
- Resource Type:
- Patent
- Resource Relation:
- Patent File Date: 2013 Aug 13
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Schrodi, Yann. Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis. United States: N. p., 2016.
Web.
Schrodi, Yann. Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis. United States.
Schrodi, Yann. Tue .
"Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis". United States. https://www.osti.gov/servlets/purl/1241345.
@article{osti_1241345,
title = {Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis},
author = {Schrodi, Yann},
abstractNote = {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.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2016},
month = {2}
}
Works referenced 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
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
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
Synthesis of Trisubstituted Alkenes via Olefin Cross-Metathesis
journal, December 1999
- Chatterjee, Arnab K.; Grubbs, Robert H.
- Organic Letters, Vol. 1, Issue 11
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
1,3-Diolein and 1,3-Distearin Esters of Fumaric, Succinic and Adipic Acids
journal, December 1958
- Feuge, R. O.; Ward, T. L.
- Journal of the American Chemical Society, Vol. 80, Issue 23, p. 6338-6341
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
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
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
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
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 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
Glycol Esters of Dibasic Acids. The Di-β-hydroxyethyl Esters 1
journal, January 1935
- Shorland, F. B.
- Journal of the American Chemical Society, Vol. 57, Issue 1
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
New fat products: Glyceride esters of adipic acid
journal, December 1959
- Ward, Truman L.; Gros, Audrey T.; Feuge, R. O.
- Journal of the American Oil Chemists Society, Vol. 36, Issue 12
Metathesis Activity and Stability of New Generation Ruthenium Polymerization Catalysts
journal, November 2003
- Courchay, Florence C.; Sworen, John C.; Wagener, Kenneth B.
- Macromolecules, Vol. 36, Issue 22