Methods of refining and producing dibasic esters and acids from natural oil feedstocks
Abstract
Methods are provided for refining natural oil feedstocks and producing dibasic esters and/or dibasic acids. The methods comprise reacting a terminal olefin with an internal olefin in the presence of a metathesis catalyst to form a dibasic ester and/or dibasic acid. In certain embodiments, the olefin esters are formed by reacting the feedstock in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters, separating the olefins from the esters in the metathesized product, and transesterifying the esters in the presence of an alcohol to form a transesterified product having olefin esters.
- Inventors:
- Issue Date:
- Research Org.:
- Elevance Renewable Sciences, Inc., Woodridge, IL (United States)
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1177513
- Patent Number(s):
- 9000246
- Application Number:
- 13/647,809
- Assignee:
- Elevance Renewable Sciences, Inc. (Woodridge, IL)
- Patent Classifications (CPCs):
-
C - CHEMISTRY C10 - PETROLEUM, GAS OR COKE INDUSTRIES C10G - CRACKING HYDROCARBON OILS
C - CHEMISTRY C11 - ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES C11C - FATTY ACIDS FROM FATS, OILS OR WAXES
- DOE Contract Number:
- EE0002872/001
- Resource Type:
- Patent
- Resource Relation:
- Patent File Date: 2012 Oct 09
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 09 BIOMASS FUELS
Citation Formats
Snead, Thomas E, Cohen, Steven A, and Gildon, Demond L. Methods of refining and producing dibasic esters and acids from natural oil feedstocks. United States: N. p., 2015.
Web.
Snead, Thomas E, Cohen, Steven A, & Gildon, Demond L. Methods of refining and producing dibasic esters and acids from natural oil feedstocks. United States.
Snead, Thomas E, Cohen, Steven A, and Gildon, Demond L. Tue .
"Methods of refining and producing dibasic esters and acids from natural oil feedstocks". United States. https://www.osti.gov/servlets/purl/1177513.
@article{osti_1177513,
title = {Methods of refining and producing dibasic esters and acids from natural oil feedstocks},
author = {Snead, Thomas E and Cohen, Steven A and Gildon, Demond L},
abstractNote = {Methods are provided for refining natural oil feedstocks and producing dibasic esters and/or dibasic acids. The methods comprise reacting a terminal olefin with an internal olefin in the presence of a metathesis catalyst to form a dibasic ester and/or dibasic acid. In certain embodiments, the olefin esters are formed by reacting the feedstock in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters, separating the olefins from the esters in the metathesized product, and transesterifying the esters in the presence of an alcohol to form a transesterified product having olefin esters.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2015},
month = {4}
}
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Works referenced in this record:
High Oxidation State Multiple Metal−Carbon Bonds
journal, January 2002
- Schrock, Richard R.
- Chemical Reviews, Vol. 102, Issue 1
Molybdenum and Tungsten Imido Alkylidene Complexes as Efficient Olefin-Metathesis Catalysts
journal, October 2003
- Schrock, Richard R.; Hoveyda, Amir H.
- Angewandte Chemie International Edition, Vol. 42, Issue 38, p. 4592-4633
Recent Advances in High Oxidation State Mo and W Imido Alkylidene Chemistry
journal, August 2009
- Schrock, Richard R.
- Chemical Reviews, Vol. 109, Issue 8
Cross-metathesis of fatty acid derivatives with methyl acrylate: renewable raw materials for the chemical industry
journal, January 2007
- Rybak, Anastasiya; Meier, Michael A. R.
- Green Chemistry, Vol. 9, Issue 12
Improved cross-metathesis of acrylate esters catalyzed by 2nd generation ruthenium carbene complexes
journal, December 2005
- Forman, Grant S.; Tooze, Robert P.
- Journal of Organometallic Chemistry, Vol. 690, Issue 24-25, p. 5863-5866
A Convenient Method for the Efficient Removal of Ruthenium Byproducts Generated during Olefin Metathesis Reactions
journal, May 2001
- Ahn, Yu Mi; Yang, KyoungLang; Georg, Gunda I.
- Organic Letters, Vol. 3, Issue 9
Metathesis of fatty acid esters
journal, February 1984
- Boelhouwer, C.; Mol, J. C.
- Journal of the American Oil Chemists' Society, Vol. 61, Issue 2
The Cl2(PCy3)(IMes)Ru(CHPh) catalyst: olefin metathesis versus olefin isomerization
journal, February 2002
- Bourgeois, Damien; Pancrazi, Ange; Nolan, Steven P.
- Journal of Organometallic Chemistry, Vol. 643-644
An Efficient Method for Removal of Ruthenium Byproducts from Olefin Metathesis Reactions
journal, February 2003
- Cho, Jong Hyun; Kim, B. Moon
- Organic Letters, Vol. 5, Issue 4
Reactivity of Grubbs' Catalysts with Urea- and Amide-Substituted Olefins. Metathesis and Isomerization
journal, September 2005
- Formentín, Pilar; Gimeno, Nélida; Steinke, Joachim H. G.
- The Journal of Organic Chemistry, Vol. 70, Issue 20
A Rapid and Simple Cleanup Procedure for Metathesis Reactions
journal, March 2007
- Galan, Brandon R.; Kalbarczyk, Kyle P.; Szczepankiewicz, Steven
- Organic Letters, Vol. 9, Issue 7
Phenylphosphoric Acid as a New Additive to Inhibit Olefin Isomerisation in Ruthenium-Catalysed Metathesis Reactions
journal, February 2007
- Gimeno, Nélida; Formentín, Pilar; Steinke, Joachim H. G.
- European Journal of Organic Chemistry, Vol. 2007, Issue 6
Prevention of Undesirable Isomerization during Olefin Metathesis
journal, December 2005
- Hong, Soon Hyeok; Sanders, Daniel P.; Lee, Choon Woo
- Journal of the American Chemical Society, Vol. 127, Issue 49
Developments in the chemistry of tris(hydroxymethyl)phosphine
journal, March 2010
- James, Brian R.; Lorenzini, Fabio
- Coordination Chemistry Reviews, Vol. 254, Issue 5-6, p. 420-430
A simple oxidative procedure for the removal of ruthenium residues from metathesis reaction products
journal, January 2010
- Knight, David W.; Morgan, Ian R.; Proctor, Anthony J.
- Tetrahedron Letters, Vol. 51, Issue 4, p. 638-640
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
Functionalized Mesoporous Silicates for the Removal of Ruthenium from Reaction Mixtures
journal, June 2006
- McEleney, Kevin; Allen, Daryl P.; Holliday, Alison E.
- Organic Letters, Vol. 8, Issue 13
A Convenient Method for Removing All Highly-Colored Byproducts Generated during Olefin Metathesis Reactions
journal, May 2000
- Paquette, Leo A.; Schloss, Jeffrey D.; Efremov, Ivan
- Organic Letters, Vol. 2, Issue 9
Applications of Olefin Cross Metathesis to Commercial Products
journal, August 2002
- Pederson, Richard L.; Fellows, Ingrid M.; Ung, Thay A.
- Advanced Synthesis & Catalysis, Vol. 344, Issue 6-7
Development of a Robust Ring-Closing Metathesis Reaction in the Synthesis of SB-462795, a Cathepsin K Inhibitor
journal, March 2008
- Wang, Huan; Goodman, Steven N.; Dai, Qunying
- Organic Process Research & Development, Vol. 12, Issue 2
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
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
Catalytic Metathesis of Unsaturated Fatty Acid Esters and Oils
journal, February 2004
- Mol, J. C.
- Topics in Catalysis, Vol. 27, Issue 1-4
Cross-metathesis of unsaturated natural oils with 2-butene. High conversion and productive catalyst turnovers
journal, January 2005
- Patel, Jim; Elaridi, Jomana; Jackson, W. Roy
- Chemical Communications, Issue 44
Ozonolysis of Unsaturated Fatty Acids: i. Ozonolysis of Oleic acid
journal, October 1961
- Ackman, R. G.; Retson, M. E.; Gallay, L. R.
- Canadian Journal of Chemistry, Vol. 39, Issue 10
Reductive ozonolysis of soybean oil: Laboratory optimization of process variables
journal, November 1972
- Throckmorton, P. E.; Pryde, E. H.
- Journal of the American Oil Chemists' Society, Vol. 49, Issue 11
Oxidation of unsaturated fatty acids with ruthenium and osmium tetroxide
journal, November 1977
- Foglia, T. A.; Barr, P. A.; Malloy, A. J.
- Journal of the American Oil Chemists' Society, Vol. 54, Issue 11
Transition-metal Catalyzed Oxidative Cleavage of Unsaturated Fatty Acids
journal, January 1995
- Rüsch, M.; Klaas, Gen.; Bavaj, P.
- Fett Wissenschaft Technologie/Fat Science Technology, Vol. 97, Issue 10
Practical dihydroxylation and C–C cleavage of unsaturated fatty acids
journal, December 1999
- Oakley, Michael A.; Woodward, Simon; Coupland, Keith
- Journal of Molecular Catalysis A: Chemical, Vol. 150, Issue 1-2, p. 105-111
Liquid-phase catalytic oxidation of unsaturated fatty acids
journal, March 1999
- Noureddini, H.; Kanabur, M.
- Journal of the American Oil Chemists' Society, Vol. 76, Issue 3
Double bond oxidative cleavage of monoenic fatty chains
journal, April 2003
- Santacesaria, E.; Ambrosio, M.; Sorrentino, A.
- Catalysis Today, Vol. 79-80, p. 59-65
High conversion and productive catalyst turnovers in cross-metathesis reactions of natural oils with 2-butene
journal, January 2006
- Patel, Jim; Mujcinovic, S.; Jackson, W. Roy
- Green Chemistry, Vol. 8, Issue 5