skip to main content
DOE Patents title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Methods of refining natural oils and methods of producing fuel compositions

Abstract

A method of refining a natural oil includes: (a) providing a feedstock that includes a natural oil; (b) reacting the feedstock in the presence of a metathesis catalyst to form a metathesized product that includes olefins and esters; (c) passivating residual metathesis catalyst with an agent selected from the group consisting of phosphorous acid, phosphinic acid, and a combination thereof; (d) separating the olefins in the metathesized product from the esters in the metathesized product; and (e) transesterifying the esters in the presence of an alcohol to form a transesterified product and/or hydrogenating the olefins to form a fully or partially saturated hydrogenated product. Methods for suppressing isomerization of olefin metathesis products produced in a metathesis reaction, and methods of producing fuel compositions are described.

Inventors:
; ;
Issue Date:
Research Org.:
Elevance Renewable Sciences, Inc., Woodridge, IL (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1224887
Patent Number(s):
9,175,231
Application Number:
13/335,538
Assignee:
Elevance Renewable Sciences, Inc.
DOE Contract Number:  
EE0002872
Resource Type:
Patent
Resource Relation:
Patent File Date: 2011 Dec 22
Country of Publication:
United States
Language:
English
Subject:
02 PETROLEUM

Citation Formats

Firth, Bruce E, Kirk, Sharon E, and Gavaskar, Vasudeo S. Methods of refining natural oils and methods of producing fuel compositions. United States: N. p., 2015. Web.
Firth, Bruce E, Kirk, Sharon E, & Gavaskar, Vasudeo S. Methods of refining natural oils and methods of producing fuel compositions. United States.
Firth, Bruce E, Kirk, Sharon E, and Gavaskar, Vasudeo S. Wed . "Methods of refining natural oils and methods of producing fuel compositions". United States. https://www.osti.gov/servlets/purl/1224887.
@article{osti_1224887,
title = {Methods of refining natural oils and methods of producing fuel compositions},
author = {Firth, Bruce E and Kirk, Sharon E and Gavaskar, Vasudeo S},
abstractNote = {A method of refining a natural oil includes: (a) providing a feedstock that includes a natural oil; (b) reacting the feedstock in the presence of a metathesis catalyst to form a metathesized product that includes olefins and esters; (c) passivating residual metathesis catalyst with an agent selected from the group consisting of phosphorous acid, phosphinic acid, and a combination thereof; (d) separating the olefins in the metathesized product from the esters in the metathesized product; and (e) transesterifying the esters in the presence of an alcohol to form a transesterified product and/or hydrogenating the olefins to form a fully or partially saturated hydrogenated product. Methods for suppressing isomerization of olefin metathesis products produced in a metathesis reaction, and methods of producing fuel compositions are described.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2015},
month = {11}
}

Patent:

Save / Share:

Works referenced in this record:

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
  • DOI: 10.1002/ejoc.200600908

Metathesis of fatty acid esters
journal, February 1984

  • Boelhouwer, C.; Mol, J. C.
  • Journal of the American Oil Chemists' Society, Vol. 61, Issue 2
  • DOI: 10.1007/BF02678808

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
  • DOI: 10.1139/v61-262

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
  • DOI: 10.1007/BF02909058

Liquid-phase catalytic oxidation of unsaturated fatty acids
journal, March 1999


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
  • DOI: 10.1016/S1381-1169(99)00213-7

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
  • DOI: 10.1039/b600956e

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
  • DOI: 10.1002/lipi.19950971002

Oxidative Cleavage of the Double Bond of Monoenic Fatty Chains in Two Steps:  A New Promising Route to Azelaic Acid and Other Industrial Products
journal, August 2000

  • Santacesaria, E.; Sorrentino, A.; Rainone, F.
  • Industrial & Engineering Chemistry Research, Vol. 39, Issue 8
  • DOI: 10.1021/ie990920u

Double bond oxidative cleavage of monoenic fatty chains
journal, April 2003


Pilot run, plant design and cost analysis for reductive ozonolysis of methyl soyate
journal, November 1972

  • Throckmorton, P. E.; Pryde, E. H.
  • Journal of the American Oil Chemists' Society, Vol. 49, Issue 11
  • DOI: 10.1007/BF02609378

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
  • DOI: 10.1007/BF02609377

Improved cross-metathesis of acrylate esters catalyzed by 2nd generation ruthenium carbene complexes
journal, December 2005


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
  • DOI: 10.1002/anie.200300576

Recent Advances in High Oxidation State Mo and W Imido Alkylidene Chemistry
journal, August 2009


Metathesis of fatty acid esters
journal, February 1984

  • Boelhouwer, C.; Mol, J. C.
  • Journal of the American Oil Chemists' Society, Vol. 61, Issue 2
  • DOI: 10.1007/BF02678808

Metathesis of unsaturated fatty acid esters and fatty oils
journal, May 1994


Catalytic Metathesis of Unsaturated Fatty Acid Esters and Oils
journal, February 2004


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
  • DOI: 10.1039/b511626k

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
  • DOI: 10.1021/ol010045k

The Cl2(PCy3)(IMes)Ru(CHPh) catalyst: olefin metathesis versus olefin isomerization
journal, February 2002


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
  • DOI: 10.1021/ol027423l

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
  • DOI: 10.1021/jo051120y

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
  • DOI: 10.1021/ol0631399

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
  • DOI: 10.1002/ejoc.200600908

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
  • DOI: 10.1021/ja052939w

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
  • DOI: 10.1016/j.ccr.2009.07.008

A simple oxidative procedure for the removal of ruthenium residues from metathesis reaction products
journal, January 2010


Purification technique for the removal of ruthenium from olefin metathesis reaction products
journal, May 1999


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
  • DOI: 10.1021/ol060389g

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
  • DOI: 10.1021/ol000036w

Applications of Olefin Cross Metathesis to Commercial Products
journal, August 2002


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
  • DOI: 10.1021/op700288p