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Title: Methods for suppressing isomerization of olefin metathesis products

Abstract

A method for suppressing isomerization of an olefin metathesis product produced in a metathesis reaction includes adding an isomerization suppression agent that includes nitric acid to a mixture that includes the olefin metathesis product and residual metathesis catalyst from the metathesis reaction under conditions that are sufficient to passivate at least a portion of the residual metathesis catalyst. Methods of refining a natural oil are described.

Inventors:
;
Issue Date:
Research Org.:
Elevance Renewable Sciences, Inc., Woodridge, IL (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1224450
Patent Number(s):
9,169,174
Application Number:
13/335,495
Assignee:
Elevance Renewable Sciences, Inc. (Woodridge, IL)
DOE Contract Number:  
EE0002872
Resource Type:
Patent
Resource Relation:
Patent File Date: 2011 Dec 22
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Firth, Bruce E., and Kirk, Sharon E. Methods for suppressing isomerization of olefin metathesis products. United States: N. p., 2015. Web.
Firth, Bruce E., & Kirk, Sharon E. Methods for suppressing isomerization of olefin metathesis products. United States.
Firth, Bruce E., and Kirk, Sharon E. Tue . "Methods for suppressing isomerization of olefin metathesis products". United States. https://www.osti.gov/servlets/purl/1224450.
@article{osti_1224450,
title = {Methods for suppressing isomerization of olefin metathesis products},
author = {Firth, Bruce E. and Kirk, Sharon E.},
abstractNote = {A method for suppressing isomerization of an olefin metathesis product produced in a metathesis reaction includes adding an isomerization suppression agent that includes nitric acid to a mixture that includes the olefin metathesis product and residual metathesis catalyst from the metathesis reaction under conditions that are sufficient to passivate at least a portion of the residual metathesis catalyst. Methods of refining a natural oil are described.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2015},
month = {10}
}

Patent:

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Works referenced in this record:

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


Nitric Acid, Nitrous Acid, and Nitrogen Oxides
book, June 2000

  • Thiemann, Michael; Scheibler, Erich; Wiegand, Karl Wilhelm
  • Ullmann's Encyclopedia of Industrial Chemistry
  • DOI: 10.1002/14356007.a17_293

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

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
  • DOI: 10.1039/B712293D

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


High Oxidation State Multiple Metal−Carbon Bonds
journal, January 2002


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


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

Reactions of Ozonides: iii. Ozonolysis of Ethyl 10-Undecenoate in Ethanol
journal, February 1965

  • Diaper, D. G. M.; Mitchell, D. L.
  • Canadian Journal of Chemistry, Vol. 43, Issue 2
  • DOI: 10.1139/v65-042

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


Phase-transfer catalytic reaction of 2,4,6-tribromophenol and dibromomethane: effect of potassium hydroxide
journal, December 1999


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