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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 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. The isomerization suppression agent is phosphorous acid, a phosphorous acid ester, phosphinic acid, a phosphinic acid ester or combinations thereof. Methods of refining natural oils are described.

Inventors:
; ;
Issue Date:
Research Org.:
Elevance Renewable Sciences, Inc., Woodridge, IL (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1221387
Patent Number(s):
9139493
Application Number:
13/335,466
Assignee:
Elevance Renewable Sciences, Inc. (Woodridge, IL)
Patent Classifications (CPCs):
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
C - CHEMISTRY C11 - ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES C11B - PRODUCING
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., Kirk, Sharon E., and Gavaskar, Vasudeo S. Methods for suppressing isomerization of olefin metathesis products. United States: N. p., 2015. Web.
Firth, Bruce E., Kirk, Sharon E., & Gavaskar, Vasudeo S. Methods for suppressing isomerization of olefin metathesis products. United States.
Firth, Bruce E., Kirk, Sharon E., and Gavaskar, Vasudeo S. Tue . "Methods for suppressing isomerization of olefin metathesis products". United States. https://www.osti.gov/servlets/purl/1221387.
@article{osti_1221387,
title = {Methods for suppressing isomerization of olefin metathesis products},
author = {Firth, Bruce E. and Kirk, Sharon E. and Gavaskar, Vasudeo S.},
abstractNote = {A method for suppressing isomerization of an olefin metathesis product produced in a metathesis reaction includes adding an isomerization suppression agent 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. The isomerization suppression agent is phosphorous acid, a phosphorous acid ester, phosphinic acid, a phosphinic acid ester or combinations thereof. Methods of refining natural oils are described.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2015},
month = {9}
}

Works referenced in this record:

Total isomerization process
patent, July 1980


Production of hydrocarbons with a relatively high cetane rating
patent, February 1991


Process for the hydrogenation of fatty acid methyl ester mixtures
patent, August 1991


Methods for treatment of edible oils
patent, February 1992


High viscosity index lubricant compositions
patent, May 1992


Homogeneous rhenium catalysts for metathesis of olefins
patent, September 1992


Synthetic lubricating oils
patent, November 1993


Process for the preparation of polyvinyl compounds
patent, November 1993


Method of preventing edible oils and fats from deteriorating
patent, March 1994


Ruthenium and osmium metal carbene complexes for olefin metathesis polymerization
patent, August 1994


Alkane disproportionation
patent, May 1995


Enzymatic method for removing oxygen from oils and fats
patent, July 1995


Process for refining oil and fat
patent, July 1996


Free fatty acid removal from used frying fat
patent, October 1996


Method for preparation of carboxylic acids
patent, January 1997


Treatment of cooking oils and fats with magnesium silicate and alkali materials
patent, January 1997


Lubricating oil compositions and concentrates and the use thereof
patent, July 1997


Lipid composition for cosmetic products
patent, August 1997


Catalytic composition and olefin disproportion process
patent, October 1997


Process for reducing sterols and free fatty acids from animal fat
patent, October 1998


Refining of edible oil rich in natural carotenes and vitamin E
patent, August 1999


Method for preparation of carboxylic acids
patent, August 1999


Fractionation of triglyceride oils
patent, September 1999


Method and apparatus for producing diesel fuel oil from waste edible oil
patent, October 1999


Refining of edible oil retaining maximum antioxidative potency
patent, March 2000


Transesterification process
patent, June 2000


Method for preparing a lower alkyl ester product from vegetable oil
patent, October 2000


Fortification of a vegetable fat with antioxidants
patent, December 2000


Methods for refining vegetable oils and byproducts thereof
patent, January 2001


Cooking oil additive and method of using
patent, April 2001


Paraffin-isomerization catalyst and process
patent, April 2001


Synthesis of 5-decenyl acetate and other pheromone components
patent, April 2001


Refining of vegetable oil
patent, June 2001


Method for production of esterified product
patent, July 2001


Preparation of propene
patent, August 2001


Process for synthesizing .alpha.-substituted ring systems
patent, October 2001


Adsorbent filtration system for treating used cooking oil or fat in frying operations
patent, April 2002


Method of removing transition metals
patent, April 2002


Method for producing polycarboxylic acid for cement dispersant and cement composition
patent, May 2002


Catalyst component and system
patent, May 2002


Additive for biodiesel and biofuel oils
patent, June 2002


Process for the catalytically carrying out multiphase reactions, in particular hydroformylations
patent, December 2002


Preparation of substituted olefins
patent, January 2003


Fractionation process
patent, April 2003


Reaction mixtures for metathesis
patent, August 2003


Methods and compositions for purifying edible oil
patent, October 2003


Preparation of propene
patent, November 2003


Metathesis syntheses of pheromones or their components
patent, February 2004


Process for the preparation of rice bran oil low in phosphorous content
patent, March 2004


Method for fractionating cooking oil
patent, October 2004


Hydrogenation catalysts
patent, January 2005


Method for carrying out a metathesis reaction of unsaturated organic compounds
patent, February 2005


Impurity inhibition in olefin metathesis reactions
patent, May 2005


Contact metathesis polymerization
patent, November 2005


Contact metathesis polymerization
patent, November 2005


Process for producing fatty acid lower alcohol ester
patent, January 2006


Method of treating fats and oils
patent, February 2006


Contact metathesis polymerization
patent, April 2006


Oil or fat composition
patent, June 2006


Solvent-containing coating material and the use thereof
patent, June 2006


Metathesis of unsaturated fatty acid esters or unsaturated fatty acids with lower olefins
patent, October 2006


Process for the synthesis of unsaturated alcohols
patent, February 2007


Phosphorous containing ligands for metathesis catalysts
patent, October 2007


Cooking oil antioxidant composition, method of preparation and use
patent, January 2008


Magnesium halide/alcohol adduct, its preparation and use
patent, April 2008


Cementitious composition
patent, October 2008


Process of removing transition metals
patent, November 2008


System for creating a biofuel
patent, November 2008


Impurity reduction in Olefin metathesis reactions
patent, March 2009


Green biodiesel
patent, July 2009


Integrate chemical processes for industrial utilization of seed oils
patent, August 2009


Low trans-fatty acid fat compositions; low-temperature hydrogenation, e.g., of edible oils
patent, September 2009


Method for processing vegetable oils
patent, October 2009


Metathesis unit pretreatment process with formation of octene
patent, October 2009


Production of fatty acid alkyl esters
patent, November 2009


Method of producing fatty acid alkyl ester for diesel fuel oil
patent, December 2009


Production of biodiesel and a side stream of crude glycerol which is converted to methanol
patent, January 2010


Process for the preparation of fatty acid methyl ester from triglyceride oil by transesterification
patent, February 2010


Method for transesterifying vegetable oils
patent, April 2010


Stabilization of olefin metathesis product mixtures
patent, April 2010


Catalyst systems and their use for metathesis reactions
patent, June 2010


Integrated chemical processes for industrial utilization of seed oils
patent, June 2010


High metathesis activity ruthenium and osmium carbene complexes
patent, July 2010


Porous silica and metal oxide composite-based catalysts for conversion of fatty acids and oils to biodiesel
patent, September 2010


Production of biodiesel and glycerin from high free fatty acid feedstocks
patent, October 2010


Metathesis process for preparing an alpha, omega-functionalized olefin
patent, October 2010


Process for continuous ruthenium-catalysed metathesis
patent, November 2010


Process for the transesterification of esters
patent, January 2011


Metathesis of unsaturated fatty acid esters or unsaturated fatty acids with lower olefins
patent-application, March 2005


Fuel products from plant or animal lipids
patent-application, March 2006


Methods, compositions, and apparatuses for forming macrocyclic compounds
patent-application, September 2007


Synthesis of Liquid Fuels and Chemicals from Oxygenated Hydrocarbons
patent-application, December 2008


Method of Making Hydrogenated Metathesis Products
patent-application, February 2009


Metathesis Methods Involving Hydrogenation and Compositions Relating to Same
patent-application, April 2010


Methods for Producing Biodiesel
patent-application, October 2010


Phenylphosphoric Acid as a New Additive to Inhibit Olefin Isomerisation in Ruthenium-Catalysed Metathesis Reactions
journal, February 2007


Functionalized Mesoporous Silicates for the Removal of Ruthenium from Reaction Mixtures
journal, June 2006


A Convenient Method for the Efficient Removal of Ruthenium Byproducts Generated during Olefin Metathesis Reactions
journal, May 2001


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


Reactivity of Grubbs' Catalysts with Urea- and Amide-Substituted Olefins. Metathesis and Isomerization
journal, September 2005


A Rapid and Simple Cleanup Procedure for Metathesis Reactions
journal, March 2007


Prevention of Undesirable Isomerization during Olefin Metathesis
journal, December 2005


Developments in the chemistry of tris(hydroxymethyl)phosphine
journal, March 2010


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


A Convenient Method for Removing All Highly-Colored Byproducts Generated during Olefin Metathesis Reactions
journal, May 2000


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


Ozonolysis of Unsaturated Fatty Acids: i. Ozonolysis of Oleic acid
journal, October 1961


Oxidation of unsaturated fatty acids with ruthenium and osmium tetroxide
journal, November 1977


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


Practical dihydroxylation and C–C cleavage of unsaturated fatty acids
journal, December 1999


Transition-metal Catalyzed Oxidative Cleavage of Unsaturated Fatty Acids
journal, January 1995


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


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


Reductive ozonolysis of soybean oil: Laboratory optimization of process variables
journal, November 1972


Cross-metathesis of fatty acid derivatives with methyl acrylate: renewable raw materials for the chemical industry
journal, January 2007


Cross-metathesis of fatty acid derivatives with methyl acrylate: renewable raw materials for the chemical industry
journal, January 2007


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


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