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Title: Methods of making organic compounds by metathesis

Abstract

Described are methods of making organic compounds by metathesis chemistry. The methods of the invention are particularly useful for making industrially-important organic compounds beginning with starting compositions derived from renewable feedstocks, such as natural oils. The methods make use of a cross-metathesis step with an olefin compound to produce functionalized alkene intermediates having a pre-determined double bond position. Once isolated, the functionalized alkene intermediate can be self-metathesized or cross-metathesized (e.g., with a second functionalized alkene) to produce the desired organic compound or a precursor thereto. The method may be used to make bifunctional organic compounds, such as diacids, diesters, dicarboxylate salts, acid/esters, acid/amines, acid/alcohols, acid/aldehydes, acid/ketones, acid/halides, acid/nitriles, ester/amines, ester/alcohols, ester/aldehydes, ester/ketones, ester/halides, ester/nitriles, and the like.

Inventors:
; ; ; ; ;
Issue Date:
Research Org.:
Elevance Renewable Sciences, Inc., Woodridge, IL (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1213457
Patent Number(s):
9120742
Application Number:
12/422,096
Assignee:
Elevance Renewable Sciences, Inc. (Woodridge, IL)
Patent Classifications (CPCs):
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
B - PERFORMING OPERATIONS B01 - PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL B01J - CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY
DOE Contract Number:  
FG36-04GO14016
Resource Type:
Patent
Resource Relation:
Patent File Date: 2009 Apr 10
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Abraham, Timothy W., Kaido, Hiroki, Lee, Choon Woo, Pederson, Richard L., Schrodi, Yann, and Tupy, Michael John. Methods of making organic compounds by metathesis. United States: N. p., 2015. Web.
Abraham, Timothy W., Kaido, Hiroki, Lee, Choon Woo, Pederson, Richard L., Schrodi, Yann, & Tupy, Michael John. Methods of making organic compounds by metathesis. United States.
Abraham, Timothy W., Kaido, Hiroki, Lee, Choon Woo, Pederson, Richard L., Schrodi, Yann, and Tupy, Michael John. Tue . "Methods of making organic compounds by metathesis". United States. https://www.osti.gov/servlets/purl/1213457.
@article{osti_1213457,
title = {Methods of making organic compounds by metathesis},
author = {Abraham, Timothy W. and Kaido, Hiroki and Lee, Choon Woo and Pederson, Richard L. and Schrodi, Yann and Tupy, Michael John},
abstractNote = {Described are methods of making organic compounds by metathesis chemistry. The methods of the invention are particularly useful for making industrially-important organic compounds beginning with starting compositions derived from renewable feedstocks, such as natural oils. The methods make use of a cross-metathesis step with an olefin compound to produce functionalized alkene intermediates having a pre-determined double bond position. Once isolated, the functionalized alkene intermediate can be self-metathesized or cross-metathesized (e.g., with a second functionalized alkene) to produce the desired organic compound or a precursor thereto. The method may be used to make bifunctional organic compounds, such as diacids, diesters, dicarboxylate salts, acid/esters, acid/amines, acid/alcohols, acid/aldehydes, acid/ketones, acid/halides, acid/nitriles, ester/amines, ester/alcohols, ester/aldehydes, ester/ketones, ester/halides, ester/nitriles, and the like.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2015},
month = {9}
}

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Works referenced in this record:

Metathesis of unsaturated fatty acids: Synthesis of long-chain unsaturated-α,ω-dicarboxylic acids
journal, July 2006


Synthesis and Reactivity of Olefin Metathesis Catalysts Bearing Cyclic (Alkyl)(Amino)Carbenes
journal, September 2007


Natural Fats and Oils—Renewable Raw Materials for the Chemical Industry
journal, January 1988


New Syntheses with Oils and Fats as Renewable Raw Materials for the Chemical Industry
journal, July 2000


Metathesis reactions of fatty acid esters
journal, January 1985


Olefin Metathesis Involving Ruthenium Enoic Carbene Complexes
journal, October 2001


A solid-Supported phosphine-Free ruthenium alkylidene for olefin metathesis in methanol and water
journal, July 2002


A highly efficient olefin metathesis initiator: improved synthesis and reactivity studies
journal, March 2003


Drying properties of metathesized soybean oil
journal, June 1997


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


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


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


Metathesis in Oleochemistry
journal, January 1998


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


Ruthenium-catalyzed metathesis of vegetable oils
journal, January 1999


Synthesis of Highly Substituted Cyclopentane and Tetrahydrofuran Derivatives by Crossed Olefin Metathesis
journal, March 1996


Model studies and the ADMET polymerization of soybean oil
journal, May 2002


Metathese ungesättigter Fettsäureester – ein einfacher Zugang zu langkettigen Dicarbonsäuren
journal, January 1992


Polymers and surfactants on the basis of renewable resources
journal, April 2001


The chemistry of metathesized soybean oil
journal, January 1999


Synthesis of Trisubstituted Alkenes via Olefin Cross-Metathesis
journal, December 1999