DOE Patents title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Methods for the synthesis of olefins and derivatives

Abstract

The invention provides a method of producing acrylic acid. The method includes contacting fumaric acid with a sufficient amount of ethylene in the presence of a cross-metathesis transformation catalyst to produce about two moles of acrylic acid per mole of fumaric acid. Also provided is an acrylate ester. The method includes contacting fumarate diester with a sufficient amount of ethylene in the presence of a cross-metathesis transformation catalyst to produce about two moles of acrylate ester per mole of fumarate diester. An integrated process for process for producing acrylic acid or acrylate ester is provided which couples bioproduction of fumaric acid with metathesis transformation. An acrylic acid and an acrylate ester production also is provided.

Inventors:
; ; ; ;
Issue Date:
Research Org.:
Genomatica, Inc. (San Diego, CA)
Sponsoring Org.:
USDOE
OSTI Identifier:
1084354
Patent Number(s):
8455683
Application Number:
13/219,423
Assignee:
Genomatica, Inc. (San Diego, CA)
Patent Classifications (CPCs):
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
C - CHEMISTRY C12 - BIOCHEMISTRY C12P - FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE {
DOE Contract Number:  
FG02-06ER84536; FG02-07ER84865
Resource Type:
Patent
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Burk, Mark J, Pharkya, Priti, Van Dien, Stephen J, Burgard, Anthony P, and Schilling, Christophe H. Methods for the synthesis of olefins and derivatives. United States: N. p., 2013. Web.
Burk, Mark J, Pharkya, Priti, Van Dien, Stephen J, Burgard, Anthony P, & Schilling, Christophe H. Methods for the synthesis of olefins and derivatives. United States.
Burk, Mark J, Pharkya, Priti, Van Dien, Stephen J, Burgard, Anthony P, and Schilling, Christophe H. Tue . "Methods for the synthesis of olefins and derivatives". United States. https://www.osti.gov/servlets/purl/1084354.
@article{osti_1084354,
title = {Methods for the synthesis of olefins and derivatives},
author = {Burk, Mark J and Pharkya, Priti and Van Dien, Stephen J and Burgard, Anthony P and Schilling, Christophe H},
abstractNote = {The invention provides a method of producing acrylic acid. The method includes contacting fumaric acid with a sufficient amount of ethylene in the presence of a cross-metathesis transformation catalyst to produce about two moles of acrylic acid per mole of fumaric acid. Also provided is an acrylate ester. The method includes contacting fumarate diester with a sufficient amount of ethylene in the presence of a cross-metathesis transformation catalyst to produce about two moles of acrylate ester per mole of fumarate diester. An integrated process for process for producing acrylic acid or acrylate ester is provided which couples bioproduction of fumaric acid with metathesis transformation. An acrylic acid and an acrylate ester production also is provided.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {Tue Jun 04 00:00:00 EDT 2013},
month = {Tue Jun 04 00:00:00 EDT 2013}
}

Works referenced in this record:

Living Ring-Opening Metathesis Polymerization in Water
journal, February 1998


Olefin Metathesis Involving Ruthenium Enoic Carbene Complexes
journal, October 2001


Well-Defined Ruthenium Olefin Metathesis Catalysts:  Mechanism and Activity
journal, April 1997


Method and system for modeling cellular metabolism
patent-application, November 2002


Complementary Metabolizing Organisms and Methods of Making Same
patent-application, January 2009


Methods and organisms for utilizing synthesis gas or other gaseous carbon sources and methanol
patent, September 2010


Methods and systems to identify operational reaction pathways
patent-application, April 2004


In silico predictions of Escherichia coli metabolic capabilities are consistent with experimental data
journal, February 2001


Rate Enhancement by Ethylene in the Ru-Catalyzed Ring-Closing Metathesis of Enynes: Evidence for an “Ene-then-Yne” Pathway that Diverts through a Second Catalytic Cycle
journal, November 2005


Method for the evolutionary design of biochemical reaction networks
patent, October 2006


A General Model for Selectivity in Olefin Cross Metathesis
journal, September 2003


Olefin metathesis
journal, August 2004


Microorganisms for the production of adipic acid and other compounds
patent, September 2010


Titanium metallacarbene-metallacyclobutane reactions: stepwise metathesis
journal, September 1980


Esterification and extraction process
patent, April 1978


Method For Determining Gene Knockouts
patent-application, January 2004


Metabolic modelling of microbes: the flux-balance approach
journal, March 2002


Multiple metal-carbon bonds. 16. Tungsten-oxo alkylidene complexes as olefins metathesis catalysts and the crystal structure of W(O)(CHCMe3(PEt3)Cl2
journal, June 1980

  • Wengrovius, Jeffrey H.; Schrock, Richard R.; Churchill, Melvyn Rowen
  • Journal of the American Chemical Society, Vol. 102, Issue 13, p. 4515-4516
  • https://doi.org/10.1021/ja00533a035

Models and methods for determining systemic properties of regulated reaction networks
patent-application, March 2003


Titanium-mediated methylene-transfer reactions. Direct conversion of esters into vinyl ethers
journal, April 1980


Methods for identifying drug targets based on genomic sequence data
patent-application, January 2002


Catalytic Upgrading of Fermentation-Derived Organic Acids
journal, October 1999


Method for the production of dicarboxylic acids
patent, February 1999


Cationic ruthenium complexes, their production and their use
patent, December 2002


Titanium-catalyzed olefin metathesis
journal, August 1979


Microorganisms for the production of 1,4-butanediol
patent, December 2010


Wax Crystal Modifiers (LAW657)
patent-application, April 2002


The Escherichia coli MG1655 in silico metabolic genotype: Its definition, characteristics, and capabilities
journal, May 2000


Fumaric Acid Production in Airlift Loop Reactor with Porous Sparger
book, January 1997


Industrial bioconversion of renewable resources as an alternative to conventional chemistry
journal, September 2004


Feasibility of acrylic acid production by fermentation
journal, February 2005


Optknock: A bilevel programming framework for identifying gene knockout strategies for microbial strain optimization
journal, October 2003


Metabolic Flux Balancing: Basic Concepts, Scientific and Practical Use
journal, October 1994


Toward Metabolic Phenomics: Analysis of Genomic Data Using Flux Balances
journal, June 1999


Bioconversion of fumaric acid to succinic acid by recombinantE. coli
journal, March 1998


Fumaric acid production by fermentation
journal, January 2008


Human metabolic models and methods
patent-application, February 2004


Methods and organisms for the growth-coupled production of 1,4-butanediol
patent, May 2011


Fumaric acid overproduction in yeast mutants deficient in fumarase
journal, March 1992


Cross-metathesis of dimethyl maleate and ethylene catalyzed by second generation ruthenium carbene complexes: B3LYP and MPW1K comparison study
journal, December 2006


Theory for the Systemic Definition of Metabolic Pathways and their use in Interpreting Metabolic Function from a Pathway-Oriented Perspective
journal, April 2000


Compositions and methods for modeling bacillus subtilis metabolism
patent-application, December 2003


Systems and methods for constructing genomic-based phenotypic models
patent-application, December 2003