skip to main content
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 (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1484241
Patent Number(s):
10,081,587
Application Number:
15/182,245
Assignee:
Genomatica, Inc. (San Diego, CA)
DOE Contract Number:  
FG02-06ER84536; FG02-07ER84865
Resource Type:
Patent
Resource Relation:
Patent File Date: 2016 Jun 14
Country of Publication:
United States
Language:
English

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., 2018. 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/1484241.
@article{osti_1484241,
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 = {2018},
month = {9}
}

Patent:

Save / Share:

Works referenced in this record:

Escherichia coli Binary Culture Engineered for Direct Fermentation of Hemicellulose to a Biofuel
journal, October 2010

  • Shin, H.-D.; McClendon, S.; Vo, T.
  • Applied and Environmental Microbiology, Vol. 76, Issue 24, p. 8150-8159
  • DOI: 10.1128/AEM.00908-10

Fumaric acid production by fermentation
journal, January 2008

  • Roa Engel, Carol A.; Straathof, Adrie J. J.; Zijlmans, Tiemen W.
  • Applied Microbiology and Biotechnology, Vol. 78, Issue 3
  • DOI: 10.1007/s00253-007-1341-x

Lewis-acid assisted cross metathesis of acrylonitrile with functionalized olefins catalyzed by phosphine-free ruthenium carbene complex
journal, January 2005

  • Bai, Chen-Xi; Lu, Xiao-Bing; He, Ren
  • Organic & Biomolecular Chemistry, Vol. 3, Issue 22
  • DOI: 10.1039/B510776H

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

  • Burgard, Anthony P.; Pharkya, Priti; Maranas, Costas D.
  • Biotechnology and Bioengineering, Vol. 84, Issue 6
  • DOI: 10.1002/bit.10803

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

  • Chatterjee, Arnab K.; Choi, Tae-Lim; Sanders, Daniel P.
  • Journal of the American Chemical Society, Vol. 125, Issue 37
  • DOI: 10.1021/ja0214882

Olefin Metathesis Involving Ruthenium Enoic Carbene Complexes
journal, October 2001

  • Choi, Tae-Lim; Lee, Choon Woo; Chatterjee, Arnab K.
  • Journal of the American Chemical Society, Vol. 123, Issue 42, p. 10417-10418
  • DOI: 10.1021/ja016386a

A Cyclometalated Aryloxy(chloro)neopentylidenetungsten Complex: A Highly Active and Stereoselective Catalyst for the Metathesis of cis- and trans-2-Pentene, Norbornene, 1-Methyl-norbornene, and Ethyl Oleate
journal, May 1992

  • Couturier, Jean-Luc; Paillet, Christophe; Leconte, Michel
  • Angewandte Chemie International Edition in English, Vol. 31, Issue 5, p. 628-631
  • DOI: 10.1002/anie.199206281

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


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


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

  • Edwards, Jeremy S.; Ibarra, Rafael U.; Palsson, Bernhard O.
  • Nature Biotechnology, Vol. 19, Issue 2
  • DOI: 10.1038/84379

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

  • Edwards, J. S.; Palsson, B. O.
  • Proceedings of the National Academy of Sciences, Vol. 97, Issue 10
  • DOI: 10.1073/pnas.97.10.5528

The Biofine Process– Production of Levulinic Acid, Furfural, and Formic Acid from Lignocellulosic Feedstocks
book, December 2005

  • Hayes, Daniel J.; Fitzpatrick, Steve; Hayes, Michael H. B.
  • Biorefineries-Industrial Processes and Products
  • DOI: 10.1002/9783527619849.ch7

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


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

  • Lloyd-Jones, Guy C.; Margue, Robert G.; de Vries, Johannes G.
  • Angewandte Chemie International Edition, Vol. 44, Issue 45, p. 7442-7447
  • DOI: 10.1002/anie.200502243

Living Ring-Opening Metathesis Polymerization in Aqueous Media Catalyzed by Well-Defined Ruthenium Carbene Complexes
journal, January 1996

  • Lynn, David M.; Kanaoka, Shokyoku; Grubbs, Robert H.
  • Journal of the American Chemical Society, Vol. 118, Issue 4
  • DOI: 10.1021/ja950327d

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

  • Lynn, David M.; Mohr, Bernhard; Grubbs, Robert H.
  • Journal of the American Chemical Society, Vol. 120, Issue 7, p. 1627-1628
  • DOI: 10.1021/ja9736323

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

  • Pine, S. H.; Zahler, R.; Evans, D. A.
  • Journal of the American Chemical Society, Vol. 102, Issue 9, p. 3270-3272
  • DOI: 10.1021/ja00529a076

Combining pathway analysis with flux balance analysis for the comprehensive study of metabolic systems
journal, January 2000


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

  • Schilling, Christophe H.; Letscher, David; Palsson, Bernhard Ø.
  • Journal of Theoretical Biology, Vol. 203, Issue 3
  • DOI: 10.1006/jtbi.2000.1073

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

  • Schilling, C. H.; Edwards, J. S.; Palsson, B. O.
  • Biotechnology Progress, Vol. 15, Issue 3
  • DOI: 10.1021/bp9900357

Metabolic engineering of Escherichia coli for the production of fumaric acid
journal, March 2013

  • Song, Chan Woo; Kim, Dong In; Choi, Sol
  • Biotechnology and Bioengineering, Vol. 110, Issue 7
  • DOI: 10.1002/bit.24868

Feasibility of acrylic acid production by fermentation
journal, February 2005

  • Straathof, Adrie J. J.; Sie, Susana; Franco, Telma T.
  • Applied Microbiology and Biotechnology, Vol. 67, Issue 6
  • DOI: 10.1007/s00253-005-1942-1

Titanium-catalyzed olefin metathesis
journal, August 1979

  • Tebbe, F. N.; Parshall, G. W.; Ovenall, D. W.
  • Journal of the American Chemical Society, Vol. 101, Issue 17, p. 5074-5075
  • DOI: 10.1021/ja00511a053

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


Development of an antibiotic-free plasmid selection system based on glycine auxotrophy for recombinant protein overproduction in Escherichia coli
journal, March 2008


Bioconversion of Fumaric Acid to Succinic Acid by Recombinant E. coli
book, January 1998


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