Methods for the synthesis of olefins and derivatives

Burk, Mark J; Pharkya, Priti; Van Dien, Stephen J; Burgard, Anthony P; Schilling, Christophe H

Title: Methods for the synthesis of olefins and derivatives

Patent · Tue Jun 04 00:00:00 EDT 2013

OSTI ID:1084354

Burk, Mark J; Pharkya, Priti; Van Dien, Stephen J; Burgard, Anthony P; Schilling, Christophe H

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.

View Patent

Cite

Export

Save

Research Organization:: Genomatica, Inc. (San Diego, CA)

Sponsoring Organization:: USDOE

DOE Contract Number:: FG02-06ER84536; FG02-07ER84865

Assignee:: Genomatica, Inc. (San Diego, CA)

Patent Number(s):: 8,455,683

Application Number:: 13/219,423

OSTI ID:: 1084354

Country of Publication:: United States

Language:: English

References (47)

Living Ring-Opening Metathesis Polymerization in Water Lynn, David M.; Mohr, Bernhard; Grubbs, Robert H. Journal of the American Chemical Society, Vol. 120, Issue 7, p. 1627-1628 https://doi.org/10.1021/ja9736323	journal	February 1998
Olefin Metathesis Involving Ruthenium Enoic Carbene Complexes Choi, Tae-Lim; Lee, Choon Woo; Chatterjee, Arnab K. Journal of the American Chemical Society, Vol. 123, Issue 42, p. 10417-10418 https://doi.org/10.1021/ja016386a	journal	October 2001
Well-Defined Ruthenium Olefin Metathesis Catalysts: Mechanism and Activity Dias, Eric L.; Nguyen, SonBinh T.; Grubbs, Robert H. Journal of the American Chemical Society, Vol. 119, Issue 17 https://doi.org/10.1021/ja963136z	journal	April 1997
Method and system for modeling cellular metabolism Maranas, Costas D.; Burgard, Anthony P. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20020168654 US Patent Application 10/043440; 20020168654	patent-application	November 2002
Complementary Metabolizing Organisms and Methods of Making Same Schilling, Christophe H. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20090023182 US Patent Application 11/779865; 20090023182	patent-application	January 2009
Methods and organisms for utilizing synthesis gas or other gaseous carbon sources and methanol Burk, Mark J.; Schilling, Christophe H.; Burgard, Anthony P. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7803589 US Patent Document 7,803,589	patent	September 2010
Methods and systems to identify operational reaction pathways Palsson, Bernhard O.; Covert, Markus W.; Herrgard, Markus https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20040072723 US Patent Application 10/367248; 20040072723	patent-application	April 2004
In silico predictions of Escherichia coli metabolic capabilities are consistent with experimental data Edwards, Jeremy S.; Ibarra, Rafael U.; Palsson, Bernhard O. Nature Biotechnology, Vol. 19, Issue 2 https://doi.org/10.1038/84379	journal	February 2001
Preparation and reactivity of several alkylidene complexes of the type W(CHR')(N-2,6-C₆H₃-iso-Pr₂)(OR)₂ and related tungstacyclobutane complexes. Controlling metathesis activity through the choice of alkoxide ligand Schrock, Richard R.; DePue, R. T.; Feldman, J. Journal of the American Chemical Society, Vol. 110, Issue 5, p. 1423-1435 https://doi.org/10.1021/ja00213a014	journal	March 1988
First direct observation of the simultaneous presence and of the interconversion of chain-propagating metal-carbene and metallacyclobutane complexes in a catalytic olefin metathesis reaction: the ring-opening polymerization of norbornene Kress, J.; Osborn, J. A.; Greene, R. M. E. Journal of the American Chemical Society, Vol. 109, Issue 3, p. 899-901 https://doi.org/10.1021/ja00237a045	journal	February 1987
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 Lloyd-Jones, Guy C.; Margue, Robert G.; de Vries, Johannes G. Angewandte Chemie International Edition, Vol. 44, Issue 45, p. 7442-7447 https://doi.org/10.1002/anie.200502243	journal	November 2005
Method for the evolutionary design of biochemical reaction networks Palsson, Bernhard O.; Edwards, Jeremy Scott https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7127379 US Patent Document 7,127,379	patent	October 2006
A General Model for Selectivity in Olefin Cross Metathesis Chatterjee, Arnab K.; Choi, Tae-Lim; Sanders, Daniel P. Journal of the American Chemical Society, Vol. 125, Issue 37 https://doi.org/10.1021/ja0214882	journal	September 2003
Olefin metathesis Grubbs, Robert H. Tetrahedron, Vol. 60, Issue 34 https://doi.org/10.1016/j.tet.2004.05.124	journal	August 2004
Microorganisms for the production of adipic acid and other compounds Burgard, Anthony P.; Pharkya, Priti; Osterhout, Robin E. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7799545 US Patent Document 7,799,545	patent	September 2010
Titanium metallacarbene-metallacyclobutane reactions: stepwise metathesis Howard, T. R.; Lee, J. B.; Grubbs, R. H. Journal of the American Chemical Society, Vol. 102, Issue 22, p. 6876-6878 https://doi.org/10.1021/ja00542a050	journal	September 1980
Esterification and extraction process Mims, Samuel S. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/4082788 US Patent Document 4,082,788	patent	April 1978
Method For Determining Gene Knockouts Maranas, Costas D.; Burgard, Anthony P.; Pharkya, Priti https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20040009466 US Patent Application 10/616659; 20040009466 A1	patent-application	January 2004
Metabolic modelling of microbes: the flux-balance approach Edwards, Jeremy S.; Covert, Markus; Palsson, Bernhard Environmental Microbiology, Vol. 4, Issue 3 https://doi.org/10.1046/j.1462-2920.2002.00282.x	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 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	journal	June 1980
Models and methods for determining systemic properties of regulated reaction networks Palsson, Bernhard O.; Covert, Markus W.; Schilling, Christophe H. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20030059792 US Patent Application 10/087441; 20030059792	patent-application	March 2003
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 Couturier, Jean-Luc; Paillet, Christophe; Leconte, Michel Angewandte Chemie International Edition in English, Vol. 31, Issue 5, p. 628-631 https://doi.org/10.1002/anie.199206281	journal	May 1992
Titanium-mediated methylene-transfer reactions. Direct conversion of esters into vinyl ethers Pine, S. H.; Zahler, R.; Evans, D. A. Journal of the American Chemical Society, Vol. 102, Issue 9, p. 3270-3272 https://doi.org/10.1021/ja00529a076	journal	April 1980
Systems and methods for constructing genomic-based phenotypic models Schilling, Christophe H. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7856317 US Patent Document 7,856,317	patent	December 2010
Methods for identifying drug targets based on genomic sequence data Palsson, Bernhard https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20020012939 US Patent Application 09/923870; 20020012939	patent-application	January 2002
Catalytic Upgrading of Fermentation-Derived Organic Acids Varadarajan, S.; Miller, D. J. Biotechnology Progress, Vol. 15, Issue 5 https://doi.org/10.1021/bp9900965	journal	October 1999
Method for the production of dicarboxylic acids Nghiem, Nhuan P.; Donnelly, Mark; Millard, Cynthia S. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/5869301 US Patent Document 5,869,301	patent	February 1999
Cationic ruthenium complexes, their production and their use Schwab, Peter; Schulz, Michael; Wolf, Jurgen https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6500975 US Patent Document 6,500,975	patent	December 2002
Titanium-catalyzed olefin metathesis Tebbe, F. N.; Parshall, G. W.; Ovenall, D. W. Journal of the American Chemical Society, Vol. 101, Issue 17, p. 5074-5075 https://doi.org/10.1021/ja00511a053	journal	August 1979
Microorganisms for the production of 1,4-butanediol Burk, Mark J.; Burgard, Anthony P.; Osterhout, Robin E. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7858350 US Patent Document 7,858,350	patent	December 2010
Wax Crystal Modifiers (LAW657) Patil, Abhimanyu Onkar; Zushma, Stephen; Berluche, Enock https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20020040123 US Patent Application 09/087257; 20020040123	patent-application	April 2002
The Escherichia coli MG1655 in silico metabolic genotype: Its definition, characteristics, and capabilities Edwards, J. S.; Palsson, B. O. Proceedings of the National Academy of Sciences, Vol. 97, Issue 10 https://doi.org/10.1073/pnas.97.10.5528	journal	May 2000
Fumaric Acid Production in Airlift Loop Reactor with Porous Sparger Du, Jianxin; Cao, Ningjun; Gong, Cheng S. Biotechnology for Fuels and Chemicals, p. 541-556 https://doi.org/10.1007/978-1-4612-2312-2_46	book	January 1997
Industrial bioconversion of renewable resources as an alternative to conventional chemistry Willke, Th.; Vorlop, K. -D. Applied Microbiology and Biotechnology, Vol. 66, Issue 2 https://doi.org/10.1007/s00253-004-1733-0	journal	September 2004
Feasibility of acrylic acid production by fermentation Straathof, Adrie J. J.; Sie, Susana; Franco, Telma T. Applied Microbiology and Biotechnology, Vol. 67, Issue 6 https://doi.org/10.1007/s00253-005-1942-1	journal	February 2005
Optknock: A bilevel programming framework for identifying gene knockout strategies for microbial strain optimization Burgard, Anthony P.; Pharkya, Priti; Maranas, Costas D. Biotechnology and Bioengineering, Vol. 84, Issue 6 https://doi.org/10.1002/bit.10803	journal	October 2003
Metabolic Flux Balancing: Basic Concepts, Scientific and Practical Use Varma, Amit; Palsson, Bernhard O. Bio/Technology, Vol. 12, Issue 10 https://doi.org/10.1038/nbt1094-994	journal	October 1994
Toward Metabolic Phenomics: Analysis of Genomic Data Using Flux Balances Schilling, C. H.; Edwards, J. S.; Palsson, B. O. Biotechnology Progress, Vol. 15, Issue 3 https://doi.org/10.1021/bp9900357	journal	June 1999
Bioconversion of fumaric acid to succinic acid by recombinantE. coli Wang, Xiaohai; Gong, C. S.; Tsao, George T. Applied Biochemistry and Biotechnology, Vol. 70-72, Issue 1 https://doi.org/10.1007/BF02920202	journal	March 1998
Fumaric acid production by fermentation Roa Engel, Carol A.; Straathof, Adrie J. J.; Zijlmans, Tiemen W. Applied Microbiology and Biotechnology, Vol. 78, Issue 3 https://doi.org/10.1007/s00253-007-1341-x	journal	January 2008
Human metabolic models and methods Palsson, Bornhard O.; Famili, Imandokht; Covert, Markus W. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20040029149 US Patent Application 10/402854; 20040029149	patent-application	February 2004
Methods and organisms for the growth-coupled production of 1,4-butanediol Burgard, Anthony P.; Van Dien, Stephen J.; Burk, Mark J. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7947483 US Patent Document 7,947,483	patent	May 2011
Fumaric acid overproduction in yeast mutants deficient in fumarase KaclÃkovÃ¡, E.; Lachowicz, T. M.; GbelskÃ¡, Y. FEMS Microbiology Letters, Vol. 91, Issue 2 https://doi.org/10.1111/j.1574-6968.1992.tb05192.x	journal	March 1992
Cross-metathesis of dimethyl maleate and ethylene catalyzed by second generation ruthenium carbene complexes: B3LYP and MPW1K comparison study Fomine, Serguei; Tlenkopatchev, Mikhail A. Journal of Organometallic Chemistry, Vol. 691, Issue 24-25, p. 5189-5196 https://doi.org/10.1016/j.jorganchem.2006.07.039	journal	December 2006
Theory for the Systemic Definition of Metabolic Pathways and their use in Interpreting Metabolic Function from a Pathway-Oriented Perspective Schilling, Christophe H.; Letscher, David; Palsson, Bernhard Ø. Journal of Theoretical Biology, Vol. 203, Issue 3 https://doi.org/10.1006/jtbi.2000.1073	journal	April 2000
Compositions and methods for modeling bacillus subtilis metabolism Park, Sung M.; Schilling, Christophe H.; Palsson, Bernhard O. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20030224363 US Patent Application 10/102022; 20030224363	patent-application	December 2003
Systems and methods for constructing genomic-based phenotypic models Schilling, Christophe H. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20030233218 US Patent Application 10/173547; 20030233218	patent-application	December 2003

Similar Records

Methods for synthesis of olefins and derivatives

Patent · Tue Jun 14 00:00:00 EDT 2016 · OSTI ID:1084354

Burk, Mark J.; Pharkya, Priti; Van Dien, Stephen J.; +2 more

Methods for the synthesis of olefins and derivatives

Patent · Tue Sep 25 00:00:00 EDT 2018 · OSTI ID:1084354

Burk, Mark J.; Pharkya, Priti; Van Dien, Stephen J.; +2 more

Methods for the synthesis of olefins and derivatives

Patent · Tue Sep 27 00:00:00 EDT 2011 · OSTI ID:1084354

Burk, Mark J; Pharkya, Priti; Van Dien, Stephen J; +2 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Title: Methods for the synthesis of olefins and derivatives

Citation Formats

References (47)

Similar Records

Related Subjects