Preparation By Isomerization Patents (Class 562/591)
  • Patent number: 10913702
    Abstract: A method for cycloaddition of dimethyl muconate is disclosed. According to the method, a direct transferring of a solid phase trans,trans-dimehtyl muconate into a reactor pre-filled with ethylene gas increases the efficiency of the reaction and suppress side reactions resulting an improvements in yield and purity. Furthermore, the method is capable of obtaining a high yield of dimethylcyclohex-2-en-1,4-dicarboxylate at a lower cost, and therefore is also useful for the mass synthesis of dimethyl terephthalate.
    Type: Grant
    Filed: December 14, 2018
    Date of Patent: February 9, 2021
    Assignee: SK CHEMICALS CO.. LTD.
    Inventors: Jae Kyun Park, Jeong Ho Park, Hee-il Chae
  • Patent number: 10337034
    Abstract: This disclosure relates to compositions and methods for converting biomass to various chemical intermediates and final products including fuels. Aspects include the depolymerization of lignin, cellulose, and hemicellulose to a wide slate of depolymerization compounds that can be subsequently metabolized by genetically modified bacterium, and converted to cis,cis-muconic acid. Other aspects include the use of monometallic catalysts for converting the cis,cis-muconic acid to commodity chemicals and fuels, for example adipic acid and/or nylon.
    Type: Grant
    Filed: April 27, 2018
    Date of Patent: July 2, 2019
    Assignee: Alliance for Sustainable Energy, LLC
    Inventors: Gregg Tyler Beckham, Christopher W. Johnson, Derek Richard Vardon, Mary Ann Franden
  • Patent number: 8809583
    Abstract: A method for producing cis,trans- and trans,trans-isomers of muconate by providing cis,cis -muconate produced from a renewable carbon source through biocatalytic conversion; isomerizing cis,cis-muconate to cis,trans-muconate under reaction conditions in which substantially all of the cis,cis-muconate is isomerized to cis,trans -muconate; separating the cis,trans-muconate; and crystallizing the cis,trans-muconate. The cis,trans-isomer can be further isomerized to the trans,trans-isomer. In one example, the method includes culturing recombinant cells that express 3-dehydroshikimate dehydratase, protocatechuate decarboxylase and catechol 1,2-dioxygenase in a medium comprising the renewable carbon source and under conditions in which the renewable carbon source is converted to 3-dehydroshikimate by enzymes in the common pathway of aromatic amino acid biosynthesis of the cell, and the 3-dehydroshikimate is biocatalytically converted to cis,cis-muconate.
    Type: Grant
    Filed: January 10, 2011
    Date of Patent: August 19, 2014
    Assignee: Amyris, Inc.
    Inventors: Vu Bui, Man Kit Lau, Doug MacRae, Dirk Schweitzer
  • Patent number: 8426639
    Abstract: The present invention relates to the isomerization of cis,cis and/or cis,trans muconic acid or esters thereof to trans,trans muconic acid or esters thereof and to the esterification of such muconic acids.
    Type: Grant
    Filed: June 16, 2010
    Date of Patent: April 23, 2013
    Assignee: Amyris, Inc.
    Inventors: John W. Frost, Adeline Miermont, Dirk Schweitzer, Vu Bui
  • Publication number: 20130030215
    Abstract: A method for producing cis,trans- and trans,trans-isomers of muconate by providing cis,cis-muconate produced from a renewable carbon source through biocatalytic conversion; isomerizing cis,cis-muconate to cis,trans-muconate under reaction conditions in which substantially all of the cis,cis-muconate is isomerized to cis,trans-muconate; separating the cis,trans-muconate; and crystallizing the cis,trans-muconate. The cis,trans-isomer can be further isomerized to the trans,trans-isomer. In one example, the method includes culturing recombinant cells that express 3-dehydroshikimate dehydratase, protocatechuate decarboxylase and catechol 1,2-dioxygenase in a medium comprising the renewable carbon source and under conditions in which the renewable carbon source is converted to 3-dehydroshikimate by enzymes in the common pathway of aromatic amino acid biosynthesis of the cell, and the 3-dehydroshikimate is biocatalytically converted to cis,cis-muconate.
    Type: Application
    Filed: January 10, 2011
    Publication date: January 31, 2013
    Applicant: Amyris, Inc.
    Inventors: Vu Bui, Man Kit Lau, Doug MacRae, Dirk Schweitzer
  • Publication number: 20100314243
    Abstract: The present invention relates to the isomerization of cis,cis and/or cis,trans muconic acid or esters thereof to trans,trans muconic acid or esters thereof and to the esterification of such muconic acids.
    Type: Application
    Filed: June 16, 2010
    Publication date: December 16, 2010
    Applicant: Draths Corporation
    Inventors: John W. Frost, Adeline Miermont, Dirk Schweitzer, Vu Bui
  • Publication number: 20030120110
    Abstract: Processes for producing citraconic anhydride and citraconic acid using porous materials with specific surface acidities and surface areas are described. The preferred catalyst is a porous gamma alumina. Itaconic acid is produced from citraconic acid. Itaconic acid is an intermediate to a variety of compounds including polymers.
    Type: Application
    Filed: August 23, 2002
    Publication date: June 26, 2003
    Applicant: Board of Trustees operating Michigan State University
    Inventors: Dennis J. Miller, Dushyant Shekhawat, Kirthivasan Nagarajan, James E. Jackson
  • Patent number: 6372942
    Abstract: The invention discloses pentenoic acid hydroxycarbonylation into adipic acid. More particularly, it concerns one pentenoic acid hydroxycarbonylation method involving reaction water and carbon monoxide, in the presence of a catalyst comprising at least rhodium and/or iridium and an iodinated or brominated catalytic promoter. In the method, the catalyst is derived at least in part from a previous pentenoic acid hydroxycarbonylation operation. The reaction is effected in the presence of an amount of branched carboxylic diacids having 6 carbon atoms not exceeding 200 grams per kilogram reaction mixture.
    Type: Grant
    Filed: March 17, 1999
    Date of Patent: April 16, 2002
    Assignee: Rhodia Fiber & Resin Intermediates
    Inventors: Jacques Brivet, Eric B. Henriet, Carl Patois, Robert Perron
  • Publication number: 20020022745
    Abstract: A process produces sorbic acid by hydrolyzing a polyester with an aqueous hydrochloric acid solution having a concentration of 15% by weight or less under the application of pressure or at a temperature of 100° C. or higher, which polyester is obtained by reaction between crotonaldehyde and ketene. In this process, the polyester may be hydrolyzed with a 3 to 10% by weight aqueous hydrochloric acid solution at a temperature of from 115° C. to 140° C. A reaction mixture after hydrolysis of the polyester may be subjected to solid-liquid separation and the resulting filtrate may be recycled and reused in the hydrolysis reaction of the polyester. This process can significantly reduce the amount of tar formed during decomposition of the polyester, can produce sorbic acid in a high yield, and can reduce the load on the treatment of waste filtrates formed during purification operation.
    Type: Application
    Filed: August 7, 2001
    Publication date: February 21, 2002
    Inventors: Mitsuhiro Kouno, Tadayuki Mitani, Noboru Kamei
  • Publication number: 20020002306
    Abstract: A method for isomerizing a maleate, or a maleate containing a 2-propenyloxy group in the molecule at a high selectivity is provided which employs an isomerizing catalyst containing a Group VIII element. This method produces a fumarate, or a fumarate containing a 1-propenyloxy group in a high yield, which is useful in the fields of resin source materials and plasticizer. This method gives high-purity fumarates containing no catalyst residue by use of a heterogeneous catalyst which is readily separable and non-corrosive.
    Type: Application
    Filed: February 14, 2001
    Publication date: January 3, 2002
    Inventors: Yasushi Kadowaki, Keisuke Ohta, Kazufumi Kai
  • Patent number: 6222069
    Abstract: The invention discloses a method for purifying adipic acid in water. More precisely it discloses an improvement in adipic acid crystallization or recrystallization in water, characterised in that the said crystallization or recrystallization is effected in presence of a strong proton acid and/or in the presence of carbon monoxide. This crystallization or recrystallization particularly enables the content of metal catalyst traces in the adipic acid to be reduced.
    Type: Grant
    Filed: March 17, 1999
    Date of Patent: April 24, 2001
    Assignee: Rhodia Fiber and Resin Intermediates
    Inventors: Eric B. Henriet, Philippe Leconte, Carl Patois, Robert Perron
  • Patent number: 6103935
    Abstract: The present invention relates to a process for the production of fumaric acid by the isomerization of maleic acid at high conversions which comprises heating maleic acid in the presence of phosphoric acid at a temperature sufficient to isomerize the maleic acid to fumaric acid.
    Type: Grant
    Filed: April 21, 1999
    Date of Patent: August 15, 2000
    Assignee: BP Amoco Corporation
    Inventor: Muin S. Haddad
  • Patent number: 5929255
    Abstract: The present invention provides a process for recovering fumaric acid formed as a by-product during the production of maleic anhydride so that both fumaric acid and maleic anhydride are obtained. The process of the present invention further eliminates the wasting of MAN that occurs when fumaric acid is incinerated and improves the production of maleic anhydride by eliminating a source of fouling caused by the fumaric acid which leads to down-time in the reaction process to clean out the fumaric acid.
    Type: Grant
    Filed: July 9, 1997
    Date of Patent: July 27, 1999
    Assignee: BP Amoco Corporation
    Inventor: John M. Forgac
  • Patent number: 5847204
    Abstract: An iridium-based solution is prepared by contacting components in a liquid phase containing (a) a carbonylated iridium compound, (b) hydriodic acid, a precursor of such an acid, or mixture thereof, and (c) a solvent; under a total pressure of between 1 and 10 bar at a temperature not greater than the boiling temperature of the solvent under conditions in which the components are brought into contact. The iridium-based solution can be used as a catalyst for carrying out carbonylation, hydroformylation or isomerization reactions.
    Type: Grant
    Filed: September 27, 1996
    Date of Patent: December 8, 1998
    Assignee: Acetex Chimie
    Inventor: Dominique Nobel
  • Patent number: 5414115
    Abstract: An improved process for the isomerization of saturated alkyl carboxylic acids is obtained by using aluminum iodide or aluminum bromide promoted rhodium or iridium catalysts.
    Type: Grant
    Filed: August 19, 1993
    Date of Patent: May 9, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Patrick M. Burke
  • Patent number: 5218144
    Abstract: A process for the preparation of adipic acid from pentenoic compounds by hydrocarboxylation using an iridium catalyst, an iodide promoter, water, carbon monoxide and a carboxylic acid solvent.
    Type: Grant
    Filed: September 15, 1992
    Date of Patent: June 8, 1993
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Erdem M. Atadan
  • Patent number: 5166421
    Abstract: A process for the manufacture of adipic acid by reacting 1,3-butadiene or an allylic butenol or the like with carbon monoxide and water using a rhodium catalyst and an HI or HBr promoter, removing adipic acid from the reaction mixture, and reacting at least part of the remaining portion of the reaction mixture to form additional adipic acid.
    Type: Grant
    Filed: March 18, 1991
    Date of Patent: November 24, 1992
    Assignee: E. I. du Pont De Nemours and Company
    Inventor: Harold S. Bruner, Jr.
  • Patent number: 4939298
    Abstract: Isomerization of branched saturated alkyl carboxylic acids to linear or isomeric branched alkyl carboxylic acids, or vice versa, by heating in the presence of a iodide or bromide promoted rhodium catalyst and carbon monoxide.
    Type: Grant
    Filed: August 10, 1989
    Date of Patent: July 3, 1990
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Patrick M. Burke
  • Patent number: 4918226
    Abstract: A process for converting formic acid esters or transesterification products thereof to carboxylic acids comprising contacting a formic acid ester of the formula (HCOO).sub.n --R where R is aliphatic, cycloaliphatic or aralkyl and n is 1 or 2 with a catalytically effective amount of a soluble iridium salt and an iodide promoter at a temperature of from about 100.degree. C. to about 300.degree. C. in the presence of an organic solvent containing at least one carboxylic acid.
    Type: Grant
    Filed: June 22, 1981
    Date of Patent: April 17, 1990
    Assignee: Exxon Research and Engineering Company
    Inventor: Roy L. Pruett
  • Patent number: 4448702
    Abstract: The freezing point of an aqueous system is lowered by adding to the system a freezing point lowering quantity of at least one and preferably two or more water soluble salts of dicarboxylic acids having at least three carbon atoms, specifically a dicarboxylic acid selected from the group which consists of adipic, glutaric, succinic and malonic acids, the salt being a sodium, potassium, ammonium or organoamine salt.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: May 15, 1984
    Assignee: Lang & Co., Chemisch-Technische Produkte Kommanditgesellschaft
    Inventor: Gertrude Kaes
  • Patent number: 4182806
    Abstract: Process for the manufacture of a salt of a poly-alpha-hydroxyacrylic acid, which salt contains monomeric units of the formula: ##STR1## in which R.sub.1 and R.sub.2 independently represent hydrogen or an alkyl group containing from 1 to 3 carbon atoms, and in which M represents the cationic radical resulting from the dissociation of a base, by reacting, with the base, in the presence of water, a solid polylactone derived from the corresponding poly-alpha-hydroxyacrylic acid, in which process the reaction is carried out in a liquid medium containing water and a diluent, the diluent being one which does not dissolve the polylactone and the salt produced and being present in an amount such that the polylactone and salt produced do not dissolve in the medium. In the process, an oxidizing agent is added to the liquid medium.
    Type: Grant
    Filed: April 18, 1978
    Date of Patent: January 8, 1980
    Assignee: Solvay & Cie.
    Inventors: Noel Vanlautem, Julien Mulders