Preparation By Isomerization Patents (Class 562/591)
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Patent number: 10913702Abstract: 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: GrantFiled: December 14, 2018Date of Patent: February 9, 2021Assignee: SK CHEMICALS CO.. LTD.Inventors: Jae Kyun Park, Jeong Ho Park, Hee-il Chae
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Patent number: 10337034Abstract: 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: GrantFiled: April 27, 2018Date of Patent: July 2, 2019Assignee: Alliance for Sustainable Energy, LLCInventors: Gregg Tyler Beckham, Christopher W. Johnson, Derek Richard Vardon, Mary Ann Franden
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Patent number: 8809583Abstract: 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: GrantFiled: January 10, 2011Date of Patent: August 19, 2014Assignee: Amyris, Inc.Inventors: Vu Bui, Man Kit Lau, Doug MacRae, Dirk Schweitzer
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Patent number: 8426639Abstract: 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: GrantFiled: June 16, 2010Date of Patent: April 23, 2013Assignee: Amyris, Inc.Inventors: John W. Frost, Adeline Miermont, Dirk Schweitzer, Vu Bui
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Publication number: 20130030215Abstract: 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: ApplicationFiled: January 10, 2011Publication date: January 31, 2013Applicant: Amyris, Inc.Inventors: Vu Bui, Man Kit Lau, Doug MacRae, Dirk Schweitzer
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Publication number: 20100314243Abstract: 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: ApplicationFiled: June 16, 2010Publication date: December 16, 2010Applicant: Draths CorporationInventors: John W. Frost, Adeline Miermont, Dirk Schweitzer, Vu Bui
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Publication number: 20030120110Abstract: 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: ApplicationFiled: August 23, 2002Publication date: June 26, 2003Applicant: Board of Trustees operating Michigan State UniversityInventors: Dennis J. Miller, Dushyant Shekhawat, Kirthivasan Nagarajan, James E. Jackson
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Patent number: 6372942Abstract: 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: GrantFiled: March 17, 1999Date of Patent: April 16, 2002Assignee: Rhodia Fiber & Resin IntermediatesInventors: Jacques Brivet, Eric B. Henriet, Carl Patois, Robert Perron
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Publication number: 20020022745Abstract: 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: ApplicationFiled: August 7, 2001Publication date: February 21, 2002Inventors: Mitsuhiro Kouno, Tadayuki Mitani, Noboru Kamei
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Publication number: 20020002306Abstract: 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: ApplicationFiled: February 14, 2001Publication date: January 3, 2002Inventors: Yasushi Kadowaki, Keisuke Ohta, Kazufumi Kai
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Patent number: 6222069Abstract: 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: GrantFiled: March 17, 1999Date of Patent: April 24, 2001Assignee: Rhodia Fiber and Resin IntermediatesInventors: Eric B. Henriet, Philippe Leconte, Carl Patois, Robert Perron
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Patent number: 6103935Abstract: 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: GrantFiled: April 21, 1999Date of Patent: August 15, 2000Assignee: BP Amoco CorporationInventor: Muin S. Haddad
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Patent number: 5929255Abstract: 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: GrantFiled: July 9, 1997Date of Patent: July 27, 1999Assignee: BP Amoco CorporationInventor: John M. Forgac
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Patent number: 5847204Abstract: 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: GrantFiled: September 27, 1996Date of Patent: December 8, 1998Assignee: Acetex ChimieInventor: Dominique Nobel
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Patent number: 5414115Abstract: 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: GrantFiled: August 19, 1993Date of Patent: May 9, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventor: Patrick M. Burke
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Patent number: 5218144Abstract: 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: GrantFiled: September 15, 1992Date of Patent: June 8, 1993Assignee: E. I. du Pont de Nemours and CompanyInventor: Erdem M. Atadan
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Patent number: 5166421Abstract: 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: GrantFiled: March 18, 1991Date of Patent: November 24, 1992Assignee: E. I. du Pont De Nemours and CompanyInventor: Harold S. Bruner, Jr.
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Patent number: 4939298Abstract: 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: GrantFiled: August 10, 1989Date of Patent: July 3, 1990Assignee: E. I. du Pont de Nemours and CompanyInventor: Patrick M. Burke
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Patent number: 4918226Abstract: 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: GrantFiled: June 22, 1981Date of Patent: April 17, 1990Assignee: Exxon Research and Engineering CompanyInventor: Roy L. Pruett
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Patent number: 4448702Abstract: 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: GrantFiled: September 30, 1982Date of Patent: May 15, 1984Assignee: Lang & Co., Chemisch-Technische Produkte KommanditgesellschaftInventor: Gertrude Kaes
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Patent number: 4182806Abstract: 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: GrantFiled: April 18, 1978Date of Patent: January 8, 1980Assignee: Solvay & Cie.Inventors: Noel Vanlautem, Julien Mulders