Plural -c(=x)x- Groups Bonded Directly To The Hetero Ring Patents (Class 549/485)
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Patent number: 9617234Abstract: A process to produce furandicarboxylic acid (FDCA). The process includes the steps of reacting a C6 sugar-containing reactant in a reaction solution comprising a first organic solvent selected from the group consisting of beta-, gamma-, and delta-lactones, hydrofurans, hydropyrans, and combinations thereof, in the presence of an acid catalyst for a time and under conditions wherein at least a portion of the C6 sugar present in the reactant is converted to 5-(hydroxymethyl)furfural (HMF); oxidizing the HMF into FDCA with or without separating the HMF from the reaction solution; and extracting the FDCA by adding an aprotic organic solvent having a dipole moment of about 1.0 D or less to the reaction solution.Type: GrantFiled: December 18, 2015Date of Patent: April 11, 2017Assignee: Wisconsin Alumni Research FoundationInventors: James A. Dumesic, Ali Hussain Motagamwala
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Patent number: 9586923Abstract: A process is provided for carrying out an oxidation on a sprayable feed including a furanic substrate to be oxidized and a catalytically effective combination of cobalt, manganese, and bromide components for catalyzing the oxidation of the furanic substrate, which process comprises spraying the feed into a reactor vessel as a mist, supplying an oxidant, reacting the furanic substrate and the oxidant, and managing the exothermic temperature rise due to the reaction through a selection and control of the operating pressure within the reactor vessel. A crude dehydration product from the dehydration of fructose, glucose or both, including 5-hydroxymethylfurfural, can be directly oxidized by the process to produce 2,5-furandicarboxylic acid in surprisingly increased yields.Type: GrantFiled: August 28, 2012Date of Patent: March 7, 2017Assignees: University of Kansas, Archer Daniels Midland CompanyInventors: Bala Subramaniam, Xiaobin Zuo, Daryle H. Busch, Padmesh Venkitasubramanian
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Patent number: 9573120Abstract: Disclosed is an oxidation process to produce a crude carboxylic acid product carboxylic acid product. The process comprises oxidizing a feed stream comprising at least one oxidizable compound to generate a crude carboxylic acid slurry comprising furan-2,5-dicarboxylic acid (FDCA) and compositions thereof. Also disclosed is a process to produce a dry purified carboxylic acid product by utilizing various purification methods on the crude carboxylic acid.Type: GrantFiled: June 27, 2014Date of Patent: February 21, 2017Assignee: EASTMAN CHEMICAL COMPANYInventors: Kenny Parker, Mesfin Janka, Ashfaq Shaikh, Lee Partin
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Patent number: 9499506Abstract: A method for preparing 2,5-furandicarboxylic acid (FDCA) by oxidizing 5-hydroxymethylfurfural (HMF) in water in the presence of a weak base and a supported catalyst comprising platinum and bismuth, in which the Bi/Pt molar ratio in the catalyst is between 0.1 and 0.3, and preferably between 0.15 and 0.3.Type: GrantFiled: February 11, 2014Date of Patent: November 22, 2016Assignees: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (C.N.R.S), UNIVERSITE CLAUDE BERNARD LYON 1Inventors: Michele Besson, Nadine Essayem, Hicham Ait Rass
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Patent number: 9458122Abstract: A process to produce a dry purified furan-2,5-dicarboxylic acid (FDCA) is described. After oxidation of 5-(hydroxymethyl)furfural (5-HMF), a crude FDCA stream is produced that is fed to a crystallization zone followed by a solid-liquid displacement zone to form a low impurity slurry stream. The solids in the low impurity slurry stream are dissolved in a dissolution zone to produce a hydrogenation feed that is hydrogenated in a hydrogenation reactor to generate a hydrogenated FDCA composition. The hydrogenated FDCA composition is routed to a crystallization zone to form a crystallized produce stream that is separated from liquid in a solid-liquid separation zone to generate a purified wet cake stream containing FDCA that can be dried in a drying zone to generate a dry purified FDCA product stream.Type: GrantFiled: September 1, 2015Date of Patent: October 4, 2016Assignee: Eastman Chemical CompanyInventors: Ashfaq Shahanawaz Shaikh, Kenny Randolph Parker, Mesfin Ejerssa Janka, Lee Reynolds Partin
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Patent number: 9428480Abstract: Disclosed is an oxidation process to produce a crude carboxylic acid product carboxylic acid product. The process comprises oxidizing a feed stream comprising at least one oxidizable compound to generate a crude carboxylic acid slurry comprising furan-2,5-dicarboxylic acid (FDCA) and compositions thereof. Also disclosed is a process to produce a dry purified carboxylic acid product by utilizing various purification methods on the crude carboxylic acid.Type: GrantFiled: September 24, 2014Date of Patent: August 30, 2016Assignee: Eastman Chemical CompanyInventors: Mesfin Janka, David Lange, Michael Morrow, Bradford Bowers, Kenny Parker, Ashfaq Shaikh, Lee Partin, Jason Jenkins, Paula Moody, Thomas Shanks, Charles Sumner
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Patent number: 9388152Abstract: A method for synthesizing 2,5-furandicarboxylic acid (FDCA) from furan-2,5-dialdehyde (DFF). The method is industrially applicable due to the simplicity and availability of the reagents used, and due to the experimental conditions on which the method is based: the method requires low temperatures and enables a reaction under atmospheric pressure, the reaction times being relatively short. Furthermore, the method does not lead to the formation of salts that need to be treated downstream from the method, and the catalytic ratio relative to the initial product is particularly low.Type: GrantFiled: September 26, 2013Date of Patent: July 12, 2016Assignee: ROQUETTE FRERESInventors: Mathias Ibert, Flora Chambon, Laurent Dambrine
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Patent number: 9376414Abstract: Disclosed is a method of making 5-formyl-2-furoic acid and furan-2,5-dicarboxylic acid. The method involves the use of 5-keto-aldonic acids as intermediates, as these can be subjected to ring formation by a cyclodehydration reaction under mild conditions. The 5-formyl-2-furoic acid or carboxylic derivative thereof is subjected to oxidation so as to form furan-2,5-dicarboxylic acid. The 5-keto-aldonic acid intermediates can be obtained by isomerization of uronic acids which can be obtained from sugar beet pulp, chicory pulp, fruit peals including orange peels, or non-terrestrial sources like seaweeds. A preferred source is sugar beet pulp.Type: GrantFiled: May 8, 2014Date of Patent: June 28, 2016Assignee: Stichting Dienst Landbouwkundig OnderzoekInventors: Jacobus van Haveren, Daniël Stephan van Es, Frits van der Klis, Henricus Wilhelmus Carolina Raaijmakers
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Patent number: 9266850Abstract: Disclosed is a process to produce a dry purified carboxylic acid product comprising furan-2,5-dicarboxylic acid (FDCA). The process comprises oxidizing at least one oxidizable compound selected from the following group: 5-(hydroxymethyl)furfural (5-HMF), 5-HMF esters (5-R(CO)OCH2-furfural where R is alkyl, cycloalkyl, or aryl), 5-HMF ethers (5-R?OCH2-furfural where R? is alkyl, cycloalkyl, or aryl), 5-alkyl furfurals (5-R?-furfural where R? is alkyl, cycloalkyl, or aryl), mixed feedstocks of 5-HMF and 5-HMF esters, mixed feedstocks of 5-HMF and 5-HMF ethers, and mixed feedstocks of 5-HMF and 5-alkyl furfurals to generate a crude carboxylic acid slurry comprising FDCA.Type: GrantFiled: April 21, 2015Date of Patent: February 23, 2016Assignee: Eastman Chemical CompanyInventors: Mesfin Ejerssa Janka, Kenny Randolph Parker, Paula Moody, Ashfaq Shahanawaz Shaikh, Lee Reynolds Partin, Bradford Russell Bowers, Michael Charles Morrow
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Patent number: 9249118Abstract: A process for purifying a crude furan 2,5-dicarboxylic acid composition (cFDCA) by hydrogenation of a FDCA composition dissolved in a hydrogenation solvent such as water, and hydrogenating under mild conditions, such as at a temperature within a range of 130° C. to 225° C. by contacting the solvated FDCA composition with hydrogen in the presence of a hydrogenation catalyst under a hydrogen partial pressure within a range of 10 psi to 900 psi. A product FDCA composition is produced having a low amount of tetrahydrofuran dicarboxylic acid, a low b*, and a low amount of 5-formyl furan-2-carboxylic acid (FFCA).Type: GrantFiled: June 19, 2014Date of Patent: February 2, 2016Assignee: Eastman Chemical CompanyInventors: Mesfin Ejerssa Janka, Charles Edwan Sumner, Jr., Shane Kipley Kirk, Ashfaq Shahanawaz Shaikh, Kenny Randolph Parker
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Patent number: 9206149Abstract: Disclosed is a process to produce a dry purified carboxylic acid product comprising furan-2,5-dicarboxylic acid (FDCA). The process comprises oxidizing at least one oxidizable compound selected from the following group: 5-(hydroxymethyl)furfural (5-HMF), 5-HMF esters (5-R(CO)OCH2-furfural where R=alkyl, cycloalkyl and aryl), 5-HMF ethers (5-R?OCH2-furfural, where R?=alkyl, cycloalkyl and aryl), 5-alkyl furfurals (5-R?-furfural, where R?=alkyl, cycloalkyl and aryl), mixed feed-stocks of 5-HMF and 5-HMF esters and mixed feed-stocks of 5-HMF and 5-HMF ethers and mixed feed-stocks of 5-HMF and 5-alkyl furfurals to generate a crude carboxylic acid slurry comprising FDCA, cooling a crude carboxylic acid slurry in cooling zone to form a cooled slurry stream. The cooled slurry stream is routed to a solid-liquid separation zone to generate a crude wet cake stream comprising FDCA that is dried in a drying zone to generate a dry carboxylic acid product stream comprising crude FDCA (cFDCA).Type: GrantFiled: May 20, 2014Date of Patent: December 8, 2015Assignee: Eastman Chemical CompanyInventors: Mesfin Ejerssa Janka, Kenny Randolph Parker, Ashfaq Shahanawaz Shaikh, Lee Reynolds Partin
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Patent number: 9199958Abstract: Disclosed is an oxidation process to produce a crude carboxylic acid product carboxylic acid product. The process comprises oxidizing a feed stream comprising at least one oxidizable compound to generate a crude carboxylic acid slurry comprising furan-2,5-dicarboxylic acid (FDCA) and compositions thereof. Also disclosed is a process to produce a dry purified carboxylic acid product by utilizing various purification methods on the crude carboxylic acid.Type: GrantFiled: October 28, 2014Date of Patent: December 1, 2015Assignee: Eastman Chemical CompanyInventors: Mesfin Ejerssa Janka, David Lange, Michael C. Morrow, Bradford Russell Bowers, Kenny Randolph Parker, Ashfaq Shaikh, Lee Reynolds Partin, Charles Sumner
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Patent number: 9199957Abstract: A two-step 2.5 FDCA integrated production process is described, comprising a first step for generating 5-HMF from streams comprising an aqueous carbohydrate solution wherein sub-critical water works as a catalyst by dehydrating the carbohydrates and generating 5-HMF, and a second step wherein 5-HMF is oxidized into 2.5 FDCA.Type: GrantFiled: October 17, 2013Date of Patent: December 1, 2015Assignee: PETROLEO BRASILEIRO S.A.-PETROBRASInventors: Bernardo Galvao Siqueira, Raphael Bezerra De Menezes, Carlos Rene Klotz Rabello, Marlito Gomes, Jr.
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Patent number: 9169229Abstract: A process to produce a purified dimethyl-furan-2,5-dicarboxylate (DMFD) by feeding furan dicarboxylic acid and methanol to an esterification zone to generate a crude diester composition, and purifying the crude diester composition with a physical separation process followed by crystallization, solid liquid separation, and optionally drying to produce a purified DMFD composition. A portion of the stream generated by solid liquid separation can be dissolved and subjected to crystallization and solid liquid separation repeatedly. The process is useful to produce a purified DMFD composition having a low b*, at least 98 wt. % DAFD solids, and a low concentration of 5-(methoxycarbonyl)furan-2-carboxylic acid (MCFC) and methyl 5-formylfuran-2-carboxylate (MFFC).Type: GrantFiled: November 7, 2014Date of Patent: October 27, 2015Assignee: Eastman Chemical CompanyInventors: Kenny Randolph Parker, Ashfaq Shaikh, Lee Reynolds Parton, Mesfin Ejerssa Janka
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Patent number: 9169228Abstract: The invention relates to mixtures of isodecyl furan-2,5-dicarboxylate of formula I, methods for producing said mixtures of isodecyl furan-2,5-dicarboxylate of formula I, compositions containing mixtures of isodecyl furan-2,5-dicarboxylate of formula I, uses of the mixtures of isodecyl furan-2,5-dicarboxylate of formula I as plasticizers, and uses of the aforementioned compositions containing isodecyl furan-2,5-dicarboxylate of formula I.Type: GrantFiled: July 30, 2010Date of Patent: October 27, 2015Assignee: EVONIK DEGUSSA GmbHInventors: Michael Grass, Hinnerk Gordon Becker
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Patent number: 9145379Abstract: The invention relates to mixtures of isononyl furan-2,5-dicarboxylate of formula (I), methods for producing said mixtures of isononyl furan-2,5-dicarboxylate of formula (I), compositions containing mixtures of isononyl furan-2,5-dicarboxylate of formula (I), uses of the mixtures of isononyl furan-2,5-dicarboxylate of formula (I) as plasticizers, and uses of the aforementioned compositions containing isononyl furan-2,5-dicarboxylate of formula (I).Type: GrantFiled: August 17, 2010Date of Patent: September 29, 2015Assignee: Evonik Degussa GmbHInventors: Michael Graβ, Hinnerk Gordon Becker
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Patent number: 9061986Abstract: A method for preparing a carboxylic acid, includes the steps of: providing magnesium carboxylate, wherein the carboxylic acid corresponding with the carboxylate is selected from the group made of 2,5-furandicarboxylic acid, fumaric acid, adipic acid, itaconic acid, citric acid, glutaric acid, maleic acid, malonic acid, oxalic acid and fatty acids having more than 10 carbon atoms; acidifying the magnesium carboxylate with hydrogen chloride (HCl), thereby obtaining a solution including carboxylic acid and magnesium chloride (MgCl2); optionally a concentration step, wherein the solution including carboxylic acid and MgCl2 is concentrated; and precipitating the carboxylic acid from the solution including the carboxylic acid and MgCl2, thereby obtaining a carboxylic acid precipitate and a MgCl2 solution.Type: GrantFiled: August 16, 2012Date of Patent: June 23, 2015Assignee: PURAC BIOCHEM B.V.Inventors: André Banier De Haan, Jan Van Breugel, Paulus Loduvicus Johannes Van Der Weide, Peter Paul Jansen, José María Vidal Lancis, Agustín Cerdà Baró
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Patent number: 9029581Abstract: A process for the manufacture of dialkyl furan-2,5-dicarboxylate (DAFD) vapor composition by feeding furan-2,5-dicarboxylic acid (“FDCA”) to an esterification reactor and in the presence of an alcohol compound such as methanol, conducting an esterification reaction to form an esterification vapor containing DAFD, unreacted alcohol compound, 5-(alkoxycarbonyl)furan-2-carboxylic acid (ACFC), and water, and continuously passing the esterification vapor through an ACFC condensing zone, that can be integral with the esterification reactor, in which at least a portion of the ACFC in the esterification vapor is converted to a liquid phase condensate, and continuously discharging the esterification vapor from the ACFC condensing zone as a DAFD vapor. There is also a DAFD vapor composition containing DAFD, water, unreacted alcohol, and by-products.Type: GrantFiled: September 19, 2014Date of Patent: May 12, 2015Assignee: Eastman Chemical CompanyInventors: Lee Reynolds Partin, Ashfaq Shaikh, Mesfin Ejerssa Janka, Kenny Randolph Parker
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Patent number: 9029579Abstract: The present invention relates to a method of making low colored bis(2-ethylhexyl) furan-2,5-dicarboxylate (BEHFD) plasticizer via mild hydrogenation of highly colored BEHFD.Type: GrantFiled: November 8, 2012Date of Patent: May 12, 2015Assignee: Eastman Chemical CompanyInventors: Mesfin Ejerssa Janka, John Dayton Baker, Jr., Stephanie Nicole Rollins
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Patent number: 9029580Abstract: Disclosed is a process to produce a dry purified carboxylic acid product comprising furan-2,5-dicarboxylic acid (FDCA). The process comprises oxidizing at least one oxidizable compound selected from the following group: 5-(hydroxymethyl)furfural (5-HMF), 5-HMF esters (5-R(CO)OCH2-furfural were R alkyl, cycloalkyl and aryl), 5-HMF ethers (5-R?OCH2-furfural, where R?=alkyl, cycloalkyl and aryl), 5-alkyl furfurals (5-R?-furfural, where R?=alkyl, cycloalkyl and aryl), mixed feed-stocks of 5-HMF and 5-HMF esters and mixed feed-stocks of 5-HMF and 5-HMF ethers and mixed feed-stocks of 5-HMF and 5-alkyl furfurals to generate a crude carboxylic acid slurry comprising FDCA.Type: GrantFiled: February 4, 2013Date of Patent: May 12, 2015Assignee: Eastman Chemical CompanyInventors: Mesfin Ejerssa Janka, Kenny Randolph Parker, Paula Moody, Ashfaq Shahanawaz Shaikh, Lee Reynolds Partin, Bradford Russell Bowers, Michael Charles Morrow
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Publication number: 20150119588Abstract: The present invention refers to a process for production of a mixture including 2,4-furandicarboxylic acid (2,4-FDCA) and 2,5 furandicarboxylic acid (2,5-FDCA) through the disproportionation route, using as base compounds oxidation products of furfural. This invention also relates to a process for production of 2,4-FDCA as a result of a disproportionation route and the use of 2,4-FDCA as a monomer or comonomer to synthesize esters or any compounds which can generate macromolecules, such as polyesters.Type: ApplicationFiled: December 29, 2011Publication date: April 30, 2015Applicants: BRASKEM S.A., STICHTING DIENST LANDBOUWKUNDIG ONDERZOEKInventors: Jacco van Haveren, Shanmugam Thiyagarajan, Augusto Teruo Morita
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Patent number: 9006470Abstract: The present invention relates to a method of synthesizing a low colored furan-2,5-dicarboxylate derivative plasticizer by utilizing purified FDCA (pFDCA), which has very low level 5-formyl furan-2-carboxyic acid (FFCA) and very low level colored bodies, and an alcohol.Type: GrantFiled: November 8, 2012Date of Patent: April 14, 2015Assignee: Eastman Chemical CompanyInventors: Mesfin Ejerssa Janka, John Dayton Baker, Jr., Stephanie Nicole Rollins
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Publication number: 20150065735Abstract: A process to produce a purified dimethyl-furan-2,5-dicarboxylate (DMFD) by feeding furan dicarboxylic acid and methanol to an esterification zone to generate a crude diester composition, and purifying the crude diester composition with a physical separation process followed by crystallization, solid liquid separation, and optionally drying to produce a purified DMFD composition. A portion of the stream generated by solid liquid separation can be dissolved and subjected to crystallization and solid liquid separation repeatedly. The process is useful to produce a purified DMFD composition having a low b*, at least 98 wt. % DAFD solids, and a low concentration of 5-(methoxycarbonyl)furan-2-carboxylic acid (MCFC) and methyl 5-formylfuran-2-carboxylate (MFFC).Type: ApplicationFiled: November 7, 2014Publication date: March 5, 2015Inventors: Kenny Randolph Parker, Ashfaq Shaikh, Lee Raynolds Parton, Mesfin Ejerssa Janka
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Patent number: 8969404Abstract: A process for purifying a crude furan 2,5-dicarboxylic acid composition (cFDCA) by hydrogenation of a FDCA composition dissolved in a hydrogenation solvent such as water, and hydrogenating under mild conditions, such as at a temperature within a range of 130° C. to 225° C. by contacting the solvated FDCA composition with hydrogen in the presence of a hydrogenation catalyst under a hydrogen partial pressure within a range of 10 psi to 900 psi. A product FDCA composition is produced having a low amount of tetrahydrofuran dicarboxylic acid, a low b*, and a low amount of 5-formyl furan-2-carboxylic acid (FFCA).Type: GrantFiled: February 4, 2013Date of Patent: March 3, 2015Assignee: Eastman Chemical CompanyInventors: Mesfin Ejerssa Janka, Charles Edwan Sumner, Jr., Shane Kipley Kirk, Ashfaq Shahanawaz Shaikh, Kenny Randolph Parker
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Publication number: 20150051412Abstract: Disclosed is an oxidation process to produce a crude carboxylic acid product carboxylic acid product. The process comprises oxidizing a feed stream comprising at least one oxidizable compound to generate a crude carboxylic acid slurry comprising furan-2,5-dicarboxylic acid (FDCA) and compositions thereof. Also disclosed is a process to produce a dry purified carboxylic acid product by utilizing various purification methods on the crude carboxylic acid.Type: ApplicationFiled: October 28, 2014Publication date: February 19, 2015Applicant: Eastman Chemical CompanyInventors: Mesfin Ejerssa Janka, David Lange, Michael C. Morrow, Bradford Russell Bowers, Kenny Randolph Parker, Ashfaq Shaikh, Lee Reynolds Partin, Charles Sumner
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Publication number: 20150031903Abstract: A process for the manufacture of dialkyl furan-2,5-dicarboxylate (DAFD) vapor composition by feeding furan-2,5-dicarboxylic acid (“FDCA”) to an esterification reactor and in the presence of an alcohol compound such as methanol, conducting an esterification reaction to form an esterification vapor containing DAFD, unreacted alcohol compound, 5-(alkoxycarbonyl)furan-2-carboxylic acid (ACFC), and water, and continuously passing the esterification vapor through an ACFC condensing zone, that can be integral with the esterification reactor, in which at least a portion of the ACFC in the esterification vapor is converted to a liquid phase condensate, and continuously discharging the esterification vapor from the ACFC condensing zone as a DAFD vapor. There is also a DAFD vapor composition containing DAFD, water, unreacted alcohol, and by-products.Type: ApplicationFiled: September 19, 2014Publication date: January 29, 2015Inventors: Lee Reynolds Partin, Ashfaq Shaikh, Mesfin Ejerssa Janka, Kenny Randolph Parker
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Publication number: 20150011783Abstract: Disclosed is an oxidation process to produce a crude carboxylic acid product carboxylic acid product. The process comprises oxidizing a feed stream comprising at least one oxidizable compound to generate a crude carboxylic acid slurry comprising furan-2,5-dicarboxylic acid (FDCA) and compositions thereof. Also disclosed is a process to produce a dry purified carboxylic acid product by utilizing various purification methods on the crude carboxylic acid.Type: ApplicationFiled: September 24, 2014Publication date: January 8, 2015Applicant: EASTMAN CHEMICAL COMPANYInventors: Mesfin Janka, David Lange, Michael Morrow, Bradford Bowers, Kenny Parker, Ashfaq Shaikh, Lee Partin, Jason Jenkins, Paula Moody, Thomas Shanks, Charles Sumner
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Patent number: 8916720Abstract: Disclosed is a process for producing a dry, purified carboxylic acid product comprising furan-2,5-dicarboxylic acid (FDCA). Also disclosed is a method for treating an oxidation off-gas stream from such a process. The method features solvent as well as energy recovery from the off-gas stream.Type: GrantFiled: March 13, 2013Date of Patent: December 23, 2014Assignee: Eastman Chemical CompanyInventors: Ashfaq Shahanawaz Shaikh, Kenny Randolph Parker, Mesfin Ejerssa Janka, Lee Reynolds Partin
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Patent number: 8916719Abstract: Disclosed is a process for producing a dry, purified carboxylic acid product comprising furan-2,5-dicarboxylic acid (FDCA). Also disclosed is a method for treating an oxidation off-gas stream from such a process. The method features solvent as well as energy recovery from the off-gas stream.Type: GrantFiled: March 13, 2013Date of Patent: December 23, 2014Assignee: Eastman Chemical CompanyInventors: Ashfaq Shahanawaz Shaikh, Kenny Randolph Parker, Mesfin Ejerssa Janka, Lee Reynolds Partin
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Method for producing purified dialkyl-furan-2,5-dicarboxylate separation and solid liquid separation
Patent number: 8912349Abstract: A process to produce a purified dimethyl-furan-2,5-dicarboxylate (DMFD) by feeding furan dicarboxylic acid and methanol to an esterification zone to generate a crude diester composition, and purifying the crude diester composition with a physical separation process followed by crystallization, solid liquid separation, and optionally drying to produce a purified DMFD composition. A portion of the stream generated by solid liquid separation can be dissolved and subjected to crystallization and solid liquid separation repeatedly. The process is useful to produce a purified DMFD composition having a low b*, at least 98 wt. % DAFD solids, and a low concentration of 5-(methoxycarbonyl)furan-2-carboxylic acid (MCFC) and methyl 5-formylfuran-2-carboxylate (MFFC).Type: GrantFiled: June 22, 2012Date of Patent: December 16, 2014Assignee: Eastman Chemical CompanyInventors: Ashfaq Shaikh, Kenny Randolph Parker, Lee Reynolds Partin, Mesfin Ejerssa Janka -
Publication number: 20140364633Abstract: A process for purifying a crude furan 2,5-dicarboxylic acid composition (cFDCA) by hydrogenation of a FDCA composition dissolved in a hydrogenation solvent such as water, and hydrogenating under mild conditions, such as at a temperature within a range of 130° C. to 225° C. by contacting the solvated FDCA composition with hydrogen in the presence of a hydrogenation catalyst under a hydrogen partial pressure within a range of 10 psi to 900 psi. A product FDCA composition is produced having a low amount of tetrahydrofuran dicarboxylic acid, a low b*, and a low amount of 5-formyl furan-2-carboxylic acid (FFCA).Type: ApplicationFiled: June 19, 2014Publication date: December 11, 2014Applicant: EASTMAN CHEMICAL COMPANYInventors: Mesfin Ejerssa Janka, Charles Edwan Sumner, JR., Shane Kipley Kirk, Ashfaq Shahanawaz Shaikh, Kenny Randolph Parker
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Publication number: 20140364632Abstract: The invention provides a method for preparing a carboxylic acid, which method includes the steps of providing magnesium carboxylate, wherein the carboxylic acid corresponding with the carboxylate has a solubility in water at 20° C. of 80 g/100 g water or less; acidifying the magnesium carboxylate with HCl, thereby obtaining a solution comprising carboxylic acid and magnesium chloride (MgCl2); optionally a concentration step, wherein the solution comprising carboxylic acid and MgCl2 is concentrated; precipitating the carboxylic acid from the solution comprising the carboxylic acid and MgCl2, thereby obtaining a carboxylic acid precipitate and a MgCl2 solution.Type: ApplicationFiled: August 16, 2012Publication date: December 11, 2014Applicant: PURAC BIOCHEM B.V.Inventors: André Banier De Haan, Jan Van Breugel, Paulus Loduvicus Johannes Van Der Weide, Peter Paul Jansen, José María Vidal Lancis, Agustín Cerdà Baró
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Publication number: 20140357877Abstract: A method for preparing a carboxylic acid, includes the steps of: providing magnesium carboxylate, wherein the carboxylic acid corresponding with the carboxylate is selected from the group made of 2,5-furandicarboxylic acid, fumaric acid, adipic acid, itaconic acid, citric acid, glutaric acid, maleic acid, malonic acid, oxalic acid and fatty acids having more than 10 carbon atoms; acidifying the magnesium carboxylate with hydrogen chloride (HCl), thereby obtaining a solution including carboxylic acid and magnesium chloride (MgCl2); optionally a concentration step, wherein the solution including carboxylic acid and MgCl2 is concentrated; and precipitating the carboxylic acid from the solution including the carboxylic acid and MgCl2, thereby obtaining a carboxylic acid precipitate and a MgCl2 solution.Type: ApplicationFiled: August 16, 2012Publication date: December 4, 2014Applicant: PURAC BIOCHEM B.V.Inventors: André Banier De Haan, Jan Van Breugel, Paulus Loduvicus Johannes Van Der Weide, Peter Paul Jansen, José María Vidal Lancis, Agustín Cerdà Baró
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Publication number: 20140343305Abstract: A process is provided for carrying out an oxidation on a feed including levulinic acid and/or a levulinic acid oxidation precursor to succinic acid, one or more furanic oxidation precursors of 2,5-furandicarboxylic acid and a catalytically effective combination of cobalt, manganese, and bromide components for catalyzing the oxidation of the levulinic acid component and of the one or more furanic oxidation precursors to produce both succinic acid and 2,5-furandicarboxylic acid products, which process comprises supplying the feed to a reactor vessel, supplying an oxidant, reacting the levulinic acid component and the one or more furanic oxidation precursors with the oxidant to produce both succinic acid and 2,5-furandicarboxylic acid (FDCA) and then recovering the succinic acid and FDCA products. A crude dehydration product from the dehydration of fructose, glucose or both, including 5-hydroxymethylfurfural, can be directly oxidized by the process to produce 2,5-furandicarboxylic acid and succinic acid.Type: ApplicationFiled: August 28, 2012Publication date: November 20, 2014Applicant: The University of KansasInventors: Bala Subramaniam, Xiaobin Zuo, Daryle H. Busch, Padmesh Venkitasubramaniam
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Patent number: 8865921Abstract: A method for the preparation of 2,5-furan dicarboxylic acid includes the step of contacting a feed comprising a compound selected from the group consisting of 5-hydroxymethylfurfural (“HMF”), an ester of 5-hydroxymethyl-furfural, 5-methylfurfural, 5-(chloromethyl)furfural, 5-methylfuroic acid, 5-(chloromethyl)furoic acid, 2,5-dimethylfuran and a mixture of two or more of these compounds with an oxidant in the presence of an oxidation catalyst at a temperature higher than 140° C.Type: GrantFiled: October 6, 2010Date of Patent: October 21, 2014Assignee: Furanix Technologies B.V.Inventors: Cesar Muñoz De Diego, Matheus Adrianus Dam, Gerardus Johannes Maria Gruter
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Patent number: 8859788Abstract: A process for the manufacture of dialkyl furan-2,5-dicarboxylate (DAFD) vapor composition by feeding furan-2,5-dicarboxylic acid (“FDCA”) to an esterification reactor and in the presence of an alcohol compound such as methanol, conducting an esterification reaction to form an esterification vapor containing DAFD, unreacted alcohol compound, 5-(alkoxycarbonyl)furan-2-carboxylic acid (ACFC), and water, and continuously passing the esterification vapor through an ACFC condensing zone, that can be integral with the esterification reactor, in which at least a portion of the ACFC in the esterification vapor is converted to a liquid phase condensate, and continuously discharging the esterification vapor from the ACFC condensing zone as a DAFD vapor. There is also a DAFD vapor composition containing DAFD, water, unreacted alcohol, and by-products.Type: GrantFiled: June 22, 2012Date of Patent: October 14, 2014Assignee: Eastman Chemical CompanyInventors: Lee Reynolds Partin, Ashfaq Shaikh, Mesfin Ejerssa Janka, Kenny Randolph Parker
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Publication number: 20140295508Abstract: Provided are methods of producing 2,5-furandicarboxylic acid (FDCA) from renewable sources such as seaweed, alginate, oligoalginate, pectin, oligopectin, polygalacturonate, galacturonate, and/or oligogalacturonate. The sugars in the renewable sources can be converted into one or more intermediates such as 4-deoxy-L-erythro-5-hexoseulose uronate (DEHU), 4-deoxy-L-threo-5-hexosulose uronate (DTHU), 5-hydroxymethyl furfural (HMF), 2,5-dihydroxymethyl furan (DHMF), and 5-formyl-2-furancarboxylic acid (FFA), which can be converted into FDCA by dehydration and cyclization to produce 5-formyl-2-furancarboxylic acid (FFA), followed by oxidation to produce FDCA. DEHU or DTHU may also be converted into FDCA by oxidation to produce 2,3-dihydroxy-5-oxohexanedioic acid (DOHA), which then undergoes dehydration and cyclization to produce FDCA.Type: ApplicationFiled: March 28, 2014Publication date: October 2, 2014Inventors: Yasuo Yoshikuni, Susan R. Cooper, Adam J. Wargacki, Leo E. Manzer, James F. White, Lou Kapicak, Dennis J. Miller, Lars Peereboom
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Patent number: 8846960Abstract: Disclosed is an oxidation process to produce a crude carboxylic acid product carboxylic acid product. The process comprises oxidizing a feed stream comprising at least one oxidizable compound to generate a crude carboxylic acid slurry comprising furan-2,5-dicarboxylic acid (FDCA) and compositions thereof. Also disclosed is a process to produce a dry purified carboxylic acid product by utilizing various purification methods on the crude carboxylic acid.Type: GrantFiled: September 9, 2011Date of Patent: September 30, 2014Assignee: Eastman Chemical CompanyInventors: Mesfin Ejerssa Janka, David Milton Lange, Michael C. Morrow, Bradford Russell Bowers, Kenny Randolph Parker, Ashfaq Shaikh, Lee Reynolds Partin, Charles Edwan Sumner, Jr.
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Publication number: 20140256964Abstract: Disclosed is a process to produce a dry purified carboxylic acid product comprising furan-2,5-dicarboxylic acid (FDCA). The process comprises oxidizing at least one oxidizable compound selected from the following group: 5-(hydroxymethyl)furfural (5-HMF), 5-HMF esters (5-R(CO)OCH2-furfural where R=alkyl, cycloalkyl and aryl), 5-HMF ethers (5-R?OCH2-furfural, where R?=alkyl, cycloalkyl and aryl), 5-alkyl furfurals (5-R?-furfural, where R?=alkyl, cycloalkyl and aryl), mixed feed-stocks of 5-HMF and 5-HMF esters and mixed feed-stocks of 5-HMF and 5-HMF ethers and mixed feed-stocks of 5-HMF and 5-alkyl furfurals to generate a crude carboxylic acid slurry comprising FDCA, cooling a crude carboxylic acid slurry in cooling zone to form a cooled slurry stream. The cooled slurry stream is routed to a solid-liquid separation zone to generate a crude wet cake stream comprising FDCA that is dried in a drying zone to generate a dry carboxylic acid product stream comprising crude FDCA (cFDCA).Type: ApplicationFiled: May 20, 2014Publication date: September 11, 2014Applicant: EASTMAN CHEMICAL COMPANYInventors: Mesfin Ejerssa Janka, Kenny Randolph Parker, Ashfaq Shahanawaz Shaikh, Lee Reynolds Partin
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Publication number: 20140235880Abstract: A process to produce a dry purified furan-2,5-dicarboxylic acid (FDCA) is described. After oxidation of 5-(hydroxymethyl)furfural (5-HMF), a crude FDCA stream is produced that is fed to a crystallization zone followed by a solid-liquid displacement zone to form a low impurity slurry stream. The solids in the low impurity slurry stream are dissolved in a dissolution zone to produce a hydrogenation feed that is hydrogenated in a hydrogenation reactor to generate a hydrogenated FDCA composition. The hydrogenated FDCA composition is routed to a crystallization zone to form a crystallized produce stream that is separated from liquid in a solid-liquid separation zone to generate a purified wet cake stream containing FDCA that can be dried in a drying zone to generate a dry purified FDCA product stream.Type: ApplicationFiled: April 23, 2014Publication date: August 21, 2014Applicant: EASTMAN CHEMICAL COMPANYInventors: Ashfaq Schahanawaz Shaikh, Kenny Randolph Parker, Mesfin Ejerssa Janka, Lee Reynolds Partin
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Patent number: 8809556Abstract: Disclosed is a process to produce a dry purified carboxylic acid product comprising furan-2,5-dicarboxylic acid (FDCA). The process comprises oxidizing at least one oxidizable compound to generate a crude carboxylic acid slurry comprising FDCA, removing impurities from a crude carboxylic acid slurry in a liquid displacement zone to form a low impurity slurry stream. The low impurity slurry stream is further treated in a secondary oxidation zone to produce a secondary oxidation slurry stream which is routed to a crystallization zone to form a crystallized slurry stream. The crystallized slurry stream is cooled in a cooling zone and the resulting cooled crystallized slurry stream is routed to a solid-liquid separation zone to generate a purified wet cake stream comprising FDCA that is dried in a drying zone to generate a dry carboxylic acid product stream comprising purified FDCA (pFDCA).Type: GrantFiled: July 20, 2012Date of Patent: August 19, 2014Assignee: Eastman Chemical CompanyInventors: Mesfin Ejerssa Janka, Kenny Randolph Parker, Paula Moody, Ashfaq Shaikh, Lee Reynolds Partin, Bradford Russell Bowers, Michael Charles Morrow
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Patent number: 8796477Abstract: Disclosed is an oxidation process to produce a crude carboxylic acid product carboxylic acid product. The process comprises oxidizing a feed stream comprising at least one oxidizable compound to generate a crude carboxylic acid slurry comprising furan-2,5-dicarboxylic acid (FDCA) and compositions thereof. Also disclosed is a process to produce a dry purified carboxylic acid product by utilizing various purification methods on the crude carboxylic acid.Type: GrantFiled: September 9, 2011Date of Patent: August 5, 2014Assignee: Eastman Chemical CompanyInventors: Mesfin Ejerssa Janka, David Milton Lange, Michael C. Morrow, Bradford Russell Bowers, Kenny Randolph Parker, Ashfaq Shaikh, Lee Reynolds Partin, Jason Christopher Jenkins, Paula Moody, Thomas Elbert Shanks, Charles Edwan Sumner, Jr.
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Patent number: 8791277Abstract: Disclosed is an oxidation process to produce a crude carboxylic acid product carboxylic acid product. The process comprises oxidizing a feed stream comprising at least one oxidizable compound to generate a crude carboxylic acid slurry comprising furan-2,5-dicarboxylic acid (FDCA) and compositions thereof. Also disclosed is a process to produce a dry purified carboxylic acid product by utilizing various purification methods on the crude carboxylic acid.Type: GrantFiled: September 9, 2011Date of Patent: July 29, 2014Assignee: Eastman Chemical CompanyInventors: Mesfin Ejerssa Janka, David Milton Lange, Michael C. Morrow, Bradford Russell Bowers, Kenny Randolph Parker, Ashfaq Shaikh, Lee Reynolds Partin, Charles Edwan Sumner, Jr.
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Patent number: 8791278Abstract: Disclosed is an oxidation process to produce a crude carboxylic acid product carboxylic acid product. The process comprises oxidizing a feed stream comprising at least one oxidizable compound to generate a crude carboxylic acid slurry comprising furan-2,5-dicarboxylic acid (FDCA) and compositions thereof. Also disclosed is a process to produce a dry purified carboxylic acid product by utilizing various purification methods on the crude carboxylic acid.Type: GrantFiled: September 9, 2011Date of Patent: July 29, 2014Assignee: Eastman Chemical CompanyInventors: Ashfaq Shaikh, Mesfin Ejerssa Janka, David Milton Lange, Michael C. Morrow, Bradford Russell Bowers, Kenny Randolph Parker, Lee Reynolds Partin, Jason Christopher Jenkins, Paula Moody, Thomas Elbert Shanks, Charles Edwan Sumner, Jr.
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Patent number: 8785667Abstract: Alcohols are catalytically oxidized to aldehydes, in particular to benzaldehyde and diformylfuran, which are useful as intermediates for a multiplicity of purposes. The invention also relates to the polymerization of the dialdehyde and to the decarbonylation of the dialdehyde to furan.Type: GrantFiled: July 25, 2013Date of Patent: July 22, 2014Assignee: E I du Pont de Nemours and CompanyInventors: Vladimir Grushin, Leo Ernest Manzer, Walter Partenheimer
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Patent number: 8772513Abstract: Disclosed is a process to produce a dry purified carboxylic acid product comprising furan-2,5-dicarboxylic acid (FDCA). The process comprises oxidizing at least one oxidizable compound selected from the following group: 5-(hydroxymethyl)furfural (5-HMF), 5-HMF esters (5-R(CO)OCH2-furfural where R=alkyl, cycloalkyl and aryl), 5-HMF ethers (5-R?OCH2-furfural, where R?=alkyl, cycloalkyl and aryl), 5-alkyl furfurals (5-R?-furfural, where R?=alkyl, cycloalkyl and aryl), mixed feed-stocks of 5-HMF and 5-HMF esters and mixed feed-stocks of 5-HMF and 5-HMF ethers and mixed feed-stocks of 5-HMF and 5-alkyl furfurals to generate a crude carboxylic acid slurry comprising FDCA, cooling a crude carboxylic acid slurry in cooling zone to form a cooled slurry stream. The cooled slurry stream is routed to a solid-liquid separation zone to generate a crude wet cake stream comprising FDCA that is dried in a drying zone to generate a dry carboxylic acid product stream comprising crude FDCA (cFDCA).Type: GrantFiled: February 4, 2013Date of Patent: July 8, 2014Assignee: Eastman Chemical CompanyInventors: Mesfin Ejerssa Janka, Kenny Randolph Parker, Ashfaq Shahanawaz Shaikh, Lee Reynolds Partin
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Patent number: 8748479Abstract: A process to produce a dry purified furan-2,5-dicarboxylic acid (FDCA) is described. After oxidation of 5-(hydroxymethyl)furfural (5-HMF), a crude FDCA stream is produced that is fed to a crystallization zone followed by a solid-liquid displacement zone to form a low impurity slurry stream. The solids in the low impurity slurry stream are dissolved in a dissolution zone to produce a hydrogenation feed that is hydrogenated in a hydrogenation reactor to generate a hydrogenated FDCA composition. The hydrogenated FDCA composition is routed to a crystallization zone to form a crystallized produce stream that is separated from liquid in a solid-liquid separation zone to generate a purified wet cake stream containing FDCA that can be dried in a drying zone to generate a dry purified FDCA product stream.Type: GrantFiled: February 4, 2013Date of Patent: June 10, 2014Assignee: Eastman Chemical CompanyInventors: Ashfaq Shaikh, Kenny Randolph Parker, Mesfin Ejerssa Janka, Lee Reynolds Partin
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Patent number: 8748637Abstract: Alcohols are catalytically oxidized to aldehydes, in particular to benzaldehyde and diformylfuran, which are useful as intermediates for a multiplicity of purposes. The invention also relates to the polymerization of the dialdehyde and to the decarbonylation of the dialdehyde to furan.Type: GrantFiled: July 25, 2013Date of Patent: June 10, 2014Assignee: E I du Pont de Nemours and CompanyInventors: Vladimir Grushin, Leo Ernest Manzer, Walter Partenheimer
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Publication number: 20140142328Abstract: Disclosed is a process to produce a dry purified carboxylic acid product comprising furan-2,5-dicarboxylic acid (FDCA). The process comprises oxidizing a feed stream comprising at least one oxidizable compound to generate a crude carboxylic acid slurry comprising FDCA, removing impurities from a crude carboxylic acid slurry via oxidative purification in a low temperature post-oxidation zone to form a low impurity slurry stream. The low impurity slurry stream is further treated in a high temperature post oxidation zone to produce a secondary oxidation slurry stream which is routed to a crystallization zone to from a crystallized slurry stream.Type: ApplicationFiled: November 19, 2013Publication date: May 22, 2014Applicant: EASTMAN CHEMICAL COMPANYInventors: Ashfaq Shaikh, Kenny R. Parker, Mesfin Ejerssa Janka, Lee R. Partin
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Publication number: 20140142327Abstract: Disclosed is a process for producing a dry, purified carboxylic acid product comprising furan-2,5-dicarboxylic acid (FDCA). Also disclosed is a method for treating an oxidation off-gas stream from such a process. The method features solvent as well as energy recovery from the off-gas stream.Type: ApplicationFiled: March 13, 2013Publication date: May 22, 2014Applicant: Eastman Chemical CompanyInventors: Ashfaq Shahanawaz Shaikh, Kenny Randolph Parker, Mesfin Ejerssa Janka, Lee Reynolds Partin