Plural -c(=x)x- Groups Bonded Directly To The Hetero Ring Patents (Class 549/485)
  • Patent number: 9617234
    Abstract: 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: Grant
    Filed: December 18, 2015
    Date of Patent: April 11, 2017
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: James A. Dumesic, Ali Hussain Motagamwala
  • Patent number: 9586923
    Abstract: 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: Grant
    Filed: August 28, 2012
    Date of Patent: March 7, 2017
    Assignees: University of Kansas, Archer Daniels Midland Company
    Inventors: Bala Subramaniam, Xiaobin Zuo, Daryle H. Busch, Padmesh Venkitasubramanian
  • Patent number: 9573120
    Abstract: 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: Grant
    Filed: June 27, 2014
    Date of Patent: February 21, 2017
    Assignee: EASTMAN CHEMICAL COMPANY
    Inventors: Kenny Parker, Mesfin Janka, Ashfaq Shaikh, Lee Partin
  • Patent number: 9499506
    Abstract: 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: Grant
    Filed: February 11, 2014
    Date of Patent: November 22, 2016
    Assignees: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (C.N.R.S), UNIVERSITE CLAUDE BERNARD LYON 1
    Inventors: Michele Besson, Nadine Essayem, Hicham Ait Rass
  • Patent number: 9458122
    Abstract: 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: Grant
    Filed: September 1, 2015
    Date of Patent: October 4, 2016
    Assignee: Eastman Chemical Company
    Inventors: Ashfaq Shahanawaz Shaikh, Kenny Randolph Parker, Mesfin Ejerssa Janka, Lee Reynolds Partin
  • Patent number: 9428480
    Abstract: 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: Grant
    Filed: September 24, 2014
    Date of Patent: August 30, 2016
    Assignee: Eastman Chemical Company
    Inventors: Mesfin Janka, David Lange, Michael Morrow, Bradford Bowers, Kenny Parker, Ashfaq Shaikh, Lee Partin, Jason Jenkins, Paula Moody, Thomas Shanks, Charles Sumner
  • Patent number: 9388152
    Abstract: 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: Grant
    Filed: September 26, 2013
    Date of Patent: July 12, 2016
    Assignee: ROQUETTE FRERES
    Inventors: Mathias Ibert, Flora Chambon, Laurent Dambrine
  • Patent number: 9376414
    Abstract: 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: Grant
    Filed: May 8, 2014
    Date of Patent: June 28, 2016
    Assignee: Stichting Dienst Landbouwkundig Onderzoek
    Inventors: Jacobus van Haveren, Daniël Stephan van Es, Frits van der Klis, Henricus Wilhelmus Carolina Raaijmakers
  • Patent number: 9266850
    Abstract: 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: Grant
    Filed: April 21, 2015
    Date of Patent: February 23, 2016
    Assignee: Eastman Chemical Company
    Inventors: Mesfin Ejerssa Janka, Kenny Randolph Parker, Paula Moody, Ashfaq Shahanawaz Shaikh, Lee Reynolds Partin, Bradford Russell Bowers, Michael Charles Morrow
  • Patent number: 9249118
    Abstract: 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: Grant
    Filed: June 19, 2014
    Date of Patent: February 2, 2016
    Assignee: Eastman Chemical Company
    Inventors: Mesfin Ejerssa Janka, Charles Edwan Sumner, Jr., Shane Kipley Kirk, Ashfaq Shahanawaz Shaikh, Kenny Randolph Parker
  • Patent number: 9206149
    Abstract: 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: Grant
    Filed: May 20, 2014
    Date of Patent: December 8, 2015
    Assignee: Eastman Chemical Company
    Inventors: Mesfin Ejerssa Janka, Kenny Randolph Parker, Ashfaq Shahanawaz Shaikh, Lee Reynolds Partin
  • Patent number: 9199958
    Abstract: 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: Grant
    Filed: October 28, 2014
    Date of Patent: December 1, 2015
    Assignee: Eastman Chemical Company
    Inventors: Mesfin Ejerssa Janka, David Lange, Michael C. Morrow, Bradford Russell Bowers, Kenny Randolph Parker, Ashfaq Shaikh, Lee Reynolds Partin, Charles Sumner
  • Patent number: 9199957
    Abstract: 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: Grant
    Filed: October 17, 2013
    Date of Patent: December 1, 2015
    Assignee: PETROLEO BRASILEIRO S.A.-PETROBRAS
    Inventors: Bernardo Galvao Siqueira, Raphael Bezerra De Menezes, Carlos Rene Klotz Rabello, Marlito Gomes, Jr.
  • Patent number: 9169229
    Abstract: 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: Grant
    Filed: November 7, 2014
    Date of Patent: October 27, 2015
    Assignee: Eastman Chemical Company
    Inventors: Kenny Randolph Parker, Ashfaq Shaikh, Lee Reynolds Parton, Mesfin Ejerssa Janka
  • Patent number: 9169228
    Abstract: 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: Grant
    Filed: July 30, 2010
    Date of Patent: October 27, 2015
    Assignee: EVONIK DEGUSSA GmbH
    Inventors: Michael Grass, Hinnerk Gordon Becker
  • Patent number: 9145379
    Abstract: 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: Grant
    Filed: August 17, 2010
    Date of Patent: September 29, 2015
    Assignee: Evonik Degussa GmbH
    Inventors: Michael Graβ, Hinnerk Gordon Becker
  • Patent number: 9061986
    Abstract: 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: Grant
    Filed: August 16, 2012
    Date of Patent: June 23, 2015
    Assignee: 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
  • Patent number: 9029581
    Abstract: 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: Grant
    Filed: September 19, 2014
    Date of Patent: May 12, 2015
    Assignee: Eastman Chemical Company
    Inventors: Lee Reynolds Partin, Ashfaq Shaikh, Mesfin Ejerssa Janka, Kenny Randolph Parker
  • Patent number: 9029579
    Abstract: 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: Grant
    Filed: November 8, 2012
    Date of Patent: May 12, 2015
    Assignee: Eastman Chemical Company
    Inventors: Mesfin Ejerssa Janka, John Dayton Baker, Jr., Stephanie Nicole Rollins
  • Patent number: 9029580
    Abstract: 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: Grant
    Filed: February 4, 2013
    Date of Patent: May 12, 2015
    Assignee: Eastman Chemical Company
    Inventors: Mesfin Ejerssa Janka, Kenny Randolph Parker, Paula Moody, Ashfaq Shahanawaz Shaikh, Lee Reynolds Partin, Bradford Russell Bowers, Michael Charles Morrow
  • Publication number: 20150119588
    Abstract: 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: Application
    Filed: December 29, 2011
    Publication date: April 30, 2015
    Applicants: BRASKEM S.A., STICHTING DIENST LANDBOUWKUNDIG ONDERZOEK
    Inventors: Jacco van Haveren, Shanmugam Thiyagarajan, Augusto Teruo Morita
  • Patent number: 9006470
    Abstract: 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: Grant
    Filed: November 8, 2012
    Date of Patent: April 14, 2015
    Assignee: Eastman Chemical Company
    Inventors: Mesfin Ejerssa Janka, John Dayton Baker, Jr., Stephanie Nicole Rollins
  • Publication number: 20150065735
    Abstract: 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: Application
    Filed: November 7, 2014
    Publication date: March 5, 2015
    Inventors: Kenny Randolph Parker, Ashfaq Shaikh, Lee Raynolds Parton, Mesfin Ejerssa Janka
  • Patent number: 8969404
    Abstract: 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: Grant
    Filed: February 4, 2013
    Date of Patent: March 3, 2015
    Assignee: Eastman Chemical Company
    Inventors: Mesfin Ejerssa Janka, Charles Edwan Sumner, Jr., Shane Kipley Kirk, Ashfaq Shahanawaz Shaikh, Kenny Randolph Parker
  • Publication number: 20150051412
    Abstract: 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: Application
    Filed: October 28, 2014
    Publication date: February 19, 2015
    Applicant: Eastman Chemical Company
    Inventors: Mesfin Ejerssa Janka, David Lange, Michael C. Morrow, Bradford Russell Bowers, Kenny Randolph Parker, Ashfaq Shaikh, Lee Reynolds Partin, Charles Sumner
  • Publication number: 20150031903
    Abstract: 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: Application
    Filed: September 19, 2014
    Publication date: January 29, 2015
    Inventors: Lee Reynolds Partin, Ashfaq Shaikh, Mesfin Ejerssa Janka, Kenny Randolph Parker
  • Publication number: 20150011783
    Abstract: 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: Application
    Filed: September 24, 2014
    Publication date: January 8, 2015
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Mesfin Janka, David Lange, Michael Morrow, Bradford Bowers, Kenny Parker, Ashfaq Shaikh, Lee Partin, Jason Jenkins, Paula Moody, Thomas Shanks, Charles Sumner
  • Patent number: 8916720
    Abstract: 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: Grant
    Filed: March 13, 2013
    Date of Patent: December 23, 2014
    Assignee: Eastman Chemical Company
    Inventors: Ashfaq Shahanawaz Shaikh, Kenny Randolph Parker, Mesfin Ejerssa Janka, Lee Reynolds Partin
  • Patent number: 8916719
    Abstract: 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: Grant
    Filed: March 13, 2013
    Date of Patent: December 23, 2014
    Assignee: Eastman Chemical Company
    Inventors: Ashfaq Shahanawaz Shaikh, Kenny Randolph Parker, Mesfin Ejerssa Janka, Lee Reynolds Partin
  • Patent number: 8912349
    Abstract: 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: Grant
    Filed: June 22, 2012
    Date of Patent: December 16, 2014
    Assignee: Eastman Chemical Company
    Inventors: Ashfaq Shaikh, Kenny Randolph Parker, Lee Reynolds Partin, Mesfin Ejerssa Janka
  • Publication number: 20140364633
    Abstract: 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: Application
    Filed: June 19, 2014
    Publication date: December 11, 2014
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Mesfin Ejerssa Janka, Charles Edwan Sumner, JR., Shane Kipley Kirk, Ashfaq Shahanawaz Shaikh, Kenny Randolph Parker
  • Publication number: 20140364632
    Abstract: 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: Application
    Filed: August 16, 2012
    Publication date: December 11, 2014
    Applicant: 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
  • Publication number: 20140357877
    Abstract: 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: Application
    Filed: August 16, 2012
    Publication date: December 4, 2014
    Applicant: 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
  • Publication number: 20140343305
    Abstract: 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: Application
    Filed: August 28, 2012
    Publication date: November 20, 2014
    Applicant: The University of Kansas
    Inventors: Bala Subramaniam, Xiaobin Zuo, Daryle H. Busch, Padmesh Venkitasubramaniam
  • Patent number: 8865921
    Abstract: 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: Grant
    Filed: October 6, 2010
    Date of Patent: October 21, 2014
    Assignee: Furanix Technologies B.V.
    Inventors: Cesar Muñoz De Diego, Matheus Adrianus Dam, Gerardus Johannes Maria Gruter
  • Patent number: 8859788
    Abstract: 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: Grant
    Filed: June 22, 2012
    Date of Patent: October 14, 2014
    Assignee: Eastman Chemical Company
    Inventors: Lee Reynolds Partin, Ashfaq Shaikh, Mesfin Ejerssa Janka, Kenny Randolph Parker
  • Publication number: 20140295508
    Abstract: 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: Application
    Filed: March 28, 2014
    Publication date: October 2, 2014
    Inventors: Yasuo Yoshikuni, Susan R. Cooper, Adam J. Wargacki, Leo E. Manzer, James F. White, Lou Kapicak, Dennis J. Miller, Lars Peereboom
  • Patent number: 8846960
    Abstract: 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: Grant
    Filed: September 9, 2011
    Date of Patent: September 30, 2014
    Assignee: Eastman Chemical Company
    Inventors: Mesfin Ejerssa Janka, David Milton Lange, Michael C. Morrow, Bradford Russell Bowers, Kenny Randolph Parker, Ashfaq Shaikh, Lee Reynolds Partin, Charles Edwan Sumner, Jr.
  • Publication number: 20140256964
    Abstract: 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: Application
    Filed: May 20, 2014
    Publication date: September 11, 2014
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Mesfin Ejerssa Janka, Kenny Randolph Parker, Ashfaq Shahanawaz Shaikh, Lee Reynolds Partin
  • Publication number: 20140235880
    Abstract: 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: Application
    Filed: April 23, 2014
    Publication date: August 21, 2014
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Ashfaq Schahanawaz Shaikh, Kenny Randolph Parker, Mesfin Ejerssa Janka, Lee Reynolds Partin
  • Patent number: 8809556
    Abstract: 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: Grant
    Filed: July 20, 2012
    Date of Patent: August 19, 2014
    Assignee: Eastman Chemical Company
    Inventors: Mesfin Ejerssa Janka, Kenny Randolph Parker, Paula Moody, Ashfaq Shaikh, Lee Reynolds Partin, Bradford Russell Bowers, Michael Charles Morrow
  • Patent number: 8796477
    Abstract: 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: Grant
    Filed: September 9, 2011
    Date of Patent: August 5, 2014
    Assignee: Eastman Chemical Company
    Inventors: 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.
  • Patent number: 8791277
    Abstract: 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: Grant
    Filed: September 9, 2011
    Date of Patent: July 29, 2014
    Assignee: Eastman Chemical Company
    Inventors: Mesfin Ejerssa Janka, David Milton Lange, Michael C. Morrow, Bradford Russell Bowers, Kenny Randolph Parker, Ashfaq Shaikh, Lee Reynolds Partin, Charles Edwan Sumner, Jr.
  • Patent number: 8791278
    Abstract: 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: Grant
    Filed: September 9, 2011
    Date of Patent: July 29, 2014
    Assignee: Eastman Chemical Company
    Inventors: 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.
  • Patent number: 8785667
    Abstract: 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: Grant
    Filed: July 25, 2013
    Date of Patent: July 22, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Vladimir Grushin, Leo Ernest Manzer, Walter Partenheimer
  • Patent number: 8772513
    Abstract: 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: Grant
    Filed: February 4, 2013
    Date of Patent: July 8, 2014
    Assignee: Eastman Chemical Company
    Inventors: Mesfin Ejerssa Janka, Kenny Randolph Parker, Ashfaq Shahanawaz Shaikh, Lee Reynolds Partin
  • Patent number: 8748479
    Abstract: 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: Grant
    Filed: February 4, 2013
    Date of Patent: June 10, 2014
    Assignee: Eastman Chemical Company
    Inventors: Ashfaq Shaikh, Kenny Randolph Parker, Mesfin Ejerssa Janka, Lee Reynolds Partin
  • Patent number: 8748637
    Abstract: 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: Grant
    Filed: July 25, 2013
    Date of Patent: June 10, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Vladimir Grushin, Leo Ernest Manzer, Walter Partenheimer
  • Publication number: 20140142328
    Abstract: 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: Application
    Filed: November 19, 2013
    Publication date: May 22, 2014
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Ashfaq Shaikh, Kenny R. Parker, Mesfin Ejerssa Janka, Lee R. Partin
  • Publication number: 20140142327
    Abstract: 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: Application
    Filed: March 13, 2013
    Publication date: May 22, 2014
    Applicant: Eastman Chemical Company
    Inventors: Ashfaq Shahanawaz Shaikh, Kenny Randolph Parker, Mesfin Ejerssa Janka, Lee Reynolds Partin