Plural -c(=x)x- Groups Bonded Directly To The Hetero Ring Patents (Class 549/485)
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Patent number: 12049456Abstract: The present disclosure provides processes for the purification of 2,5-furandicarboxylic acid (FDCA). The present disclosure further provides crystalline preparations of purified FDCA, as well as processes for making the same. In addition, the present disclosure provides mixtures used in processes for the purification of FDCA.Type: GrantFiled: November 30, 2021Date of Patent: July 30, 2024Assignee: Stora Enso OyjInventors: Henricus Johannes Cornelis Den Ouden, Valery Sokolovskii, Thomas R. Boussie, Gary M. Diamond, Eric L. Dias, Guang Zhu, Staffan Torssell, Vincent J. Murphy
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Patent number: 11958804Abstract: The present invention relates to the use of 2,5-furanedicarboxylate-based MOFs, such as, MIL-160(AI) metal-organic framework, for separating C6 alkane isomers into linear, mono-branched and di-branched isomers. The present invention also relates to the use of 2,5-furanedicarboxylate-based MOFs, such as, MIL-160(AI) metal-organic framework, preferably in combination with Zeolite 5A for producing higher research octane number gasoline blends. Also within the scope of the invention is a system for separating C6 and C5 alkane isomer mixtures into linear, mono-branched and di-branched fractions.Type: GrantFiled: January 7, 2020Date of Patent: April 16, 2024Assignees: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, INSTITUTO POLITÉCNICO DE BRAGANÇA, ÉCOLE SUPÉRIEURE DE PHYSIQUE ET DE CHIMIE INDUSTRIELLES DE LA VILLE DE PARIS, ÉCOLE NORMALE SUPÉRIEURE DE PARIS, UNIVERSIDADE DO PORTOInventors: Christian Serre, Farid Nouar, José Silva, Alírio Rodrigues, Pedro Brântuas
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Patent number: 11891370Abstract: The present disclosure provides processes for the production of 2-5-furandicarboxylic acid (FDCA) and intermediates thereof by the chemocatalytic conversion of a furanic oxidation substrate. The present disclosure further provides processes for preparing derivatives of FDCA and FDCA-based polymers. In addition, the present disclosure provides crystalline preparations of FDCA, as well as processes for making the same.Type: GrantFiled: February 15, 2023Date of Patent: February 6, 2024Assignee: Stora Enso OjyInventors: Valery Sokolovskii, Vincent J. Murphy, Thomas R. Boussie, Gary M. Diamond, Eric L. Dias, Guang Zhu, James M. Longmire, Stanley Herrmann, Staffan Torssell, Mayya Lavrenko
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Patent number: 11787774Abstract: A process for preparing 5-(alkoxycarbonyl)furan-2-carboxylic acids (ACFC) by oxidizing various furcates in the presence of a catalyst containing cobalt, manganese, and bromine, and a solvent while simultaneously removing water vapor from the reaction chamber. The process can produce ACFC with high purity and low color, and in high yield.Type: GrantFiled: August 25, 2020Date of Patent: October 17, 2023Assignee: Eastman Chemical CompanyInventor: Mesfin Ejerssa Janka
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Patent number: 11708343Abstract: A process for carboxylation of a furoate slurry to produce FDCA, especially 2,5-FDCA, includes the steps of: feeding a slurry containing a suspension fluid, furoate, a surfactant and an alkali metal carbonate to a carboxylation reactor; and feeding a flow of CO2 to the carboxylation reactor at flow conditions sufficient to suspend the slurry in the reactor and react the furoate with CO2 to form 2,5-FDCA. A fully integrated process is also disclosed.Type: GrantFiled: July 16, 2021Date of Patent: July 25, 2023Assignee: KSE, Inc.Inventors: James R. Kittrell, Carl R. Dupre, Keith D. Kittrell, Leonard T. McDonald, Jeffrey A. Kittrell
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Patent number: 11702395Abstract: Bimetal oxide catalyst and methods, a method comprises: mixing and grinding to obtain a mixture comprising a manganese salt (a), at least one of other metal salt (b), and an additive (c), wherein the other metal salt comprises at least one of a copper salt, a cobalt salt, a cerium salt, an iron salt, or a nickel salt, and the additive comprises at least one of polyol or organic acid, and calcining the mixture to obtain the bimetal oxide catalyst.Type: GrantFiled: September 10, 2021Date of Patent: July 18, 2023Assignee: Xiamen UniversityInventors: Xing Tang, Huai Liu, Lu Lin, Xianhai Zeng, Yong Sun
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Patent number: 11697642Abstract: The present invention relates to a method for the production of 5-hydroxymethylfurfural (HMF), which converts a fructose-containing component using a catalytically active anolyte fraction, which has been produced by electrolysis of water, at a temperature of 90 to 200° C. and for obtaining an HMF-containing product mixture, wherein advantageously a high HMF selectivity is achieved with significantly lower by-product formation.Type: GrantFiled: May 28, 2019Date of Patent: July 11, 2023Assignee: SÜDZUCKER AGInventors: Alireza Haji Begli, Christine Kröner, Waldemar Tschilingiri, Ralf Riemenschnitter, Kay Mantyk
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Patent number: 11655227Abstract: Disclosed is a process to produce a purified vapor comprising dialkyl-furan-2,5-dicarboxylate (DAFD). Furan-2,5-dicarboxylic acid (FDCA) and an alcohol in an esterification zone to generate a crude diester stream containing dialkyl furan dicarboxylate (DAFD), unreacted alcohol, 5-(alkoxycarbonyl)furan-2-carboxylic acid (ACFC), and alkyl furan-2-carboxylate (AFC). The esterification zone comprises at least one reactor that has been previously used in an DMT process.Type: GrantFiled: March 22, 2021Date of Patent: May 23, 2023Assignee: Eastman Chemical CompanyInventors: Kevin John Fontenot, Mesfin Ejerssa Janka, Kenny Randolph Parker, Ashfaq Shahanawaz Shaikh
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Patent number: 11613523Abstract: The present disclosure provides processes for the production of 2-5-furandicarboxylic acid (FDCA) and intermediates thereof by the chemocatalytic conversion of a furanic oxidation substrate. The present disclosure further provides processes for preparing derivatives of FDCA and FDCA-based polymers. In addition, the present disclosure provides crystalline preparations of FDCA, as well as processes for making the same.Type: GrantFiled: November 13, 2020Date of Patent: March 28, 2023Assignee: Stora Enso OyjInventors: Valery Sokolovskii, Vincent J. Murphy, Thomas R. Boussie, Gary M. Diamond, Eric L. Dias, Guang Zhu, James M. Longmire, Stanley Herrmann, Staffan Torssell, Mayya Lavrenko
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Patent number: 11603361Abstract: The invention is directed to a method for the preparation, in particular for the purification of 2,5-furandicarboxylic acid or a salt thereof, comprising crystallization of a 2,5-furandicarboxylic acid mono salt and then crystallizing 2,5-furandicarboxylic diacid from this mono salt. Preferably, the method is at least partially carried out in a continuous or semi-continuous manner, preferably at least partially in one or more continuous mixed-suspension mixed product removal (MSMPR) crystallizers in series.Type: GrantFiled: September 30, 2019Date of Patent: March 14, 2023Assignee: Nederlandse Organisatie voor toegepastnatuurwetensInventors: Marc Crockatt, Carol Andrea Roa Engel, Cornelis Petrus Marcus Roelands, Johannes Van Der Meer
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Patent number: 11597709Abstract: The present disclosure provides a preparing method for 5-alkoxymethylfurfural, including steps of (a) preparing fructose, (b) mixing the fructose, an organic acid catalyst, and an organic solvent, thereby preparing mixing solution, and (c) heating the mixing solution, thereby preparing 5-alkoxymethylfurfural. Therefore, 5-alkoxymethylfurfural may be effectively prepared without by-products from fructose.Type: GrantFiled: February 4, 2021Date of Patent: March 7, 2023Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGYInventors: Dong Won Hwang, Young Kyu Hwang, Ma Eum Lee, Pravin Pandharinath Upare, Do Young Hong
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Dehydration and cyclization of ?-, ?-dihydroxy carbonyl compounds to 2-substituted furan derivatives
Patent number: 11578048Abstract: Processes are disclosed for the synthesis of 2-substituted furan derivatives, such as furan dicarboxylic acid (FDCA), from a starting compound or substrate having a carbonyl functional group (C?O), with hydroxy-substituted carbon atoms at alpha (?) and beta (?) positions, relative to the carbonyl functional group. According a particular embodiment, an ?-, ?-dihydroxy carboxylate is dehydrated to form a dicarbonyl intermediate by transformation of the ?-hydroxy group to a second carbonyl group and removal of the ?-hydroxy group. The dicarbonyl intermediate undergoes cyclization and dehydration, to produce the 2-substituted furan derivative. Optionally, a further step of oxidation may be carried out, for example to convert a hydroxymethyl group, as a 5-substituted about the furan ring, to a carboxy group of FDCA.Type: GrantFiled: April 4, 2019Date of Patent: February 14, 2023Assignee: ARCHER DANIELS MIDLAND COMPANYInventors: James Brazdil, Donald Rogness -
Patent number: 11446586Abstract: According to an example aspect of the present invention, there is provided a method for separating and purifying furan carboxylates from a crude reaction mixture comprising furans, by utilizing high vacuum distillation in a total heating environment.Type: GrantFiled: February 11, 2019Date of Patent: September 20, 2022Assignee: TEKNOLOGIAN TUTKIMUSKESKUS VTT OYInventors: David Thomas, Juha Linnekoski
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Patent number: 11440895Abstract: Disclosed herein is a very efficient method to make 5-(alkoxycarbonyl)furan-2-carboxylic acids (ACFC) from feedstocks comprised of furoates. When a feedstock comprised of methyl 5-methylfuran-2-carboxylate (MMFC) is used a product comprised of (5-(methoxycarbonyl)furan-2-carboxylic acid (MCFC) is obtained in high yield.Type: GrantFiled: June 4, 2019Date of Patent: September 13, 2022Assignee: Eastman Chemical CompanyInventor: Mesfin Ejerssa Janka
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Patent number: 11267796Abstract: The invention is directed to the to the electrochemical preparation of 2,5-furandicarboxylic acid (FDCA) from 5-hydroxymethylfurfural (HMF) by electrochemical oxidation, comprising a first oxidation step of oxidizing HMF to 5-hydroxymethyl-2-furan-carboxylic acid (HMFCA) in an electrochemical cell, subsequently a first isolation step of isolating HMFCA, followed by a second oxidation step of HMFCA to FDCA.Type: GrantFiled: February 28, 2018Date of Patent: March 8, 2022Assignee: Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek TNOInventors: Marc Crockatt, Roel Johannes Martinus Bisselink, Roman Latsuzbaia, Cornelis Petrus Marcus Roelands, Earl Lawrence Vincent Goetheer
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Patent number: 11220475Abstract: Compounds derived from biomass, e.g., cellulose and lignins, methods of forming such compounds and polymers and products formed using such compounds.Type: GrantFiled: December 20, 2019Date of Patent: January 11, 2022Assignee: NDSU RESEARCH FOUNDATIONInventors: Mukund P. Sibi, Selvakumar Sermadurai, Nicolas Zimmermann, Eric Serum, Gaoyuan Ma, Ramkumar Moorthy, Krystal Kalliokoski
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Patent number: 11192872Abstract: The present disclosure provides processes for the purification of 2,5-furandicarboxylic acid (FDCA). The present disclosure further provides crystalline preparations of purified FDCA, as well as processes for making the same. In addition, the present disclosure provides mixtures used in processes for the purification of FDCA.Type: GrantFiled: July 11, 2018Date of Patent: December 7, 2021Assignee: Stora Enso OyjInventors: Henricus Johannes Cornelis Den Ouden, Valery Sokolovskii, Thomas R. Boussie, Gary M. Diamond, Eric L. Dias, Guang Zhu, Staffan Torssell, Vincent J. Murphy
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Patent number: 11104656Abstract: The invention is based on the finding that when conducting crystallization of FDCA at high temperatures, the formation of significant amounts of colored byproduct can be reduced or even avoided when the FDCA mixture is kept at temperatures above 100° C. for less than 15 minutes. This is achieved by conducting the crystallization process in a continuous reactor. Accordingly, the method comprises the steps of feeding a mixture comprising undissolved FDCA and a solvent to a reactor; and dissolving FDCA by superheating the mixture in the reactor to a temperature of at least 130° C.; and crystallizing FDCA by cooling the mixture in the reactor, wherein the reactor is a continuous reactor and the residence time in the reactor zone wherein the FDCA mixture has a temperature above 100° C. is less than 15 minutes.Type: GrantFiled: December 31, 2018Date of Patent: August 31, 2021Assignee: Nederlandse Organisatie voor toegepast-natuurwetenschappelijk onderzoek TNOInventors: Carol Andrea Roa Engel, Johannes Van Der Meer, Leonard Ferdinand Gerard Geers, Marc Crockatt
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Patent number: 11066376Abstract: Disclosed is a process to produce a purified vapor comprising dialkyl-furan-2,5-dicarboxylate (DAFD). Furan-2,5-dicarboxylic acid (FDCA) and an alcohol in an esterification zone to generate a crude diester stream containing dialkyl furan dicarboxylate (DAFD), unreacted alcohol, 5-(alkoxycarbonyl)furan-2-carboxylic acid (ACFC), and alkyl furan-2-carboxylate (AFC). The esterification zone comprises at least one reactor that has been previously used in an DMT process.Type: GrantFiled: December 18, 2019Date of Patent: July 20, 2021Assignee: Eastman Chemical CompanyInventors: Kevin John Fontenot, Mesfin Ejerssa Janka, Kenny Randolph Parker, Ashfaq Shahanawaz Shaikh
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Patent number: 11028063Abstract: An integrated process is useful for producing 2,5-furandicarboxylic acid (FDCA) and/or a derivative thereof from a six-carbon sugar-containing feed. The process includes a) dehydrating a feed containing a six-carbon sugar unit, in the presence of a bromine source and of a solvent, to generate an oxidation feed that contains at least one of 5-hydroxymethylfurfural (HMF) and/or a derivative or derivatives of HMF in the solvent, together with at least one bromine containing species; b) contacting the oxidation feed from step (a) with a metal catalyst and with an oxygen source under oxidation conditions to produce an oxidation product mixture of at least FDCA and/or a derivative thereof, the solvent, and a residual catalyst; c) purifying and separating the mixture obtained in step (b) to obtain FDCA and/or a derivative thereof and the solvent; and d) recycling at least a portion of the solvent obtained in step (c) to step (a).Type: GrantFiled: July 9, 2020Date of Patent: June 8, 2021Assignees: DUPONT INDUSTRIAL BIOSCIENCES USA, LLC, ARCHER-DANIELS-MIDLAND COMPANYInventors: Stephen J. Howard, Kristina A. Kreutzer, Bhuma Rajagopalan, Eric R. Sacia, Alexandra Sanborn, Brennan Smith
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Patent number: 10954207Abstract: Disclosed is a process to produce a purified vapor comprising dialkyl-furan-2,5-dicarboxylate (DAFD). Furan-2,5-dicarboxylic acid (FDCA) and an alcohol in an esterification zone to generate a crude diester stream containing dialkyl furan dicarboxylate (DAFD), unreacted alcohol, 5-(alkoxycarbonyl) furan-2-carboxylic acid (ACFC), and alkyl furan-2-carboxylate (AFC). The esterification zone comprises at least one reactor that has been previously used in an DMT process.Type: GrantFiled: July 27, 2020Date of Patent: March 23, 2021Assignee: Eastman Chemical CompanyInventors: Kevin John Fontenot, Mesfin Ejerssa Janka, Kenny Randolph Parker, Ashfaq Shahanawaz Shaikh
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Patent number: 10947209Abstract: An embodiment of the present invention provides a method of preparing 2,5-furandimethylcarboxylate (FDMC), including preparing 2,5-furandimethylcarboxylate (FDMC) by subjecting a reaction mixture including 5-hydroxymethylfurfural (HMF), air, and an alcohol solvent to oxidative esterification in the presence of a gold (Au)-nanoparticle-supported catalyst, in which the gold (Au)-nanoparticle-supported catalyst includes a support and gold (Au) nanoparticles supported on the support.Type: GrantFiled: June 29, 2018Date of Patent: March 16, 2021Assignees: Korea Institute of Industrial Technology, SK CHEMICALS CO., LTD.Inventors: Yong Jin Kim, Dinesh Kumar Mishra, Jin Ku Cho, Yong Jin Yi, Han Seok Kim, Jong Ryang Kim
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Patent number: 10882032Abstract: 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: July 22, 2016Date of Patent: January 5, 2021Assignee: Eastman Chemical CompanyInventors: Kevin John Fontenot, Mesfin Ejerssa Janka, Kenny Randolph Parker, Ashfaq Shahanawaz Shaikh, Lee Reynolds Partin, Charles Edwan Sumner, Jr., Shane Kipley Kirk, Paula Moody, Bradford Russell Bowers, Michael Charles Morrow
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Patent number: 10865190Abstract: A process for producing furan dicarboxylic acid or an ester thereof from a feedstock comprising hydroxymethyl furfural (HMF) and humins is disclosed. Humins are a byproduct from reactions forming HMF from sugars and are typically removed from the HMF prior to any further processing. A humins-containing HMF feedstock is utilized to produce furan dicarboxylic acids and ester substantially free from humins.Type: GrantFiled: June 20, 2019Date of Patent: December 15, 2020Assignee: E I DU PONT DE NEMOURS AND COMPANYInventors: Pranit S Metkar, Ronnie Ozer, Bhuma Rajagopalan
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Patent number: 10858332Abstract: A method for purifying a crude 2,5-furandicarboxylic acid composition including 2,5-furandicarboxylic acid and 5-formylfuran-2-carboxylic acid is disclosed. The method includes the steps of: (a) subjecting the crude 2,5-furandicarboxylic acid composition to complete dissolution in a solvent solution to obtain a mixture, the solvent solution including an organic solvent and water; (b) subjecting 5-formylfuran-2-carboxylic acid in the mixture to an addition reaction with sodium hydrogen sulfite to obtain an addition product; and (c) subjecting 2,5-furandicarboxylic acid to precipitation after step (b) to obtain purified 2,5-furandicarboxylic acid.Type: GrantFiled: January 7, 2020Date of Patent: December 8, 2020Assignee: FAR EASTERN NEW CENTURY CORPORATIONInventors: Shu-Wei Liu, Ruey-Fen Liao, Xin-An Lu
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Patent number: 10851074Abstract: The present disclosure provides processes for the production of 2-5-furandicarboxylic acid (FDCA) and intermediates thereof by the chemocatalytic conversion of a furanic oxidation substrate. The present disclosure further provides processes for preparing derivatives of FDCA and FDCA-based polymers. In addition, the present disclosure provides crystalline preparations of FDCA, as well as processes for making the same.Type: GrantFiled: April 6, 2020Date of Patent: December 1, 2020Assignee: Stora Enso OyjInventors: Valery Sokolovskii, Vincent J. Murphy, Thomas R. Boussie, Gary M. Diamond, Eric L. Dias, Guang Zhu, James M. Longmire, Stanley Herrmann, Staffan Torssell, Mayya Lavrenko
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Patent number: 10787748Abstract: An aromatic dicarboxylic acid of chemical formula HOOC—Ar1—COOH is prepared in a process wherein a feedstock comprising at least an aromatic aldehyde compound of chemical formula (1): OHC—Ar1—COOH, wherein Ar1 represents an arylene or heteroarylene moiety, and an aqueous electrolyte are provided; the feedstock and the aqueous electrolyte are introduced into an electrolytic cell comprising electrodes, wherein at least one of the electrodes comprises a non-noble metal and/or an oxide and/or a hydroxide thereof and/or carbon; and the aromatic aldehyde compound of formula (1) is oxidized electrochemically to yield the aromatic dicarboxylic acid.Type: GrantFiled: May 20, 2016Date of Patent: September 29, 2020Assignee: Avantium Knowledge Centre B.V.Inventors: Klaas Jan Pieter Schouten, Jan Cornelis Van Der Waal, Maria Varini, Gerardus Johannes Maria Gruter
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Patent number: 10723712Abstract: Disclosed is a process to produce a purified vapor comprising dialkyl-furan-2,5-dicarboxylate (DAFD). Furan-2,5-dicarboxylic acid (FDCA) and an alcohol in an esterification zone to generate a crude diester stream containing dialkyl furan dicarboxylate (DAFD), unreacted alcohol, 5-(alkoxycarbonyl)furan-2-carboxylic acid (ACFC), and alkyl furan-2-carboxylate (AFC). The esterification zone comprises at least one reactor that has been previously used in an DMT process.Type: GrantFiled: September 6, 2019Date of Patent: July 28, 2020Assignee: Eastman Chemical CompanyInventors: Kevin John Fontenot, Mesfin Ejerssa Janka, Kenny Randolph Parker, Ashfaq Shahanawaz Shaikh
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Patent number: 10695755Abstract: 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: March 15, 2018Date of Patent: June 30, 2020Assignee: Eastman Chemical CompanyInventors: Mesfin Ejerssa Janka, Kenny Randolph Parker, Ashfaq Shahanawaz Shaikh, Lee Reynolds Partin
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Patent number: 10654819Abstract: The present disclosure provides processes for the production of 2-5-furandicarboxylic acid (FDCA) and intermediates thereof by the chemocatalytic conversion of a furanic oxidation substrate. The present disclosure further provides processes for preparing derivatives of FDCA and FDCA-based polymers. In addition, the present disclosure provides crystalline preparations of FDCA, as well as processes for making the same.Type: GrantFiled: August 27, 2019Date of Patent: May 19, 2020Assignee: Stora Enso OyjInventors: Valery Sokolovskii, Vincent J. Murphy, Thomas R. Boussie, Gary M. Diamond, Eric L. Dias, Guang Zhu, James M. Longmire, Stanley Herrmann, Staffan Torssell, Mayya Lavrenko
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Patent number: 10544118Abstract: Disclosed herein is a very efficient method to make 5-(alkoxycarbonyl)furan-2-carboxylic acids (ACFC) from feedstocks comprised of furoates. When a feedstock comprised of methyl 5-methylfuran-2-carboxylate (MMFC) is used a product comprised of (5-(methoxycarbonyl)furan-2-carboxylic acid (MCFC) is obtained in high yield.Type: GrantFiled: June 4, 2019Date of Patent: January 28, 2020Assignee: Eastman Chemical CompanyInventor: Mesfin Ejerssa Janka
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Patent number: 10538499Abstract: An integrated process is described for producing 2,5-furandicarboxylic acid and/or a derivative thereof from a six carbon sugar-containing feed, comprising: a) dehydrating a feed comprising a six-carbon sugar unit, in the presence of a bromine source and of a solvent, to generate an oxidation feed comprised of at least one of 5-hydroxymethylfurfural and/or a derivative or derivatives of 5-hydroxymethylfurfural in the solvent, together with at least one bromine containing species; b) contacting the oxidation feed from step (a) with a metal catalyst and with an oxygen source under oxidation conditions to produce an oxidation product mixture comprising 2,5-furandicarboxylic acid (FDCA) and/or a derivative thereof, the solvent, and a residual catalyst; c) purifying and separating the mixture obtained in step (b) to obtain FDCA and/or a derivative thereof and the solvent; and d) recycling at least a portion of the solvent obtained in step (c) to step (a).Type: GrantFiled: April 13, 2016Date of Patent: January 21, 2020Assignees: DUPONT INDUSTRIAL BIOSCIENCES USA, LLC, ARCHER DANIELS MIDLAND COMPANYInventors: Stephen J. Howard, Kristina A. Kreutzer, Bhuma Rajagopalan, Eric R. Sacia, Alexandra Sanborn, Brennan Smith
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Patent number: 10526301Abstract: Disclosed is a process to produce a purified vapor comprising dialkyl-furan-2,5-dicarboxylate (DAFD). Furan-2,5-dicarboxylic acid (FDCA) and an alcohol in an esterification zone to generate a crude diester stream containing dialkyl furan dicarboxylate (DAFD), unreacted alcohol, 5-(alkoxycarbonyl)furan-2-carboxylic acid (ACFC), and alkyl furan-2-carboxylate (AFC). The esterification zone comprises at least one reactor that has been previously used in an DMT process.Type: GrantFiled: May 10, 2019Date of Patent: January 7, 2020Assignee: Eastman Chemical CompanyInventors: Kevin John Fontenot, Mesfin Ejerssa Janka, Kenny Randolph Parker, Ashfaq Shahanawaz Shaikh
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Patent number: 10457657Abstract: A process for producing furan dicarboxylic acid or an ester thereof from a feedstock comprising hydroxymethyl furfural (HMF) and humins is disclosed. Humins are a byproduct from reactions forming HMF from sugars and are typically removed from the HMF prior to any further processing. A humins-containing HMF feedstock is utilized to produce furan dicarboxylic acids and ester substantially free from humins.Type: GrantFiled: October 15, 2018Date of Patent: October 29, 2019Assignees: DUPONT INDUSTRIAL BIOSCIENCES USA, LLC, ARCHER DANIELS MIDLAND COMPANYInventors: Pranit S. Metkar, Ronnie Ozer, Bhuma Rajagopalan
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Patent number: 10442780Abstract: The present disclosure provides processes for the production of 2-5-furandicarboxylic acid (FDCA) and intermediates thereof by the chemocatalytic conversion of a furanic oxidation substrate. The present disclosure further provides processes for preparing derivatives of FDCA and FDCA-based polymers. In addition, the present disclosure provides crystalline preparations of FDCA, as well as processes for making the same.Type: GrantFiled: January 31, 2019Date of Patent: October 15, 2019Assignee: Stora Enso OYJInventors: Valery Sokolovskii, Vincent J. Murphy, Thomas R. Boussie, Gary M. Diamond, Eric L. Dias, Guang Zhu, James M. Longmire, Stanley Herrmann, Staffan Torssell, Mayya Lavrenko
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Patent number: 10421736Abstract: Disclosed is a process to produce a purified vapor comprising dialkyl-furan-2,5-dicarboxylate (DAFD). Furan-2,5-dicarboxylic acid (FDCA) and an alcohol in an esterification zone to generate a crude diester stream containing dialkyl furan dicarboxylate (DAFD), unreacted alcohol, 5-(alkoxycarbonyl)furan-2-carboxylic acid (ACFC), and alkyl furan-2-carboxylate (AFC). The esterification zone comprises at least one reactor that has been previously used in an DMT process.Type: GrantFiled: March 20, 2018Date of Patent: September 24, 2019Assignee: Eastman Chemical CompanyInventors: Kevin John Fontenot, Mesfin Ejerssa Janka, Kenny Randolph Parker, Ashfaq Shahanawaz Shaikh
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Patent number: 10406454Abstract: 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, 2018Date of Patent: September 10, 2019Assignee: Eastman Chemical CompanyInventors: Kenny Parker, Mesfin Janka, Ashfaq Shaikh, Lee Partin
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Patent number: 10385033Abstract: A process for preparing furan-2,5-dicarboxylic acid is disclosed. The process includes the following steps: preparing or providing a starting mixture including 5-(hydroxy-methyl)furfural (HMF), 5,5?-[oxy-bis(methylene)]bis-2-furfural (di-HMF), and water; subjecting said starting mixture to oxidation conditions in the presence of an oxygen-containing gas and a catalytically effective amount of a heterogeneous catalyst including one or more noble metals on a support so that both HMF and di-HMF react to give furane-2,5-dicarboxylic acid in a product mixture also including water and oxidation by-products. The use of a catalyst is also disclosed, the catalyst including one or more noble metals on a support as an heterogeneous oxidation catalyst for catalyzing in an aqueous starting mixture the reaction of both HMF and di-HMF to furane-2,5-dicarboxylic acid.Type: GrantFiled: July 1, 2016Date of Patent: August 20, 2019Assignee: BASF SEInventors: Alvaro Gordillo, Holger Werhan, Richard Dehn, Benoit Blank, Joaquim Henrique Teles, Stephan A Schunk, Markus Piepenbrink, Rene Backes, Lei Zhang
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Patent number: 10350584Abstract: 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: April 12, 2016Date of Patent: July 16, 2019Assignee: Eastman Chemical CompanyInventors: Kenny Randolph Parker, Mesfin Ejerssa Janka, Ashfaq Shahanawaz Shaikh, Lee Reynolds Partin
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Patent number: 10344011Abstract: 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: May 4, 2018Date of Patent: July 9, 2019Assignee: Eastman Chemical CompanyInventors: Kenny Raldolph Parker, Mesfin Ejerssa Janka
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Patent number: 10344010Abstract: Method for purifying a crude of 2,5-furandicarboxylic acid (cFDCA) by crystallization is provided. The method includes (a) mixing the cFDCA and a solvent to form a mixture, wherein the solvent has a dipole moment of 3.7D (Debye) to 4.1D; (b) heating the mixture; (c) after step (b), cooling the mixture to precipitate a solid; and (d1) after step (c), filtering the mixture to collect a wet filter cake of the solid, and drying the wet filter cake to obtain purified FDCA. The purified FDCA has a higher FDCA purity than that of the cFDCA.Type: GrantFiled: December 4, 2017Date of Patent: July 9, 2019Assignee: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTEInventors: Ying-Ting Huang, Jinn-Jong Wong, Jau-Hong Chen
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Patent number: 10167268Abstract: An ester composition including at least 90% wt of the dialkyi ester of 2,5-furandicarboxylic acid as starting dialkyi ester concentration and up to 5% wt of the monoalkyi ester of 2,5-furandicarboxylic acid as starting monoalkyi ester concentration, the percentages being based on the weight of the ester composition, is purified in a process which includes subjecting the ester composition to melt crystallization to yield a purified dialkyi ester composition containing a dialkyi ester concentration higher than the starting dialkyi ester concentration and a melt residue containing a monoalkyi ester concentration higher than the starting monoalkyi ester concentration. From the melt residue a purified monoalkyi ester composition and a contaminants-rich residue can be prepared via melt crystallization. The purified dialkyi ester composition and/or the purified monoalkyi ester composition can be hydrolyzed to yield purified 2,5-furandicarboxylic acid.Type: GrantFiled: November 10, 2015Date of Patent: January 1, 2019Assignee: Synvina C.V.Inventors: Benjamin McKay, Gerardus Johannes Maria Gruter, Johannes Maria Franciscus Sijben
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Patent number: 10118908Abstract: A method for manufacturing furan-2,5-dicarboxylic acid (FDCA) by converting a furan-2,5-dicarboxylate salt (MFDC) into furan-2,5-dicarboxylic acid (FDCA), includes the steps of combining solid MFDC with an inorganic acid (HY), to form a reaction mixture having solid FDCA in a concentration of 1-15 wt. % in a solution of a salt resulting from the cation of the furan-2,5-dicarboxylate salt and the anion of the inorganic acid (MY solution), removing solid FDCA from the reaction mixture in a solid/liquid separation step, and providing at least 40 vol. % of the MY solution resulting from the solid/liquid separation step to the step of combining MFDC with HY. The step of providing part of the MY salt solution resulting from the solid/liquid separation step to the step of combining MFDC with HY makes it possible to obtain a stable and economic process which results in an FDCA product with good quality, and obtained in high yield.Type: GrantFiled: March 17, 2016Date of Patent: November 6, 2018Assignee: PURAC BIOCHEM B.V.Inventors: Jan Van Krieken, Andre Banier De Haan
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Patent number: 10087162Abstract: Dialkyil esters of 2,5-furandicarboxylic acid are prepared in a process including: contacting an acid starting composition having 2,5-furandicarboxylic acid with an excess of alkanol to form an esterification product having the dialkyil ester of 2,5-furan dicarboxylic acid, water and unreacted alkanol; separating at least part of the unreacted alkanol and water from the esterification product to yield a solid crude product composition having the dialkyil ester of 2,5-furandicarboxylic acid; and subjecting at least part of the solid crude product composition to an evaporation step, where the dialkyil ester of 2,5-furandicarboxylic acid is evaporated and subsequently condensed to yield purified dialkyil ester of 2,5-furandicarboxylic acid.Type: GrantFiled: November 10, 2015Date of Patent: October 2, 2018Assignee: Synvina C.V.Inventors: Ana Sofia Vagueiro De Sousa Dias, Benjamin McKay, Victor Peter Charles Vreeken, Gerardus Johannes Maria Gruter, Johannes Maria Franciscus Sijben
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Patent number: 10053442Abstract: Dialkyl esters of 2,5-furandicarboxylic acid are prepared from a 2,5-furandicarboxylic acid-containing starting material in a process, which includes: contacting a vaporous stream of an alkanol countercurrently with the at least partially liquid starting material having the 2,5-furandicarboxylic acid, in a reaction zone to conduct an esterification reaction to yield the dialkyl ester of 2,5-furandicarboxylic acid and water; withdrawing a reaction vapor comprising the alkanol and water from the reaction zone; and discharging a liquid phase having at least the dialkyl ester of 2,5-furandicarboxylic acid, from the bottom part of the reaction zone, to obtain the dialkyl ester of 2,5-furandicarboxylic acid.Type: GrantFiled: November 10, 2015Date of Patent: August 21, 2018Assignee: Synvina C.V.Inventors: Ana Sofia Vagueiro De Sousa Dias, Benjamin McKay, Victor Peter Charles Vreeken, Johannes Maria Franciscus Sijben
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Patent number: 10030120Abstract: The invention relates to a softener composition containing at least one tetrahydrofurane derivative and at least one 1,2-cyclohexane dicarboxylic acid ester, molding compounds which contain a thermoplastic polymer or an elastomer and said type of softener composition, and to the use of said softener compositions and molding compounds.Type: GrantFiled: December 5, 2014Date of Patent: July 24, 2018Assignee: BASF SEInventors: Jochen Wagner, Boris Breitscheidel, Martin A. Bohn, Benoit Blank, Alois Kindler
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Patent number: 10011579Abstract: 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: May 22, 2017Date of Patent: July 3, 2018Assignee: 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: 10005748Abstract: The present invention relates to a process for producing a water cleavage product, a water cleavage product thus produced, a process for producing at least one water cleavage secondary product, a water cleavage secondary product thus produced and the use of a multi-fluorinated alcohol compound for the extraction of at least one water cleavage product from an aqueous phase.Type: GrantFiled: October 9, 2015Date of Patent: June 26, 2018Assignees: Klaus-Dieter Vorlop, Ulf PruesseInventors: Klaus-Dieter Vorlop, Ulf Prüsse
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Patent number: 9994539Abstract: The disclosure relates to a method for forming 2,5-furan dicarboxylic acid (FDCA) from aldaric acids. The aldaric acids are dehydrating and cyclizing via acid catalysis to form the FDCA product. Aldaric acids such as galactaric acid, gularic acid, mannaric acid, and glucaric acid can be used in the disclosed method, and the aldaric acids can be obtained from form renewable biomass sources which contain pectin, alginate, and/or other biomass carbohydrates. The FDCA can be used as a renewable feedstock for consumer product polymeric materials such as polyalkylene furoate polymers.Type: GrantFiled: July 11, 2017Date of Patent: June 12, 2018Assignee: BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITYInventors: Dennis J. Miller, Lars Peereboom, Evan Wegener, Matthew Gattinger
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Patent number: 9890266Abstract: Plasticizers comprising a dialkyl 2,5-furandicarboxylate and plasticized polymeric compositions comprising such plasticizers. Such plasticized polymeric compositions can be employed in forming various articles of manufacture, such as coated conductors.Type: GrantFiled: May 12, 2014Date of Patent: February 13, 2018Assignee: Dow Global Technologies LLCInventor: Bharat I. Chaudhary