Plural -c(=x)x- Groups Bonded Directly To The Hetero Ring Patents (Class 549/485)
  • Patent number: 11958804
    Abstract: 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: Grant
    Filed: January 7, 2020
    Date of Patent: April 16, 2024
    Assignees: 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 PORTO
    Inventors: Christian Serre, Farid Nouar, José Silva, Alírio Rodrigues, Pedro Brântuas
  • Patent number: 11891370
    Abstract: 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: Grant
    Filed: February 15, 2023
    Date of Patent: February 6, 2024
    Assignee: Stora Enso Ojy
    Inventors: 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
  • Patent number: 11787774
    Abstract: 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: Grant
    Filed: August 25, 2020
    Date of Patent: October 17, 2023
    Assignee: Eastman Chemical Company
    Inventor: Mesfin Ejerssa Janka
  • Patent number: 11708343
    Abstract: 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: Grant
    Filed: July 16, 2021
    Date of Patent: July 25, 2023
    Assignee: KSE, Inc.
    Inventors: James R. Kittrell, Carl R. Dupre, Keith D. Kittrell, Leonard T. McDonald, Jeffrey A. Kittrell
  • Patent number: 11702395
    Abstract: 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: Grant
    Filed: September 10, 2021
    Date of Patent: July 18, 2023
    Assignee: Xiamen University
    Inventors: Xing Tang, Huai Liu, Lu Lin, Xianhai Zeng, Yong Sun
  • Patent number: 11697642
    Abstract: 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: Grant
    Filed: May 28, 2019
    Date of Patent: July 11, 2023
    Assignee: SÜDZUCKER AG
    Inventors: Alireza Haji Begli, Christine Kröner, Waldemar Tschilingiri, Ralf Riemenschnitter, Kay Mantyk
  • Patent number: 11655227
    Abstract: 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: Grant
    Filed: March 22, 2021
    Date of Patent: May 23, 2023
    Assignee: Eastman Chemical Company
    Inventors: Kevin John Fontenot, Mesfin Ejerssa Janka, Kenny Randolph Parker, Ashfaq Shahanawaz Shaikh
  • Patent number: 11613523
    Abstract: 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: Grant
    Filed: November 13, 2020
    Date of Patent: March 28, 2023
    Assignee: Stora Enso Oyj
    Inventors: 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
  • Patent number: 11603361
    Abstract: 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: Grant
    Filed: September 30, 2019
    Date of Patent: March 14, 2023
    Assignee: Nederlandse Organisatie voor toegepastnatuurwetens
    Inventors: Marc Crockatt, Carol Andrea Roa Engel, Cornelis Petrus Marcus Roelands, Johannes Van Der Meer
  • Patent number: 11597709
    Abstract: 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: Grant
    Filed: February 4, 2021
    Date of Patent: March 7, 2023
    Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY
    Inventors: Dong Won Hwang, Young Kyu Hwang, Ma Eum Lee, Pravin Pandharinath Upare, Do Young Hong
  • Patent number: 11578048
    Abstract: 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: Grant
    Filed: April 4, 2019
    Date of Patent: February 14, 2023
    Assignee: ARCHER DANIELS MIDLAND COMPANY
    Inventors: James Brazdil, Donald Rogness
  • Patent number: 11446586
    Abstract: 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: Grant
    Filed: February 11, 2019
    Date of Patent: September 20, 2022
    Assignee: TEKNOLOGIAN TUTKIMUSKESKUS VTT OY
    Inventors: David Thomas, Juha Linnekoski
  • Patent number: 11440895
    Abstract: 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: Grant
    Filed: June 4, 2019
    Date of Patent: September 13, 2022
    Assignee: Eastman Chemical Company
    Inventor: Mesfin Ejerssa Janka
  • Patent number: 11267796
    Abstract: 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: Grant
    Filed: February 28, 2018
    Date of Patent: March 8, 2022
    Assignee: Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek TNO
    Inventors: Marc Crockatt, Roel Johannes Martinus Bisselink, Roman Latsuzbaia, Cornelis Petrus Marcus Roelands, Earl Lawrence Vincent Goetheer
  • Patent number: 11220475
    Abstract: Compounds derived from biomass, e.g., cellulose and lignins, methods of forming such compounds and polymers and products formed using such compounds.
    Type: Grant
    Filed: December 20, 2019
    Date of Patent: January 11, 2022
    Assignee: NDSU RESEARCH FOUNDATION
    Inventors: Mukund P. Sibi, Selvakumar Sermadurai, Nicolas Zimmermann, Eric Serum, Gaoyuan Ma, Ramkumar Moorthy, Krystal Kalliokoski
  • Patent number: 11192872
    Abstract: 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: Grant
    Filed: July 11, 2018
    Date of Patent: December 7, 2021
    Assignee: Stora Enso Oyj
    Inventors: Henricus Johannes Cornelis Den Ouden, Valery Sokolovskii, Thomas R. Boussie, Gary M. Diamond, Eric L. Dias, Guang Zhu, Staffan Torssell, Vincent J. Murphy
  • Patent number: 11104656
    Abstract: 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: Grant
    Filed: December 31, 2018
    Date of Patent: August 31, 2021
    Assignee: Nederlandse Organisatie voor toegepast-natuurwetenschappelijk onderzoek TNO
    Inventors: Carol Andrea Roa Engel, Johannes Van Der Meer, Leonard Ferdinand Gerard Geers, Marc Crockatt
  • Patent number: 11066376
    Abstract: 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: Grant
    Filed: December 18, 2019
    Date of Patent: July 20, 2021
    Assignee: Eastman Chemical Company
    Inventors: Kevin John Fontenot, Mesfin Ejerssa Janka, Kenny Randolph Parker, Ashfaq Shahanawaz Shaikh
  • Patent number: 11028063
    Abstract: 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: Grant
    Filed: July 9, 2020
    Date of Patent: June 8, 2021
    Assignees: DUPONT INDUSTRIAL BIOSCIENCES USA, LLC, ARCHER-DANIELS-MIDLAND COMPANY
    Inventors: Stephen J. Howard, Kristina A. Kreutzer, Bhuma Rajagopalan, Eric R. Sacia, Alexandra Sanborn, Brennan Smith
  • Patent number: 10954207
    Abstract: 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: Grant
    Filed: July 27, 2020
    Date of Patent: March 23, 2021
    Assignee: Eastman Chemical Company
    Inventors: Kevin John Fontenot, Mesfin Ejerssa Janka, Kenny Randolph Parker, Ashfaq Shahanawaz Shaikh
  • Patent number: 10947209
    Abstract: 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: Grant
    Filed: June 29, 2018
    Date of Patent: March 16, 2021
    Assignees: 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
  • Patent number: 10882032
    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: July 22, 2016
    Date of Patent: January 5, 2021
    Assignee: Eastman Chemical Company
    Inventors: 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
  • Patent number: 10865190
    Abstract: 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: Grant
    Filed: June 20, 2019
    Date of Patent: December 15, 2020
    Assignee: E I DU PONT DE NEMOURS AND COMPANY
    Inventors: Pranit S Metkar, Ronnie Ozer, Bhuma Rajagopalan
  • Patent number: 10858332
    Abstract: 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: Grant
    Filed: January 7, 2020
    Date of Patent: December 8, 2020
    Assignee: FAR EASTERN NEW CENTURY CORPORATION
    Inventors: Shu-Wei Liu, Ruey-Fen Liao, Xin-An Lu
  • Patent number: 10851074
    Abstract: 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: Grant
    Filed: April 6, 2020
    Date of Patent: December 1, 2020
    Assignee: Stora Enso Oyj
    Inventors: 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
  • Patent number: 10787748
    Abstract: 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: Grant
    Filed: May 20, 2016
    Date of Patent: September 29, 2020
    Assignee: Avantium Knowledge Centre B.V.
    Inventors: Klaas Jan Pieter Schouten, Jan Cornelis Van Der Waal, Maria Varini, Gerardus Johannes Maria Gruter
  • Patent number: 10723712
    Abstract: 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: Grant
    Filed: September 6, 2019
    Date of Patent: July 28, 2020
    Assignee: Eastman Chemical Company
    Inventors: Kevin John Fontenot, Mesfin Ejerssa Janka, Kenny Randolph Parker, Ashfaq Shahanawaz Shaikh
  • Patent number: 10695755
    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: March 15, 2018
    Date of Patent: June 30, 2020
    Assignee: Eastman Chemical Company
    Inventors: Mesfin Ejerssa Janka, Kenny Randolph Parker, Ashfaq Shahanawaz Shaikh, Lee Reynolds Partin
  • Patent number: 10654819
    Abstract: 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: Grant
    Filed: August 27, 2019
    Date of Patent: May 19, 2020
    Assignee: Stora Enso Oyj
    Inventors: 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
  • Patent number: 10544118
    Abstract: 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: Grant
    Filed: June 4, 2019
    Date of Patent: January 28, 2020
    Assignee: Eastman Chemical Company
    Inventor: Mesfin Ejerssa Janka
  • Patent number: 10538499
    Abstract: 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: Grant
    Filed: April 13, 2016
    Date of Patent: January 21, 2020
    Assignees: DUPONT INDUSTRIAL BIOSCIENCES USA, LLC, ARCHER DANIELS MIDLAND COMPANY
    Inventors: Stephen J. Howard, Kristina A. Kreutzer, Bhuma Rajagopalan, Eric R. Sacia, Alexandra Sanborn, Brennan Smith
  • Patent number: 10526301
    Abstract: 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: Grant
    Filed: May 10, 2019
    Date of Patent: January 7, 2020
    Assignee: Eastman Chemical Company
    Inventors: Kevin John Fontenot, Mesfin Ejerssa Janka, Kenny Randolph Parker, Ashfaq Shahanawaz Shaikh
  • Patent number: 10457657
    Abstract: 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: Grant
    Filed: October 15, 2018
    Date of Patent: October 29, 2019
    Assignees: DUPONT INDUSTRIAL BIOSCIENCES USA, LLC, ARCHER DANIELS MIDLAND COMPANY
    Inventors: Pranit S. Metkar, Ronnie Ozer, Bhuma Rajagopalan
  • Patent number: 10442780
    Abstract: 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: Grant
    Filed: January 31, 2019
    Date of Patent: October 15, 2019
    Assignee: Stora Enso OYJ
    Inventors: 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
  • Patent number: 10421736
    Abstract: 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: Grant
    Filed: March 20, 2018
    Date of Patent: September 24, 2019
    Assignee: Eastman Chemical Company
    Inventors: Kevin John Fontenot, Mesfin Ejerssa Janka, Kenny Randolph Parker, Ashfaq Shahanawaz Shaikh
  • Patent number: 10406454
    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, 2018
    Date of Patent: September 10, 2019
    Assignee: Eastman Chemical Company
    Inventors: Kenny Parker, Mesfin Janka, Ashfaq Shaikh, Lee Partin
  • Patent number: 10385033
    Abstract: 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: Grant
    Filed: July 1, 2016
    Date of Patent: August 20, 2019
    Assignee: BASF SE
    Inventors: Alvaro Gordillo, Holger Werhan, Richard Dehn, Benoit Blank, Joaquim Henrique Teles, Stephan A Schunk, Markus Piepenbrink, Rene Backes, Lei Zhang
  • Patent number: 10350584
    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: April 12, 2016
    Date of Patent: July 16, 2019
    Assignee: Eastman Chemical Company
    Inventors: Kenny Randolph Parker, Mesfin Ejerssa Janka, Ashfaq Shahanawaz Shaikh, Lee Reynolds Partin
  • Patent number: 10344010
    Abstract: 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: Grant
    Filed: December 4, 2017
    Date of Patent: July 9, 2019
    Assignee: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE
    Inventors: Ying-Ting Huang, Jinn-Jong Wong, Jau-Hong Chen
  • Patent number: 10344011
    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: May 4, 2018
    Date of Patent: July 9, 2019
    Assignee: Eastman Chemical Company
    Inventors: Kenny Raldolph Parker, Mesfin Ejerssa Janka
  • Patent number: 10167268
    Abstract: 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: Grant
    Filed: November 10, 2015
    Date of Patent: January 1, 2019
    Assignee: Synvina C.V.
    Inventors: Benjamin McKay, Gerardus Johannes Maria Gruter, Johannes Maria Franciscus Sijben
  • Patent number: 10118908
    Abstract: 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: Grant
    Filed: March 17, 2016
    Date of Patent: November 6, 2018
    Assignee: PURAC BIOCHEM B.V.
    Inventors: Jan Van Krieken, Andre Banier De Haan
  • Patent number: 10087162
    Abstract: 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: Grant
    Filed: November 10, 2015
    Date of Patent: October 2, 2018
    Assignee: Synvina C.V.
    Inventors: Ana Sofia Vagueiro De Sousa Dias, Benjamin McKay, Victor Peter Charles Vreeken, Gerardus Johannes Maria Gruter, Johannes Maria Franciscus Sijben
  • Patent number: 10053442
    Abstract: 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: Grant
    Filed: November 10, 2015
    Date of Patent: August 21, 2018
    Assignee: Synvina C.V.
    Inventors: Ana Sofia Vagueiro De Sousa Dias, Benjamin McKay, Victor Peter Charles Vreeken, Johannes Maria Franciscus Sijben
  • Patent number: 10030120
    Abstract: 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: Grant
    Filed: December 5, 2014
    Date of Patent: July 24, 2018
    Assignee: BASF SE
    Inventors: Jochen Wagner, Boris Breitscheidel, Martin A. Bohn, Benoit Blank, Alois Kindler
  • Patent number: 10011579
    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: May 22, 2017
    Date of Patent: July 3, 2018
    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: 10005748
    Abstract: 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: Grant
    Filed: October 9, 2015
    Date of Patent: June 26, 2018
    Assignees: Klaus-Dieter Vorlop, Ulf Pruesse
    Inventors: Klaus-Dieter Vorlop, Ulf Prüsse
  • Patent number: 9994539
    Abstract: 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: Grant
    Filed: July 11, 2017
    Date of Patent: June 12, 2018
    Assignee: BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITY
    Inventors: Dennis J. Miller, Lars Peereboom, Evan Wegener, Matthew Gattinger
  • Patent number: 9890266
    Abstract: 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: Grant
    Filed: May 12, 2014
    Date of Patent: February 13, 2018
    Assignee: Dow Global Technologies LLC
    Inventor: Bharat I. Chaudhary
  • Patent number: 9676740
    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: January 14, 2016
    Date of Patent: June 13, 2017
    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