Preparing By Hydrogenation Of Furfural Patents (Class 549/503)
-
Patent number: 11628422Abstract: Disclosed are a catalyst including copper (Cu) particles having specific properties as an active metal dispersed and supported on an alumina support, a method of preparing the same, and a method of hydrogenating furan-based compounds such as 5-(hydroxymethyl)furfural (HMF) derived from biomass with a high selective conversion and high efficiency using the catalyst.Type: GrantFiled: November 12, 2020Date of Patent: April 18, 2023Assignee: IUCF-HYU (INDUSTRY-UNIVERSITY COOPERATION FOUNDATION HANYANG UNIVERSITY)Inventors: Young Woong Suh, Jin Sung Kim
-
Patent number: 11548863Abstract: The present invention relates to a method for the production of 5-hydroxymethylfurfural (HMF), which converts a fructose-containing component using a catalyst system comprising a solution of a salt and acid mixture at a temperature of 90 to 200° C. and leads to obtaining an HMF-containing product mixture, wherein advantageously a high HMF selectivity with significantly lower by-product formation is achieved at the same time.Type: GrantFiled: May 28, 2019Date of Patent: January 10, 2023Assignee: SÜDZUCKER AGInventors: Alireza Haji Begli, Christine Kröner, Kay Mantyk, Ralf Riemenschnitter
-
Patent number: 10493438Abstract: A process for purifying an olefin-containing hydrocarbon feedstock comprising the steps of: (a) passing the said hydrocarbon feedstock in the presence of hydrogen over a first catalyst bed material comprising nickel deposited on a support material wherein said nickel is present as both nickel oxide and metallic nickel (b) recovering the feedstock having a substantially reduced acetylenics (in particular methylacetylene) and allenes (in particular propadiene) content.Type: GrantFiled: December 22, 2009Date of Patent: December 3, 2019Assignee: TOTAL RESEARCH & TECHNOLOGY FELUYInventors: William J. Gauthier, Olivier Miserque, George Vulpescu, Francine Genin, Kai Hortmann, Jean-Pierre Dath
-
Patent number: 9428479Abstract: Biomass feedstocks (e.g., plant biomass, animal biomass, and municipal waste biomass) are processed to produce useful products, such as fuels. For example, systems are described that can convert feedstock materials to a sugar solution, especially, xylose, which can then be chemically converted to furfural and furfural-derived products.Type: GrantFiled: July 3, 2013Date of Patent: August 30, 2016Assignee: Xyleco, Inc.Inventors: Marshall Medoff, Thomas Craig Masterman, Christopher Cooper, Jihan Khan
-
Publication number: 20140256966Abstract: A method for stabilizing a metal or metal-containing particle supported on a surface is described, along with the resulting composition of matter. The method includes the steps of depositing upon the surface a protective thin film of a material of sufficient thickness to overcoat the metal or metal-containing particle and the surface, thereby yielding an armored surface; and then calcining the armored surface for a time and at a temperature sufficient to form channels in the protective thin film, wherein the channels so formed expose a portion of the metal- or metal-containing particle to the surrounding environment. Also described is a method of performing a heterogeneous catalytic reaction using the stabilized, supported catalyst.Type: ApplicationFiled: March 8, 2013Publication date: September 11, 2014Applicant: Wisconsin Alumni Research FoundationInventors: James A. Dumesic, Brandon J. O'Neill
-
Patent number: 8742144Abstract: A method of reducing hydroxymethylfurfural (HMF) where a starting material containing HMF in a solvent comprising water is provided. H2 is provided into the reactor and the starting material is contacted with a catalyst containing at least one metal selected from Ni, Co, Cu, Pd, Pt, Ru, Ir, Re and Rh, at a temperature of less than or equal to 250° C. A method of hydrogenating HMF includes providing an aqueous solution containing HMF and fructose. H2 and a hydrogenation catalyst are provided. The HMF is selectively hydrogenated relative to the fructose at a temperature at or above 30° C. A method of producing tetrahydrofuran dimethanol (THFDM) includes providing a continuous flow reactor having first and second catalysts and providing a feed comprising HMF into the reactor. The feed is contacted with the first catalyst to produce furan dimethanol (FDM) which is contacted with the second catalyst to produce THFDM.Type: GrantFiled: June 30, 2011Date of Patent: June 3, 2014Assignee: Battelle Memorial InstituteInventors: Michael A. Lilga, Richard T. Hallen, James F. White, Michel J. Gray
-
Publication number: 20140011248Abstract: Biomass feedstocks (e.g., plant biomass, animal biomass, and municipal waste biomass) are processed to produce useful products, such as fuels. For example, systems are described that can convert feedstock materials to a sugar solution, especially, xylose, which can then be chemically converted to furfural and furfural-derived products.Type: ApplicationFiled: July 3, 2013Publication date: January 9, 2014Inventors: Marshall Medoff, Thomas Craig Masterman, Christopher Cooper, Jihan Khan
-
Patent number: 8604225Abstract: The present invention relates to a method of producing 5-hydroxymethylfurfural by dehydration of fructose and/or glucose and/or mannose.Type: GrantFiled: April 7, 2011Date of Patent: December 10, 2013Assignee: Novozymes, A/SInventors: Sven Pedersen, Troels B. Christensen, Astrid Boisen, Vibeke W. Jurgensen, Thomas S. Hansen, Soeren Kegnaes, Anders Riisager, John M. Woodley, Jacob S. Jensen, Wenjing Fu
-
Patent number: 8399688Abstract: A method to make levulinic acid (LA), furfural, or gamma-valerolactone (GVL). React cellulose (and/or other C6 carbohydrates) or xylose (and/or other C5 carbohydrates) or combinations thereof in a monophasic reaction medium comprising GVL and an acid; or (ii) a biphasic reaction system comprising an organic layer comprising GVL, and a substantially immiscible aqueous layer. At least a portion of the cellulose (and/or other C6 carbohydrates), if present, is converted to LA and at least a portion of the xylose (and/or other C5 carbohydrates), if present, is converted into furfural.Type: GrantFiled: April 12, 2012Date of Patent: March 19, 2013Assignee: Wisconsin Alumni Research FoundationInventors: James A. Dumesic, David Martin Alonso, Elif I. Gürbüz, Stephanie G. Wettstein
-
Patent number: 8389749Abstract: Described is a catalytic process for converting biomass to furan derivatives (e.g., furfural, furfuryl alcohol, etc.) using a biphasic reactor containing a reactive aqueous phase and an organic extracting phase containing an alkylphenol. The process provides a cost-effective route for producing furfural, furfuryl alcohol, levulinic acid hydroxymethylfurfural, ?-valerolactone, and the like. The products formed are useful as value-added intermediates to produce polymers, as precursors to diesel fuel, and as fuel additives.Type: GrantFiled: May 25, 2011Date of Patent: March 5, 2013Assignee: Wisconsin Alumni Research FoundationInventors: James Dumesic, David Alonso, Jesse Bond, Thatcher Root, Mei Chia
-
Patent number: 8367851Abstract: A method of reducing hydroxymethylfurfural (HMF) where a starting material containing HMF in a solvent comprising water is provided. H2 is provided into the reactor and the starting material is contacted with a catalyst containing at least one metal selected from Ni, Co, Cu, Pd, Pt, Ru, Ir, Re and Rh, at a temperature of less than or equal to 250° C. A method of hydrogenating HMF includes providing an aqueous solution containing HMF and fructose. H2 and a hydrogenation catalyst are provided. The HMF is selectively hydrogenated relative to the fructose at a temperature at or above 30° C. A method of producing tetrahydrofuran dimethanol (THFDM) includes providing a continuous flow reactor having first and second catalysts and providing a feed comprising HMF into the reactor. The feed is contacted with the first catalyst to produce furan dimethanol (FDM) which is contacted with the second catalyst to produce THFDM.Type: GrantFiled: June 30, 2011Date of Patent: February 5, 2013Assignee: Battelle Memorial InstituteInventors: Michael A. Lilga, Richard T. Hallen, James F. White, Michel J. Gray
-
Publication number: 20120302767Abstract: A method to make levulinic acid (LA), furfural, or gamma-valerolactone (GVL). React cellulose (and/or other C6 carbohydrates) or xylose (and/or other C5 carbohydrates) or combinations thereof in a monophasic reaction medium comprising GVL and an acid; or (ii) a biphasic reaction system comprising an organic layer comprising GVL, and a substantially immiscible aqueous layer. At least a portion of the cellulose (and/or other C6 carbohydrates), if present, is converted to LA and at least a portion of the xylose (and/or other C5 carbohydrates), if present, is converted into furfural.Type: ApplicationFiled: April 12, 2012Publication date: November 29, 2012Inventors: James A. Dumesic, David Martin Alonso, Elif I. Gürbüz, Stephanie G. Wettstein
-
Publication number: 20120302765Abstract: Described is a catalytic process for converting biomass to furan derivatives (e.g., furfural, furfuryl alcohol, etc.) using a biphasic reactor containing a reactive aqueous phase and an organic extracting phase containing an alkylphenol. The process provides a cost-effective route for producing furfural, furfuryl alcohol, levulinic acid hydroxymethylfurfural, ?-valerolactone, and the like. The products formed are useful as value-added intermediates to produce polymers, as precursors to diesel fuel, and as fuel additives.Type: ApplicationFiled: May 25, 2011Publication date: November 29, 2012Inventors: James Dumesic, David Alonso, Jesse Bond, Thatcher Root, Mei Chia
-
Publication number: 20110257419Abstract: A method of reducing hydroxymethylfurfural (HMF) where a starting material containing HMF in a solvent comprising water is provided. H2 is provided into the reactor and the starting material is contacted with a catalyst containing at least one metal selected from Ni, Co, Cu, Pd, Pt, Ru, Ir, Re and Rh, at a temperature of less than or equal to 250° C. A method of hydrogenating HMF includes providing an aqueous solution containing HMF and fructose. H2 and a hydrogenation catalyst are provided. The HMF is selectively hydrogenated relative to the fructose at a temperature at or above 30° C. A method of producing tetrahydrofuran dimethanol (THFDM) includes providing a continuous flow reactor having first and second catalysts and providing a feed comprising HMF into the reactor. The feed is contacted with the first catalyst to produce furan dimethanol (FDM) which is contacted with the second catalyst to produce THFDM.Type: ApplicationFiled: June 30, 2011Publication date: October 20, 2011Inventors: Michael A. Lilga, Richard T. Hallen, Todd A. Werpy, James F. White, Johnathan E. Holladay, John G. Frye, JR., Alan H. Zacher
-
Publication number: 20110201820Abstract: Disclosed is a practical method for efficiently producing an alcohol compound by hydrogenating an aldehyde by using a homogeneous copper catalyst which is an easily-available low-cost metal species. Specifically disclosed is a method for producing an alcohol compound, which is characterized in that a hydrogenation reaction of an aldehyde compound is performed in the presence of a homogeneous copper catalyst, a monophosphine compound and an alcohol selected from the group consisting of primary alcohols, secondary alcohols and mixtures of those.Type: ApplicationFiled: December 11, 2008Publication date: August 18, 2011Applicant: TAKASAGO INTERNATIONAL CORPORATIONInventor: Hideo Shimizu
-
Patent number: 7994347Abstract: A method of reducing hydroxymethylfurfural (HMF) where a starting material containing HMF in a solvent comprising water is provided. H2 is provided into the reactor and the starting material is contacted with a catalyst containing at least one metal selected from Ni, Co, Cu, Pd, Pt, Ru, Ir, Re and Rh, at a temperature of less than or equal to 250° C. A method of hydrogenating HMF includes providing an aqueous solution containing HMF and fructose. H2 and a hydrogenation catalyst are provided. The HMF is selectively hydrogenated relative to the fructose at a temperature at or above 30° C. A method of producing tetrahydrofuran dimethanol (THFDM) includes providing a continuous flow reactor having first and second catalysts and providing a feed comprising HMF into the reactor. The feed is contacted with the first catalyst to produce furan dimethanol (FDM) which is contacted with the second catalyst to produce THFDM.Type: GrantFiled: June 8, 2007Date of Patent: August 9, 2011Assignee: Battelle Memorial InstituteInventors: Michael A. Lilga, Richard T. Hallen, Todd A. Werpy, James F. White, Johnathan E. Holladay, John G. Frye, Jr., Alan H. Zacher
-
Publication number: 20100137615Abstract: Provide that a useful catalyst for homogeneous hydrogenation, particularly a catalyst for homogeneous asymmetric hydrogenation for hydrogenation, particularly asymmetric hydrogenation, which is obtainable with comparative ease and is excellent in economically and workability, and a process for producing a hydrogenated compound of an unsaturated compound, particularly an optically active compound using said catalyst with a high yield and optical purity.Type: ApplicationFiled: February 9, 2010Publication date: June 3, 2010Applicant: Takasago International CorporationInventors: Hideo SHIMIZU, Daisuke Igarashi, Wataru Kuriyama, Yukinori Yusa
-
Patent number: 7579490Abstract: A method of preparing 2,5-bis(hydroxymethyl)tetrahydrofuran comprises heating a reaction mixture comprising 2,5-(hydroxymethyl)furaldehyde, an organic solvent, and a catalyst system comprising nickel and zirconium at a temperature, for a time, and at a pressure sufficient to promote reduction of the 2,5-(hydroxymethyl)furaldehyde to 2,5-bis(hydroxymethyl)tetrahydrofuran to produce a product mixture comprising 2,5-bis(hydroxymethyl)tetrahydrofuran.Type: GrantFiled: November 15, 2005Date of Patent: August 25, 2009Assignee: Archer-Daniels-Midland CompanyInventors: Alexandra J. Sanborn, Paul D. Bloom
-
Patent number: 7015359Abstract: The present invention provides a catalytic process for the synthesis of furfuryl alcohol and cyclohexanone simultaneously over a copper based catalyst in vapour phase conditions by hydrogenation of furfural and dehydrogenation of cyclohexanol respectively.Type: GrantFiled: December 23, 2004Date of Patent: March 21, 2006Assignee: Council of Scientific and Industrial ResearchInventors: Kamaraju Seetha Rama Rao, David Raju Burri, Narayanan Sankarasubbier, Mallanna Nagaraja Bhari, Hari Padmasri Aytam, Sivakumar Vasireddy, Shashikala Veldurthi, Seetharamulu Podila, Sanapureddy Sreevardhan Reddy
-
Patent number: 6852868Abstract: Processes are disclosed for the preparation of 2-methylfuran and 2-methyltetrahydrofuran. The continuous vapor-phase processes are commercially viable and efficient because they permit the preparation of 2-methylfuran and 2-methyltetrahydrofuran using commercially-available catalysts, namely, a reduced copper-based catalyst consisting essentially of cupric oxide, chromium (III) oxide, manganese oxide and barium chromate and a reduced nickel-based catalyst consisting essentially of nickel, nickel (II) oxide, aluminum oxide and silica. An apparatus comprising two inline hydrogenators is used for preparing the 2-methylfuran or 2-methyltetrahydrofuran.Type: GrantFiled: August 21, 2002Date of Patent: February 8, 2005Assignee: Pure Energy CorporationInventor: Irshad Ahmed
-
Patent number: 6600078Abstract: A heterogeneous liquid-phase process for the hydrogenation of aldehydes of Formula (I) and (III) to the corresponding alcohols of Formula (II) and (IV) which process comprises contacting alcoholic or aqueous-alcoholic solution of aldehydes and hydrogen gas with a catalyst comprising a reduced mixture of CuO and ZnO in presence of a metal of group IIIA of the Periodic Table, such as aluminium, as a promoter at a temperature of between about 110° and 180° C. and a pressure of between about 20 and 500 psig.Type: GrantFiled: August 12, 2002Date of Patent: July 29, 2003Assignee: Saudi Basic Industries CorporationInventors: Meftahuddin Mahmud, Ahmad Kamal Faizi, Vidyasagar Anchoori, Abdullah Al-Qahtani
-
Patent number: 6054627Abstract: Disclosed are catalysts in powdered form comprising a major amount of the oxides of a first metal selected from copper or zinc, a second metal selected from chromium, molybdenum, tungsten and vanadium, and optionally, a minor amount of the oxide of a promoter metal selected from the group consisting of manganese, barium, zinc, nickel, cobalt, cadmium, iron and any combination thereof provided that the promoter metal is not zinc if the first metal is zinc, wherein the average particle diameter of the powder is from about 6 to about 20 microns; and the particle surface area is from about 20 to about 70 m.sup.2 /g. Also disclosed is a process for preparing such catalysts and a process for hydrogenating aldehydes, ketones, carboxylic acids and carboxylic acid esters with catalysts of the type described.Type: GrantFiled: May 27, 1992Date of Patent: April 25, 2000Assignee: Engelhard CorporationInventors: Deepak S. Thakur, Eugene Palka, Thomas I. Sullivan, Eugene Nebesh, Brian D. Roberts
-
Patent number: 5691362Abstract: Compounds represented by the structural formula ##STR1## or a pharmaceutically acceptable salt thereof, wherein the variables are as defined in the specification; methods of treating asthma, cough, bronchospasm, inflammatory diseases, and gastrointestinal disorders with said compounds, and pharmaceutical compositions comprising said compounds are disclosed.Type: GrantFiled: June 5, 1996Date of Patent: November 25, 1997Assignee: Schering-Plough CorporationInventors: Kevin D. McCormick, Andrew T. Lupo, Jr.
-
Patent number: 5591873Abstract: A formed copper catalyst for the hydrogenation of organic compounds is disclosed, especially for the selective hydrogenation of furfural to furfuryl alcohol. The catalyst contains an intimate mixture of a pyrogenic silica, reduced copper and, optionally, a basic oxide as promotor. The catalyst is distinguished by a high specific catalytic activity, selectivities and yields.Type: GrantFiled: February 1, 1995Date of Patent: January 7, 1997Assignee: Degussa AktiengesellschaftInventors: Martin Bankmann, Johannes Ohmer, Thomas Tacke
-
Patent number: 5345005Abstract: In one embodiment, the invention relates to a catalyst in powdered form which comprises a major amount of the oxides of copper and zinc, and a minor amount of aluminum oxide wherein the pore volume of pores of said catalysts having a diameter between about 120 and about 1000 .ANG. is at least about 40% of the total pore volume. In another embodiment, the invention relates to a process for preparing hydrogenation catalysts comprising the oxides of copper, zinc and aluminum which comprises the steps of(A) preparing a first aqueous solution containing at least one water-soluble copper salt and at least one water-soluble zinc salt;(B) preparing a second solution containing at least one water-soluble basic aluminum salt and at least one alkaline precipitating agent;(C) mixing the first and second solutions whereby an insoluble solid is formed;(D) recovering the insoluble solid.Type: GrantFiled: September 18, 1992Date of Patent: September 6, 1994Assignee: Engelhard CorporationInventors: Deepak S. Thakur, Brian L. Roberts, Thomas J. Sullivan, Anita L. Vichek
-
Patent number: 5198592Abstract: The invention concerns a method of performing a chemical reaction in which hydrogenation and/or dehydrogenation occurs, in the presence of a supported catalyst comprising a carrier material with copper as active component and iron as a promotor. According to the invention, the proporation of iron, calculated on the amount of copper and iron jointly, on an atomic basis, is no more than 25%. The invention also relates to a catalyst for carrying out the reaction, and to a process for preparing a supported catalyst.Type: GrantFiled: October 15, 1990Date of Patent: March 30, 1993Assignee: Engelhard De Meern B.V.Inventors: Johannes van Beijnum, Adrianus J. van Dillen, John W. Geus
-
Patent number: 4728671Abstract: The present invention relates to a process for producing alcohols comprising hydrogenating compounds selected from the group consisting of acids, esters and aldehydes under sufficient hydrogen pressure and temperature in the presence of a catalyst comprising a copper chromite first component and a second component consisting essentially of copper deposited on a support.Type: GrantFiled: April 25, 1985Date of Patent: March 1, 1988Assignee: Oleofina, S.A.Inventor: Herve Hinnekens
-
Patent number: 4626604Abstract: A continuous multi-stage hydrogenation process is described.This is effected in at least three catalytic stages connected in series. All stages up to and including the penultimate stage are operated adiabatically and in the vapor phase. Aldehyde (or other unsaturated organic compound) is fed to all stages up to and including the penultimate stage. The rate of supply of the aldehyde or other unsaturated organic compound to the penultimate stage is controlled in relation to the catalyst volume in the penultimate catalytic stage so that the degree of hydrogenation in that stage is less than 100%. The remaining chemically unsaturated material in the product mixture from the penultimate stage is hydrogenated, after cooling that product mixture, in the final catalytic stage to produce a substantially completely hydrogenated product mixture. In this way the dwell time of the reactants and product(s) at "hot spot" temperatures is minimized, thus reducing byproduct formation.Type: GrantFiled: September 11, 1985Date of Patent: December 2, 1986Assignee: Davy McKee (London) LimitedInventors: Andrew G. Hiles, John E. Logsdon
-
Patent number: H918Abstract: Carbohydrates, especially aldose or ketose sugars, including those whose carbonyl group is masked by hemi-acetal or hemi-ketal formation, are decarbonylated by heating the feed carbohydrate together with a transition metal complex in a suitable solvent. Also, primary alcohols, including sugar alditols are simultaneously dehydrogenated and decarbonylated by heating a mixture of rhodium and ruthenium complexes and the alcohol and optionally a hydrogen acceptor in an acceptable solvent. Such defarbonylation and/or dehydrogenation of sugars provides a convenient procedure for the synthesis of certain carbohydrates and may provide a means for the conversion of biomass into useful products.Type: GrantFiled: October 5, 1988Date of Patent: May 7, 1991Assignee: The United States of America as represented by the United States Department of EnergyInventors: Mark A. Andrews, Stephen A. Klaeren