Preparation By Degradation Of Carbohydrates Patents (Class 562/515)
  • Patent number: 10821422
    Abstract: In a first aspect, the present invention is directed to a process for forming a metal alloy catalyst. Another aspect of the present invention is directed to a process for oxidizing a substrate that includes contacting a substrate with an oxidant in the presence of a metal alloy catalyst to form one or more carboxylic acids. Suitable substrates include sugars, polyols, furfural alcohols, and polyhydroxycarboxylic acids. The oxidation process may use the alloy catalyst formed from the process of the first aspect of the invention.
    Type: Grant
    Filed: November 17, 2016
    Date of Patent: November 3, 2020
    Assignee: UNIVERSITY OF KANSAS
    Inventors: Raghunath V. Chaudhari, Xin Jin, Bala Subramaniam
  • Patent number: 10807074
    Abstract: Disclosed are catalysts comprised of platinum and gold. The catalysts are generally useful for the selective oxidation of compositions comprised of a primary alcohol group and at least one secondary alcohol group wherein at least the primary alcohol group is converted to a carboxyl group. More particularly, the catalysts are supported catalysts including particles comprising gold and particles comprising platinum, wherein the molar ratio of platinum to gold is in the range of about 100:1 to about 1:4, the platinum is essentially present as Pt(0) and the platinum-containing particles are of a size in the range of about 2 to about 50 nm. Also disclosed are methods for the oxidative chemocatalytic conversion of carbohydrates to carboxylic acids or derivatives thereof. Additionally, methods are disclosed for the selective oxidation of glucose to glucaric acid or derivatives thereof using catalysts comprising platinum and gold. Further, methods are disclosed for the production of such catalysts.
    Type: Grant
    Filed: November 3, 2017
    Date of Patent: October 20, 2020
    Assignee: Archer-Daniels-Midland Company
    Inventors: Vincent J. Murphy, James Shoemaker, Guang Zhu, Raymond Archer, George Frederick Salem, Eric L. Dias
  • Patent number: 10702792
    Abstract: A process for the isolation of levulinic acid obtained by acid catalyzed hydrolysis of a C6-carbohydrate-containing feedstock, including the following steps: a) providing a solution 1 comprising at least 5 wt. % of levulinic acid, at least 0.1 wt. % of formic acid and at most 94.9 wt. % of solvent, relative to the total weight of solution 1, b) feeding solution 1 to a first evaporation step to treat solution 1 and to obtain solution 2, comprising at least 25 wt. % of levulinic acid, less than 20 wt. % of solvent and at least 1 wt. % of formic acid, relative to the total weight of solution 2, c) feeding solution 2 to a second evaporation step to treat solution 2 and to obtain solution 3, comprising at least 30 wt. % of levulinic acid and less than 1.0 wt. % of formic acid, relative to the total weight of solution 3, d) feeding solution 3 to a third evaporation step to treat solution 3 and to obtain levulinic acid with a purity of at least 90 wt. % and containing less than 1000 wppm angelica lactone.
    Type: Grant
    Filed: June 26, 2019
    Date of Patent: July 7, 2020
    Assignee: GFBIOCHEMICALS IP ASSETS B.V.
    Inventors: Aris De Rijke, Rudy Francois Maria Jozef Parton, Donato Santoro
  • Patent number: 10550067
    Abstract: A levulinic acid composition A having: a. at least 95 wt. % of levulinic acid; b. between 5 wppm and 5000 wppm of formic acid; and c. less than 1000 wppm of angelica lactone, based on the total weight of the composition. A process for the isolation of a levulinic acid composition, having the following steps: a. performing acid catalyzed hydrolysis of a C6 carbohydrate-containing feedstock to obtain reaction product X, b. subjecting of reaction product X to solid-liquid separation to provide a composition 1, c. feeding composition 1 to at least two purification steps to treat composition 1 to obtain a levulinic acid composition, wherein a second or a further purification step is a melt crystallization step.
    Type: Grant
    Filed: July 8, 2016
    Date of Patent: February 4, 2020
    Assignee: GFBIOCHEMICALS IP ASSETS B.V.
    Inventors: Rudy Francois Maria Jozef Parton, Aris De Rijke
  • Patent number: 10369492
    Abstract: A process for the isolation of levulinic acid obtained by acid catalyzed hydrolysis of a C6-carbohydrate-containing feedstock, including the following steps: a) providing a solution 1 comprising at least 5 wt. % of levulinic acid, at least 0.1 wt. % of formic acid and at most 94.9 wt. % of solvent, relative to the total weight of solution 1, b) feeding solution 1 to a first evaporation step to treat solution 1 and to obtain solution 2, comprising at least 25 wt. % of levulinic acid, less than 20 wt. % of solvent and at least 1 wt. % of formic acid, relative to the total weight of solution 2, c) feeding solution 2 to a second evaporation step to treat solution 2 and to obtain solution 3, comprising at least 30 wt. % of levulinic acid and less than 1.0 wt. % of formic acid, relative to the total weight of solution 3, d) feeding solution 3 to a third evaporation step to treat solution 3 and to obtain levulinic acid with a purity of at least 90 wt. % and containing less than 1000 wppm angelica lactone.
    Type: Grant
    Filed: July 8, 2016
    Date of Patent: August 6, 2019
    Assignee: GFBIOCHEMICALS IP ASSETS B.V.
    Inventors: Aris De Rijke, Rudy Francois Maria Jozef Parton, Donato Santoro
  • Patent number: 9809773
    Abstract: A methodology for the removal of the harmful components of ash from urban/industrial wastes and sludges from the sewage treatment plants is invented. The harmful components are alkaline metals, chlorine, sulphur, zinc, lead, and chromium. They are removed before the thermochemical conversion and therefore the corrosion problems, scaling/deposition, ash agglomeration, dioxin and furan emissions, alkaline metal, chlorine, sulphur emissions are minimized if not diminished. The emissions of heavy metals such as zinc, lead, copper, and chromium are reduced. The removal is achieved with prepyrolysis/pregasification at 250-320° C. for 5 min to 2 h of urban/industrial wastes and sludges from the sewage treatment plants. Then the prepyrolyzed/pregasified sample is washed with a 0.5%-5% weight basis aqueous calcium acetate and/or magnesium acetate and/or aluminum acetate solution.
    Type: Grant
    Filed: September 9, 2010
    Date of Patent: November 7, 2017
    Assignee: Thermorefinery Technologies LLC
    Inventor: Emmanouil Koukios
  • Patent number: 9695253
    Abstract: Compositions comprising oxidized poly alpha-1,3-glucan compounds are disclosed herein. Oxidized poly alpha-1,3-glucan compounds are produced by contacting poly alpha-1,3-glucan under aqueous conditions with at least one N-oxoammonium salt.
    Type: Grant
    Filed: March 9, 2015
    Date of Patent: July 4, 2017
    Assignee: E I DU PONT DE NEMOURS AND COMPANY
    Inventors: Rakesh Nambiar, Jayme L Paullin, Andrea M Perticone, T Joseph Dennes
  • Patent number: 9682912
    Abstract: Provided is a method for preparing levulinic acid using a solid acid catalyst in the presence of an ethylene glycol-based compound. The levulinic acid according to the present invention can be prepared by using a linear or cyclic ethylene glycol-based compound as a solvent and preparing the levulinic acid from fructose in the presence of the solid acid catalyst at a reaction temperature of 100 to 200° C., thereby reducing the dependency on petroleum in response to greenhouse gas emission regulations. Also, a high yield of levulinic acid can be obtained from fructose, and the solvent and the catalyst can be efficiently separated, collected, and reused after the reaction has completed.
    Type: Grant
    Filed: August 28, 2014
    Date of Patent: June 20, 2017
    Assignee: KOREA INSTITUTE OF INDUSTRIAL TECHNOLOGY
    Inventors: Jin Ku Cho, Sang Yong Kim, Do Hoon Lee, Jae Won Jeong
  • Patent number: 9422216
    Abstract: The present disclosure provides a catalyst for preparing lactic acid and derivatives thereof, comprising at least one of metallic compounds MXn, wherein M is selected from Na, K, Mg, Ca, Sr, Ba, Al, Ga, In, Sn, Sb, Bi, Cr, Mn, Fe, Co, Ni and Zn, and n is an integer of 1 to 6. The present disclosure further provides a method for synthesis of lactic acid and derivatives thereof, wherein at least one raw material including carbohydrates, at least one alcohol, at least one of the aforesaid catalysts and at least one solvent are heated to react to prepare lactic acid and derivatives thereof.
    Type: Grant
    Filed: August 27, 2013
    Date of Patent: August 23, 2016
    Assignee: Microvast Power Systems Co., Ltd
    Inventor: Xiaoping Zhou
  • Patent number: 9346731
    Abstract: A method and integrated system for producing levulinic acid from the sludge of a pulp and paper mill and other lignocellulosic biomass is provided.
    Type: Grant
    Filed: September 16, 2014
    Date of Patent: May 24, 2016
    Assignee: Georgia-Pacific LLC
    Inventors: John Patrick Kelly, Michael Eugene Carroll, Paul Topping
  • Patent number: 9334224
    Abstract: This invention relates to a process for the preparation of alkenoic acid esters comprising contacting a lactone with an alcohol and an acidic catalyst in the gas phase, characterized in that the process is carried out in the presence of at least 0.26 wt. % water, relative to the amount of the lactone. The process may result in a good production yield and selectivity with respect to the production of alkenoic acid esters and may also result in less formation of dialkylethers. The improved yield advantageously allows energy conservation.
    Type: Grant
    Filed: September 21, 2012
    Date of Patent: May 10, 2016
    Assignee: DSM IP ASSETS B.V.
    Inventor: Anna Maria Cornelia Francisca Castelijns
  • Patent number: 9328052
    Abstract: This invention relates to a process for the preparation of alkenoic acid esters comprising contacting a lactone with an alcohol and an acidic heterogeneous catalyst, characterized in that the process is carried out in the presence of at least 20 ppm of an acid having a pKa of 5 or less, relative to the amount of the lactone. The presence of at least 20 ppm of an acid having a pKa of 5 or less may stabilize the catalyst during the reaction and may also be used for reactivating an acidic heterogeneous catalyst. The improved yield advantageously allows energy conservation.
    Type: Grant
    Filed: December 20, 2012
    Date of Patent: May 3, 2016
    Assignee: DSM IP ASSETS B.V.
    Inventor: Anna Maria Cornelia Francisca Castelijns
  • Patent number: 9073841
    Abstract: The invention describes processes to prepare levulinic acid, formic acid and/or hydroxymethyl furfural from various biomass materials.
    Type: Grant
    Filed: March 14, 2013
    Date of Patent: July 7, 2015
    Assignee: SEGETIS, INC.
    Inventors: Brian D. Mullen, Dorie Janine Yontz, Cora M. Leibig
  • Patent number: 9067903
    Abstract: Described is a method to make liquid chemicals. The method includes deconstructing cellulose to yield a product mixture comprising levulinic acid and formic acid, converting the levulinic acid to ?-valerolactone, and converting the ?-valerolactone to pentanoic acid. Alternatively, the ?-valerolactone can be converted to a mixture of n-butenes. The pentanoic acid can be decarboxylated yield 1-butene or ketonized to yield 5-nonanone. The 5-nonanone can be hydrodeoxygenated to yield nonane, or 5-nonanone can be reduced to yield 5-nonanol. The 5-nonanol can be dehydrated to yield nonene, which can be dimerized to yield a mixture of C9 and C18 olefins, which can be hydrogenated to yield a mixture of alkanes.
    Type: Grant
    Filed: December 2, 2013
    Date of Patent: June 30, 2015
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: James A. Dumesic, Juan Carlos Serrano Ruiz, Ryan M. West
  • Patent number: 9012682
    Abstract: The invention relates to a process for transformation of lignocellulosic biomass or cellulose using stable non-zeolitic heterogeneous catalysts that are based on tin and/or antimony, preferably dispersed on a substrate. The use of these catalysts makes it possible to obtain directly lactic acid with high selectivity while limiting the production of oligosaccharides and soluble polymers.
    Type: Grant
    Filed: December 16, 2011
    Date of Patent: April 21, 2015
    Assignee: Centre National de la Recherche Scientifique
    Inventors: Flora Chambon, Nadine Essayem, Franck Rataboul, Catherine Pinel, Amandine Cabiac, Emmanuelle Guillon
  • Publication number: 20150080603
    Abstract: A method and integrated reactor system are provided for producing one or more organic acids, organic acid degradation compounds, and combinations thereof, from various types of biomass, including sludge from a pulp and paper mill.
    Type: Application
    Filed: September 16, 2014
    Publication date: March 19, 2015
    Applicant: Georgia-Pacific LLC
    Inventors: John Patrick Kelly, Michael Eugene Carroll, Paul Topping
  • Publication number: 20150080602
    Abstract: A method and integrated system for producing levulinic acid from the sludge of a pulp and paper mill and other lignocellulosic biomass is provided.
    Type: Application
    Filed: September 16, 2014
    Publication date: March 19, 2015
    Applicant: Georgia-Pacific LLC
    Inventors: John Patrick Kelly, Michael Eugene Carroll, Paul Topping
  • Publication number: 20150052806
    Abstract: A method for producing levulinic acid from lignocellulosic biomass comprising hemicellulose including one or more six carbon chain compound precursors comprises the steps of hydrolyzing the lignocellulosic biomass to form a first phase comprising partially hydrolyzed lignocellulosic biomass including cellulose and lignin and a second phase comprising one or more five carbon chain sugars and one or more six carbon chain sugars from degradation of the hemicellulose, separating the first phase from the second phase, and converting at least a portion of the one or more six carbon chain sugars to levulinic acid.
    Type: Application
    Filed: March 11, 2013
    Publication date: February 26, 2015
    Inventors: William A. Frey, Jeffrey Wayne Brown, John Patrick Kelly, Michael Eugene Carroll, Peter Chester Guion
  • Patent number: 8962867
    Abstract: A method to produce levulinic acid (LA) and gamma-valerolactone (GVL) from biomass-derived cellulose or lignocellulose by selective extraction of LA using GVL and optionally converting the LA so isolated into GVL, with no purifications steps required to yield the GVL.
    Type: Grant
    Filed: December 15, 2011
    Date of Patent: February 24, 2015
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: James A. Dumesic, Stephanie G. Wettstein, David Martin Alonso, Elif Ispir Gurbuz
  • Publication number: 20150045576
    Abstract: Unique methods have been developed to convert saccharides into value-added products such as alkyl lactates, lactic acid, alkyl levulinates, levulinic acid, and optionally alkyl formate esters and/or hydroxymethylfurfural (HMF). Useful catalysts include Lewis acid catalysts and Brønsted acid catalysts including mineral acids, metal halides, immobilized heterogeneous catalysts functionalized with a Brønsted acid group or a Lewis acid group, or combinations thereof. The saccharides are contacted with the catalyst in the presence of various alcohols.
    Type: Application
    Filed: August 6, 2014
    Publication date: February 12, 2015
    Inventors: Herman P. Benecke, Daniel Garbark
  • Publication number: 20140323759
    Abstract: Processes for producing formic acid from a carbohydrate-containing material include hydrolyzing a carbohydrate-containing material (e.g., cellulose) in the presence of a mineral acid to form an intermediate hydrolysate comprising one or more sugars, and hydrolyzing the intermediate hydrolysate to form a hydrolysate product including formic acid.
    Type: Application
    Filed: June 30, 2014
    Publication date: October 30, 2014
    Inventor: Stephen W. Fitzpatrick
  • Publication number: 20140316159
    Abstract: A process is described wherein a feed of a six-carbon carbohydrate-containing material or of a furanic dehydration product from a six-carbon carbohydrate-containing material or of a combination of these is supplied to a reactor in a controlled manner over time up to a desired combined or total feed level, and the feed is acid-hydrolyzed to produce levulinic acid. In certain embodiments, derivatives of the levulinic acid are prepared.
    Type: Application
    Filed: November 28, 2012
    Publication date: October 23, 2014
    Applicant: ARCHER DANIELS MIDLAND COMPANY
    Inventors: Alexandra Sanborn, Thomas Binder
  • Publication number: 20140316158
    Abstract: A method of obtaining an aqueous solution of an alkali acetate from lignocellulose, wherein lignocellulose is treated with a first aqueous extraction solution having a pH value in the range of 12 to 14 and a content of a C1-4 alcohol, in particular ethanol or isopropanol, in the range of 40% to 90%, in particular of from 75% to 85%, whereby a first aqueous solution of an alkali acetate is obtained, and wherein said first solution of an alkali acetate is used to treat additional lignocellulose in order to enrich additional acetate in said first solution.
    Type: Application
    Filed: September 5, 2012
    Publication date: October 23, 2014
    Applicant: Annikki GmbH
    Inventors: Thomas Ters, Karin Fackler, Kurt Messner, Ortwin Ertl
  • Publication number: 20140309454
    Abstract: There are provided methods for the valorization of carbohydrates. The methods comprise reacting a fluid comprising at least one carbohydrate with at least one metal catalyst or at least one metal catalytic system in a fluidized bed reactor so as to obtain at least one organic acid or a derivative thereof.
    Type: Application
    Filed: August 22, 2012
    Publication date: October 16, 2014
    Applicant: POLYVALOR SOCIETE EN COMMANDITE
    Inventors: Gregory Patience, Ali Shekari, Youssef Farrie
  • Patent number: 8835670
    Abstract: A method for synthesis of lactic acid and its derivatives is provided. First, a mixture is prepared, which includes: at least one carbohydrate-containing raw material, at least one alcohol, at least one composite catalyst containing metal chloride(s) (MCln) and tin-containing compound(s), and at least one solvent, wherein M is selected from a group consisting of Li+, Na+ K+, Mg2+, Ca2+, Sr2+, Ga3+, In3+, Sb3+, Bi3+, Cr3+, Mn2+, Fe2+, Co2+, Ni2+, Zn2+, and n represents 1, 2 or 3. Then, the mixture is heated to obtain lactic acid and its derivatives. By using the above catalyst and method, it is capable of converting carbohydrate-containing raw material to lactic acid and its derivatives directly in a more efficient and economical way.
    Type: Grant
    Filed: December 26, 2012
    Date of Patent: September 16, 2014
    Assignee: Microvast Power Systems Co., Ltd.
    Inventors: Xiaoping Zhou, Rui Bi
  • Patent number: 8785683
    Abstract: The present invention generally relates to processes for the chemocatalytic conversion of a pentose source to a glutaric acid product. The present invention includes processes for the conversion of pentose to a glutaric acid product via pentaric acid or derivatives thereof. The present invention also includes processes comprising the catalytic oxidation of pentose to pentaric acid and catalytic hydrodeoxygenation of pentaric acid or derivatives thereof to a glutaric acid product.
    Type: Grant
    Filed: June 11, 2010
    Date of Patent: July 22, 2014
    Assignee: Rennovia, Inc.
    Inventors: Thomas R. Boussie, Eric L. Dias, Zachary M. Fresco, Vincent J. Murphy
  • Publication number: 20140186903
    Abstract: In some variations, the invention provides a process for producing furfural, 5-hydroxymethylfurfural, and/or levulinic acid from cellulosic biomass, comprising: fractionating the feedstock in the presence of a solvent for lignin, sulfur dioxide, and water, to produce a liquor containing hemicellulose, cellulose-rich solids, and lignin; hydrolyzing the hemicellulose contained in the liquor, to produce hemicellulosic monomers; dehydrating the hemicellulose to convert at least a portion of C5 hemicelluloses to furfural and to convert at least a portion of C6 hemicelluloses to 5-hydroxymethylfurfural; converting at least some of the 5-hydroxymethylfurfural to levulinic acid and formic acid; and recovering at least one of the furfural, the 5-hydroxymethylfurfural, or the levulinic acid. Other embodiments provide a process for dehydrating hemicellulose to convert oligomeric C5 hemicelluloses to furfural and to convert oligomeric C6 hemicelluloses to 5-hydroxymethylfurfural.
    Type: Application
    Filed: November 18, 2013
    Publication date: July 3, 2014
    Applicant: API Intellectual Property Holdings, LLC
    Inventors: Theodora RETSINA, Vesa PYLKKANEN, Kimberly NELSON, Ryan O'CONNOR
  • Patent number: 8765998
    Abstract: Processes for producing formic acid from a carbohydrate-containing material include hydrolyzing a carbohydrate-containing material (e.g., cellulose) in the presence of a mineral acid to form an intermediate hydrolysate comprising one or more sugars, and hydrolyzing the intermediate hydrolysate to form a hydrolysate product including formic acid.
    Type: Grant
    Filed: March 16, 2012
    Date of Patent: July 1, 2014
    Assignee: Biofine Technology, LLC
    Inventor: Stephen W. Fitzpatrick
  • Patent number: 8759575
    Abstract: The invention relates to a method for catalytically producing formic acid. A polyoxometallate ion, which is used as a catalyst, of the general formula [PMoxVyO40]5? is brought into contact with an alpha-hydroxyaldehyde, an alpha-hydroxycarboxylic acid, a carbohydrate, or a glycoside in a liquid solution at a temperature below 120° C., wherein 6<x<11, 1<y<6, x+y=12, and x and y are each a whole number.
    Type: Grant
    Filed: August 26, 2011
    Date of Patent: June 24, 2014
    Assignee: JBACH GmbH
    Inventors: Andreas Bösmann, René Wölfel, Peter Wasserscheid, Nicola Taccardi, Jakob Albert
  • Patent number: 8716522
    Abstract: Methods are disclosed for producing, from renewable carbon sources, acetic acid in an economical manner. In particular, these methods are directed to the separation and recovery of acetic acid as a substantial product (e.g., as much as 5% by weight or more) of biomass pyrolysis. For a given commercial biomass pyrolysis unit, the acetic acid yield can represent a significant quantity of that used in a major industrial applications such as purified terephthalic acid (PTA) production. According to some embodiments, pyrolysis conditions and/or flow schemes advantageously improve the recovery of acetic acid for a given purity level.
    Type: Grant
    Filed: December 30, 2010
    Date of Patent: May 6, 2014
    Assignee: UOP LLC
    Inventor: Joseph Anthony Kocal
  • Patent number: 8703450
    Abstract: The present invention relates to a process for the production of polymers, such as water-absorbing polymer structures, by radical polymerization of acrylic acid, whereby the acrylic acid has been obtained by a synthesis process which comprises as a process step the splitting of an organic material by means of an enzyme or at least one component of an enzyme. The invention also relates to the water-absorbing polymers obtainable by this process, water-absorbing polymers which are based to at least about 25 wt % upon partially neutralized acrylic acid, a composite, a process for the production of a composite, the composite obtainable by this production, the use of acrylic acid in the production of polymers, preferably in the production of water-absorbing polymer structures, a device for the production of acrylic acid, and a process for the production of acrylic acid.
    Type: Grant
    Filed: February 28, 2006
    Date of Patent: April 22, 2014
    Assignee: Evonik Degussa GmbH
    Inventors: Günther Bub, Jürgen Mosler, Andreas Sabbagh, Franz-Felix Kuppinger, Franck Furno
  • Patent number: 8679364
    Abstract: The formulation of the current invention provides better deicing and anti-icing performance than commercial acetate-based deicing solutions. The performance is consistently better in all testing categories including melting, penetration, undercutting, and friction. The corrosiveness is similar to commercial deicers, which may include corrosion inhibitors. Chemical analysis reveals that a potassium acetate solution provided by the invention contains formate and lactate in the prepared deicer.
    Type: Grant
    Filed: August 16, 2013
    Date of Patent: March 25, 2014
    Assignee: API Intellectual Property Holdings, LLC
    Inventor: Vesa Pylkkanen
  • Publication number: 20140058130
    Abstract: A method for synthesis of lactic acid and its derivatives is provided. First, a mixture is prepared, which includes: at least one carbohydrate-containing raw material, at least one alcohol, at least one composite catalyst containing metal chloride(s) (MCln) and tin-containing compound(s), and at least one solvent, wherein M is selected from a group consisting of Li+, Na+ K+, Mg2+, Ca2+, Sr2+, Ga3+, In3+, Sb3+, Bi3+, Cr3+, Mn2+, Fe2+, Co2+, Ni2+, Zn2+, and n represents 1, 2 or 3. Then, the mixture is heated to obtain lactic acid and its derivatives. By using the above catalyst and method, it is capable of converting carbohydrate-containing raw material to lactic acid and its derivatives directly in a more efficient and economical way.
    Type: Application
    Filed: December 26, 2012
    Publication date: February 27, 2014
    Applicant: MICROVAST NEW MATERIALS (HUZHOU) CO., LTD.
    Inventor: MICROVAST NEW MATERIALS (HUZHOU) CO., LTD
  • Patent number: 8624058
    Abstract: The invention relates to a process for transformation of lignocellulosic biomass or cellulose that uses tungsten-based heterogeneous catalysts that are dispersed on an oxide-based substrate, preferably with a base of oxide(s) of aluminum and/or zirconium and/or titanium and/or niobium. The use of these catalysts makes it possible to obtain directly lactic acid with high selectivity while limiting the production of oligosaccharides and soluble polymers.
    Type: Grant
    Filed: February 1, 2011
    Date of Patent: January 7, 2014
    Assignees: Centre National de la Recherche Scientifique, IFP Energies nouvelles
    Inventors: Flora Chambon, Nadine Essayem, Franck Rataboul, Catherine Pinel, Amandine Cabiac, Emmanuelle Guillon
  • Patent number: 8624043
    Abstract: Described is a method to make liquid chemicals. The method includes deconstructing cellulose to yield a product mixture comprising levulinic acid and formic acid, converting the levulinic acid to ?-valerolactone, and converting the ?-valerolactone to pentanoic acid. Alternatively, the ?-valerolactone can be converted to a mixture of n-butenes. The pentanoic acid can be decarboxylated yield 1-butene or ketonized to yield 5-nonanone. The 5-nonanone can be hydrodeoxygenated to yield nonane, or 5-nonanone can be reduced to yield 5-nonanol. The 5-nonanol can be dehydrated to yield nonene, which can be dimerized to yield a mixture of C9 and C18 olefins, which can be hydrogenated to yield a mixture of alkanes.
    Type: Grant
    Filed: February 9, 2012
    Date of Patent: January 7, 2014
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: James A. Dumesic, Juan Carlos Serrano Ruiz, Ryan M. West
  • Publication number: 20130338397
    Abstract: A catalyst for synthesis of lactic acid and it derivatives is provided. The catalyst includes SnY2.mH2O and at least one of NH4X or quaternary ammonium salts, wherein X and Y are selected from F—, Cl—, Br—, I—, CH3SO3—, C6H5SO3—, CH3C6H4SO3— or CN—, m represents an integer of 1 to 15. A method for synthesis of lactic acid and it derivatives with the above catalyst is also provided. By using the above catalyst and method, it is capable of converting carbohydrate-containing raw material to lactic acid and its derivatives directly in a more efficient and economical way.
    Type: Application
    Filed: August 27, 2012
    Publication date: December 19, 2013
    Applicant: Microvast New Materials (Huzhou) Co., LTD.
    Inventors: Xiaoping Zhou, Rui Bi
  • Patent number: 8598383
    Abstract: The present invention relates to a pharmaceutical composition useful for treating or preventing inflammatory disease and cell damage, and a method for treating or preventing inflammatory disease and cell damage. The present invention uses the 2-hydroxybenzoic acid derivative represented by the specific chemical formula or its pharmaceutically acceptable salt. The compound of the present invention is useful for treating or preventing cell damage and inflammatory disease including gastritis, gastric ulcer, pancreatitis, colitis, arthritis, diabetes, arteriosclerosis, nephritis, hepatitis, Alzheimer's disease, Parkinson's disease and Lou Gehrig's disease.
    Type: Grant
    Filed: April 23, 2012
    Date of Patent: December 3, 2013
    Assignee: Neurotech Pharmaceuticals Co., Ltd.
    Inventors: Byoung-Joo Gwag, Sung-Ig Cho, Jae-Young Cho, Young-Ae Lee, Han-Yeol Byun, Doo-Soon Lim, Ki-Baik Hahm, Young-Bae Kwon, Jin-Hwan Lee, Bok-Seon Yoon, Chun-San An, Keun-Sil Ryu
  • Publication number: 20130281734
    Abstract: The invention relates to a process for transformation of lignocellulosic biomass or cellulose using stable non-zeolitic heterogeneous catalysts that are based on tin and/or antimony, preferably dispersed on a substrate. The use of these catalysts makes it possible to obtain directly lactic acid with high selectivity while limiting the production of oligosaccharides and soluble polymers.
    Type: Application
    Filed: December 16, 2011
    Publication date: October 24, 2013
    Applicant: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE
    Inventors: Flora Chambon, Nadine Essayem, Franck Rataboul, Catherine Pinel, Amandine Cabiac, Emmanuelle Guillon
  • Publication number: 20130281733
    Abstract: Embodiments of the present invention include methods and compositions related to catabolic conversion of cellulosic biomass to glycolic acid using molybdenum-containing acidic catalysts. The invention includes the use of heteropoly and isopoly acids and salts as the molybdenum-containing multi-functional catalysts for biomass conversion. In embodiments of the invention, the reactions employ successive hydrolysis, retro-aldol fragmentation, and selective oxidation in a noble metal-free system.
    Type: Application
    Filed: April 10, 2013
    Publication date: October 24, 2013
    Applicant: King Abdullah University of Science and Technology
    Inventors: Yu Han, Jizhe Zhang, Xin Liu
  • Patent number: 8530695
    Abstract: The invention relates to a process for the recovery of concentrated high purity formic acid having a concentration of at least 50%, most preferably at least 95%, from biomass wherein an aqueous liquid mixture containing levulinic acid and possibly furfural is subjected to a liquid-liquid extraction step, followed by the recovery of furfural, formic acid and levulinic acid.
    Type: Grant
    Filed: April 21, 2009
    Date of Patent: September 10, 2013
    Assignee: Kemira Oyj
    Inventors: Jarmo Reunanen, Pekka Oinas, Timo Nissinen
  • Publication number: 20130231497
    Abstract: A method for synthesizing lactic acid and lactate is invented from carbohydrates, such as monosaccharides and/or polysaccharides in the presence of the catalyst that is the combinations of nitrogen-heterocycle aromatic ring cation salts and metal compounds. In the reaction, at least one alcohol and at least one solvent are used. Specifically, in the presence of [SnCl4-1-ethyl-3-methylimidazolium chloride ([EMIM]Cl)], SnCl4-1, 3-dimethylimidazolium methyl sulfate ([DMIM] CH3SO4)], [SnCl2-1-ethyl-3-methylimidazolium chloride ([EMIM]Cl)], or SnCl2-1, 3-dimethylimidazolium methyl sulfate ([DMIM] CH3SO4)] in methanol.
    Type: Application
    Filed: November 10, 2011
    Publication date: September 5, 2013
    Applicant: MICROVAST, INC.
    Inventors: Xiaoping Zhou, Jiaruo Huang, Whensheng Li
  • Publication number: 20130204039
    Abstract: A method of producing levulinic acid from biomass is described. The method includes two acid treatment steps: first, treating biomass with a first aqueous acidic solution at a pH, for a time, and temperature such that at least a portion of pentosans contained within the biomass is extracted from the biomass, to yield pentosan-extracted biomass; second, treating the pentosan-extracted biomass with a second aqueous acidic solution at a pH, for a time, and a temperature, such that at least a portion of hexosans contained within the pentosan-extracted biomass are converted to levulinic acid.
    Type: Application
    Filed: February 2, 2012
    Publication date: August 8, 2013
    Inventor: Troy M. Runge
  • Publication number: 20130197183
    Abstract: A process for the production of a complex of lactic acid and either ammonia or an amine, comprising reacting one or more saccharides with barium hydroxide to produce a first reaction mixture comprising barium lactate, and contacting at least part of the first reaction mixture with ammonia or an amine and with carbon dioxide, or with the carbonate and/or bicarbonate salt of ammonia or an amine, to produce a second reaction mixture comprising said complex and barium carbonate.
    Type: Application
    Filed: October 17, 2011
    Publication date: August 1, 2013
    Applicant: Plaxica Limited
    Inventor: Edward Leslie Marshall
  • Patent number: 8492586
    Abstract: Processes for the recovery of formate salt from biomass and the product obtained thereof generally include subjecting an aqueous liquid mixture containing levulinic acid, formic acid and possibly furfural to a liquid-liquid extraction process, followed by the recovery of the furfural, the formate salt and the levulinic acid or the levulinate salt.
    Type: Grant
    Filed: April 21, 2009
    Date of Patent: July 23, 2013
    Assignee: Kemira Oyj
    Inventors: Jarmo Reunanen, Pekka Oinas, Timo Nissinen, Esko Tirronen
  • Patent number: 8399688
    Abstract: 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: Grant
    Filed: April 12, 2012
    Date of Patent: March 19, 2013
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: James A. Dumesic, David Martin Alonso, Elif I. Gürbüz, Stephanie G. Wettstein
  • Patent number: 8389761
    Abstract: A method to produce levulinic acid (LA) and ?-valerolactone (GVL) from biomass-derived cellulose by selective extraction of LA by alkylphenol (AP) and hydrogenation of LA, in which mineral acid used in the method is recycled and the final concentration of GVL is increased by successive extraction/hydrogenation steps to allow for effective separation by distillation.
    Type: Grant
    Filed: May 25, 2011
    Date of Patent: March 5, 2013
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: James Dumesic, Jesse Bond, David Alonso, Thatcher Root
  • Publication number: 20120302767
    Abstract: 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: Application
    Filed: April 12, 2012
    Publication date: November 29, 2012
    Inventors: James A. Dumesic, David Martin Alonso, Elif I. Gürbüz, Stephanie G. Wettstein
  • Publication number: 20120302765
    Abstract: 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: Application
    Filed: May 25, 2011
    Publication date: November 29, 2012
    Inventors: James Dumesic, David Alonso, Jesse Bond, Thatcher Root, Mei Chia
  • Publication number: 20120264908
    Abstract: The present invention generally relates to processes for the conversion of glucose to caprolactam employing chemocatalytic oxidation and reduction reactions. The present invention also includes processes for the conversion of glucose to caprolactam via amido polyhydroxy acid products and amidocaproic acid or derivatives thereof. The present invention also includes processes that catalytically oxidize an amidopolyol to amidopolyhydroxy acid or derivatives thereof, and processes that catalytically hydrodeoxygenate amino or amido polyhydroxy acid or derivatives thereof to an amino or amidocaproic acid product. The amino or amidocaproic acid product may then be converted to caprolactam. The present invention also includes products produced by such processes and products producable from such products.
    Type: Application
    Filed: March 29, 2012
    Publication date: October 18, 2012
    Applicant: Rennovia, Inc.
    Inventors: Vincent J. MURPHY, Eric L. DIAS, James A. W. SHOEMAKER, Thomas R. BOUSSIE, Zachary M. FRESCO
  • Publication number: 20120172625
    Abstract: Processes for producing formic acid from a carbohydrate-containing material include hydrolyzing a carbohydrate-containing material (e.g., cellulose) in the presence of a mineral acid to form an intermediate hydrolysate comprising one or more sugars, and hydrolyzing the intermediate hydrolysate to form a hydrolysate product including formic acid.
    Type: Application
    Filed: March 16, 2012
    Publication date: July 5, 2012
    Inventor: Stephen W. Fitzpatrick