Preparation By Degradation Of Carbohydrates Patents (Class 562/515)
  • Patent number: 8148553
    Abstract: Described is a method to make liquid chemicals, such as functional intermediates, solvents, and liquid fuels from biomass-derived cellulose. The method is cascading; the product stream from an upstream reaction can be used as the feedstock in the next downstream reaction. The method includes the steps of 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 so formed can be further reacted to yield a host of valuable products. For example, 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.
    Type: Grant
    Filed: June 23, 2009
    Date of Patent: April 3, 2012
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: James A. Dumesic, Juan Carlos Serrano Ruiz, Ryan M. West
  • Patent number: 8138371
    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 11, 2009
    Date of Patent: March 20, 2012
    Assignee: Biofine Technologies LLC
    Inventor: Stephen W. Fitzpatrick
  • Publication number: 20120035356
    Abstract: Compositions which inhibit corrosion and alter the physical properties of concrete (admixtures) are prepared from salt mixtures of hydroxycarboxylic acids, carboxylic acids, and nitric acid. The salt mixtures are prepared by neutralizing acid product mixtures from the oxidation of polyols using nitric acid and oxygen as the oxidizing agents. Nitric acid is removed from the hydroxycarboxylic acids by evaporation and diffusion dialysis.
    Type: Application
    Filed: October 20, 2011
    Publication date: February 9, 2012
    Inventors: Donald E. Kiely, Kirk R. Hash, Kylie Kramer-Presta, Tyler Smith
  • Publication number: 20110277378
    Abstract: A process for liquefying a cellulosic material to produce a liquefied product from cellulosic material is provided. Products obtained from such process and use of such products to prepare biofuels is also provided.
    Type: Application
    Filed: May 12, 2011
    Publication date: November 17, 2011
    Applicant: SHELL OIL COMPANY
    Inventors: Klaas Lambertus VON HEBEL, Jean-Paul LANGE
  • Patent number: 8058458
    Abstract: A method for utilizing an industrially convenient fructose source for a dehydration reaction converting a carbohydrate to a furan derivative is provided. Recovery methods also are provided. Embodiments of the methods improve upon the known methods of producing furan derivatives.
    Type: Grant
    Filed: July 13, 2009
    Date of Patent: November 15, 2011
    Assignee: Archer Daniels Midland Company
    Inventor: Alexandra J. Sanborn
  • Patent number: 7938981
    Abstract: A composition for deicing or for the preparation of a heat transfer fluid is provided. The composition comprises a mixture of at least two carboxylic acid salts having a t/c ratio of 2 or lower, including a dicarboxylic salt and a monocarboxylic salt, said dicarboxylic salt being present in the mixture in an amount of at least 50 wt % of the weight of the mixture, on a dry basis. More particularly, said mixture is including a succinate and a formate, wherein the succinate is in an amount of at least 50 wt %, on a dry basis. Also provided is a method for deicing a surface or preventing the accumulation of ice, snow or a mixture thereof on a surface, comprising a step of applying on a surface covered by ice, snow or a mixture thereof, or susceptible of being covered by ice, snow or a mixture thereof, the above composition. The composition is also useful for the preparation of a heat transfer fluid coolant to be used in a heat transfer system comprising a heat transfer fluid provided with a cooling system.
    Type: Grant
    Filed: September 24, 2010
    Date of Patent: May 10, 2011
    Assignee: Bioamber S.A.S.
    Inventors: Dilum Dunuwila, Roger L. Bernier
  • Publication number: 20110098490
    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: Application
    Filed: April 21, 2009
    Publication date: April 28, 2011
    Applicant: KEMIRA OYJ
    Inventors: Jarmo Reunanen, Pekka Oinas, Timo Nissinen, Esko Tirronen
  • Publication number: 20100324310
    Abstract: Described is a method to make liquid chemicals, such as functional intermediates, solvents, and liquid fuels from biomass-derived cellulose. The method is cascading; the product stream from an upstream reaction can be used as the feedstock in the next downstream reaction. The method includes the steps of 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 so formed can be further reacted to yield a host of valuable products. For example, 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.
    Type: Application
    Filed: June 23, 2009
    Publication date: December 23, 2010
    Inventors: James A. Dumesic, Juan Carlos Serrano Ruiz, Ryan M. West
  • Publication number: 20100317822
    Abstract: The present invention generally relates to processes for the chemocatalytic conversion of a carbohydrate source to an adipic acid product. The present invention includes processes for the conversion of a carbohydrate source to an adipic acid product via a furanic substrate, such as 2,5-furandicarboxylic acid or derivatives thereof. The present invention also includes processes for producing an adipic acid product comprising the catalytic hydrogenation of a furanic substrate to produce a tetrahydrofuranic substrate and the catalytic hydrodeoxygenation of at least a portion of the tetrahydrofuranic substrate to an adipic acid product. The present invention also includes products produced from adipic acid product and processes for the production thereof from such adipic acid product.
    Type: Application
    Filed: June 11, 2010
    Publication date: December 16, 2010
    Applicant: RENNOVIA, INC.
    Inventors: Thomas R. Boussie, Eric L. Dias, Zachary M. Fresco, Vincent J. Murphy
  • Patent number: 7838700
    Abstract: A process for the recovery of substituted tartaric acid resolving agents from resolution process liquors comprising organic solvents, wherein the substituted tartaric acid derivatives are neutralised by adding a base, extracted into an aqueous phase and crystallized from the aqueous phase by addition of a mineral acid in the presence of an organic solvent.
    Type: Grant
    Filed: November 8, 2002
    Date of Patent: November 23, 2010
    Assignee: Aesica Pharmaceuticals
    Inventors: Steve Martin, Daniele Piergentili
  • Publication number: 20100234638
    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 11, 2009
    Publication date: September 16, 2010
    Inventor: Stephen W. Fitzpatrick
  • Patent number: 7723540
    Abstract: The object is to provide a method and apparatus for producing a polyhydroxy carboxylic acid according to which an annular dimer can be efficiently obtained in the production of polyhydroxy carboxylic acid which is small in distribution breadth of molecular weight in depolymerization and opening ring polymerization steps. There are provided a depolymerization device 11 which depolymerizes hydroxy carboxylic acid or a polycondensate thereof into an annular dimer, a upper distillation column 13 which condenses the annular dimer vaporized in the depolymerization device 11, and lower distillation column 12 which refluxes the annular dimer and is provided between the depolymerization device 11 and the upper distillation column 13, said depolymerization device 11 having a polycondensate feed opening 54 and an annular dimer discharge opening 55 which are provided at a casing 50, a liquid film being formed inside the casing 50 and heated by a heating part.
    Type: Grant
    Filed: June 28, 2007
    Date of Patent: May 25, 2010
    Assignee: Hitachi Plant Technologies, Ltd.
    Inventors: Masayuki Kamikawa, Toshiaki Matsuo, Kenichiro Oka, Naruyasu Okamoto, Ryuji Kaziya
  • Publication number: 20100121096
    Abstract: A process for the production of lactic acid and 2-hydroxy-3-butenoic acid or esters thereof by conversion of glucose, fructose, sucrose, xylose and glycolaldehyde dissolved in a solvent in presence of a solid Lewis acidic catalyst.
    Type: Application
    Filed: November 6, 2009
    Publication date: May 13, 2010
    Inventors: Esben Taarning, Saravanamurugan Shunmugavel, Martin Spangsberg Holm
  • Patent number: 7692041
    Abstract: A controlled nitric acid process employing oxygen and nitric acid as co-oxidants is used to oxidize organic compounds subject to nitric acid oxidation, to their corresponding carboxylic acids. Oxidation of some carbohydrates by this process can produce one or more of their corresponding acid forms. The process is carried out at moderate temperatures, typically in the range of 20° C. to 45° C. in a closed reactor, with oxygen gas being introduced into the reaction chamber as needed in order to sustain the reaction. Computer controlled reactors allow for careful and reproducible control of reaction parameters. Nitric acid can be recovered by a distillation/evaporation process, or by diffusion dialysis, the aqueous solution made basic with inorganic hydroxide, and the residual inorganic nitrate removed using a filtration (nanofiltration) device.
    Type: Grant
    Filed: August 6, 2007
    Date of Patent: April 6, 2010
    Assignee: The University of Montana
    Inventors: Donald E. Kiely, Kirk R. Hash, Sr.
  • Publication number: 20090281338
    Abstract: A method for utilizing an industrially convenient fructose source for a dehydration reaction converting a carbohydrate to a furan derivative is provided. Recovery methods also are provided. Embodiments of the methods improve upon the known methods of producing furan derivatives.
    Type: Application
    Filed: July 13, 2009
    Publication date: November 12, 2009
    Inventor: Alexandra J. Sanborn
  • Patent number: 7579489
    Abstract: A method for utilizing an industrially convenient fructose source for a dehydration reaction converting a carbohydrate to a furan derivative is provided. Recovery methods also are provided. Embodiments of the methods improve upon the known methods of producing furan derivatives.
    Type: Grant
    Filed: September 28, 2007
    Date of Patent: August 25, 2009
    Assignee: Archer-Daniels-Midland Company
    Inventor: Alexandra J. Sanborn
  • Publication number: 20090156841
    Abstract: A method of producing substantially pure HMF, HMF esters and other derivatives from a carbohydrate source by contacting the carbohydrate source with a solid phase catalyst. A carbohydrate starting material is heated in a solvent in a column and continuously flowed through a solid phase catalyst in the presence of an organic acid, or heated with the organic acid and a solid catalyst in solution to form a HMF ester. Heating without organic acid forms HMF. The resulting product is purified by filtration to remove the unreacted starting materials and catalyst. The HMF ester or a mixture of HMF and HMF ester may then be oxidized to 2,5-furandicarboxylic acid (FDCA) by combining the HMF ester with an organic acid, cobalt acetate, manganese acetate and sodium bromide under pressure. Alternatively, the HMF ester may be reduced to form a furan or tetrahydrofuran diol.
    Type: Application
    Filed: December 12, 2008
    Publication date: June 18, 2009
    Inventors: Alexandra J. SANBORN, Stephen J. Howard
  • Patent number: 7520905
    Abstract: Aqueous sulfuric acid is used for hydrolysis of a biomass, constituting a hydrolysate, to produce organic compounds. Organic compounds such as furfural and hyroxymethylfurfural are formed within the hydrolysate. Heterocyclic ring opening within hyroxymethylfurfural forms levulinic acid within the hydrolysate. Furfural and levulinic acid are extracted by a biodiesel fuel oil to increase content of biodiesel fuel oil. Biodiesel fuel oil generally consists of vegetable oils, insoluble in aqueous sulfuric acid, and affords access to, extraction of furfural and levulinic acid. Extracted hydrolysate is recycled for further hydrolysis of biomass.
    Type: Grant
    Filed: February 6, 2006
    Date of Patent: April 21, 2009
    Inventor: Gene E Lightner
  • Patent number: 7459584
    Abstract: Hexose and pentose monosaccharides are degraded to lactic acid and glyceric acid in an aqueous solution in the presence of an excess of a strongly anionic exchange resin, such as AMBERLITE IRN78 and AMBERLITE IRA400. The glyceric acid and lactic acid can be separated from the aqueous solution. Lactic acid and glyceric acid are staple articles of commerce.
    Type: Grant
    Filed: September 22, 2005
    Date of Patent: December 2, 2008
    Assignee: Board of Trustees of Michigan State University
    Inventors: James E. Jackson, Dennis J. Miller, Simona Marincean
  • Publication number: 20080161601
    Abstract: The invention provides a process for the recovery of citric acid from an aqueous solution feed stream originating in germination of carbohydrates and utilizing an amine solvent extraction step for separation of impurities comprising: subjecting said aqueous solution feed stream A to a treatment for partial recovery of citric acid, wherein said treatment is other than amine solvent extraction, to form a first portion of purified citric acid B and a secondary feed stream F; subjecting at least a portion G of said secondary feed stream F to a treatment consisting of amine solvent extraction to form a second portion of purified citric acid solution and to reject substantial of impurities initially present in said portion of said secondary feed stream; subjecting said second portion of purified citric acid solution to crystallization; and recycling mother liquor from said crystallization.
    Type: Application
    Filed: March 17, 2008
    Publication date: July 3, 2008
    Applicant: A.E. STALEY MANUFACTURING COMPANY
    Inventors: Avraham BANIEL, Asher Vitner, David Gonen, David Heidel
  • Publication number: 20070197825
    Abstract: A process for converting lactose into carbon dioxide and/or carbon monoxide using catalytic wet oxidation. Oxygen gas and an aqueous solution of lactose are fed to a reactor comprising a Pt/Al2O3 catalyst, a Mn/Ce catalyst or a Pt/Mn—Ce catalyst, and the lactose is oxidized in the reactor at elevated temperature and pressure to produce at least one of small organic acids, carbon dioxide, carbon monoxide, water and combinations thereof. The small organic acids may be further degraded by feeding the small organic acids and oxygen gas into a reactor containing a Mn/Ce catalyst and oxidizing the small organic acids to water and at least one of carbon dioxide, carbon monoxide and combinations thereof.
    Type: Application
    Filed: February 21, 2007
    Publication date: August 23, 2007
    Applicant: MICHIGAN TECHNOLOGICAL UNIVERSITY
    Inventor: Joseph Holles
  • Publication number: 20040002597
    Abstract: The invention relates to the industrial conversion of carbohydrates, alcohols, aldehydes or polyhydroxy compounds in aqueous phase. According to the invention a catalytic method is used for the conversion, using a metal catalyst consisting of polymer-stabilized nanoparticles. A catalyst of this type is not deactivated by the conversion reaction as long as the stabilizing interaction between the polymer and the nanoparticles is maintained.
    Type: Application
    Filed: January 10, 2003
    Publication date: January 1, 2004
    Applicant: SUDZUCKER AKTIENGESELLSCHAFT
    Inventors: Emine Capan, Marc Sascha Hahnlein, Ulf Prusse, Klaus-Dieter Vorlop, Alireza Haji Begli
  • Patent number: 6608229
    Abstract: A simplified process for oxidizing starch and other polysaccharides in an aqueous solution or suspension using hypochlorite in the presence of a catalytic amount of a nitroxyl compound is described. The oxidation is process is bromide-free and is carried out at a pH between 7 and 8.3 and at a temperature between 15 and 25° C.
    Type: Grant
    Filed: April 25, 2001
    Date of Patent: August 19, 2003
    Assignee: SCA Hygiene Products Zeist B.V.
    Inventors: Petter Bragd, Arie Cornelis Besemer, Jeffrey Wilson Thornton
  • Patent number: 6498269
    Abstract: A method for the oxidation of substrates comprising treating an aqueous, basic solution of a substrate having an oxidizable functionality using an elemental halogen as terminal oxidant in the presence of an oxoammonium catalyst/halide co-catalyst system. Use of elemental halogen, preferably chlorine gas or elemental bromine, unexpectedly allows oxidation without significant degradation of the substrate. The substrate is preferably a monosaccharide, oligosaccharide, or polysaccharide, and the oxidizable functionality is preferably an aldehyde, hemiacetal, or a primary alcohol. An effective source of the oxoammonium catalyst is 2,2,6,6-tetramethylpiperidinyl-1-oxy (TEMPO) and a particularly economical and effective catalyst is 4-acetylamino-2,2,6,6-tetramethylpiperidinyl-1-oxy.
    Type: Grant
    Filed: October 17, 2000
    Date of Patent: December 24, 2002
    Assignee: The University of Connecticut
    Inventors: Nabyl Merbouh, James M. Bobbitt, Christian Brückner
  • Patent number: 6465690
    Abstract: A process for preparing polyamino monosuccinic acids, salts or chelates thereof by (a) reacting a maleic or fumaric acid ester or mixtures thereof with a polyamino compound in a primary alcohol as a solvent, (b) hydrolyzing the product obtained in step (a), and (c) separating the primary alcohol. The use of a primary alcohol as the solvent results in a markedly purer polyamino monosuccinic acid product and simpler reaction conditions than when the solvent is a secondary or tertiary alcohol.
    Type: Grant
    Filed: February 23, 2000
    Date of Patent: October 15, 2002
    Assignee: The Dow Chemical Company
    Inventors: Alan D. Strickland, David A. Wilson, Brian D. Burkholder, Druce K. Crump
  • Publication number: 20020115886
    Abstract: A stable compound having a vapor pressure higher by 1 order than that of Ta(NtBu)(NEt2)3 is provided as a starting material for forming a TaN film as a barrier film by the CVD method. There are further provided a process for producing the same and a method of forming a TaN film by using the same. The novel compound, tantalum tertiary amylimido tris(dimethylamide) [Ta(NtAm)(NMe2)3] has a vapor pressure of 1 Torr at 80 ° C., and its melting point is 36° C. This compound is obtained by allowing 1 mole of TaCl5, 4 moles of LiNMe2 and 1 mole of LiNHtAm to react with one another in an organic solvent in the vicinity of room temperature, then separating byproducts by filtration, distilling the solvent away, and distilling the product in vacuo. This compound can be used as a starting material in CVD to form a cubic TaN film on a SiO2/Si substrate at 550° C. at 0.05 Torr.
    Type: Application
    Filed: November 9, 2001
    Publication date: August 22, 2002
    Inventors: Sakiko Yasuhara, Hidekimi Kadokura
  • Patent number: 6384276
    Abstract: The invention relates to a process for the preparation of high purity lactic acid from an aqueous solution containing said acid in the form of salt(s), characterised in that the aqueous solution is treated with a strong acid in order to liberate lactic acid in the free form and to produce salts of the corresponding strong acid, said salts of the strong acid are crystallised by evaporative crystallisation and lactic acid is recovered in the free form in solution.
    Type: Grant
    Filed: May 22, 2001
    Date of Patent: May 7, 2002
    Assignee: Roquette Freres
    Inventors: Eric Dubois, Catherine Fouache
  • Patent number: 6288244
    Abstract: A process for the preparation of 3,4-dihydroxybutanoic acid (I) and 3-hydroxy-&ggr;-butyrolactone (V) thereof from a 3-leaving group substituted pentose source is described. In particular, the process relates to the synthesis of (R)-3,4-dihydroxybutanoic acid and (R)-3-hydroxy-&ggr;-butyrolactone from a 3-leaving group substituted L-pentose sugars. The process uses a base and a peroxide to convert the pentose source to the chiral 3,4-dihydroxybutanoic acid compound. The chiral 3,4-dihydroxybutanoic acid can be further converted to 3-hydroxy-&ggr;-butyrolactone by acidification. The chiral compound is useful as a chemical intermediate to the synthesis of various drugs and other products.
    Type: Grant
    Filed: September 21, 2000
    Date of Patent: September 11, 2001
    Assignee: Board of Trustees operating Michigan State University
    Inventor: Rawle I. Hollingsworth
  • Patent number: 6288272
    Abstract: The present invention relates to a continuous process for preparing optically pure (S)-3,4-dihydroxybutyric acid derivatives expressed by the following Formula 1 and more particularly, to the continuous process which enables preparing optically pure (S)-3,4-dihydroxybutyric acid derivatives economically in large quantities, by: (a) Preparing &agr;-(1,4) linked oligosaccharide having adequate sugar distribution by reacting amylopectin which is easily available from natural product with enzyme under a specific condition; and (b) Performing oxidatioin by running basic anion exchange resin with an oxidant to give (S)-3,4-dihydroxybutyric acid-anion exchange resin complex, dissociating the (S)-3,4-dihydroxybutyric acid from anion exchange resin complex and esterification sequentially under a specific condition.  wherein Represents linear or branched alkyl group with 1˜5 carbon atoms.
    Type: Grant
    Filed: July 23, 1999
    Date of Patent: September 11, 2001
    Assignee: Samsung Fine Chemicals Co., Ltd.
    Inventors: Kyoung Rok Roh, Jongpil Chun, Yik-haeng Cho, Young Mi Park, Hosung Yu, Dae Il Hwang
  • Patent number: 6245940
    Abstract: The invention relates to a method of manufacturing an acid derivative of ose containing n carbon atoms on the carbonic chain, characterised by the fact that an acid derivative of ose with n+1 carbon atoms containing at least one &agr; ketone function, and/or one of its salts, is brought into contact with hydrogen peroxide in a reaction medium without pH regulation.
    Type: Grant
    Filed: March 14, 2000
    Date of Patent: June 12, 2001
    Assignee: Roquette Freres
    Inventor: Rodolphe Tamion
  • Patent number: 6239311
    Abstract: An improved process for the preparation of 3,4-dihydroxybutanoic acid (1) and salts thereof from a D- or L-hexose source is described. The process uses an alkali metal or alkaline earth metal hydroxide and peroxide oxidizing agent to convert the D- or L-hexose source to (1) by maintaining a low concentration of base and oxidizing agent in the reaction mixture at any one time and by maintaining a temperature between about 25° C. and 80° C. Upon acidification of the reaction mixture the 3-hydroxylactone is produced. The compound (1) is useful as a chemical intermediate to naturally occurring fatty acids and is used to prepare 3,4-dihydroxybutanoic acid-gamma-lactone (2) and furanone (3), particularly stereoisomers of these compounds.
    Type: Grant
    Filed: April 24, 2000
    Date of Patent: May 29, 2001
    Assignee: Board of Trustees operating Michigan State University
    Inventor: Rawle I. Hollingsworth
  • Patent number: 6235930
    Abstract: A process for the preparation of 3,4-dihydroxybutanoic acid (I) and 3-hydroxy-&ggr;-butyrolactone (V) thereof from a 3-leaving group substituted pentose source is described. In particular, the process relates to the synthesis of (R)-3,4-dihydroxybutanoic acid and (R)-3-hydroxy-&ggr;-butyrolactone from a 3-leaving group substituted L-pentose sugars. The process uses a base and a peroxide to convert the pentose source to the chiral 3,4-dihydroxybutanoic acid compound. The chiral 3,4-dihydroxybutanoic acid can be further converted to 3-hydroxy-&ggr;-butyrolactone by acidification. The chiral compound is useful as a chemical intermediate to the synthesis of various drugs and other products.
    Type: Grant
    Filed: March 31, 1999
    Date of Patent: May 22, 2001
    Assignee: Board of Trustees operating Michigan State University
    Inventor: Rawle I. Hollingsworth
  • Patent number: 6204396
    Abstract: A method produces calcium fulvate from naturally-occurring humus material, such as leonardite, or humic shales. The humus material containing solid fulvic acid and solid humic acid is mixed with water and sodium hydroxide for a first selected period of time to form a solution having a pH of approximately 10.0 thereby solubilizing the fulvic acid and the humic acid. The pH of the solution is reduced to approximately 4.5 and is maintained at the approximately pH 4.5 for second selected period of time thereby precipitating the humic acid as a solid while the fulvic acid remains in solution. The fulvic acid solution is separated from the solid humic acid. The pH of the fulvic acid solution is increased to approximately 13 with calcium hydroxide thereby precipitating the solubilized fulvic acid as calcium fulvate.
    Type: Grant
    Filed: December 29, 1999
    Date of Patent: March 20, 2001
    Assignee: Electrolytes, Inc.
    Inventors: Hans W. Rasmussen, Lawrence H. Allen
  • Patent number: 6147229
    Abstract: A method produces magnesium fulvate from naturally-occurring humus material, such as leonardite, or humic shales. The humus material containing solid fulvic acid and solid humic acid is mixed with water and sodium hydroxide for a first selected period of time to form a solution having a pH of approximately 10.0 thereby solubilizing the fulvic acid and the humic acid. The pH of the solution is reduced to approximately 4.5 and is maintained at the approximately pH 4.5 for second selected period of time thereby precipitating the humic acid as a solid while the fulvic acid remains in solution. The fulvic acid solution is separated from the solid humic acid. The pH of the fulvic acid solution is increased to approximately 13 with magnesium hydroxide thereby precipitating the solubilized fulvic acid as magnesium fulvate.
    Type: Grant
    Filed: December 27, 1999
    Date of Patent: November 14, 2000
    Assignee: Electrolytes, Inc.
    Inventors: Hans W. Rasmussen, Lawrence H. Allen
  • Patent number: 6054611
    Abstract: A method of producing dehydration products from one more 5-carbon or 6-carbon sugars includes reacting said one or more sugars at 40-240.degree. C. for 1 to 96 hours in the presence of 5-90% sulfuric acid, separating the reaction products, and recovering levulinic acid. The sugars are can be generated from strong acid hydrolysis of biomass, such as rice straw, paper, cotton and other cellulosic materials.
    Type: Grant
    Filed: May 13, 1998
    Date of Patent: April 25, 2000
    Assignee: Arkenol, Inc.
    Inventors: William A. Farone, John E. Cuzens
  • Patent number: 5892107
    Abstract: A method of producing dehydration products from one or more 5-carbon or 6-carbon sugars includes reacting said one or more sugars at 40.degree.-240 .degree. C. for 1 to 96 hours in the presence of 10-90% sulfuric acid, separating the reaction products, and recovering levulinic acid. The sugars can be generated from strong acid hydrolysis of biomass, such as rice straw, paper, cotton and other cellulosic materials.
    Type: Grant
    Filed: November 8, 1996
    Date of Patent: April 6, 1999
    Assignee: Arkenol, Inc.
    Inventors: William A. Farone, John E. Cuzens
  • Patent number: 5859263
    Abstract: The present invention relates to a continuous process for preparing levulinic acid from starch in a reactive extrusion process. In a preferred embodiment, the extrusion takes place in a twin-screw extruder having a plurality of temperature zones wherein the starch slurry is preconditioned, extruded, filter pressed, reboiled, vacuum distilled, condensed, centrifuged, whereby the waste effluent from the centrifugation is reprocessed upstream to the preconditioning stage.
    Type: Grant
    Filed: August 14, 1996
    Date of Patent: January 12, 1999
    Assignee: Board of Regents University of Nebraska Lincoln
    Inventors: Viswas M. Ghorpade, Milford A. Hanna
  • Patent number: 5608105
    Abstract: A continuous process for producing levulinic acid from carbohydrate-containing materials in high yields is described. According to the process, a carbohydrate-containing material is supplied continuously to a first reactor and hydrolyzed at between 210.degree. C. and 230.degree. C. for between 13 seconds and 25 seconds in the presence of between 1% and 5% by weight mineral acid. The hydrolysis produces hydroxymethylfurfural, which is removed continuously from the first reactor and supplied continuously to a second reactor. In the second reactor, the hydroxymethylfurfural is hydrolyzed further at between 195.degree. C. and 215.degree. C. for between 15 minutes and 30 minutes to produce levulinic acid, which is continuously removed from the second reactor. The levulinic acid preferably is produced in at least 60%, and more preferably at least 70%, of the theoretical yield based on the hexose content of the carbohydrate-containing material.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: March 4, 1997
    Assignee: Biofine Incorporated
    Inventor: Stephen W. Fitzpatrick
  • Patent number: 5374773
    Abstract: A process for the preparation of 3,4-dihydroxybutanoic acid (1) and salts thereof from a glucose source containing 1,4-1inked glucose as a substituent is described. The process uses an alkali metal hdyroxide and hydrogen peroxide to convert the glucose source to (1). The compound (1) is useful as a chemical intermediate to naturally occurring fatty acids and is used to prepare 3,4-dihydroxybutanoic acid-gamma-lactone (2) and furanone (3), particularly stereoisomers of these compounds.
    Type: Grant
    Filed: October 27, 1993
    Date of Patent: December 20, 1994
    Assignee: Board of Trustees operating Michigan State University
    Inventor: Rawle I. Hollingsworth
  • Patent number: 5292939
    Abstract: A process for the preparation of 3,4-dihydroxybutanoic acid (1) and salts thereof from a glucose source containing 1,4-linked glucose as a substituent is described. The process uses an alkali metal hdyroxide and hydrogen peroxide to convert the glucose source to (1). The compound (1) is useful as a chemical intermediate to naturally occurring fatty acids and is used to prepare 3,4-dihydroxybutanoic acid-gamma-lactone (2) and furanone (3), particularly stereoisomers of these compounds.
    Type: Grant
    Filed: October 26, 1992
    Date of Patent: March 8, 1994
    Assignee: Board of Trustees Operating Michigan State University
    Inventor: Rawle I. Hollingsworth
  • Patent number: 5264623
    Abstract: Calcium salts, such as calcium acetate, calcium formate or calcium proprionate, are obtained from aqueous liquors derived from the pyrolysis of lignocellulosic biomass containing cellulose, hemicelluloses or starch. The above biomass is subjected to rapid pyrolysis to obtain a crude product containing an aqueous phase and an organic phase. The product obtained, preferably as the aqueous phase, is then distilled to produce a distillate containing at least one acid selected from acetic acid, formic acid and propionic acid as well as their esters and formaldehyde. An alkaline source of calcium is added to this distillate to adjust the pH to an alkaline level sufficient to hydrolyze the esters, cause at least partial oxidation of the formaldehyde and prevent volatilization of acetate, formate or propionate ions as acetic acid, formic acid or propionic acid respectively.
    Type: Grant
    Filed: January 4, 1993
    Date of Patent: November 23, 1993
    Assignee: Energy Mines & Resources Canada
    Inventors: Klaus H. Oehr, Donald S. Scott, Stefan Czernik
  • Patent number: 5258557
    Abstract: This invention relates to a Process for the preparation of Chelatant Organic Acids, from Pentosanes contained in corn husk, wheat seed husk, rice seed husk, oat seed husk, barley seed husk, cotton seed husk, sorgus seed husk, buffel, alfalfa and similar pastures, and harvests and residues of such.
    Type: Grant
    Filed: October 9, 1992
    Date of Patent: November 2, 1993
    Inventor: Hector Vargas-Garza
  • Patent number: 5210294
    Abstract: Purified lactic acid aqueous solutions obtained by percolating fermentation broths through columns of appropriate ion-exchange resins.
    Type: Grant
    Filed: June 3, 1992
    Date of Patent: May 11, 1993
    Assignee: Himont Incorporated
    Inventors: Giorgio Mantovani, Giuseppe Vaccari, Anna L. Campi
  • Patent number: 5024731
    Abstract: A method of manufacturing a material for medical and pharmaceutical products from pyroligneous acid extracted as water content in smoke generated by baking arbor and bark. Pyroligneous acid is heated, and resultant evaporation gas in a temperature range 98.degree. to 103.degree. C. is extracted and liquified by cooling.
    Type: Grant
    Filed: November 29, 1989
    Date of Patent: June 18, 1991
    Inventors: Katsumi Nagata, Hisako Nagata
  • Patent number: 4959494
    Abstract: A method for oxidizing organic compounds by contacting organic compounds with molecular oxygen in the presence of a noble metal pyrochlore having the formula:A.sub.2+x B.sub.2-x O.sub.7-ywherein A is a pyrochlore structure metal cation, and B is one or more of Ru, Rh, Ir, Os, and Pt; x and y are greater than or equal to 0 and less than or equal to 1.0, at a temperature up to about 200.degree. C.
    Type: Grant
    Filed: July 6, 1987
    Date of Patent: September 25, 1990
    Assignee: Monsanto Company
    Inventor: Timothy R. Felthouse
  • Patent number: 4954620
    Abstract: This material which has a hemi-cellulose content of less than 2%, a benzopyrene content of less than 2 .mu.g/kg and a calorific value which is about 20% greater than that of the starting material is obtained by isothermal treatment between 220.degree. C. and 280.degree. C. for a period of thirty minutes using crossed flows of treated material and of oxygen-free hot gases in an oven including stirring means (6,9) and a gas generator (1) with the gas being circulated by a fan (3).
    Type: Grant
    Filed: September 27, 1988
    Date of Patent: September 4, 1990
    Assignee: Association pour la Recherche et le Developpement des Methods et Processus Industriels
    Inventor: Jean-Paul Bourgeois
  • Patent number: 4897497
    Abstract: A process for producing furfural and levulinic acid from lignocellulose includes subjecting a sample of lignocellulose to acid degradation at an elevated temperature for a minute or less, during which time at least fifty percent of the furfural that theoretically can be derived from the sample is generated. The resulting mixture is then subjected to a second acid degradation at an elevated temperature to produce levulinic acid. During the second acid degradation, furfural vapors are continuously collected from the mixture.
    Type: Grant
    Filed: April 26, 1988
    Date of Patent: January 30, 1990
    Assignee: Biofine Incorporated
    Inventor: Stephen W. Fitzpatrick
  • Patent number: 4885387
    Abstract: High yields of glycolic and oxalic acids, as well as good yields of lactic, formic, and acetic acids are produced from polysaccharide-containing materials by reacting the materials in a concentrated alkaline solution at elevated temperatures.
    Type: Grant
    Filed: February 12, 1988
    Date of Patent: December 5, 1989
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventor: John M. Krochta
  • Patent number: 4816572
    Abstract: This material which has a hemi-cellulose content of less tha 2%, a benzopyrene content of less than 2 ug/kg and a calorific value which is about 20% greater than that of the starting material is obtained by isothermal treatment between 220.degree. C. and 280.degree. C. for a period of thirty minutes using crossed flows of treated material and of oxygen-free hot gases in an oven including stirring means (6,9) and a gas generator (1) with the gas being circulated by a fan (3).
    Type: Grant
    Filed: December 12, 1986
    Date of Patent: March 28, 1989
    Assignee: Association pour la Recherche et le Developpement des Methodes et Processus Industriels (Armines)
    Inventor: Jean-Paul Bourgeois
  • Patent number: 4553978
    Abstract: The present invention relates to a process for converting ligneous matter of vegetable origin by torrefaction, and to the product obtained. Wood or any other ligneous matter is subjected in a neutral atmosphere to a treatment of torrefaction at a temperature of between 200.degree. and 280.degree. C., and preferably between 240.degree. and 260.degree. C. for a duration of 30 mins. to 5 hours. The product of the invention is not fermentable, it has a specific mass close to 0.25 kg/dm.sup.3, a calorific power of at least about 5000 kcal/kg, a content of fixed carbon of 35 to 40% and can be broken up by hand; it may be used as fuel in boilers and in gas generators.
    Type: Grant
    Filed: August 23, 1982
    Date of Patent: November 19, 1985
    Assignee: Association pour la Recherche et le Developpement des Methodes et Processus Industriels
    Inventor: Schwob Yvan