Preparation By Degradation Of Carbohydrates Patents (Class 562/515)
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Publication number: 20120172625Abstract: 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: ApplicationFiled: March 16, 2012Publication date: July 5, 2012Inventor: Stephen W. Fitzpatrick
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Patent number: 8148553Abstract: 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: GrantFiled: June 23, 2009Date of Patent: April 3, 2012Assignee: Wisconsin Alumni Research FoundationInventors: James A. Dumesic, Juan Carlos Serrano Ruiz, Ryan M. West
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Patent number: 8138371Abstract: 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: GrantFiled: March 11, 2009Date of Patent: March 20, 2012Assignee: Biofine Technologies LLCInventor: Stephen W. Fitzpatrick
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Publication number: 20120035356Abstract: 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: ApplicationFiled: October 20, 2011Publication date: February 9, 2012Inventors: Donald E. Kiely, Kirk R. Hash, Kylie Kramer-Presta, Tyler Smith
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Publication number: 20110277378Abstract: 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: ApplicationFiled: May 12, 2011Publication date: November 17, 2011Applicant: SHELL OIL COMPANYInventors: Klaas Lambertus VON HEBEL, Jean-Paul LANGE
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Patent number: 8058458Abstract: 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: GrantFiled: July 13, 2009Date of Patent: November 15, 2011Assignee: Archer Daniels Midland CompanyInventor: Alexandra J. Sanborn
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Patent number: 7938981Abstract: 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: GrantFiled: September 24, 2010Date of Patent: May 10, 2011Assignee: Bioamber S.A.S.Inventors: Dilum Dunuwila, Roger L. Bernier
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Publication number: 20110098490Abstract: 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: ApplicationFiled: April 21, 2009Publication date: April 28, 2011Applicant: KEMIRA OYJInventors: Jarmo Reunanen, Pekka Oinas, Timo Nissinen, Esko Tirronen
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Publication number: 20100324310Abstract: 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: ApplicationFiled: June 23, 2009Publication date: December 23, 2010Inventors: James A. Dumesic, Juan Carlos Serrano Ruiz, Ryan M. West
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Publication number: 20100317822Abstract: 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: ApplicationFiled: June 11, 2010Publication date: December 16, 2010Applicant: RENNOVIA, INC.Inventors: Thomas R. Boussie, Eric L. Dias, Zachary M. Fresco, Vincent J. Murphy
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Patent number: 7838700Abstract: 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: GrantFiled: November 8, 2002Date of Patent: November 23, 2010Assignee: Aesica PharmaceuticalsInventors: Steve Martin, Daniele Piergentili
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Publication number: 20100234638Abstract: 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: ApplicationFiled: March 11, 2009Publication date: September 16, 2010Inventor: Stephen W. Fitzpatrick
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Patent number: 7723540Abstract: 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: GrantFiled: June 28, 2007Date of Patent: May 25, 2010Assignee: Hitachi Plant Technologies, Ltd.Inventors: Masayuki Kamikawa, Toshiaki Matsuo, Kenichiro Oka, Naruyasu Okamoto, Ryuji Kaziya
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Publication number: 20100121096Abstract: 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: ApplicationFiled: November 6, 2009Publication date: May 13, 2010Inventors: Esben Taarning, Saravanamurugan Shunmugavel, Martin Spangsberg Holm
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Patent number: 7692041Abstract: 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: GrantFiled: August 6, 2007Date of Patent: April 6, 2010Assignee: The University of MontanaInventors: Donald E. Kiely, Kirk R. Hash, Sr.
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Publication number: 20090281338Abstract: 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: ApplicationFiled: July 13, 2009Publication date: November 12, 2009Inventor: Alexandra J. Sanborn
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Patent number: 7579489Abstract: 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: GrantFiled: September 28, 2007Date of Patent: August 25, 2009Assignee: Archer-Daniels-Midland CompanyInventor: Alexandra J. Sanborn
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Publication number: 20090156841Abstract: 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: ApplicationFiled: December 12, 2008Publication date: June 18, 2009Inventors: Alexandra J. SANBORN, Stephen J. Howard
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Patent number: 7520905Abstract: 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: GrantFiled: February 6, 2006Date of Patent: April 21, 2009Inventor: Gene E Lightner
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Patent number: 7459584Abstract: 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: GrantFiled: September 22, 2005Date of Patent: December 2, 2008Assignee: Board of Trustees of Michigan State UniversityInventors: James E. Jackson, Dennis J. Miller, Simona Marincean
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Publication number: 20080161601Abstract: 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: ApplicationFiled: March 17, 2008Publication date: July 3, 2008Applicant: A.E. STALEY MANUFACTURING COMPANYInventors: Avraham BANIEL, Asher Vitner, David Gonen, David Heidel
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Publication number: 20070197825Abstract: 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: ApplicationFiled: February 21, 2007Publication date: August 23, 2007Applicant: MICHIGAN TECHNOLOGICAL UNIVERSITYInventor: Joseph Holles
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Publication number: 20040002597Abstract: 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: ApplicationFiled: January 10, 2003Publication date: January 1, 2004Applicant: SUDZUCKER AKTIENGESELLSCHAFTInventors: Emine Capan, Marc Sascha Hahnlein, Ulf Prusse, Klaus-Dieter Vorlop, Alireza Haji Begli
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Patent number: 6608229Abstract: 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: GrantFiled: April 25, 2001Date of Patent: August 19, 2003Assignee: SCA Hygiene Products Zeist B.V.Inventors: Petter Bragd, Arie Cornelis Besemer, Jeffrey Wilson Thornton
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Patent number: 6498269Abstract: 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: GrantFiled: October 17, 2000Date of Patent: December 24, 2002Assignee: The University of ConnecticutInventors: Nabyl Merbouh, James M. Bobbitt, Christian Brückner
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Patent number: 6465690Abstract: 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: GrantFiled: February 23, 2000Date of Patent: October 15, 2002Assignee: The Dow Chemical CompanyInventors: Alan D. Strickland, David A. Wilson, Brian D. Burkholder, Druce K. Crump
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Publication number: 20020115886Abstract: 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: ApplicationFiled: November 9, 2001Publication date: August 22, 2002Inventors: Sakiko Yasuhara, Hidekimi Kadokura
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Patent number: 6384276Abstract: 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: GrantFiled: May 22, 2001Date of Patent: May 7, 2002Assignee: Roquette FreresInventors: Eric Dubois, Catherine Fouache
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Patent number: 6288272Abstract: 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: GrantFiled: July 23, 1999Date of Patent: September 11, 2001Assignee: Samsung Fine Chemicals Co., Ltd.Inventors: Kyoung Rok Roh, Jongpil Chun, Yik-haeng Cho, Young Mi Park, Hosung Yu, Dae Il Hwang
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Patent number: 6288244Abstract: 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: GrantFiled: September 21, 2000Date of Patent: September 11, 2001Assignee: Board of Trustees operating Michigan State UniversityInventor: Rawle I. Hollingsworth
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Patent number: 6245940Abstract: 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: GrantFiled: March 14, 2000Date of Patent: June 12, 2001Assignee: Roquette FreresInventor: Rodolphe Tamion
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Patent number: 6239311Abstract: 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: GrantFiled: April 24, 2000Date of Patent: May 29, 2001Assignee: Board of Trustees operating Michigan State UniversityInventor: Rawle I. Hollingsworth
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Patent number: 6235930Abstract: 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: GrantFiled: March 31, 1999Date of Patent: May 22, 2001Assignee: Board of Trustees operating Michigan State UniversityInventor: Rawle I. Hollingsworth
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Patent number: 6204396Abstract: 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: GrantFiled: December 29, 1999Date of Patent: March 20, 2001Assignee: Electrolytes, Inc.Inventors: Hans W. Rasmussen, Lawrence H. Allen
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Patent number: 6147229Abstract: 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: GrantFiled: December 27, 1999Date of Patent: November 14, 2000Assignee: Electrolytes, Inc.Inventors: Hans W. Rasmussen, Lawrence H. Allen
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Patent number: 6054611Abstract: 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: GrantFiled: May 13, 1998Date of Patent: April 25, 2000Assignee: Arkenol, Inc.Inventors: William A. Farone, John E. Cuzens
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Patent number: 5892107Abstract: 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: GrantFiled: November 8, 1996Date of Patent: April 6, 1999Assignee: Arkenol, Inc.Inventors: William A. Farone, John E. Cuzens
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Patent number: 5859263Abstract: 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: GrantFiled: August 14, 1996Date of Patent: January 12, 1999Assignee: Board of Regents University of Nebraska LincolnInventors: Viswas M. Ghorpade, Milford A. Hanna
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Patent number: 5608105Abstract: 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: GrantFiled: June 7, 1995Date of Patent: March 4, 1997Assignee: Biofine IncorporatedInventor: Stephen W. Fitzpatrick
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Patent number: 5374773Abstract: 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: GrantFiled: October 27, 1993Date of Patent: December 20, 1994Assignee: Board of Trustees operating Michigan State UniversityInventor: Rawle I. Hollingsworth
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Patent number: 5292939Abstract: 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: GrantFiled: October 26, 1992Date of Patent: March 8, 1994Assignee: Board of Trustees Operating Michigan State UniversityInventor: Rawle I. Hollingsworth
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Patent number: 5264623Abstract: 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: GrantFiled: January 4, 1993Date of Patent: November 23, 1993Assignee: Energy Mines & Resources CanadaInventors: Klaus H. Oehr, Donald S. Scott, Stefan Czernik
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Patent number: 5258557Abstract: 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: GrantFiled: October 9, 1992Date of Patent: November 2, 1993Inventor: Hector Vargas-Garza
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Patent number: 5210294Abstract: Purified lactic acid aqueous solutions obtained by percolating fermentation broths through columns of appropriate ion-exchange resins.Type: GrantFiled: June 3, 1992Date of Patent: May 11, 1993Assignee: Himont IncorporatedInventors: Giorgio Mantovani, Giuseppe Vaccari, Anna L. Campi
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Patent number: 5024731Abstract: 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: GrantFiled: November 29, 1989Date of Patent: June 18, 1991Inventors: Katsumi Nagata, Hisako Nagata
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Patent number: 4959494Abstract: 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: GrantFiled: July 6, 1987Date of Patent: September 25, 1990Assignee: Monsanto CompanyInventor: Timothy R. Felthouse
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Patent number: 4954620Abstract: 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: GrantFiled: September 27, 1988Date of Patent: September 4, 1990Assignee: Association pour la Recherche et le Developpement des Methods et Processus IndustrielsInventor: Jean-Paul Bourgeois
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Patent number: 4897497Abstract: 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: GrantFiled: April 26, 1988Date of Patent: January 30, 1990Assignee: Biofine IncorporatedInventor: Stephen W. Fitzpatrick
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Patent number: 4885387Abstract: 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: GrantFiled: February 12, 1988Date of Patent: December 5, 1989Assignee: The United States of America as represented by the Secretary of AgricultureInventor: John M. Krochta
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Patent number: 4816572Abstract: 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: GrantFiled: December 12, 1986Date of Patent: March 28, 1989Assignee: Association pour la Recherche et le Developpement des Methodes et Processus Industriels (Armines)Inventor: Jean-Paul Bourgeois