Preparation Of Furfural (i.e., Furan-2-aldehyde) Patents (Class 549/489)
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Publication number: 20130317239Abstract: An object of the present invention is to provide a method for suppressing the corrosion of a reactor and reducing waste in the production of 2-furaldehyde from a sugar raw material containing a hexose as a constituent component, and another object of the invention is to provide an industrially advantageous method for producing 2-furaldehyde, which suppresses a decrease in the activity of a catalyst in a case of using an acid catalyst and provides a higher yield. The present invention relates to a method for producing 2-furaldehyde comprising heating a sugar raw material containing a hexose as a constituent component in an aprotic polar solvent in the presence of a solid acid catalyst.Type: ApplicationFiled: July 29, 2013Publication date: November 28, 2013Applicant: MITSUBISHI CHEMICAL CORPORATIONInventors: Toru Okoshi, Hideto Tsuji
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Publication number: 20130305594Abstract: A process that directly converts carbohydrates, particularly biomass derived carbohydrates and more specifically biomass (e.g., lignocellulosic biomass), to furfural-/HMF-ketone adducts for liquid hydrocarbon production under mild conditions.Type: ApplicationFiled: November 8, 2011Publication date: November 21, 2013Inventors: Li Shuai, Xuejun Pan
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Publication number: 20130295628Abstract: This invention provides processes to convert biomass into energy-dense biomass for combustion, alone or in combination with another solid fuel. In some variations, biomass is extracted to produce an extract liquor containing hemicellulosic oligomers and cellulose-rich solids; hemicellulosic oligomers are removed; and the cellulose-rich solids are torrefied to produce energy-dense biomass. In some embodiments, hydrotorrefaction is employed to produce hydrophobic, energy-dense biomass in an energy-efficient process that avoids intermediate drying between extraction/hydrolysis and torrefaction. The energy-dense biomass may be pelletized or directly combusted or gasified. The hemicellulosic oligomers may be hydrolyzed to fermentable sugars and then fermented to ethanol or other products, or further reacted to produce furfural or other products.Type: ApplicationFiled: May 1, 2013Publication date: November 7, 2013Applicant: API Intellectual Property Holdings, LLCInventors: Theodora RETSINA, Vesa PYLKKANEN, Ryan O'CONNOR
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Patent number: 8530695Abstract: 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: GrantFiled: April 21, 2009Date of Patent: September 10, 2013Assignee: Kemira OyjInventors: Jarmo Reunanen, Pekka Oinas, Timo Nissinen
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Patent number: 8524924Abstract: Furfural is produced from a lignocellulosic feedstock comprising glucan and xylan. The feedstock is contacted with water in the presence of an acid catalyst. The resulting mixture is contacted with at least one water-immiscible organic solvent to form a mixture comprising an aqueous phase and an organic phase. Under suitable reaction conditions, furfural is produced and preferentially partitions into the organic phase, from which it may be recovered.Type: GrantFiled: December 21, 2010Date of Patent: September 3, 2013Assignee: E I du Pont de Nemours and CompanyInventors: Christopher Burket, Subramaniam Sabesan
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Patent number: 8524925Abstract: Processes for producing furfural from biomass are provided. The processes use a metal halide in aqueous solutions of water-miscible and can provide a furfural yield of greater than 70%.Type: GrantFiled: October 31, 2011Date of Patent: September 3, 2013Assignee: E I du Pont de Nemours and CompanyInventors: Subramaniam Sabesan, Christina Jacy Spado
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Patent number: 8492586Abstract: 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: GrantFiled: April 21, 2009Date of Patent: July 23, 2013Assignee: Kemira OyjInventors: Jarmo Reunanen, Pekka Oinas, Timo Nissinen, Esko Tirronen
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Publication number: 20130178617Abstract: Methods and catalyst compositions for formation of furans from carbohydrates. A carbohydrate substrate is heating in the presence of a 2-substituted phenylboronic acid (or salt or hydrate thereof) and optionally a magnesium or calcium halide salt. The reaction is carried out in a polar aprotic solvent other than an ionic liquid, an ionic liquid or a mixture thereof. Additional of a selected amount of water to the reaction can enhance the yield of furans.Type: ApplicationFiled: September 27, 2012Publication date: July 11, 2013Inventors: Ronald Raines, Benjamin Caes, Michael Palte
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Publication number: 20130172582Abstract: Processes for making furfural and 5-hydroxymethylfurfural from sugars are provided. The processes can be carried out using a batch process or a continuous mode of operation. An aqueous sugar solution is pressurized with CO2, thereby producing carbonic acid in situ that catalyzes the dehydration reaction to produce furfural from C5 sugars and 5-methylhydroxyfurfural from C6 sugars.Type: ApplicationFiled: December 28, 2012Publication date: July 4, 2013Applicant: E I DU PONT DE NEMOURS AND COMPANYInventor: E I DU PONT DE NEMOURS AND COMPANY
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Publication number: 20130172581Abstract: Furfural is produced by mixing an aqueous feedstock solution containing C5 sugar and/or C6 sugar with a heated, high boiling, water-miscible solvent, such as sulfolane, and a soluble acid catalyst. Furfural product and water are distilled off through a multistage distillation column, leaving non-volatile solvent behind. Typical furfural yields with sulfolane as the reaction solvent are about 80% at as high as 99% conversion. Also, certain by-products (e.g., humins) solubilized in the reaction solvent can be precipitated by addition of water or aqueous feedstock solution and then removed by filtration, thereby providing a convenient and effective way of removing these undesirable byproducts from the reaction mixture.Type: ApplicationFiled: December 28, 2012Publication date: July 4, 2013Applicant: E I DU PONT DE NEMOURS AND COMPANYInventor: E I DU PONT DE NEMOURS AND COMPANY
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Publication number: 20130172585Abstract: Furfural is produced by contacting an aqueous feedstock solution containing C5 sugar and/or C6 sugar using a soluble acid catalyst with reactive distillation. Both high yield and high conversion are obtained in the reaction vessel. Degradation of furfural is minimized by its low residence time in contact with the acid catalyst. The use of staged distillation improves the furfural yield.Type: ApplicationFiled: December 28, 2012Publication date: July 4, 2013Applicant: E I DU PONT DE NEMOURS AND COMPANYInventor: E I DU PONT DE NEMOURS AND COMPANY
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Publication number: 20130172583Abstract: Furfural is produced by contacting a feedstock solution containing C5 sugar and/or C6 sugar with a solid acid catalyst using reactive distillation. Both high yield and high conversion are obtained, without production of insoluble char in the reaction vessel. Degradation of furfural is minimized by its low residence time in contact with the solid acid catalyst. Higher catalyst lifetime can be achieved because the catalyst is continually washed with the refluxing aqueous solution and not sitting in high-boiling byproducts like humins, which are known to be deleterious to catalyst lifetime.Type: ApplicationFiled: December 28, 2012Publication date: July 4, 2013Applicant: E I DU PONT DE NEMOURS AND COMPANYInventor: E I DU PONT DE NEMOURS AND COMPANY
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Publication number: 20130172584Abstract: Furfural is produced by mixing an aqueous feedstock solution containing C5 sugar and/or C6 sugar with a heated high boiling, water-miscible solvent, such as sulfolane, and a solid acid catalyst. Furfural product and water can be distilled off, leaving non-volatile solvent behind. Furfural yields of over 70% at as high as 99% conversion have been obtained with this process with sulfolane as the reaction solvent and zeolite beta as the solid acid catalyst. Also, certain by-products (e.g., humins) solubilized in the reaction solvent can be precipitated by addition of water or aqueous feedstock solution and then removed by filtration, thereby providing a convenient and effective way of removing these undesirable byproducts from the reaction mixture.Type: ApplicationFiled: December 28, 2012Publication date: July 4, 2013Applicant: E I DU PONT DE NEMOURS AND COMPANYInventor: E I DU PONT DE NEMOURS AND COMPANY
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Publication number: 20130158254Abstract: A method for converting a carbohydrate to a furan in a polar aprotic solvent in the presence of a chloride, bromide, or iodide salt or a mixture thereof and optionally in the presence of an acid catalyst, a metal halide catalyst and/or an ionic liquid (up to 40 wt %). The method can be employed in particular to produce furfural or 5-hydroxymethylfurfural.Type: ApplicationFiled: October 30, 2012Publication date: June 20, 2013Inventors: Joseph Bartholomew BINDER, Ronald Thaddeus Raines
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Publication number: 20130123520Abstract: Methods for the production of dehydrated sugars and derivatives of dehydrated sugars using microwave (MW) irradiation and methods of purifying the same are described. The dehydrated sugars derivatives include 5-hydroxymethyl-2-furfural (HMF) and anhydrosugar alcohols such as sorbitans and isosorbide. The derivatives include HMF ethers, levulinic acid esters, and ether derivatives of the anhydrosugar alcohols. The described methods require lower reaction temperatures and shorter reaction times than similar non microwave mediated reactions known in the art. Typical reaction conditions are 120-210° C., and typical reaction times are 30 minutes or less.Type: ApplicationFiled: July 18, 2011Publication date: May 16, 2013Applicant: Archer Daniels Midland CompanyInventors: Stephen J. Howard, Alexandra J. Sanborn
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Publication number: 20130115654Abstract: A method for utilizing agricultural biomass components, namely cellulose, hemicellose, and lignin, and converting them to value-added biobased chemical products is described herein. The present method provides treatments to obtain a plurality of component streams from agricultural biomass for producing derivative products while minimizing waste products.Type: ApplicationFiled: November 9, 2011Publication date: May 9, 2013Applicant: Thesis Chemistry, LLCInventors: John R. Peterson, Christopher M. Yost, Jian Wu
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Publication number: 20130115653Abstract: A method for utilizing woody biomass components, namely cellulose, hemicellose, and lignin, and converting them to value-added biobased chemical products is described herein. The present method provides treatments to obtain a plurality of component streams from woody biomass for producing derivative products while minimizing waste products.Type: ApplicationFiled: November 9, 2011Publication date: May 9, 2013Applicant: Thesis Chemistry, LLCInventors: John R. Peterson, Christopher M. Yost, Jian Wu
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Publication number: 20130109869Abstract: Processes for producing furfural from biomass are provided. The processes use a metal halide in aqueous solutions of water-miscible and can provide a furfural yield of greater than 70%.Type: ApplicationFiled: October 31, 2011Publication date: May 2, 2013Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: Subramaniam Sabesan, Christina Jacy Spado
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Patent number: 8426619Abstract: A process for continuously producing furfural and levulinic acid from biomass, said process comprising steps including pre-treatment of the biomass; hydrolysis and dehydration of the biomass; removing a vapor mixture by flashing the slurried biomass and a heat integration step comprising the water used being heated through a heat exchange system with the flashed vapor mixture.Type: GrantFiled: June 21, 2012Date of Patent: April 23, 2013Assignee: DSM IP Assets B.V.Inventors: Rudy Francois Maria Jozef Parton, Marinus Petrus Wihelmus Maria Rijkers, Johannes Augustinus Kroon
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Publication number: 20130085285Abstract: Method for the manufacture of furan compounds by using a heterogeneous catalyst in aqueous solution.Type: ApplicationFiled: September 28, 2012Publication date: April 4, 2013Applicant: FRAUNHOFER-GESELLSCHAFT ZUR FÖRDERUNGInventor: FRAUNHOFER-GESELLSCHAFT ZUR FÖRDERU
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Patent number: 8399688Abstract: A method to make levulinic acid (LA), furfural, or gamma-valerolactone (GVL). React cellulose (and/or other C6 carbohydrates) or xylose (and/or other C5 carbohydrates) or combinations thereof in a monophasic reaction medium comprising GVL and an acid; or (ii) a biphasic reaction system comprising an organic layer comprising GVL, and a substantially immiscible aqueous layer. At least a portion of the cellulose (and/or other C6 carbohydrates), if present, is converted to LA and at least a portion of the xylose (and/or other C5 carbohydrates), if present, is converted into furfural.Type: GrantFiled: April 12, 2012Date of Patent: March 19, 2013Assignee: Wisconsin Alumni Research FoundationInventors: James A. Dumesic, David Martin Alonso, Elif I. Gürbüz, Stephanie G. Wettstein
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Patent number: 8389749Abstract: Described is a catalytic process for converting biomass to furan derivatives (e.g., furfural, furfuryl alcohol, etc.) using a biphasic reactor containing a reactive aqueous phase and an organic extracting phase containing an alkylphenol. The process provides a cost-effective route for producing furfural, furfuryl alcohol, levulinic acid hydroxymethylfurfural, ?-valerolactone, and the like. The products formed are useful as value-added intermediates to produce polymers, as precursors to diesel fuel, and as fuel additives.Type: GrantFiled: May 25, 2011Date of Patent: March 5, 2013Assignee: Wisconsin Alumni Research FoundationInventors: James Dumesic, David Alonso, Jesse Bond, Thatcher Root, Mei Chia
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Publication number: 20130030194Abstract: The present invention relates to a metal catalyst composition for producing furfural derivatives from raw materials of lignocellulosic biomass, and method for producing furfural derivatives using the composition. The present invention comprises ruthenium chloride (RuCl3) and chromium chloride (CrCl2). The chromium chloride (CrCl2) is from 300 to 500 parts by weight on the basis of 100 parts by weight of the ruthenium chloride (RuCl3). Unlike conventional furfural derivatives producing process that should go through multi step processes such as pre-process, saccharification process, etc, the present invention has an advantage of producing furfural derivatives from lignocellulosic raw material only through simple reaction process in one reaction apparatus by mixing various kinds of metal catalyst at an optimum ratio.Type: ApplicationFiled: April 14, 2011Publication date: January 31, 2013Applicant: KOREA INSTITUTE OF INDUSTRIAL TECHNOLOGYInventors: Jin Ku Cho, Sangyong Kim, Dohoon Lee, Bora Kim, Jaewon Jeong
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Publication number: 20130029383Abstract: The present invention relates to a method of producing 5-hydroxymethylfurfural by dehydration of fructose and/or glucose and/or mannose.Type: ApplicationFiled: April 7, 2011Publication date: January 31, 2013Applicant: NOVOZYMES A/SInventors: Sven Pedersen, Troels B. Christensen, Astrid Boisen, Vibeke W. Jurgensen, Thomas S. Hansen, Soeren Kegnaes, Anders Riisager, John M. Woodley, Jacob S. Jensen, Wenjing Fu
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Publication number: 20120330040Abstract: A process for continuously producing furfural and levulinic acid from biomass, said process comprising steps including pre-treatment of the biomass; hydrolysis and dehydration of the biomass; removing a vapour mixture by flashing the slurried biomass and a heat integration step comprising the water used being heated through a heat exchange system with the flashed vapour mixture.Type: ApplicationFiled: June 21, 2012Publication date: December 27, 2012Applicant: DSM IP ASSETSInventors: Rudy Francois Maria Jozef Parton, Marinus Petrus Wihelmus Maria RIJKERS, Johannes Augustinus Kroon
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Publication number: 20120330035Abstract: The present invention relates to a method for the hydrothermolysis of a mono- and/or oligosaccharide-comprising composition which in addition comprises at least one monoalkyl and/or dialkyl ether of a polyalkylene glycol, and also relates to a hydrothermolysis device.Type: ApplicationFiled: June 22, 2012Publication date: December 27, 2012Applicant: BASF SEInventors: Alois Kindler, Andrea Schmidt, Alwin Rehfinger, Peter Bassler, Ralf Böhling
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Publication number: 20120330039Abstract: The present invention relates to a method for dehydrating a carbohydrate-comprising composition.Type: ApplicationFiled: June 21, 2012Publication date: December 27, 2012Applicant: BASF SEInventors: Alois Kindler, Klemens Massonne
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Patent number: 8338626Abstract: Method for the manufacture of 5-alkoxymethylfurfural derivatives by reacting a fructose and/or glucose-containing starting material with an alcohol in the presence of a catalytic or sub-stoechiometric amount of heterogeneous acid catalyst. The catalysts may be employed in a continuous flow fixed bed or catalytic distillation reactor. The ethers can be applied as a fuel or fuel additive.Type: GrantFiled: December 8, 2011Date of Patent: December 25, 2012Assignee: Furanix Technologies B.V.Inventors: Gerardus Johannes Maria Gruter, Frits Dautzenberg
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Publication number: 20120309060Abstract: Biomass (e.g., plant biomass, animal biomass, and municipal waste biomass) is processed to produce useful products, such as fuels. For example, systems are described that can use feedstock materials, such as cellulosic and/or lignocellulosic materials, to produce ethanol and/or butanol, e.g., by fermentation.Type: ApplicationFiled: August 20, 2012Publication date: December 6, 2012Applicant: XYLECO, INC.Inventor: Marshall Medoff
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Publication number: 20120302767Abstract: A method to make levulinic acid (LA), furfural, or gamma-valerolactone (GVL). React cellulose (and/or other C6 carbohydrates) or xylose (and/or other C5 carbohydrates) or combinations thereof in a monophasic reaction medium comprising GVL and an acid; or (ii) a biphasic reaction system comprising an organic layer comprising GVL, and a substantially immiscible aqueous layer. At least a portion of the cellulose (and/or other C6 carbohydrates), if present, is converted to LA and at least a portion of the xylose (and/or other C5 carbohydrates), if present, is converted into furfural.Type: ApplicationFiled: April 12, 2012Publication date: November 29, 2012Inventors: James A. Dumesic, David Martin Alonso, Elif I. Gürbüz, Stephanie G. Wettstein
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Publication number: 20120302765Abstract: Described is a catalytic process for converting biomass to furan derivatives (e.g., furfural, furfuryl alcohol, etc.) using a biphasic reactor containing a reactive aqueous phase and an organic extracting phase containing an alkylphenol. The process provides a cost-effective route for producing furfural, furfuryl alcohol, levulinic acid hydroxymethylfurfural, ?-valerolactone, and the like. The products formed are useful as value-added intermediates to produce polymers, as precursors to diesel fuel, and as fuel additives.Type: ApplicationFiled: May 25, 2011Publication date: November 29, 2012Inventors: James Dumesic, David Alonso, Jesse Bond, Thatcher Root, Mei Chia
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Publication number: 20120282656Abstract: Methods are disclosed for increasing the level of C5 monosaccharides produced from lignocellulosic biomass using a multistage fractionation process to handle recalcitrant C5 oligosaccharides without producing unwanted degradation products. Methods for reducing C5 monosaccharides degradation products produced from lignocellulosic biomass are also disclosed. In addition, compositions and products produced by the methods are disclosed.Type: ApplicationFiled: May 4, 2012Publication date: November 8, 2012Applicant: Renmatix, Inc.Inventor: Phillip R. Gibbs
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Publication number: 20120282655Abstract: Methods are disclosed for increasing the level of soluble C5 saccharides produced from lignocellulosic biomass comprising acidifying fractionated lignocellulosic biomass to prevent the recondensation of soluble C5 saccharides, including C5 oligosaccharides and xylose and arabinose monomers, to insoluble higher molecular weight C5 oligosaccharides.Type: ApplicationFiled: May 4, 2012Publication date: November 8, 2012Applicant: Renmatix, Inc.Inventor: Phillip R. Gibbs
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Publication number: 20120184756Abstract: Furfural is a known component of both gasoline or diesel fuels as well as a chemical raw material. We disclose a new production process from cellulose, using as a solvent and catalyst an alkyl imidazole sulphate or chloride or a mixture of both in a reaction with simultaneous extraction, using as a solvent dibuthyl ether. Furfural and dibuthyl ether are later separated by distillation.Type: ApplicationFiled: January 15, 2011Publication date: July 19, 2012Inventor: Pedro Brito Correia
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Publication number: 20120157697Abstract: Furfural is produced from a lignocellulosic feedstock comprising glucan and xylan. The feedstock is contacted with water in the presence of an acid catalyst. The resulting mixture is contacted with at least one water-immiscible organic solvent to form a mixture comprising an aqueous phase and an organic phase. Under suitable reaction conditions, furfural is produced and preferentially partitions into the organic phase, from which it may be recovered.Type: ApplicationFiled: December 21, 2010Publication date: June 21, 2012Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: CHRISTOPHER L. BURKET, SUBRAMANIAM SABESAN
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Publication number: 20120149924Abstract: The invention is directed to a process for production of furfural from pentoses and/or water-soluble pentosans, said process comprising converting said pentoses and/or water soluble pentosans in aqueous solution in a first step to furfural and in a second step feeding the aqueous solution containing furfural obtained in step one to the top of a distillation column to produce an aqueous, liquid downflow, which column is heated at the bottom part thereof, using at least one reboiler to produce an upflow steam flow, recovering a water and furfural containing vapor product stream from the top of said column, compressing said vapor flow and condensing it on the hot side of the reboiler at the bottom of said column to produce sufficient steam in said bottom part of the column to produce said upflow steam flow, and to recover an aqueous furfural containing solution as the condensate in the reboiler.Type: ApplicationFiled: December 15, 2011Publication date: June 14, 2012Applicant: TECHNISCHE UNIVERSITEIT DELFTInventors: Wiebren de Jong, Gianluca Marcotullio
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Patent number: 8193381Abstract: A method of oxidizing hydroxymethylfurfural (HMF) includes providing a starting material which includes HMF in a solvent comprising water into a reactor. At least one of air and O2 is provided into the reactor. The starting material is contacted with the catalyst comprising Pt on a support material where the contacting is conducted at a reactor temperature of from about 50° C. to about 200° C. A method of producing an oxidation catalyst where ZrO2 is provided and is calcined. The ZrO2 is mixed with platinum (II) acetylacetonate to form a mixture. The mixture is subjected to rotary evaporation to form a product. The product is calcined and reduced under hydrogen to form an activated product. The activated product is passivated under a flow of 2% O2.Type: GrantFiled: February 24, 2010Date of Patent: June 5, 2012Assignee: Battelle Memorial InstituteInventors: Michael A. Lilga, Richard T. Hallen, Jianli Hu, James F. White, Michel J. Gray
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Patent number: 8193382Abstract: A method of oxidizing hydroxymethylfurfural (HMF) includes providing a starting material which includes HMF in a solvent comprising water into a reactor. At least one of air and O2 is provided into the reactor. The starting material is contacted with the catalyst comprising Pt on a support material where the contacting is conducted at a reactor temperature of from about 50° C. to about 200° C. A method of producing an oxidation catalyst where ZrO2 is provided and is calcined. The ZrO2 is mixed with platinum (II) acetylacetonate to form a mixture. The mixture is subjected to rotary evaporation to form a product. The product is calcined and reduced under hydrogen to form an activated product. The activated product is passivated under a flow of 2% O2.Type: GrantFiled: February 24, 2010Date of Patent: June 5, 2012Assignee: Battelle Memorial InstituteInventors: Michael A. Lilga, Richard T. Hallen, Jianli Hu, James F. White, Michel J. Gray
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Publication number: 20120108829Abstract: The invention is directed to a process for the production of furfural from pentoses and/or water soluble pentosans, said process comprising converting the said pentoses and/or water soluble pentosans in aqueous solution in a first step to furfural and in a second step feeding the aqueous solution containing furfural obtained in the first step to the top of a distillation column to produce an aqueous, liquid downflow, which column is heated at the bottom to produce an upflow water vapour flow, recovering a gaseous water and furfural containing product stream from the top of the said column, compressing the said vapour flow and condensing it on the hot side of a reboiler at the bottom of the said column.Type: ApplicationFiled: November 11, 2010Publication date: May 3, 2012Applicant: TECHNISCHE UNIVERSITEIT DELFTInventors: Wiebren de Jong, Gianluca Marcotullio
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Publication number: 20120083611Abstract: A process is provided for producing furfural from solid biomass by gaseous acid catalysed hydrolysis and dehydration in the presence of superheated steam and one or more acid catalysts. The solid biomass is heated to a temperature which is sufficiently high to ensure that the superheated steam and the acid catalyst or catalysts to be used remain in gaseous form during the reaction. The heated solid biomass is contacted with a gaseous stream containing superheated steam and one or more acid catalysts to produce a furfural-containing gaseous stream containing superheated steam, one or more acid catalysts and furfural. The furfural-containing gaseous stream is recirculated to bring it into further contact with the heated solid biomass to enrich the concentration of furfural.Type: ApplicationFiled: September 29, 2011Publication date: April 5, 2012Applicant: SHELL OIL COMPANYInventors: Jeroen VAN BUIJTENEN, Jean-Paul LANGE, Wouter SPIERING
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Patent number: 8133289Abstract: Method for the manufacture of 5-alkoxymethylfurfural derivatives by reacting a fructose and/or glucose-containing starting material with an alcohol in the presence of a catalytic or sub-stoechiometric amount of solid (“heterogeneous”) acid catalyst. The catalysts may be employed in a continuous flow fixed bed or catalytic distillation reactor. The ethers can be applied as a fuel or fuel additive.Type: GrantFiled: March 12, 2007Date of Patent: March 13, 2012Assignee: Furanix Technologies B.V.Inventors: Gerardus Johannes Maria Gruter, Frits Dautzenberg
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Patent number: 8129550Abstract: Alcohols are catalytically oxidized to aldehydes, in particular to benzaldehyde and diformylfuran, which are useful as intermediates for a multiplicity of purposes. The invention also relates to the polymerization of the dialdehyde and to the decarbonylation of the dialdehyde to furan.Type: GrantFiled: May 6, 2011Date of Patent: March 6, 2012Assignee: E. I. du Pont de Nemours and CompanyInventors: Vladimir Grushin, Walter Partenheimer, Leo Ernest Manzer
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Patent number: 8119823Abstract: The invention relates to a process for producing furfural from xylose comprising: (a) mixing an aqueous xylose solution containing xylose oligosaccharides with sub-critical or near-critical water to form a mixture at a first temperature and a first pressure; (b) maintaining the mixture at the first temperature and the first pressure for a first time period; and (c) rapidly cooling the mixture to a second temperature and a second pressure, wherein furfural is produced by the process (d) process can also be carried out with or without mixing of carbon dioxide with aqueous xylose solution before it is mixed with sub-critical or near-critical water to form a mixture at a first temperature and pressure.Type: GrantFiled: July 16, 2009Date of Patent: February 21, 2012Assignee: Renmatix, Inc.Inventor: Srinivas Kilambi
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Publication number: 20110282079Abstract: The invention relates to a method for manufacture of hydrocarbon fuels and oxygenated hydrocarbon fuels such as alkyl substituted tetrahydrofurans such as 2,5-dimethyltetrahydrofuran, 2-methyltetrahydrofuran, 5-methylfurfural and mixtures thereof. The method generally entails forming a mixture of reactants that includes carbonaceous material, water, a metal catalyst and an acid reacting that mixture in the presence of hydrogen. The reaction is performed at a temperature and for a time sufficient to produce a furan type hydrocarbon fuel. The process may be adapted to provide continuous manufacture of hydrocarbon fuels such as a furan type fuel.Type: ApplicationFiled: January 11, 2011Publication date: November 17, 2011Applicant: The Penn State Research FoundationInventors: Ayusman Sen, Weiran Yang
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Publication number: 20110144359Abstract: A method for producing furfural from lignocellulosic biomass material is provided, comprising (a) contacting the lignocellulosic biomass material with a mixture comprising water and an organic acid at a temperature of at least 100° C. and a pressure of at most 10 bar (absolute) to obtain a first liquid stream comprising hydrolysed hemicellulose and a second stream comprising lignin and cellulose; (b) maintaining the first liquid stream comprising hydrolysed hemicellulose at a temperature of at least 130° C. to obtain a second liquid stream comprising furfural; and (c) separating the furfural obtained in step b) from the second liquid stream.Type: ApplicationFiled: December 16, 2010Publication date: June 16, 2011Inventors: Evert VAN DER HEIDE, Ting Zhang
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Publication number: 20110137051Abstract: 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: ApplicationFiled: April 21, 2009Publication date: June 9, 2011Applicant: KEMIRA OYJInventors: Jarmo Reunanen, Pekka Oinas, Timo Nissinen
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Patent number: 7956203Abstract: Alcohols are catalytically oxidized to aldehydes, in particular to benzaldehyde and diformylfuran, which are useful as intermediates for a multiplicity of purposes. The invention also relates to the polymerization of the dialdehyde and to the decarbonylation of the dialdehyde to furan.Type: GrantFiled: March 27, 2001Date of Patent: June 7, 2011Assignee: E. I. du Pont de Nemours and CompanyInventors: Vladimir Grushin, Walter Partenheimer, Leo E. Manzer
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Patent number: 7939681Abstract: Methods are described for converting carbohydrates including, e.g., monosaccharides, disaccharides, and polysaccharides in ionic liquids to value-added chemicals including furans, useful as chemical intermediates and/or feedstocks. Fructose is converted to 5-hydroxylmethylfurfural (HMF) in the presence of metal halide and acid catalysts. Glucose is effectively converted to HMF in the presence of chromium chloride catalysts. Yields of up to about 70% are achieved with low levels of impurities such as levulinic acid.Type: GrantFiled: July 6, 2007Date of Patent: May 10, 2011Assignee: Battelle Memorial InstituteInventors: Haibo Zhao, Johnathan E. Holladay, Zongchao C. Zhang
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Patent number: 7875664Abstract: This invention relates to a composition comprising, consisting of or alternatively consisting essentially of a stabilized furfural or glycol ester of a vegetable oil fatty acid and an antioxidant such as butylated hydroxy toluene. This invention also relates to latex film-forming compositions containing stabilized furfural or glycol esters, such as a stabilized propylene glycol monoester (PGME) mixture. This invention is also directed to methods of stabilizing furfural or glycol esters of a vegetable fatty acid by contacting the esters with an antioxidant such as butylated hydroxy toluene. This invention also includes methods of preparing film-forming compositions comprising a stabilized furfural or glycol ester, such as the stabilized PGME mixture disclosed herein.Type: GrantFiled: July 23, 2007Date of Patent: January 25, 2011Assignee: Archer Daniels Midland CompanyInventors: Paul D. Bloom, Peter K. Fuge, George B. Poppe, Teodora R. Tabuena-Salyers
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Publication number: 20100317879Abstract: Methods are described for converting carbohydrates including, e.g., monosaccharides, disaccharides, and polysaccharides in ionic liquids to value-added chemicals including furans, useful as chemical intermediates and/or feedstocks. Fructose is converted to 5-hydroxylmethylfurfural (HMF) in the presence of metal halide and acid catalysts. Glucose is effectively converted to HMF in the presence of chromium chloride catalysts. Yields of up to about 70% are achieved with low levels of impurities such as levulinic acid.Type: ApplicationFiled: August 24, 2010Publication date: December 16, 2010Applicant: BATTELLE MEMORIAL INSTITUTEInventors: Haibo Zhao, Johnathan E. Holladay, Zongchao C. Zhang