Additional Chalcogen Attached Indirectly To The Hetero Ring By Nonionic Bonding Patents (Class 549/488)
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Patent number: 11186945Abstract: The methods and compounds disclosed herein relate to the surface modification of UHMWPs by means of a catalytic C—H bond insertion catalyst using a rhodium catalysts in conjunction with carbene-generating diazo compounds. The catalytic treatment imparts covalently added functionality to the UHMWPE surface. This functionality acts as an excellent grafting mechanism for grafting, bonding, or adhering further materials to the UHMWPs surface.Type: GrantFiled: August 30, 2017Date of Patent: November 30, 2021Assignee: National Technology & Engineering Solutions of Sandia, LLCInventors: Greg O'Bryan, Mitchell Anstey, Bryan Loyola
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Patent number: 10941130Abstract: This invention relates to a novel molten salt system in chemical transformation of saccharides and a method as well as an apparatus for multi carbon production by the molten salt system. It is found that an eutectic molten salt composition is advantageous for multi-carbon productions through chemical transformation under mild conditions. This invention further provides a method and an apparatus for preparing 5-hydroxymethylfurfural (HMF) and HMF-derived chemicals from saccharides by the said molten salt system.Type: GrantFiled: March 22, 2019Date of Patent: March 9, 2021Assignee: Academia SinicaInventors: Po-Wen Chung, Prasenjit Bhaumik, Hao-Ju Chou
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Patent number: 10844030Abstract: The present invention relates to a method for producing furfural, including: obtaining a sugar solution containing at least one of a monosaccharide having 5 carbon atoms and a polysaccharide containing the monosaccharide having 5 carbon atoms by carrying out a reaction with a specific resource as a raw material in the presence of a catalyst in a solvent; converting at least one of the monosaccharide and the polysaccharide containing the monosaccharide in the sugar solution into furfural by a dehydration reaction, so as to obtain a reaction solution; and separating the reaction solution into an organic layer and an aqueous layer, wherein an aromatic hydrocarbon solvent having a density of from 0.90 g/cm3 to 1.1 g/cm3 at 25° C. and under atmospheric pressure is used, and wherein the reaction solution is separated at a temperature higher than 90° C. and lower than 150° C.Type: GrantFiled: September 24, 2018Date of Patent: November 24, 2020Assignee: Mitsubishi Chemical CorporationInventors: Yusuke Izawa, Yosuke Suzuki, Masaru Utsunomiya
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Patent number: 10781196Abstract: A method of converting a lignocellulosic biomass to monosaccharides, and optionally further converting the monosaccharides to one or both of furfural and HMF, includes contacting the biomass with a reactive liquid phase comprising LiBr, H2SO4, and water, wherein H2SO4 preferably constitutes at most 1.0 wt %, more preferably at most 0.5 wt %, and most preferably at most 0.1 wt % of the reactive liquid phase, and water preferably constitutes at most at most 60 wt %, more preferably at most 50 wt %, and most preferably at most 30 wt % of the reactive liquid phase.Type: GrantFiled: August 15, 2017Date of Patent: September 22, 2020Assignee: UNIVERSITY OF DELAWAREInventors: Basudeb Saha, Sunitha Sadula, Dionisios Vlachos
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Patent number: 10532990Abstract: The present invention relates to systems, methods, and processes for the production of conversion products such as furanic products from biomass such as lignocellulosic materials.Type: GrantFiled: December 11, 2015Date of Patent: January 14, 2020Assignee: VIRDIA, INC.Inventors: Robert Jansen, James Alan Lawson, Philip Travisano, Brendon Christopher Stout, Allison Jean Hulchanski, Neta Matis, Noa Lapidot, Michael Zviely, Adam Tyler Carden, Michael Andrew Faison, Bassem Hallac, Sterling Alexander White
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Patent number: 10526302Abstract: The invention relates to a process for the production of 5-hydroxymethylfurfural from a feedstock comprising at least one sugar using a combination of at least one catalyst selected from the homogeneous Lewis acids, the heterogeneous Lewis acids and the heterogeneous bases and at least one homogeneous Brønsted acid catalyst selected from the families of the thioureas, the sulphonic acids and the phosphorus-containing organic compounds, alone or in a mixture, in the presence of at least one aprotic polar solvent, at a temperature comprised between 30° C. and 300° C., and at a pressure comprised between 0.1 MPa and 10 MPa.Type: GrantFiled: October 17, 2016Date of Patent: January 7, 2020Assignee: IFP Energies NouvellesInventors: Myriam Souleymanou, Marc Jacquin, Damien Delcroix
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Patent number: 10428039Abstract: Provided herein is a process for preparing furan-2,5-dicarboxylic acid. The process includes the following steps: (A-1) preparing a starting mixture comprising one, two or more carbohydrate compounds selected from the group consisting of: hexoses, oligosaccharides comprising hexose units, and polysaccharides including hexose units, and as a solvent or as a co-solvent for the carbohydrate compounds an amount of one or more carboxylic acid esters of a formula (II) and (A-2) subjecting the starting mixture to reaction conditions so that at least one of the one, two or more carbohydrate compounds reacts, and a fraction of the amount of one or more carboxylic acid esters of formula (II) is hydrolyzed, resulting in a mixture including 5-(hydroxymethyl)furfural and/or the one or more HMF esters of a formula (I), one or more carboxylic acids of a formula (III) and a remaining fraction of the amount of one or more carboxylic acid esters of formula (II).Type: GrantFiled: November 3, 2016Date of Patent: October 1, 2019Assignee: BASF SEInventors: Alvaro Gordillo, Martin Alexander Bohn, Stephan A. Schunk, Ivana Jevtovikj, Rene Backes, Holger Werhan, Svenia Duefert, Richard Dehn, Markus Piepenbrink
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Patent number: 10421735Abstract: The invention relates to a novel process for the conversion of a feedstock comprising at least one sugar to 5-hydroxymethylfurfural, in which said feedstock is contacted with one or more catalysts of the family of the homogeneous sulphonic acids in the presence of at least one aprotic polar solvent, used alone or in a mixture, at a temperature comprised between 30° C. and 200° C., and at a pressure comprised between 0.Type: GrantFiled: October 17, 2016Date of Patent: September 24, 2019Assignee: IFP Energies nouvellesInventors: Myriam Souleymanou, Marc Jacquin, Damien Delcroix
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Patent number: 10399953Abstract: The present invention provides methods of making furfural fatty acids from (chloromethyl)furfural. The present invention also provides furfural fatty acids and nutritional supplements that include furfural fatty acids.Type: GrantFiled: September 14, 2016Date of Patent: September 3, 2019Assignee: THE REGENTS OF THE UNIVERSITY OF CALIFORNIAInventors: Mark Mascal, Fei Chang
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Patent number: 10259797Abstract: Provided herein is a process for preparing a mixture including 5-(hydroxy-methyl)furfural (HMF) and one or more HMF esters of formula (I), the process including the following steps: (A-1) preparing or providing a starting mixture which includes one, two or more carbohydrate compounds and as the solvent or as a co-solvent for the carbohydrate compounds an amount of one or more carboxylic acid esters of formula (II); (A-2) subjecting the starting mixture to reaction conditions so that at least one of the one, two or more carbohydrate compounds reacts, and a fraction of the amount of one or more carboxylic acid esters of formula (II) is hydrolyzed, so that a mixture results that includes 5-(hydroxy-methyl)furfural and/or the one or more HMF esters of formula (I), one or more carboxylic acids of formula (III) and a remaining fraction of the amount of one or more carboxylic acid esters of formula (II).Type: GrantFiled: November 3, 2016Date of Patent: April 16, 2019Assignee: BASF SEInventors: Alvaro Gordillo, Martin Alexander Bohn, Stephan A Schunk, Ivana Jevtovikj, Holger Werhan, Svenia Duefert, Markus Piepenbrink, Rene Backes, Richard Dehn
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Patent number: 10167267Abstract: The present invention relates to a method for synthesizing an optionally substituted furoic acid by dehydrating a biomass and oxidizing the optionally substituted furan derived from the dehydration reaction. Water extraction has been incorporated as a step between the dehydration and the oxidation in order to purify the intermediate optionally substituted furan before having it oxidized. Prior to this water extraction, the organic solvent used for dehydration may be separated by evaporation. The provision of the water extraction allows impurities to be separated from the intermediate optionally substituted furan.Type: GrantFiled: September 17, 2014Date of Patent: January 1, 2019Assignee: AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCHInventors: Guangshun Yi, Yugen Zhang
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Patent number: 10030001Abstract: The present invention relates to a process for the synthesis of 5-hydroxymethyl furfural (HMF) comprising the steps of: 1) dehydrating at least one saccharide selected from monosaccharides having 6 carbon atoms and disaccharides, oligosaccharides or polysaccharides formed from units having 6 carbon atoms or mixtures thereof in the presence of at least one quaternary ammonium salt R3R?N+X?; in which: —R, which is the same or different, represents a C1-C16 substituted or unsubstituted alkyl group; —R? belongs to the group consisting of: hydrogen, C1-C16 substituted or unsubstituted alkyl group, monocyclic substituted or unsubstituted aryl group; —X? represents an anion selected from chloride, bromide, iodide, fluoride, hydroxide, BF4? and PF6?; at a temperature of between 80 and 120° C.Type: GrantFiled: October 16, 2015Date of Patent: July 24, 2018Assignee: Novamont S.P.A.Inventors: Catia Bastioli, Luigi Capuzzi, Giuseppina Carotenuto, Anna Di Martino, Adriano Ferrari
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Patent number: 9957244Abstract: A process is described for converting hydroxymethylfurfural to furanic products inclusive of 2,5-furandicarboxylic acid, comprising combining a quantity of hydroxymethylfurfural with water to provide an aqueous solution containing at least about five percent by weight of hydroxymethylfurfural, and combining the aqueous solution with an oxygen source in the presence of a heterogeneous ruthenium-based catalyst and under conditions which are effective for oxidizing hydroxymethylfurfural to furanic oxidation products inclusive of 2,5-furandicarboxylic acid, but in the substantial absence of any solvent for either hydroxymethylfurfural or 2,5-furandicarboxylic acid other than water.Type: GrantFiled: August 5, 2015Date of Patent: May 1, 2018Assignee: Archer Daniels Midland CompanyInventor: Alexandra Sanborn
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Patent number: 9822187Abstract: Described are a method for processing cellulose-containing biomass and the use of methanesulfonic acid for processing cellulose-containing biomass, especially for the pretreatment of cellulose-containing biomass prior to saccharification.Type: GrantFiled: October 2, 2014Date of Patent: November 21, 2017Assignee: BASF SEInventors: Frank Rittig, Michael Koch, Vaidotas Navickas, Stefan Koch, Alois Kindler
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Patent number: 9707547Abstract: An oxidation catalyst includes a nickel-containing material, a manganese-containing material and a bromine-containing material, wherein the molar number of the element bromine (Br) in the oxidation catalyst to the total molar number of the element nickel (Ni) and the element manganese (Mn) in the oxidation catalyst substantially ranges from 0.01 to 7.5.Type: GrantFiled: December 10, 2015Date of Patent: July 18, 2017Assignee: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTEInventors: Ying-Ting Huang, Jinn-Jong Wong, Jau-Hong Chen
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Patent number: 9475787Abstract: A process for the production of furan derivatives from carbohydrates in the presence of an acidic catalyst, characterized in that N-methylpyrrolidone is used as a solvent and that the acidic catalyst is homogeneous.Type: GrantFiled: September 2, 2013Date of Patent: October 25, 2016Assignee: Annikki GMBHInventors: Marko Mihovilovic, Michael Schön, Johanna Hölbling
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Patent number: 9469619Abstract: Provided is a two-step method of producing a compound of chemical formula 1 in the presence of an alcohol solvent and a Group 3B metal catalyst or a salt thereof, comprising a first step comprising alkylation or isomerization of an aldohexose-containing substrate to obtain an intermediate, and a second step comprising dehydration of the intermediate to produce a compound of chemical formula 1. Preferably, additional solvent and/or catalyst are not added in the second step.Type: GrantFiled: October 29, 2013Date of Patent: October 18, 2016Assignee: SAMSUNG ELECTRONICS CO., LTD.Inventors: Jong Min Lee, Hyeon Su Heo, Moo Ho Lee, Kyung Hae Lee
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Patent number: 9260402Abstract: A process is described for the preparation of 5-hydroxymethylfurfural (HMF), which comprises the following steps: provision or preparation of a starting mixture, comprising one, two or more starting compounds selected from the group consisting of hexoses, oligosaccharides comprising hexose units, and polysaccharides comprising hexose units, one, two or more organic salts with a melting point <180° C. and a boiling point >200° C. at 1013.25 hPa, optionally additionally one or more catalysts for the conversion of the one starting compound or at least one of the two or more starting compounds to 5-hydroxymethylfurfural (HMF), optionally water, optionally further substances, adjustment of reaction conditions such that an amount of the starting compound or starting compounds converts to HMF.Type: GrantFiled: June 11, 2014Date of Patent: February 16, 2016Assignee: BASF SEInventors: Benoit Blank, Alois Kindler, Peter Bassler, Markus Piepenbrink, Ortmund Lang, Carmen Feldner
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Method for selectively preparing 5-hydroxymethylfurfual (HMF) from biomass in polar aprotic solvents
Patent number: 9242952Abstract: A method to produce 5-hydroxymethylfurfural (HMF) is described in which a reactant including cellulose, lignocellulose, or a combination thereof, in a reaction mixture of a polar, aprotic solvent and an acid is reacted for a time, at a temperature, and at a hydrogen ion concentration wherein at least a portion of the cellulose or lignocellulose present in the reactant is converted to HMF. The reaction mixture is initially substantially devoid of water. As the reaction proceeds, dehydration of intermediates causes the water concentration in the reaction mixture to rise to no more than about 0.2 wt % water.Type: GrantFiled: March 28, 2014Date of Patent: January 26, 2016Assignee: Wisconsin Alumni Research FoundationInventors: James A. Dumesic, George W. Huber, Ronen Weingarten -
Patent number: 9221777Abstract: The invention relates to a novel process for preparation of dronedarone of formula (I) and pharmaceutically acceptable salts thereof, characterized in that a compound of formula (II)—where L is leaving group—is reacted with compound of formula (III) and the obtained product is isolated and, if desired, converted into a pharmaceutically acceptable salt thereof.Type: GrantFiled: March 1, 2013Date of Patent: December 29, 2015Assignee: SANOFIInventor: Antal Friesz
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Patent number: 9206147Abstract: The present invention relates to a method for producing a furan-based compound using an ion exchange resin in the presence of an organic solvent. In the method for producing a furan-based compound according to the present invention, a furan-based compound is made from an aldose-type hexose compound in the presence of an organic solvent by using an anion exchange resin and a cation exchange resin. Thus, the aldose-type hexose compound obtained from biomass by simultaneously or consecutively using the anion/cation exchange resins as catalysts can be made into 5-hydroxymethyl-2-furfural (HMF) or alkyl ether derivatives thereof such as 5-alkoxymethyl-2-furfural (AMF) without using an expensive reagent. Also, since the selection of an organic solvent is not limitative and a heterogeneous catalyst can be used, separation and purification is easy and chemically stable AMF can be directly obtained.Type: GrantFiled: July 9, 2012Date of Patent: December 8, 2015Assignee: KOREA INSTITUTE OF INDUSTRIAL TECHNOLOGYInventors: Jin Ku Cho, Sang Yong Kim, Jae Hoon Cho, Bo Ra Kim, Paul Joo
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Patent number: 9156805Abstract: Disclosed is a process to produce a dry purified carboxylic acid product comprising furan-2,5-dicarboxylic acid (FDCA). The process comprises oxidizing a feed stream comprising at least one oxidizable compound to generate a crude carboxylic acid slurry comprising FDCA, removing impurities from a crude carboxylic acid slurry via oxidative purification in a low temperature post-oxidation zone to form a low impurity slurry stream. The low impurity slurry stream is further treated in a high temperature post oxidation zone to produce a secondary oxidation slurry stream which is routed to a crystallization zone to from a crystallized slurry stream.Type: GrantFiled: November 19, 2013Date of Patent: October 13, 2015Assignee: EASTMAN CHEMICAL COMPANYInventors: Ashfaq Shaikh, Kenny R. Parker, Mesfin Ejerssa Janka, Lee R. Partin
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Patent number: 9156802Abstract: Method for producing solutions which comprise 5-hydroxymethylfurfural (HMF) and have a reduced content of starting materials of the HMF synthesis or a reduced content of by-products of the HMF synthesis (hereinbelow called product solution), which comprises treating solutions which comprise HMF starting materials or by-products of the HMF synthesis and an organic solvent having at least two ether groups (for short polyether) (hereinbelow called starting solution) in an evaporator with steam.Type: GrantFiled: December 12, 2012Date of Patent: October 13, 2015Assignee: BASF SEInventors: Ralf Böhling, Benoit Blank, Alois Kindler, Carmen Feldner, Sandra Umlauf
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Patent number: 9090579Abstract: A process is disclosed for making dehydration products from an aqueous sugars solution including pentoses, hexoses or both, for example, an aqueous high fructose corn syrup solution, or from an aqueous solution of one or more of the alcohols of such pentoses and hexoses, for example, from an aqueous sorbitol solution, by an acid-catalyzed dehydration using substituted sulfonic acids solubilized in the aqueous sugars or sugar alcohols solution.Type: GrantFiled: March 7, 2013Date of Patent: July 28, 2015Assignee: Archer Daniels Midland Co.Inventors: Thomas P. Binder, Alexandra Sanborn
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Patent number: 9045449Abstract: Method for the manufacture of furan compounds by using a heterogeneous catalyst in aqueous solution.Type: GrantFiled: September 28, 2012Date of Patent: June 2, 2015Assignee: FRAUNHOFER-GESELLSCHAFT ZUR FOERDERUNG DER ANGEWANDTEN FORSCHUNG E.V.Inventors: Jochen Forstner, Rainer Schweppe, Gerd Unkelbach, Klemens Flick
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Publication number: 20150126731Abstract: The invention relates to a method for the isomerisation of glucose into fructose in water in the presence of a solid base catalyst characterised by its reversibility of CO2 adsorption at a low temperature, the catalyst being a catalyst comprising at least one supported or non-supported lanthanide oxide or a molecular sieve based on silicon containing the organic template thereof. The invention also relates to a method for preparing HMF from glucose, comprising the isomerisation of glucose into fructose.Type: ApplicationFiled: August 24, 2012Publication date: May 7, 2015Applicants: Université Claude Bernard Lyon 1, CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (C.N.R.S)Inventors: Nadine Essayem, Rodrigo Lopes De Souza, Franck Rataboul, Cyril Feche, Dilson Cardoso, Demian Fabiano
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Publication number: 20150111943Abstract: The hydroxymethylfurfural derivative is represented by the general formula (A) (wherein, R is selected from the group consisting of the following formula (I), (II) HOOCCH2COCO—, (III) HOOCCH2CH2COCO—, and (IV) a hydrogen atom).Type: ApplicationFiled: December 20, 2012Publication date: April 23, 2015Inventors: Hiroshi Nishioka, Tomohiro Ito, Takahiro Maeda
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Publication number: 20150087848Abstract: An acid-functionalized polyolefin material that can be used as an acid catalyst in a wide range of acid-promoted chemical reactions, wherein the acid-functionalized polyolefin material includes a polyolefin backbone on which acid groups are appended. Also described is a method for the preparation of the acid catalyst in which a precursor polyolefin is subjected to ionizing radiation (e.g., electron beam irradiation) of sufficient power and the irradiated precursor polyolefin reacted with at least one vinyl monomer having an acid group thereon. Further described is a method for conducting an acid-promoted chemical reaction, wherein an acid-reactive organic precursor is contacted in liquid form with a solid heterogeneous acid catalyst comprising a polyolefin backbone of at least 1 micron in one dimension and having carboxylic acid groups and either sulfonic acid or phosphonic acid groups appended thereto.Type: ApplicationFiled: September 20, 2013Publication date: March 26, 2015Inventors: Yatsandra Oyola, Chengcheng Tian, John Christopher Bauer, Sheng Dai
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Publication number: 20150087031Abstract: The present invention relates to methods of processing lignocellulosic material to obtain hemicellulose sugars, cellulose sugars, lignin, cellulose and other high-value products. Also provided are hemicellulose sugars, cellulose sugars, lignin, cellulose, and other high-value products.Type: ApplicationFiled: May 3, 2013Publication date: March 26, 2015Inventors: Robert Jansen, Claire Gregoire, philip Travisano, Lee Madsen, Neta Matis, Yael Har-Tal, Shay Eliahu, James Alan Lawson, Noa Lapidot, Luke Burke, Aharon M. Eyal, Timothy Allen Bauer, Hagit Sade, Paul Mcwilliams, Ziv-Vladimir Belman, Bassem Hallac, Michael Zviely, Yelena Gershinksy, Adam Carden
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Publication number: 20150065698Abstract: There is described a method of isolating one or more of pectin, d-limonene, a flavour compound, a flavonoid, a soluble monosaccharide, a decomposition product of a monosaccharide and cellulose, from citrus material wherein said method comprises the microwave assisted hydrothermal low temperature treatment of citrus material.Type: ApplicationFiled: April 4, 2013Publication date: March 5, 2015Inventors: James Hanley Clark, Lucie Anne Pfaltzgraff, Vitaliy Lvovich Budarin, Mario De Bruyn
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Patent number: 8952192Abstract: Provided are compositions and methods for modulating quorum sensing in microbes. The compounds are AI-2 analogs and as such have structures similar to 4,5-dihydroxy-2,3-pentanedione that can act as agonists/antagonists of quorum sensing. The compounds are useful for modulating quorum sensing in bacteria and can be used in methods for prophylaxis or therapy of bacterial infections and for reduction of biofilms.Type: GrantFiled: March 26, 2012Date of Patent: February 10, 2015Assignee: University of Maryland, College ParkInventors: Herman O. Sintim, William E. Bentley, Varnika Roy, Jacqueline Smith, Reza Ghodssi, Mariana Tsacoumis Meyer
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Patent number: 8952186Abstract: The present invention relates to a method for dehydrating a carbohydrate-comprising composition.Type: GrantFiled: June 21, 2012Date of Patent: February 10, 2015Assignee: BASF SEInventors: Alois Kindler, Klemens Massonne
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Patent number: 8940914Abstract: Disclosed are compositions and methods for the production of mono-esters and di-esters from the reaction of HMF and a reactant selected from a diacid or a diacid derivative; typical reactants are PAN, phthaloyl dichloride, dimethyl phthalate, maleic acid, and maleic anhydride or mono-esters that can be prepared from HMF and MAN.Type: GrantFiled: July 20, 2012Date of Patent: January 27, 2015Assignee: Battelle Memorial InstituteInventors: Herman P. Benecke, Jerry L. King, II, Alex Walter Kawczak, Donald W. Zehnder, II, Erica E. Hirschl
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Publication number: 20150025256Abstract: This invention relates to an efficient procedure for purifying HMF by crystallization at low temperature from an organic solvent.Type: ApplicationFiled: August 17, 2012Publication date: January 22, 2015Inventors: Tim Ståhlberg, Jacob Skibsted Jensen, Anders Riisager, John M. Woodley
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Publication number: 20150005516Abstract: A process is disclosed for making dehydration products from an aqueous sugars solution including pentoses, hexoses or both, for example, an aqueous high fructose corn syrup solution, or from an aqueous solution of one or more of the alcohols of such pentoses and hexoses, for example, from an aqueous sorbitol solution, by an acid-catalyzed dehydration using substituted sulfonic acids solubilized in the aqueous sugars or sugar alcohols solution.Type: ApplicationFiled: March 7, 2013Publication date: January 1, 2015Inventors: Thomas P. Binder, Alexandra Sanborn
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Publication number: 20140371473Abstract: A process is described for the preparation of 5-hydroxymethylfurfural (HMF), which comprises the following steps: provision or preparation of a starting mixture, comprising one, two or more starting compounds selected from the group consisting of hexoses, oligosaccharides comprising hexose units, and polysaccharides comprising hexose units, one, two or more organic salts with a melting point <180° C. and a boiling point >200° C. at 1013.25 hPa, optionally additionally one or more catalysts for the conversion of the one starting compound or at least one of the two or more starting compounds to 5-hydroxymethylfurfural (HMF), optionally water, optionally further substances, adjustment of reaction conditions such that an amount of the starting compound or starting compounds converts to HMF.Type: ApplicationFiled: June 11, 2014Publication date: December 18, 2014Applicant: BASF SEInventors: Benoit Blank, Alois Kindler, Peter Bassler, Markus Piepenbrink, Ortmund Lang, Carmen Feldner
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Publication number: 20140356280Abstract: Provided is a surfactant-free, single-step synthesis of delaminated aluminosilicate zeolites. The process comprises the step of heating a borosilicate zeolite precursor in a metal salt solution, e.g., an aluminum nitrate solution, zinc nitrate solution or manganese nitrate solution. The delaminated aluminosilicate zeolite product is then recovered from the solution.Type: ApplicationFiled: May 30, 2014Publication date: December 4, 2014Applicants: CHEVRON U.S.A. INC., THE REGENTS OF THE UNIVERSITY OF CALIFORNIAInventors: Xiaoying OUYANG, Alexander KATZ, Stacey Ian ZONES
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Publication number: 20140357878Abstract: Disclosed herein is a process for preparing 5-hydroxymethylfurfural comprising the step of contacting a carbohydrate and a Brønsted acid in an alcoholic solvent comprising an alcohol selected from the group consisting of secondary alcohols, tertiary alcohols, aryl alcohols and combinations thereof under conditions to dehydrate the carbohydrate thereby forming a reaction product containing 5-hydroxymethylfurfural.Type: ApplicationFiled: September 24, 2012Publication date: December 4, 2014Applicant: Agency for Science, Technology and ResearchInventors: Yugen Zhang, Linke Lai
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Publication number: 20140349351Abstract: The present invention relates to a process for producing 5-hydroxymethylfurfural (HMF) from fructose in a single-phase aqueous solution comprising an organic solvent.Type: ApplicationFiled: October 11, 2012Publication date: November 27, 2014Applicant: Novozymes A/SInventors: Jacob Skibsted Jensen, Thomas Grotkjaer, Sven Pedersen, Rolf Ringborg
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Patent number: 8889734Abstract: The subject of the present invention is a novel process for the preparation of N-[2-n-butyl-3-{4-[(3-dibutylamino)propoxy]benzoyl}-1-benzofuran-5-yl]methanesulfonamide of formula I: and the new intermediates of the preparation process.Type: GrantFiled: May 30, 2013Date of Patent: November 18, 2014Assignee: SANOFIInventors: Antal Friesz, Zsolt Dombrady, Mariann Csatarine Nagy
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Patent number: 8883824Abstract: Disclosed is a compound represented by Formula (I) or a pharmaceutically acceptable salt thereof: wherein R1 is 1: a C3-8 cycloalkyl C1-4 alkyl group, 2: a C7-14 aralkyl group, in which the aryl moiety thereof is optionally substituted with the same or different 1 to 3 groups selected from the group consisting of: (a) halogen, (b) C1-4 alkyl, which is optionally substituted with 1 to 3 fluorine atoms, (c) C1-4 alkoxy, which is optionally substituted with 1 to 3 fluorine atoms, and (d) C1-4 alkylcarbonyl, which is optionally substituted with C1-4 alkoxy, 3: a five-to ten-membered heteroaryl-C1-4 alkyl group, in which the heteroaryl moiety thereof is optionally substituted with the same or different 1 to 3 groups selected from the group consisting of: (a) halogen, and (b) C1-4 alkyl, or 4: a C6-10 aryl C2-6 alkenyl group; and R2 is a cyano group or a nitro group.Type: GrantFiled: May 12, 2010Date of Patent: November 11, 2014Assignee: Sumitomo Dainippon Pharma Co., Ltd.Inventors: Akihito Fujii, Kazumi Niidome, Chiaki Migihashi, Toshiyuki Kamei, Takafumi Matsumoto, Tomoyuki Hirata
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Patent number: 8877950Abstract: Method for the manufacture of 5-hydroxymethylfurfural derivatives by reacting a fructose and/or glucose-containing starting material with an alcohol in the presence of a catalytic or sub-stoichiometric 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: December 15, 2010Date of Patent: November 4, 2014Assignee: Furanix Technologies B.V.Inventors: Gerardus Johannes Maria Gruter, Frits Dautzenberg
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Publication number: 20140315262Abstract: Hydroxymethylfurfural is made from an aqueous hexose sugar solution, especially from a high fructose corn syrup product. By rapidly heating the sugar solution to the elevated temperatures involved as well as rapidly cooling the resultant product mixture, a limited per-pass conversion to HMF is obtained; correspondingly, however, the overall exposure of the HMF that is formed to acidic, elevated temperature conditions is also limited, so that byproducts are reduced. Separation and recovery of the products is simplified, and levels of HMF and other hexose dehydration products known to inhibit ethanol production by fermentation are reduced in the residual sugars product, to an extent whereby the residual sugars product is suited to be directly fermented to ethanol or for other uses.Type: ApplicationFiled: November 28, 2012Publication date: October 23, 2014Applicant: ARCHER DANIELS MIDLAND COMPANYInventors: Alexandra Sanborn, Thomas Binder, April Hoffart
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Publication number: 20140288230Abstract: The present invention provides methylene beta-ketoester monomers, methods for producing the same, and compositions and products formed therefrom. In the method for producing the methylene beta-ketoesters of the invention, a beta-ketoester is reacted with a source of formaldehyde in a modified Knoevenagel reaction optionally in the presence of an acidic or basic catalyst, and optionally in the presence of an acidic or non-acidic solvent, to form reaction complex. The reaction complex may be an oligomeric complex. The reaction complex is subjected to further processing, which may be vaporization by contact with an energy transfer means in order to isolate the beta-ketoester monomer. The present invention further compositions and products formed from methylene beta-ketoester monomers of the invention, including monomer-based products (e.g., inks, adhesives, coatings, sealants or reactive molding) and polymer-based products (e.g., fibers, films, sheets, medical polymers, composite polymers and surfactants).Type: ApplicationFiled: October 18, 2012Publication date: September 25, 2014Inventors: Bernard M. Malofsky, Adam G. Malofsky, Tanmoy Dey
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Publication number: 20140275400Abstract: The present invention provides methylene beta-diketone monomers, methods for producing the same, and compositions and products formed therefrom. In the method for producing the methylene beta-diketones of the invention, a beta-diketone is reacted with a source of formaldehyde in a modified Knoevenagel reaction optionally in the presence of an acidic or basic catalyst, and optionally in the presence of an acidic or non-acidic solvent, to form reaction complex. The reaction complex may be an oligomeric complex. The reaction complex is subjected to further processing, which may be vaporization by contact with an energy transfer means in order to isolate the beta-diketone monomer. The present invention further compositions and products formed from methylene beta-diketone monomers of the invention, including monomer-based products (e.g., inks, adhesives, coatings, sealants or reactive molding) and polymer-based products (e.g., fibers, films, sheets, medical polymers, composite polymers and surfactants).Type: ApplicationFiled: October 18, 2012Publication date: September 18, 2014Inventors: Yangbin Chen, Adam G. Malofsky, Jeffrey M. Sullivan, Stanley C. Wojciak, Tanmoy Dey, Bernard M. Malofsky
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Publication number: 20140235881Abstract: The present invention relates to a method for producing a furan-based compound using an ion exchange resin in the presence of an organic solvent. In the method for producing a furan-based compound according to the present invention, a furan-based compound is made from an aldose-type hexose compound in the presence of an organic solvent by using an anion exchange resin and a cation exchange resin. Thus, the aldose-type hexose compound obtained from biomass by simultaneously or consecutively using the anion/cation exchange resins as catalysts can be made into 5-hydroxymethyl-2-furfural (HMF) or alkyl ether derivatives thereof such as 5-alkoxymethyl-2-furfural (AMF) without using an expensive reagent. Also, since the selection of an organic solvent is not limitative and a heterogeneous catalyst can be used, separation and purification is easy and chemically stable AMF can be directly obtained.Type: ApplicationFiled: July 9, 2012Publication date: August 21, 2014Applicant: KOREA INSTITUTE OF INDUSTRIAL TECHNOLOGYInventors: Jin Ku Cho, Sang Yong Kim, Jae Hoon Cho, Bo Ra Kim, Paul Joo
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Patent number: 8795393Abstract: Disclosed is a method of preparing a petroleum-alternative bio fuel material such as 5-hydroxymethyl-2-furfural (HMF), 5-alkoxymethyl-2-furfural, levulinic acid alkil ester, etc. through a single process without saccharification, using a catalyst conversion reaction, from galactan that can be massively supplied at low costs and extracted from macroalgae of marine reusable resources. Thus, the macroalgae of the marine biomass resources is used so that a carbon source can be more easily extracted than that of a lignocellulosic biomass resource without a problem of having an effect on grain price like a crop-based biomass.Type: GrantFiled: April 15, 2010Date of Patent: August 5, 2014Assignee: Korea Institute of Industrial TechnologyInventors: Jin-Ku Cho, Sang-Yong Kim, Do-Hoon Lee, Bo-Ra Kim, Jae-Won Jung
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Patent number: 8785668Abstract: The present invention relates to a method for efficient conversion of carbohydrates into 5-hydroxymethylfurfural (HMF) in the presence of tantalum-containing solid acid, which shows good activity and high selectivity for HMF preparation from saccharides. The catalyst is stable in aqueous system which makes it as an ideal catalyst for HMF production. High HMF yield was obtained even in mild condition. The catalysts of the invention are advantageous in that they are environment-friendly, easy separation and recovery, can be re-used in subsequent reactions, do not corrode reaction reactors. These features make the catalyst as an ideal catalyst for HMF preparation and have strong industrial application significance.Type: GrantFiled: November 30, 2010Date of Patent: July 22, 2014Assignee: Dalian Institute of Chemical Physics, Chinese Academy of SciencesInventors: Yuguang Du, Qishun Liu, Fengli Yang, Xuefang Bai, Jingmei Zhao
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Patent number: 8765805Abstract: Novel ligand compounds having the structural formula (I): in which: Ar is a radical selected from among the radicals of formulae (a)-(c) below: are formulated into pharmaceutical compositions suited for administration in human or veterinary medicine, or, alternatively into cosmetic compositions.Type: GrantFiled: April 30, 2012Date of Patent: July 1, 2014Assignee: Galderma Research & DevelopmentInventors: Thibaud Biadatti, Jean-Marie Arlabosse
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Publication number: 20140171444Abstract: The present invention provides aryl- or heteroaryl-diketo acid compounds effective to inhibit an activity of a Mycobacterial malate synthase enzyme or to inhibit a malate synthase activity in other bacteria having the enzyme. The compounds may be phenyl- naphthyl-, or thienyl-substituted diketo acids and carboxylate derivatives thereof. Also provided are methods of treating tuberculosis or other pathophysiological conditions associated with a malate synthase enzyme with the inhibitory compounds and methods of in silico design of the inhibitory compounds. In addition, the present invention provides the inhibitory compounds designed by this method. Furthermore, three-dimensional X-ray crystal structures of the Mycobacterial malate synthase complexed with the inhibitory compounds are provided. Further still a method for stabilizing an aromatic or heteroaromatic diketo acid or its prodrug or close analog in solution by derivatizing at least the ortho position on the aromatic ring is provided.Type: ApplicationFiled: March 3, 2014Publication date: June 19, 2014Applicant: THE TEXAS A&M UNIVERSITY SYSTEMInventors: Joel S. Freundlich, James C. Sacchettini, Inna V. Kriger, Thomas R. Ioerger, Vijay Gawandi