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