Preparing From Compound Containing -coo- Group Patents (Class 549/326)
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Patent number: 11098020Abstract: Processes and reactor systems for biomass conversion are described. A continuous process for the conversion of carbo-hydrate-containing feed material into furanic compounds comprises a reaction step comprising subjecting said feed material to reaction conditions in a reaction medium comprising two immiscible liquid phases, including a reactive phase and an extractive phase, and a Brønsted acid as catalyst, wherein the reaction medium comprises a solid component comprising at least a part of a carbohydrate-containing fraction of said feed material.Type: GrantFiled: May 23, 2017Date of Patent: August 24, 2021Assignee: Nederlandse Organisatie voor toegepast-natuurwetenschappelijk onderzoek TNOInventors: Paul Mathijs Könst, Johan Urbanus
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Patent number: 10407623Abstract: The disclosure describes a one-step liquid biphasic catalytic process for converting a carbohydrate-containing feedstock, preferably lignocellulose, to light naphtha (e.g., hexane, pentane, methyl cyclopentane, cyclohexane, etc.) in the presence of an acidic reactive aqueous phase and a redox catalyst in the organic extracting/reaction phase. The process provides a cost-effective route for producing light-naphtha components, in presence or not of deoxygenates. The light naphtha components are useful as feedstock for steam and catalytic cracking to produce value-added platform molecules like ethylene and propylene, as precursor for the synthesis of bioaromatics like benzene and as gasoline fuel feedstock, and as fuel additives (e.g., the concomitantly formed oxygenates) to improve the biological origin of carbon in the fuel.Type: GrantFiled: May 12, 2015Date of Patent: September 10, 2019Assignee: Katholieke Universiteit Leuven, K.U. Leuven Research & DevelopmentInventors: Michiel Julien Dusselier, Beau Op De Beeck, Bert Frans Sels
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Patent number: 10377727Abstract: Gamma-valerolactone is prepared from a levulinic acid ester in a continuous process where a stream of the levulinic acid ester together with a gaseous stream of a hydrogen-containing gas is contacted with a hydrogenation catalyst, where the levulinic acid ester is in the liquid phase, and where the hydrogenation catalyst is a solid particulate catalyst including at least one hydrogenating metal, supported on an oxide carrier.Type: GrantFiled: October 6, 2016Date of Patent: August 13, 2019Assignee: Synvina C.V.Inventors: Nicolas André Vélu Popoff, Jan Cornelis van der Waal
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Patent number: 10221149Abstract: The present invention discloses a fast and selective process for the preparation of ?-valerolactone (Gvl) by catalytic hydrogenation of biomass-derived levulinic acid (LA) using recyclable ruthenium (Ru)-based heterogeneous catalysts in aqueous medium in stoichiometric yields (˜100%) under mild reaction conditions using nearly required amount of hydrogen.Type: GrantFiled: October 8, 2015Date of Patent: March 5, 2019Inventors: Kannan Srinivasan, Sreedhar Gundekari
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Patent number: 10195592Abstract: The present invention relates to a catalyst for transfer hydrogenation, which is formed of a metal-organic framework having an MOF-808 based X-ray diffraction pattern. A high crystalline porous MOF-808 based metal-organic framework exhibits excellent performance in the transfer hydrogenation of ethyl levulinate (EL) at high and low temperature.Type: GrantFiled: May 2, 2017Date of Patent: February 5, 2019Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGYInventors: Young Kyu Hwang, Jong San Chang, Do Young Hong, Dong Won Hwang, U Hwang Lee, Kyung Ho Cho, Anil Haribhau Valekar, Su Kyung Lee
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Patent number: 10150720Abstract: The present application relates to a device and a method for preparing alkanol. According to the present application, energy can be reduced when preparing alkanol by reducing the amount of steam used in a reboiler or cooling water used in a condenser, and steam generated from a heat exchanger for overhead stream can be utilized in a variety of fields. Also, highly pure alkanol can be prepared according to the present application.Type: GrantFiled: January 16, 2014Date of Patent: December 11, 2018Assignee: LG CHEM, LTD.Inventors: Sung Kyu Lee, Joon Ho Shin, Jong Ku Lee
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Patent number: 9944571Abstract: The present invention relates to a process for the one-pot hydrogenation and dehydration or isomerization of an organic compound, and to a catalyst composition for this process comprising transition metal particles having particle size below 50 nm supported on a material comprising at least one fluorinated polymer (P), wherein polymer (P) bears —SO2X functional groups, X being selected from X? and OM, X? being selected from the groups consisting of F, Cl, Br and I; and M being selected from the group consisting of H, and alkaline metal and NH4.Type: GrantFiled: November 16, 2015Date of Patent: April 17, 2018Assignee: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.Inventors: Claudio Oldani, Luca Merlo, Pierluigi Barbaro, Carmen Moreno-Marrodan, Francesca Liguori
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Patent number: 9878967Abstract: The present invention relates to a method of converting levulinic acid or a derivative thereof to hydrocarbons and hydrogen by providing a source of levulinic acid or a derivative thereof and converting the levulinic acid or a derivative thereof in the source to hydrocarbons and hydrogen, where converting is carried out in a single reactor. The present invention also relates to methods for producing hydrocarbons and hydrogen.Type: GrantFiled: December 22, 2016Date of Patent: January 30, 2018Assignee: Iowa State University Research Foundation, Inc.Inventors: Wenyu Huang, Chaoxian Xiao
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Patent number: 9873612Abstract: The present invention relates to methods of preparing carbon monoxide (CO) and hydrogen (H2) by reacting biomass, a biomass component (e.g., lignin, ligno-cellulose, cellulose, hemiceullose or combination thereof) or a carbohydrate from any source with a polyoxometalate catalyst such as H5PV2Mo10O40, or solvates thereof, in the presence of a concentrated acid, under conditions sufficient to yield carbon monoxide (CO); followed by electrochemical release of hydrogen (H2). The carbon monoxide (CO) and hydrogen (H2) may be combined in any desired proportion to yield synthesis gas (Syngas). The present invention further relates to methods for preparing H2, CO and formic acid/formaldehyde from biomass, a biomass component and/or from carbohydrates.Type: GrantFiled: October 28, 2014Date of Patent: January 23, 2018Assignee: YEDA RESEARCH AND DEVELOPMENT CO. LTD.Inventors: Ronny Neumann, Bidyut-Bikash Sarma
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Patent number: 9777224Abstract: Methods are disclosed for converting a biomass-derived product containing levulinic acid and/or gamma-valerolactone to a transportation fuel precursor product containing diesel like hydrocarbons. These methods are expected to produce fuel products at a reduced cost relative to conventional approaches.Type: GrantFiled: November 7, 2016Date of Patent: October 3, 2017Assignee: BATTELLE MEMORIAL INSTITUTEInventors: Michael A. Lilga, Asanga B. Padmaperuma
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Patent number: 9695140Abstract: An object of the present invention is to provide high-purity gamma-butyrolactone (GBL) capable of preventing occurrence of reaction other than the object at the time of use, which reaction is caused due to a high acidity of GBL, and the present invention relates to a gamma-butyrolactone composition containing gamma-butyrolactone and a nitrogen-containing compound, wherein a content of the gamma-butyrolactone is 99.0% by mass or more, and a total content of the nitrogen-containing compound is 0.1 ppm by mass to 1,000 ppm by mass as converted to a nitrogen atom.Type: GrantFiled: August 17, 2016Date of Patent: July 4, 2017Assignee: MITSUBISHI CHEMICAL CORPORATIONInventors: Shohei Taniguchi, Yusuke Izawa, Masaru Utsunomiya
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Patent number: 9376411Abstract: 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: January 14, 2015Date of Patent: June 28, 2016Assignee: Wisconsin Alumni Research FoundationInventors: James A. Dumesic, Stephanie G. Wettstein, David Martin Alonso, Elif Ispir Gurbuz
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Patent number: 9212320Abstract: Described are methods, reactor systems, and catalysts for converting biomass to fuels and chemicals in a batch and/or continuous process. The process generally involves the conversion of water insoluble components of biomass, such as hemicellulose, cellulose and lignin, to volatile C2+O1-2 oxygenates, such as alcohols, ketones, cyclic ethers, esters, carboxylic acids, aldehydes, and mixtures thereof. In certain applications, the volatile C2+O1-2 oxygenates can be collected and used as a final chemical product, or used in downstream processes to produce liquid fuels, chemicals and other products.Type: GrantFiled: May 23, 2012Date of Patent: December 15, 2015Assignee: Virent, Inc.Inventors: Elizabeth M. Woods, Ming Qiao, Paul Myren, Randy D. Cortright, John Kania
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Patent number: 9068120Abstract: Technologies are generally described for a system and method effective to prepare a flame retardant. In one example, a method may include copolymerizing a mixture of monomers. The mixture of monomers may include at least one dicarboxylic acid monomer, at least one diamine monomer, and at least one monomer having the formula wherein R1 is hydroxyl, halogen, alkoxy, or aryloxy; wherein R2 is hydroxyl, halogen, alkoxy, or aryloxy; wherein R3 is H or -L-R5; wherein R4 is H or L-R5; wherein if R3 is H, then R4 is L-R5; wherein L is alkyl, cycloalkyl, aryl, heteroaryl, or —(R6-O—R7)n-; wherein R6 is alkyl, cycloalkyl, aryl, or heteroaryl, wherein R7 is alkyl, cycloalkyl, aryl, or heteroaryl, wherein n is an integer from 1 to 12; wherein R5 is a flame retarding moiety comprising P, N, halogen, or B; and wherein q is an integer from 1 to 12.Type: GrantFiled: August 9, 2012Date of Patent: June 30, 2015Assignee: Empire Technology Development LLCInventor: Glen Leon Brizius
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Patent number: 9045804Abstract: A process to produce an aqueous solution of carbohydrates that contains C6-sugar-containing oligomers, C6 sugar monomers, C5-sugar-containing oligomers, C5 sugar monomers, or any combination thereof is presented. The process includes the steps of reacting biomass or a biomass-derived reactant with a solvent system including a lactone and water, and an acid catalyst. The reaction yields a product mixture containing water-soluble C6-sugar-containing oligomers, C6-sugar monomers, C5-sugar-containing oligomers, C5-sugar monomers, or any combination thereof. A solute is added to the product mixture to cause partitioning of the product mixture into an aqueous layer containing the carbohydrates and a substantially immiscible organic layer containing the lactone.Type: GrantFiled: January 8, 2013Date of Patent: June 2, 2015Assignee: Wisconsin Alumni Research FoundationInventors: James A. Dumesic, Jeremy S. Luterbacher
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Publication number: 20150073156Abstract: The present invention relates to a production method of ?-methylene lactone which comprises the following steps: (A) a step of producing an enolate intermediate by making lactone react with alkyl formate under the presence of an alkoxide base; and (B) making the enolate intermediate react with paraformaldehyde. The production method of the present invention is capable of reducing the process time, improving yield, and minimizing the contamination of a reactor.Type: ApplicationFiled: July 20, 2012Publication date: March 12, 2015Inventors: Myung Ryul Lee, Sun Dae Kim, In Sik Jeon, Won Gi Lee, Sung Hee Ahn, Sang Hyun Hong
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Patent number: 8975421Abstract: An industrially viable process for selective preparation of ?- valerolactone using recyclable non noble metal catalyst is provided. This process provides 80-100% conversion to ?-valerolactone, with selectivity in the range of 80-100%.Type: GrantFiled: February 22, 2013Date of Patent: March 10, 2015Assignee: Council of Scientific & Industrial ResearchInventors: Chandrashekhar Vasant Rode, Amol Mahalingappa Hengne
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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
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Publication number: 20140316146Abstract: A process for the production of 1,4-butanediol and tetrahydrofuran by catalytic hydrogenation of dialkyl maleates includes the following steps: a) hydrogenating a stream of dialkyl maleate in a first stage of reaction over suitable catalysts to produce dialkyl succinate; b) further hydrogenating the dialkyl succinate in a second stage of reaction, by using a different suitable catalyst, for producing mainly 1,4-butanediol, together with gamma-butyrolactone and tetrahydrofuran as co-products. In both stages of reaction the conditions, as hydrogen/organic feed ratio, pressure and temperature, are such to maintain the reactors in mixed liquid/vapor phase.Type: ApplicationFiled: November 25, 2011Publication date: October 23, 2014Applicant: CONSER SPAInventors: Flavio Simola, Marco Scarsella, Paolo De Filippis
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Publication number: 20140296466Abstract: The present invention relates to a method of producing bio-based homoserine lactone and bio-based organic acid through hydrolysis of O-acyl homoserine produced by a microorganism in the presence of an acid catalyst. According to the present invention, O-acyl homoserine produced by a microorganism is used as a raw material for producing 1,4-butanediol, gamma-butyrolactone, tetrahydrofuran and the like, which are industrially highly useful. The O-acyl homoserine produced by a microorganism can substitute conventional petrochemical products, can solve environmental concerns, including the emission of pollutants and the exhaustion of natural resources, and can be continuously renewable so as not to exhaust natural resources.Type: ApplicationFiled: March 19, 2014Publication date: October 2, 2014Inventors: Han Won Lee, Young Lyeol Yang, So Young Kim, Yong Uk Shin, Jin Sook Chang, Hye Won Um, Young Hyoung Goh, Sung Hoo Jhon
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Patent number: 8779168Abstract: The present invention relates to lactone compounds represented by the following Formulas I and II, and methods of making such lactone compounds. The present invention also relates to methods of making other materials from such lactone compounds, such as fused ring indenol compounds (e.g., indeno-fused naphthols), and fused ring indenopyran compounds (e.g., indeno-fused naphthopyrans).Type: GrantFiled: December 7, 2011Date of Patent: July 15, 2014Assignee: Transitions Optical, Inc.Inventors: Meng He, Darrin R. Dabideen, Ruisong Xu, Anil Kumar
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Publication number: 20140170714Abstract: Post purification processes and methods for making pure biobased gamma-butyrolactone from renewable carbon resources comprising filtration and/or distillation and/or peroxide treatment are described herein.Type: ApplicationFiled: August 10, 2012Publication date: June 19, 2014Applicant: METABOLIX, INC.Inventors: Johan Van Walsem, John Licata, Erik A. Anderson, Kevin A. Sparks, William R. Farmer, Christopher Mirley, Jeffrey A. Bickmeier, Frank A. Skraly, Thomas M. Ramseier, Ann D'Ambruoso, Melarkode S. Sivasubramanian, Yossef Shabtai, Derek Samuelson, Stephen Harris
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Publication number: 20140162326Abstract: Methods for forming ammonium salts of C4 diacids in a fermentation process with removal of divalent metal carbonate salts are disclosed. The pH of fermentation broths for production of C4 diacids is controlled by adding alkaline oxygen containing calcium or magnesium compounds, which forms divalent metal salts of the diacids. The divalent metal salts of the diacids are substituted with ammonium by introduction of ammonium salts at elevated temperature and pressure forming soluble ammonium salts thereof. C02 or bicarbonate is simultaneously added to the fennentation media at the elevated temperature and pressure. Reducing the temperature and pressure forms insoluble divalent metal carbonate salts that are separated from the solubilized ammonium diacid salts.Type: ApplicationFiled: July 9, 2012Publication date: June 12, 2014Inventors: ChiCheng Ma, Todd Werpy
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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
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Patent number: 8598372Abstract: The present invention relates to a method for producing a cyclic compound that has high selectivity, high yield, and stability over a long period of time depending on a metal content ratio of a catalyst, specifically a lactone compound or a heterocyclic compound including oxygen, which includes hydrogenating an organic acid, organic acid ester, or a mixture of the organic acid and organic acid ester, which are having 4 to 6 carbon atoms, by using a selective hydrogenated catalyst.Type: GrantFiled: August 27, 2010Date of Patent: December 3, 2013Assignee: Korea Research Institute of Chemical TechnologyInventors: Young Kyu Hwang, Jong San Chang, Jung Ho Lee, Jong-Min Lee
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Patent number: 8580978Abstract: A process for preparing a hydroxyacid or hydroxyester from a reactant selected from (a) a carboxylic acid having an aldehyde or keto group; and (b) an ester of a carboxylic acid having an aldehyde or keto group; by contacting the reactant with a metal catalyst in the presence of hydrogen, wherein the metal catalyst is supported on a titanium dioxide or zirconium dioxide support.Type: GrantFiled: August 5, 2010Date of Patent: November 12, 2013Assignee: Shell Oil CompanyInventors: Rene Johan Haan, Jean-Paul Lange
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Publication number: 20130296579Abstract: An industrially viable process for selective preparation of ?-valerolactone using recyclable non noble metal catalyst is provided. This process provides 80-100% conversion to ?-valerolactone, with selectivity in the range of 80-100%.Type: ApplicationFiled: February 22, 2013Publication date: November 7, 2013Applicant: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCHInventor: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH
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Publication number: 20130204015Abstract: A method for preparing a lactone is described. Also described, is the preparation of butyrolactone, valerolactone and caprolactone. The method for preparing a lactone can include a reduction of a dicarboxylic acid using hydrogen, in a gaseous phase and in the presence of an effective amount of a catalyst including an active ruthenium-tin phase including at least one Ru2Sn3 alloy and an Ru3Sn7 alloy.Type: ApplicationFiled: April 5, 2011Publication date: August 8, 2013Applicant: RHODIA OPERATIONSInventors: Roland Jacquot, Philippe Marion
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Patent number: 8466300Abstract: A process for making a hydrogenated product includes providing a clarified DAS-containing fermentation broth; distilling the broth under super atmospheric pressure at a temperature of >100° C. to about 300° C. to form an overhead that includes water and ammonia, and a liquid bottoms that includes SA, and at least about 20 wt % water; cooling the bottoms to a temperature sufficient to cause the bottoms to separate into a liquid portion in contact with a solid portion that is substantially pure SA; separating the solid portion from the liquid portion; recovering the solid portion; hydrogenating the solid portion in the presence of at least one hydrogenation catalyst to produce the hydrogenated product including at least one of THF, GBL or BDO; and recovering the hydrogenated product.Type: GrantFiled: March 18, 2011Date of Patent: June 18, 2013Assignee: BioAmber International S.a.r.l.Inventors: Olan S. Fruchey, Leo E. Manzer, Dilum Dunuwila, Brian Terry Keen, Brooke Ashley Albin, Nye A. Clinton, Bernard Duane Dombek
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Patent number: 8410291Abstract: A process for making a hydrogenated product includes providing a clarified DAS-containing fermentation broth, distilling the broth to form an overhead that includes water and ammonia, and a liquid bottoms that includes MAS, at least some DAS, and at least about 20 wt % water, cooling and/or evaporating the bottoms, and optionally adding an antisolvent to the bottoms, to attain a temperature and composition sufficient to cause the bottoms to separate into a DAS-containing liquid portion and a MAS-containing solid portion that is substantially free of DAS, separating the solid portion from the liquid portion, recovering the solid portion, hydrogenating the second solid portion in the presence of at least one hydrogenation catalyst to produce the hydrogenated product comprising at least one of THF, GBL or BDO, and recovering the hydrogenated product.Type: GrantFiled: March 18, 2011Date of Patent: April 2, 2013Assignee: BioAmber International S.á.r.l.Inventors: Olan S. Fruchey, Leo E. Manzer, Dilum Dunuwila, Brian Terry Keen, Brooke Ashley Albin, Nye A. Clinton, Bernard Duane Dombek
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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: 8399687Abstract: A process for making a hydrogenated product includes providing a clarified DAS-containing fermentation broth, distilling the broth to form an overhead that includes water and ammonia, and a liquid bottoms that includes MAS, at least some DAS, and at least about 20 wt % water, cooling and/or evaporating the bottoms, and optionally adding an antisolvent to the bottoms, to attain a temperature and composition sufficient to cause the bottoms to separate into a DAS-containing liquid portion and a MAS-containing solid portion that is substantially free of DAS, separating the solid portion from the liquid portion, recovering the solid portion, hydrogenating the second solid portion in the presence of at least one hydrogenation catalyst to produce the hydrogenated product comprising at least one of THF, GBL or BDO, and recovering the hydrogenated product.Type: GrantFiled: December 22, 2011Date of Patent: March 19, 2013Assignee: BioAmber International S.a.r.l.Inventors: Olan S. Fruchey, Leo E. Manzer, Dilum Dunuwila, Brian T. Keen, Brooke A. Albin, Nye A. Clinton, Bernard D. Dombek
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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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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
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Publication number: 20130046075Abstract: A double-walled plastic jar for cosmetic materials, having an inner compartment to hold the cosmetic, and an annular outer side wall defining the exterior of the jar. The inner compartment carries the lip that seals with a screw cap, and also carries an external skirt, which latter has the screw threads for engagement by the cap. In addition, a weight is disposed in a-concealed manner in the base of the jar, between the walls, to give the jar a heft feel, characteristic of glass or thick plastic walls.Type: ApplicationFiled: April 4, 2011Publication date: February 21, 2013Inventors: Johan van Walsem, Erik Anderson, John Licata, Kevin A. Sparks, William R. Farmer, Christopher Mirley, Jeffrey A. Bickmeier, Ann D'Ambruoso, Frank A. Skraly, Thomas M. Ramseier, M.S. Sivasubramanian, Yossef Shabtai
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Patent number: 8362306Abstract: A process for upgrading an organic acid includes neutralizing the organic acid to form a salt and thermally decomposing the resulting salt to form an energy densified product. In certain embodiments, the organic acid is levulinic acid. The process may further include upgrading the energy densified product by conversion to alcohol and subsequent dehydration.Type: GrantFiled: October 26, 2010Date of Patent: January 29, 2013Assignee: University of Maine System Board of TrusteesInventors: M. Clayton Wheeler, G. Peter van Walsum, Thomas J. Schwartz, Adriaan van Heiningen
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Publication number: 20120302764Abstract: 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: ApplicationFiled: May 25, 2011Publication date: November 29, 2012Inventors: James Dumesic, Jesse Bond, David Alonso, Thatcher Root
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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: 20120302766Abstract: 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: ApplicationFiled: December 15, 2011Publication date: November 29, 2012Inventors: James A. Dumesic, Stephanie G. Wettstein, David Martin Alonso, Elif Ispir Gurbuz
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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: 20120215014Abstract: A process for making a hydrogenated product includes providing a clarified DAS-containing fermentation broth, distilling the broth to form an overhead that includes water and ammonia, and a liquid bottoms that includes MAS, at least some DAS, and at least about 20 wt % water, cooling and/or evaporating the bottoms, and optionally adding an antisolvent to the bottoms, to attain a temperature and composition sufficient to cause the bottoms to separate into a DAS-containing liquid portion and a MAS-containing solid portion that is substantially free of DAS, separating the solid portion from the liquid portion, recovering the solid portion, hydrogenating the second solid portion in the presence of at least one hydrogenation catalyst to produce the hydrogenated product comprising at least one of THF, GBL or BDO, and recovering the hydrogenated product.Type: ApplicationFiled: April 27, 2012Publication date: August 23, 2012Applicant: BioAmber International S.a.r.l.Inventors: Olan S. Fruchey, Leo E. Manzer, Dilum Dunuwila, Brian Terry Keen, Brooke Ashley Albin, Nye A. Clinton, Bernard Duane Dombek
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Publication number: 20120197029Abstract: The present invention relates to a method for producing a cyclic compound that has high selectivity, high yield, and stability over a long period of time depending on a metal content ratio of a catalyst, specifically a lactone compound or a heterocyclic compound including oxygen, which includes hydrogenating an organic acid, organic acid ester, or a mixture of the organic acid and organic acid ester, which are having 4 to 6 carbon atoms, by using a selective hydrogenated catalyst.Type: ApplicationFiled: August 27, 2010Publication date: August 2, 2012Applicant: Korea Research Institute of Chemical TechnologyInventors: Young Kyu Hwang, Jong San Chang, Jung Ho Lee, Jong-Min Lee
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Publication number: 20120149922Abstract: 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: ApplicationFiled: February 9, 2012Publication date: June 14, 2012Inventors: James A. Dumesic, Juan Carlos Serrano Ruiz, Ryan M. West
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Patent number: 8193375Abstract: A process for making a hydrogenated product includes providing a clarified DAS-containing fermentation broth, distilling the broth to form an overhead that includes water and ammonia, and a liquid bottoms that includes MAS, at least some DAS, and at least about 20 wt % water, cooling and/or evaporating the bottoms, and optionally adding an antisolvent to the bottoms, to attain a temperature and composition sufficient to cause the bottoms to separate into a DAS-containing liquid portion and a MAS-containing solid portion that is substantially free of DAS, separating the solid portion from the liquid portion, recovering the solid portion, hydrogenating the second solid portion in the presence of at least one hydrogenation catalyst to produce the hydrogenated product comprising at least one of THF, GBL or BDO, and recovering the hydrogenated product.Type: GrantFiled: August 19, 2011Date of Patent: June 5, 2012Assignee: BioAmber International S.ä.r.l.Inventors: Olan S. Fruchey, Leo E. Manzer, Dilum Dunuwila, Brian Terry Keen, Brooke Ashley Albin, Nye A. Clinton, Bernard Duane Dombek
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Publication number: 20120095241Abstract: A process for making a hydrogenated product includes providing a clarified DAS-containing fermentation broth, distilling the broth to form an overhead that includes water and ammonia, and a liquid bottoms that includes MAS, at least some DAS, and at least about 20 wt % water, cooling and/or evaporating the bottoms, and optionally adding an antisolvent to the bottoms, to attain a temperature and composition sufficient to cause the bottoms to separate into a DAS-containing liquid portion and a MAS-containing solid portion that is substantially free of DAS, separating the solid portion from the liquid portion, recovering the solid portion, hydrogenating the second solid portion in the presence of at least one hydrogenation catalyst to produce the hydrogenated product comprising at least one of THF, GBL or BDO, and recovering the hydrogenated product.Type: ApplicationFiled: December 22, 2011Publication date: April 19, 2012Applicant: BioAmber International S.a.r.l.Inventors: Olan S. Fruchey, Leo E. Manzer, Dilum Dunuwila, Brian T. Keen, Brooke A. Albin, Nye A. Clinton, Bernard D. Dombek
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Patent number: 8148553Abstract: Described is a method to make liquid chemicals, such as functional intermediates, solvents, and liquid fuels from biomass-derived cellulose. The method is cascading; the product stream from an upstream reaction can be used as the feedstock in the next downstream reaction. The method includes the steps of deconstructing cellulose to yield a product mixture comprising levulinic acid and formic acid, converting the levulinic acid to ?-valerolactone, and converting the ?-valerolactone to pentanoic acid. Alternatively, the ?-valerolactone can be converted to a mixture of n-butenes. The pentanoic acid so formed can be further reacted to yield a host of valuable products. For example, the pentanoic acid can be decarboxylated yield 1-butene or ketonized to yield 5-nonanone. The 5-nonanone can be hydrodeoxygenated to yield nonane, or 5-nonanone can be reduced to yield 5-nonanol.Type: GrantFiled: June 23, 2009Date of Patent: April 3, 2012Assignee: Wisconsin Alumni Research FoundationInventors: James A. Dumesic, Juan Carlos Serrano Ruiz, Ryan M. West
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Patent number: 8093409Abstract: The present invention provides a method for producing a cyclic unsaturated compound, which sufficiently suppresses generation of acyclic unsaturated compounds and permits excellent yield and reaction rate. Such a method for producing a cyclic unsaturated compound is a method for producing a cyclic unsaturated compound by reacting an ?,?-unsaturated carboxylic acid with an unsaturated organic compound, wherein the method comprises a step of reacting the ?,?-unsaturated carboxylic acid with the unsaturated organic compound in the presence of a catalyst.Type: GrantFiled: August 22, 2007Date of Patent: January 10, 2012Assignee: Nippon Shokubai Co., Ltd.Inventor: Koji Yonehara
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Patent number: 8084626Abstract: A process for making a hydrogenated product includes providing a clarified DAS-containing fermentation broth; distilling the broth under super atmospheric pressure at a temperature of >100° C. to about 300° C. to form an overhead that includes water and ammonia, and a liquid bottoms that includes SA, and at least about 20 wt % water; cooling the bottoms to a temperature sufficient to cause the bottoms to separate into a liquid portion in contact with a solid portion that is substantially pure SA; separating the solid portion from the liquid portion; recovering the solid portion; hydrogenating the solid portion in the presence of at least one hydrogenation catalyst to produce the hydrogenated product including at least one of THF, GBL or BDO; and recovering the hydrogenated product.Type: GrantFiled: August 19, 2011Date of Patent: December 27, 2011Assignee: BioAmber S.A.S.Inventors: Olan S. Fruchey, Leo E. Manzer, Dilum Dunuwila, Brian Terry Keen, Brooke Ashley Albin, Nye A. Clinton, Bernard Duane Dombek
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Publication number: 20110306777Abstract: A process for making a hydrogenated product includes providing a clarified DAS-containing fermentation broth; distilling the broth under super atmospheric pressure at a temperature of >100° C. to about 300° C. to form an overhead that includes water and ammonia, and a liquid bottoms that includes SA, and at least about 20 wt % water; cooling the bottoms to a temperature sufficient to cause the bottoms to separate into a liquid portion in contact with a solid portion that is substantially pure SA; separating the solid portion from the liquid portion; recovering the solid portion; hydrogenating the solid portion in the presence of at least one hydrogenation catalyst to produce the hydrogenated product including at least one of THF, GBL or BDO; and recovering the hydrogenated product.Type: ApplicationFiled: August 19, 2011Publication date: December 15, 2011Applicant: BioAmber S.A.S.Inventors: Olan S. Fruchey, Leo E. Manzer, Dilum Dunuwila, Brian Terry Keen, Brooke Ashley Albin, Nye A. Clinton, Bernard Duane Dombek
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Publication number: 20110301364Abstract: A process for making a hydrogenated product includes providing a clarified DAS-containing fermentation broth, distilling the broth to form an overhead that includes water and ammonia, and a liquid bottoms that includes MAS, at least some DAS, and at least about 20 wt % water, cooling and/or evaporating the bottoms, and optionally adding an antisolvent to the bottoms, to attain a temperature and composition sufficient to cause the bottoms to separate into a DAS-containing liquid portion and a MAS-containing solid portion that is substantially free of DAS, separating the solid portion from the liquid portion, recovering the solid portion, hydrogenating the second solid portion in the presence of at least one hydrogenation catalyst to produce the hydrogenated product comprising at least one of THF, GBL or BDO, and recovering the hydrogenated product.Type: ApplicationFiled: August 19, 2011Publication date: December 8, 2011Applicant: BioAmber S.A.S.Inventors: Olan S. Fruchey, Leo E. Manzer, Dilum Dunuwila, Brian Terry Keen, Brooke Ashley Albin, Nye A. Clinton, Bernard Duane Dombek