Preparing From Compound Containing -coo- Group Patents (Class 549/326)
  • Patent number: 11098020
    Abstract: 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: Grant
    Filed: May 23, 2017
    Date of Patent: August 24, 2021
    Assignee: Nederlandse Organisatie voor toegepast-natuurwetenschappelijk onderzoek TNO
    Inventors: Paul Mathijs Könst, Johan Urbanus
  • Patent number: 10407623
    Abstract: 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: Grant
    Filed: May 12, 2015
    Date of Patent: September 10, 2019
    Assignee: Katholieke Universiteit Leuven, K.U. Leuven Research & Development
    Inventors: Michiel Julien Dusselier, Beau Op De Beeck, Bert Frans Sels
  • Patent number: 10377727
    Abstract: 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: Grant
    Filed: October 6, 2016
    Date of Patent: August 13, 2019
    Assignee: Synvina C.V.
    Inventors: Nicolas André Vélu Popoff, Jan Cornelis van der Waal
  • Patent number: 10221149
    Abstract: 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: Grant
    Filed: October 8, 2015
    Date of Patent: March 5, 2019
    Inventors: Kannan Srinivasan, Sreedhar Gundekari
  • Patent number: 10195592
    Abstract: 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: Grant
    Filed: May 2, 2017
    Date of Patent: February 5, 2019
    Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY
    Inventors: Young Kyu Hwang, Jong San Chang, Do Young Hong, Dong Won Hwang, U Hwang Lee, Kyung Ho Cho, Anil Haribhau Valekar, Su Kyung Lee
  • Patent number: 10150720
    Abstract: 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: Grant
    Filed: January 16, 2014
    Date of Patent: December 11, 2018
    Assignee: LG CHEM, LTD.
    Inventors: Sung Kyu Lee, Joon Ho Shin, Jong Ku Lee
  • Patent number: 9944571
    Abstract: 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: Grant
    Filed: November 16, 2015
    Date of Patent: April 17, 2018
    Assignee: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.
    Inventors: Claudio Oldani, Luca Merlo, Pierluigi Barbaro, Carmen Moreno-Marrodan, Francesca Liguori
  • Patent number: 9878967
    Abstract: 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: Grant
    Filed: December 22, 2016
    Date of Patent: January 30, 2018
    Assignee: Iowa State University Research Foundation, Inc.
    Inventors: Wenyu Huang, Chaoxian Xiao
  • Patent number: 9873612
    Abstract: 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: Grant
    Filed: October 28, 2014
    Date of Patent: January 23, 2018
    Assignee: YEDA RESEARCH AND DEVELOPMENT CO. LTD.
    Inventors: Ronny Neumann, Bidyut-Bikash Sarma
  • Patent number: 9777224
    Abstract: 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: Grant
    Filed: November 7, 2016
    Date of Patent: October 3, 2017
    Assignee: BATTELLE MEMORIAL INSTITUTE
    Inventors: Michael A. Lilga, Asanga B. Padmaperuma
  • Patent number: 9695140
    Abstract: 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: Grant
    Filed: August 17, 2016
    Date of Patent: July 4, 2017
    Assignee: MITSUBISHI CHEMICAL CORPORATION
    Inventors: Shohei Taniguchi, Yusuke Izawa, Masaru Utsunomiya
  • Patent number: 9376411
    Abstract: 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: Grant
    Filed: January 14, 2015
    Date of Patent: June 28, 2016
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: James A. Dumesic, Stephanie G. Wettstein, David Martin Alonso, Elif Ispir Gurbuz
  • Patent number: 9212320
    Abstract: 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: Grant
    Filed: May 23, 2012
    Date of Patent: December 15, 2015
    Assignee: Virent, Inc.
    Inventors: Elizabeth M. Woods, Ming Qiao, Paul Myren, Randy D. Cortright, John Kania
  • Patent number: 9068120
    Abstract: 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: Grant
    Filed: August 9, 2012
    Date of Patent: June 30, 2015
    Assignee: Empire Technology Development LLC
    Inventor: Glen Leon Brizius
  • Patent number: 9045804
    Abstract: 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: Grant
    Filed: January 8, 2013
    Date of Patent: June 2, 2015
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: James A. Dumesic, Jeremy S. Luterbacher
  • Publication number: 20150073156
    Abstract: 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: Application
    Filed: July 20, 2012
    Publication date: March 12, 2015
    Inventors: Myung Ryul Lee, Sun Dae Kim, In Sik Jeon, Won Gi Lee, Sung Hee Ahn, Sang Hyun Hong
  • Patent number: 8975421
    Abstract: 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: Grant
    Filed: February 22, 2013
    Date of Patent: March 10, 2015
    Assignee: Council of Scientific & Industrial Research
    Inventors: Chandrashekhar Vasant Rode, Amol Mahalingappa Hengne
  • Patent number: 8962867
    Abstract: 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: Grant
    Filed: December 15, 2011
    Date of Patent: February 24, 2015
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: James A. Dumesic, Stephanie G. Wettstein, David Martin Alonso, Elif Ispir Gurbuz
  • Publication number: 20140316146
    Abstract: 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: Application
    Filed: November 25, 2011
    Publication date: October 23, 2014
    Applicant: CONSER SPA
    Inventors: Flavio Simola, Marco Scarsella, Paolo De Filippis
  • Publication number: 20140296466
    Abstract: 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: Application
    Filed: March 19, 2014
    Publication date: October 2, 2014
    Inventors: Han Won Lee, Young Lyeol Yang, So Young Kim, Yong Uk Shin, Jin Sook Chang, Hye Won Um, Young Hyoung Goh, Sung Hoo Jhon
  • Patent number: 8779168
    Abstract: 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: Grant
    Filed: December 7, 2011
    Date of Patent: July 15, 2014
    Assignee: Transitions Optical, Inc.
    Inventors: Meng He, Darrin R. Dabideen, Ruisong Xu, Anil Kumar
  • Publication number: 20140170714
    Abstract: 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: Application
    Filed: August 10, 2012
    Publication date: June 19, 2014
    Applicant: 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
  • Publication number: 20140162326
    Abstract: 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: Application
    Filed: July 9, 2012
    Publication date: June 12, 2014
    Inventors: ChiCheng Ma, Todd Werpy
  • Patent number: 8624043
    Abstract: 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: Grant
    Filed: February 9, 2012
    Date of Patent: January 7, 2014
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: James A. Dumesic, Juan Carlos Serrano Ruiz, Ryan M. West
  • Patent number: 8598372
    Abstract: 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: Grant
    Filed: August 27, 2010
    Date of Patent: December 3, 2013
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Young Kyu Hwang, Jong San Chang, Jung Ho Lee, Jong-Min Lee
  • Patent number: 8580978
    Abstract: 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: Grant
    Filed: August 5, 2010
    Date of Patent: November 12, 2013
    Assignee: Shell Oil Company
    Inventors: Rene Johan Haan, Jean-Paul Lange
  • Publication number: 20130296579
    Abstract: 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: Application
    Filed: February 22, 2013
    Publication date: November 7, 2013
    Applicant: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH
    Inventor: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH
  • Publication number: 20130204015
    Abstract: 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: Application
    Filed: April 5, 2011
    Publication date: August 8, 2013
    Applicant: RHODIA OPERATIONS
    Inventors: Roland Jacquot, Philippe Marion
  • Patent number: 8466300
    Abstract: 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: Grant
    Filed: March 18, 2011
    Date of Patent: June 18, 2013
    Assignee: 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
  • Patent number: 8410291
    Abstract: 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: Grant
    Filed: March 18, 2011
    Date of Patent: April 2, 2013
    Assignee: 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
  • Patent number: 8399687
    Abstract: 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: Grant
    Filed: December 22, 2011
    Date of Patent: March 19, 2013
    Assignee: 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
  • Patent number: 8399688
    Abstract: 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: Grant
    Filed: April 12, 2012
    Date of Patent: March 19, 2013
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: James A. Dumesic, David Martin Alonso, Elif I. Gürbüz, Stephanie G. Wettstein
  • Patent number: 8389749
    Abstract: 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: Grant
    Filed: May 25, 2011
    Date of Patent: March 5, 2013
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: James Dumesic, David Alonso, Jesse Bond, Thatcher Root, Mei Chia
  • Patent number: 8389761
    Abstract: 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: Grant
    Filed: May 25, 2011
    Date of Patent: March 5, 2013
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: James Dumesic, Jesse Bond, David Alonso, Thatcher Root
  • Publication number: 20130046075
    Abstract: 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: Application
    Filed: April 4, 2011
    Publication date: February 21, 2013
    Inventors: 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
  • Patent number: 8362306
    Abstract: 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: Grant
    Filed: October 26, 2010
    Date of Patent: January 29, 2013
    Assignee: University of Maine System Board of Trustees
    Inventors: M. Clayton Wheeler, G. Peter van Walsum, Thomas J. Schwartz, Adriaan van Heiningen
  • Publication number: 20120302767
    Abstract: 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: Application
    Filed: April 12, 2012
    Publication date: November 29, 2012
    Inventors: James A. Dumesic, David Martin Alonso, Elif I. Gürbüz, Stephanie G. Wettstein
  • Publication number: 20120302764
    Abstract: 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: Application
    Filed: May 25, 2011
    Publication date: November 29, 2012
    Inventors: James Dumesic, Jesse Bond, David Alonso, Thatcher Root
  • Publication number: 20120302765
    Abstract: 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: Application
    Filed: May 25, 2011
    Publication date: November 29, 2012
    Inventors: James Dumesic, David Alonso, Jesse Bond, Thatcher Root, Mei Chia
  • Publication number: 20120302766
    Abstract: 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: Application
    Filed: December 15, 2011
    Publication date: November 29, 2012
    Inventors: James A. Dumesic, Stephanie G. Wettstein, David Martin Alonso, Elif Ispir Gurbuz
  • Publication number: 20120215014
    Abstract: 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: Application
    Filed: April 27, 2012
    Publication date: August 23, 2012
    Applicant: 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
  • Publication number: 20120197029
    Abstract: 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: Application
    Filed: August 27, 2010
    Publication date: August 2, 2012
    Applicant: Korea Research Institute of Chemical Technology
    Inventors: Young Kyu Hwang, Jong San Chang, Jung Ho Lee, Jong-Min Lee
  • Publication number: 20120149922
    Abstract: 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: Application
    Filed: February 9, 2012
    Publication date: June 14, 2012
    Inventors: James A. Dumesic, Juan Carlos Serrano Ruiz, Ryan M. West
  • Patent number: 8193375
    Abstract: 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: Grant
    Filed: August 19, 2011
    Date of Patent: June 5, 2012
    Assignee: 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
  • Publication number: 20120095241
    Abstract: 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: Application
    Filed: December 22, 2011
    Publication date: April 19, 2012
    Applicant: 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
  • Patent number: 8148553
    Abstract: 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: Grant
    Filed: June 23, 2009
    Date of Patent: April 3, 2012
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: James A. Dumesic, Juan Carlos Serrano Ruiz, Ryan M. West
  • Patent number: 8093409
    Abstract: 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: Grant
    Filed: August 22, 2007
    Date of Patent: January 10, 2012
    Assignee: Nippon Shokubai Co., Ltd.
    Inventor: Koji Yonehara
  • Patent number: 8084626
    Abstract: 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: Grant
    Filed: August 19, 2011
    Date of Patent: December 27, 2011
    Assignee: 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
  • Publication number: 20110306777
    Abstract: 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: Application
    Filed: August 19, 2011
    Publication date: December 15, 2011
    Applicant: 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
  • Publication number: 20110301364
    Abstract: 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: Application
    Filed: August 19, 2011
    Publication date: December 8, 2011
    Applicant: 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