Having -c(=x)-, Wherein X Is Chalcogen, Bonded Directly To The Hetero Ring Patents (Class 549/483)
  • Patent number: 11352336
    Abstract: Disclosed is a cost-effective process for catalytic conversion of simple C6-based sugars (such as glucose and fructose) and industrial-grade sugar syrups derived from starch (such as different grades of High Fructose Corn Syrup) and cellulosic biomass to 5-HydroxyMethylFurfural (5-HMF) in a continuous-flow tubular reactor in bi-phasic media using inexpensive heterogeneous solid catalysts. Commercial and synthesized heterogeneous solid catalysts were used and their activities in terms of sugar conversion and HMF selectivity and yield were compared. Continuous dehydration of fructose, glucose and industrial-grade sugar syrups derived from corn and wood to HMF was achieved and the stability of selected catalysts and feasibility of catalyst recycling and regeneration were demonstrated.
    Type: Grant
    Filed: June 29, 2017
    Date of Patent: June 7, 2022
    Assignee: THE UNIVERSITY OF WESTERN ONTARIO
    Inventors: Chunbao Xu, Sadra Souzanchi, Tirumala Venkateswara Rao Kasanneni, Zhongshun Yuan
  • Patent number: 11299468
    Abstract: The present disclosure provides methods to produce 5-(halomethyl)furfural, including 5-(chloromethyl)furfural, by acid-catalyzed conversion of C6 saccharides, including isomers thereof, polymers thereof, and certain derivatives thereof. The methods make use of acids with lower concentrations, and allows for conversion of sugars into 5-(halomethyl)furfural at higher temperatures and faster reaction or residence times.
    Type: Grant
    Filed: June 5, 2020
    Date of Patent: April 12, 2022
    Assignee: Origin Materials Operating, Inc.
    Inventors: Alex B. Wood, Makoto N. Masuno, Ryan L. Smith, John Bissell, Dimitri A. Hirsch-Weil, Robert Joseph Araiza, Daniel R. Henton, James H. Plonka
  • Patent number: 10875834
    Abstract: Prodrugs and derivatives of 5-hydoxymethyl-2-furfural (5-HMF) with protected or modified aldehyde and/or alcohol moieties are provided. The prodrugs or derivatives exhibit increased bioavailability, e.g. due to having extended half-lives in circulation. The drugs are therefore administered i) at lower doses and/or ii) less frequently than 5-HMF, while still maintaining the beneficial therapeutic effects of 5-HMF.
    Type: Grant
    Filed: July 24, 2017
    Date of Patent: December 29, 2020
    Assignees: Virginia Commonwealth University, The Children's Hospital of Philadelphia
    Inventors: Martin K. Safo, Guoyan Xu, Yan Zhang, Osheiza Abdulmalik
  • Patent number: 10662167
    Abstract: The invention relates to a method for producing 5-hydroxymethylfurfural (HMF) in a continuous process, which leads to the obtainment of an HMF fraction, a carbohydrate/acid fraction, a fructose fraction, and a levulinic-acid and formic-acid fraction and advantageously makes it possible, because of the purity of the obtained fractions, to return the fructose fraction obtained by means of the method directly to the production process and to use the other fractions in further-processing processes without the need for complex, additional purification steps.
    Type: Grant
    Filed: December 1, 2017
    Date of Patent: May 26, 2020
    Assignee: SUDZUCKER AG
    Inventors: Markwart Kunz, Alireza Haji Begli, Christine Kröner, Wolfgang Wach, Alain-Michel Graf, Wolfgang Kraus
  • Patent number: 10562874
    Abstract: A process for the extraction of furfural from a composition comprising furfural, water, at least one organic acid and an oxygenate solvent with a boiling point higher than that of furfural. The process includes: (a) subjecting the composition to a first liquid-liquid separation step to provide: (i) an organic phase; (b) subjecting the organic phase of step (a) to a first distillation step to provide: (i) a first top stream; (c) subjecting the first top stream of step (b) to a second liquid-liquid separation step to provide: (i) a second top stream; and (d) subjecting the second top stream of step (c) to a second distillation step to provide: (i) a third top stream comprising a furfural-water azeotrope, and (ii) a third bottom stream comprising furfural.
    Type: Grant
    Filed: October 30, 2017
    Date of Patent: February 18, 2020
    Assignee: SHELL OIL COMPANY
    Inventors: Juben Nemchand Chheda, Charu Ehrenreich-Gureja, Jean Paul Andre Marie Joseph Ghislain Lange
  • Patent number: 10479773
    Abstract: Implementations of the disclosed subject matter provide a process for converting biomass into furfural. The process may include subjecting a pentosan-containing biomass material to an acid catalyzed digestion process in a digestion vessel to produce a digested product stream comprising C5-carbohydrates and solids comprising cellulose. The digested product stream may be separated into a liquid product stream and a solid product stream comprising lignin and cellulose. The solids product stream may be contacted with water and an organic solvent, thereby converting at least part of the lignin to a phenolic solvent. The C5-carbohydrate in the liquid product stream may be subjected to a dehydration reaction in the presence of an acid catalyst and a biphasic mixture comprising an aqueous phase and a water-immiscible organic phase, wherein the water-immiscible organic phase includes at least a portion of the phenolic solvent, to produce furfural or a furan derivative.
    Type: Grant
    Filed: May 2, 2017
    Date of Patent: November 19, 2019
    Assignee: SHELL OIL COMPANY
    Inventors: Juben Nemchand Chheda, Jean Paul Andre Marie Joseph Ghislain Lange
  • Patent number: 10351543
    Abstract: A furfural derivative having the chemical formula (1) wherein R represents hydrogen, an alkyl group or an acyl group, is prepared in a process, which process includes reacting a fructose- and/or glucose-containing starting material with a liquid hydroxyl group-containing compound of formula R—OH in the presence of an acid catalyst at a reaction temperature in the range of 150 to 300° C. to produce an acid reaction mixture including the furfural derivative of chemical formula (1), which acid reaction mixture has a pH-value of smaller than 3; neutralizing the acid reaction mixture to a pH-value in the range of 3 to 6.5 to provide a partially neutralized reaction mixture; and purifying the partially neutralized reaction mixture to recover the furfural derivative of chemical formula (1).
    Type: Grant
    Filed: July 1, 2016
    Date of Patent: July 16, 2019
    Assignee: Synvina C.V.
    Inventors: Johannes Maria Franciscus Sijben, Etienne Mazoyer, Ana Sofia Vagueiro De Sousa Dias, Gerardus Johannes Maria Gruter
  • Patent number: 10266508
    Abstract: A furfural derivative having the chemical formula (1) where R represents hydrogen, an alkyl group or an acyl group, is prepared in a process, which process includes reacting a fructose- and/or glucose-containing starting material with a liquid hydroxyl group-containing compound of formula R—OH in the presence of an acid catalyst at a reaction temperature in the range of 150 to 300° C. to produce a primary acid reaction mixture including the furfural derivative of chemical formula (1); separating part of the liquid hydroxyl group-containing compound from the primary acid reaction mixture to yield a secondary acid reaction mixture; neutralizing the secondary acid reaction mixture to a pH-value of at least 3 to obtain a neutralized reaction mixture; and purifying the neutralized reaction mixture to recover the furfural derivative of chemical formula (1).
    Type: Grant
    Filed: July 1, 2016
    Date of Patent: April 23, 2019
    Assignee: Synvina C.V.
    Inventors: Johannes Maria Franciscus Sijben, Etienne Mazoyer, Ana Sofia Vagueiro De Sousa Dias, Gerardus Johannes Maria Gruter
  • Patent number: 10011577
    Abstract: The present disclosure provides methods to produce 5-(halomethyl)furfural, including 5-(chloromethyl)furfural, by acid-catalyzed conversion of C6 saccharides, including isomers thereof, polymers thereof, and certain derivatives thereof. The methods make use of acids with lower concentrations, and allows for conversion of sugars into 5-(halomethyl)furfural at higher temperatures and faster reaction or residence times.
    Type: Grant
    Filed: September 19, 2014
    Date of Patent: July 3, 2018
    Assignee: MICROMIDAS, INC.
    Inventors: Alex B. Wood, Makoto N. Masuno, Ryan L. Smith, John Bissell, Dimitri A. Hirsch-Weil, Robert Joseph Araiza, Daniel R. Henton, James H. Plonka
  • Patent number: 9522898
    Abstract: The present invention concerns a process for the production of an aldehyde compound by an oxidation reaction of an alcohol compound in the presence of a mesostructured vanadium phosphorus mixed oxide catalyst, at a temperature comprised between 50° C. and 200° C., in presence of an oxidant. The reaction medium may also comprise a solvent.
    Type: Grant
    Filed: February 5, 2014
    Date of Patent: December 20, 2016
    Assignees: RHODIA OPERATIONS, CENTRE NATIONAL DE LA RECHERECHE SCIENTIFIQUE
    Inventors: Jean-Marc Clacens, Floryan Decampo, Fabien Grasset, Benjamin Katryniok, Franck Dumeignil, Sebastien Paul, Veronique Rataj
  • Patent number: 9416030
    Abstract: Within the scope of hydrothermal carbonization of biomass, not only the main product, coal, but also the platform chemical 5-hydroxymethyl furfural, as well as furfural and levulinic acid, are formed. These are extracted from the process water of the carbonization reaction. However, in this connection, the problem exists that humic substances deposit on the container walls of the extraction column and can only be removed again by means of great cleaning effort. Furthermore, oligomers clearly worsen the purity of the product. This problem is solved by a filtration cascade through which the process water passes before extraction. In this connection, first the impurities mentioned are removed in a first filtration stage, and the remaining products and educts are separated from one another in a second filtration stage. Only the products are passed to extraction.
    Type: Grant
    Filed: December 10, 2014
    Date of Patent: August 16, 2016
    Assignee: AVA-CO2 Schweiz AG
    Inventors: Jan Vyskocil, Stephan Koehler, François Badoux
  • Patent number: 9388150
    Abstract: The present invention relates to a method for preparing 5-acetoxymethylfurfural, comprising a step of synthesizing 5-acetoxymethylfurfural by reacting 5-halomethyl furfural with alkylammonium acetate. The present invention can provide a method for preparing 5-acetoxymethylfurfural which is economic and has high reaction efficiency even without using an additional base.
    Type: Grant
    Filed: March 15, 2013
    Date of Patent: July 12, 2016
    Assignees: KOREA INSTITUTE OF INDUSTRIAL TECHNOLOGY, SEOUL NATIONAL UNIVERSITY R&DB FOUNDATION
    Inventors: Baek Jin Kim, Jin Ku Cho, Sangyong Kim, Do Hoon Lee, Young Gyu Kim, Eun-Sil Kang, Yeon-Woo Hong, Da Won Chae
  • Patent number: 9388151
    Abstract: The present disclosure provides methods to produce 5-(halomethyl)furfural, including 5-(chloromethyl)furfural, by acid-catalyzed conversion of biomass. The methods make use of certain organic solvents with temperature-dependent solubility for 5-(halomethyl)furfural. This allows for temperature-dependent phase separation of the 5-(halomethyl)furfural from the reaction mixture. In certain embodiments, solid 5-(halomethyl)furfural may be obtained. The solid 5-(halomethyl)furfural obtained may be amorphous or crystalline.
    Type: Grant
    Filed: October 25, 2013
    Date of Patent: July 12, 2016
    Assignee: Micromidas, Inc.
    Inventors: Shawn M. Browning, John Bissell, II, Ryan L. Smith, Makoto N. Masuno, Benjamin F. Nicholson, Alex B. Wood
  • Patent number: 9206148
    Abstract: Provided herein is a method for producing 5-hydroxymethyl-2-furfural (HMF) from maize syrup containing fructose including a conversion step in which a reaction product containing the 5-hydroxymethyl-2-furfural is produced by mixing and heating the maize syrup, a dioxane solvent and a solid acid catalyst, thus providing an advantage that the solvent can be easily isolated and the isolated solvent can be reused because dioxane is used as the solvent, and an advantage that the catalyst can be easily isolated and the isolated catalyst can be easily reused because a nonuniform solid acid catalyst is used.
    Type: Grant
    Filed: July 26, 2012
    Date of Patent: December 8, 2015
    Assignee: Korea Institute of Industrial Technology
    Inventors: Jin Ku Cho, Jaewon Jeong, Sangyong Kim, Bora Kim, Baek-Jin Kim, Seunghan Shin, Dohoon Lee
  • Patent number: 9102644
    Abstract: The present invention describes methods and apparatuses for the synthesis of 5-(chloromethyl)-2-furaldehyde (CMF) from saccharides in pure or crude form, the method comprising: (a) continuously contacting saccharides in pure or crude form, hydrochloric acid, and an organic solvent, by way of a continuous, biphasic-flow reactor assembly at a temperature from about 60 degrees C. to about 200 degrees C. and pressures from about 1 atmosphere to about 20 atmospheres, such that CMF is produced; (b) separating 5-(chloromethyl)-2-furaldehyde by liquid/liquid and solid/liquid phase separation; (c) producing at least five kilograms per day with at least 50% yield. Embodiments of the present invention can produce CMF in a continuous fashion, with high yield and without degradation of CMF to such side products as 5-(hydroxymethyl)furfural (HMF), 2-(2-hydroxyacetyl)furan (HAF) and levulinic acid (LA).
    Type: Grant
    Filed: March 3, 2014
    Date of Patent: August 11, 2015
    Assignee: XF Technologies Inc.
    Inventors: Peter Mikochik, Aviad Cahana, Edward Nikitin, Jeremy Standiford, Kyle Ellis, Luzheng Zhang, Timothy George
  • Publication number: 20150112086
    Abstract: A process is disclosed for the preparation of a compound of formula and/or an addition salt of a proton acid, wherein R1 and R2 independently represent alkyl, cycloalkyl, aryl or aralkyl, each aryl or aralkyl being optionally further substituted with alkyl, alkoxy and/or halogen.
    Type: Application
    Filed: December 23, 2014
    Publication date: April 23, 2015
    Inventors: Dominique Michel, Rudolf Fuchs
  • Publication number: 20150087031
    Abstract: The present invention relates to methods of processing lignocellulosic material to obtain hemicellulose sugars, cellulose sugars, lignin, cellulose and other high-value products. Also provided are hemicellulose sugars, cellulose sugars, lignin, cellulose, and other high-value products.
    Type: Application
    Filed: May 3, 2013
    Publication date: March 26, 2015
    Inventors: Robert Jansen, Claire Gregoire, philip Travisano, Lee Madsen, Neta Matis, Yael Har-Tal, Shay Eliahu, James Alan Lawson, Noa Lapidot, Luke Burke, Aharon M. Eyal, Timothy Allen Bauer, Hagit Sade, Paul Mcwilliams, Ziv-Vladimir Belman, Bassem Hallac, Michael Zviely, Yelena Gershinksy, Adam Carden
  • Patent number: 8889734
    Abstract: The subject of the present invention is a novel process for the preparation of N-[2-n-butyl-3-{4-[(3-dibutylamino)propoxy]benzoyl}-1-benzofuran-5-yl]methanesulfonamide of formula I: and the new intermediates of the preparation process.
    Type: Grant
    Filed: May 30, 2013
    Date of Patent: November 18, 2014
    Assignee: SANOFI
    Inventors: Antal Friesz, Zsolt Dombrady, Mariann Csatarine Nagy
  • Patent number: 8877950
    Abstract: Method for the manufacture of 5-hydroxymethylfurfural derivatives by reacting a fructose and/or glucose-containing starting material with an alcohol in the presence of a catalytic or sub-stoichiometric amount of solid (“heterogeneous”) acid catalyst. The catalysts may be employed in a continuous flow fixed bed or catalytic distillation reactor. The ethers can be applied as a fuel or fuel additive.
    Type: Grant
    Filed: December 15, 2010
    Date of Patent: November 4, 2014
    Assignee: Furanix Technologies B.V.
    Inventors: Gerardus Johannes Maria Gruter, Frits Dautzenberg
  • Publication number: 20140296527
    Abstract: The present invention relates to processes for the enantio-selective preparation of spyrrolidine derivatives useful in the manufacture of pesticidally active compounds, as well as to intermediates in the processes. The processes include those comprising (a-i) reacting a compound of formula Ia wherein P is alkyl, aryl or heteroaryl, each optionally substituted, wherein the heteroaryl is connected at P via a ring carbon atom; R1 is chlorodifluoromethyl or trifluoromethyl; R2 is aryl or heteroaryl, each optionally substituted; with a source of cyanide in the presence a chiral catalyst to give a compound of formula IIa wherein P, R1 and R2 are as defined for the compound of formula Ia; and (a-ii) oxidising the compound of formula IIa with a peroxy acid, or peroxide in the presence of an acid to give a compound of formula VI wherein R1 and R2 are as defined for the compound of formula Ia.
    Type: Application
    Filed: September 28, 2012
    Publication date: October 2, 2014
    Applicant: SYNGENTA PARTICIPATIONS AG
    Inventors: Tomas Smejkal, Helmars Smits, Sebastian Volker Wendeborn, Guillaume Berthon, Jerome Yves Cassayre, Myriem El Qacemi
  • Publication number: 20140271537
    Abstract: The present invention generally relates to deuterium-enriched aldehydes, compositions comprising deuterium-enriched aldehydes, and methods for slowing the rate of aldehyde autoxidation. In one aspect, the present invention provides a composition comprising a compound of structure 1: wherein: there are at least 6×1018 molecules of the aldehyde and Rx is hydrogen, wherein the deuterium isotope in Rx is in an amount greater than 0.10 percent of the hydrogen atoms present in Rx.
    Type: Application
    Filed: March 15, 2014
    Publication date: September 18, 2014
    Inventor: Anthony W. Czarnik
  • Patent number: 8835467
    Abstract: Compounds are disclosed which inhibit SIR2 base exchange more than deacetylation, thus enhancing SIR2 deacetylation activity. Methods of using the compounds for enhancing SIR2 deacetylation activity and increasing longevity of an organism are also disclosed. Methods for screening for compounds that enhance SIR2 deacetylation activity and increase longevity of an organism are additionally disclosed.
    Type: Grant
    Filed: January 23, 2013
    Date of Patent: September 16, 2014
    Assignee: Albert Einstein College of Medicine of Yeshiva University
    Inventors: Vern L. Schramm, Anthony A. Sauve
  • Patent number: 8772515
    Abstract: Described is a process to produce hydroxymethyl furfural (HMF) from biomass-derived sugars. The process includes the steps of reacting a C5 and/or C6 sugar-containing reactant derived from biomass in a monophasic or biphasic reaction solution comprising water and a co-solvent. The co-solvent can be beta-, gamma-, and/or delta-lactones derived from biomass, tetrahydrofuran (THF) derived from biomass, and/or methyltetrahydrofuran (MTHF) derived from biomass. The reaction takes place in the presence of an acid catalyst and a dehydration catalyst for a time and under conditions such that at least a portion of glucose or fructose present in the reactant is converted to HMF.
    Type: Grant
    Filed: October 11, 2012
    Date of Patent: July 8, 2014
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: James A. Dumesic, Jean Marcel Ribeiro Gallo, David Alonso
  • Publication number: 20140187802
    Abstract: The present invention describes methods and apparatuses for the synthesis of 5-(chloromethyl)-2-furaldehyde (CMF) from saccharides in pure or crude form, the method comprising: (a) continuously contacting saccharides in pure or crude form, hydrochloric acid, and an organic solvent, by way of a continuous, biphasic-flow reactor assembly at a temperature from about 60 degrees C. to about 200 degrees C. and pressures from about 1 atmosphere to about 20 atmospheres, such that CMF is produced; (b) separating 5-(chloromethyl)-2-furaldehyde by liquid/liquid and solid/liquid phase separation; (c) producing at least five kilograms per day with at least 50% yield. Embodiments of the present invention can produce CMF in a continuous fashion, with high yield and without degradation of CMF to such side products as 5-(hydroxymethyl)furfural (HMF), 2-(2-hydroxyacetyl)furan (HAF) and levulinic acid (LA).
    Type: Application
    Filed: March 3, 2014
    Publication date: July 3, 2014
    Inventors: Peter Mikochik, Aviad Cahana, Edward Nikitin, Jeremy Standiford, Kyle Ellis, Luzheng Zhang, Timothy George
  • Patent number: 8748637
    Abstract: Alcohols are catalytically oxidized to aldehydes, in particular to benzaldehyde and diformylfuran, which are useful as intermediates for a multiplicity of purposes. The invention also relates to the polymerization of the dialdehyde and to the decarbonylation of the dialdehyde to furan.
    Type: Grant
    Filed: July 25, 2013
    Date of Patent: June 10, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Vladimir Grushin, Leo Ernest Manzer, Walter Partenheimer
  • Patent number: 8729281
    Abstract: The invention provides a process for making hydroxymethylfurfural comprising exposing a saccharide, e.g. glucose or fructose, to a metal complex of an N-heterocyclic carbene.
    Type: Grant
    Filed: June 18, 2008
    Date of Patent: May 20, 2014
    Assignee: Agency for Science, Technology and Research
    Inventors: Yugen Zhang, Jackie Y. Ying, Gen Yong
  • Publication number: 20140100378
    Abstract: The present disclosure provides methods to produce substituted furans (e.g., halomethylfurfural, hydroxymethylfurfural, and furfural), by acid-catalyzed conversion of biomass using a gaseous acid in a multiphase reactor, such as a fluidized bed reactor.
    Type: Application
    Filed: June 6, 2012
    Publication date: April 10, 2014
    Applicant: MICROMIDAS, INC.
    Inventors: Makoto N. Masuno, John Bissell, Ryan L. Smith, Brian Higgins, Alex Benjamin Wood, Marc Foster
  • Publication number: 20130305594
    Abstract: A process that directly converts carbohydrates, particularly biomass derived carbohydrates and more specifically biomass (e.g., lignocellulosic biomass), to furfural-/HMF-ketone adducts for liquid hydrocarbon production under mild conditions.
    Type: Application
    Filed: November 8, 2011
    Publication date: November 21, 2013
    Inventors: Li Shuai, Xuejun Pan
  • Publication number: 20130310574
    Abstract: A process is disclosed for the preparation of a compound of formula and/or an addition salt of a proton acid, wherein R1 and R2 independently represent alkyl, cycloalkyl, aryl or aralkyl, each aryl or aralkyl being optionally further substituted with alkyl, alkoxy and/or halogen.
    Type: Application
    Filed: July 25, 2013
    Publication date: November 21, 2013
    Applicant: Lonza AG
    Inventors: Dominique Michel, Rudolf Fuchs
  • Publication number: 20130298291
    Abstract: The present invention relates to cyanoenamine derivatives, their process of preparation, intermediate compounds, their use as fungicide active agents, particularly in the form of fungicide compositions, and methods for the control of phytopathogenic fungi, notably of plants and in material protection, using these compounds or compositions.
    Type: Application
    Filed: November 11, 2011
    Publication date: November 7, 2013
    Applicant: BAYER INTELLECTUAL PROPERTY GMBH
    Inventors: Jürgen Benting, Ulrike Wachendorff-Neumann, Philippe Desbordes, Christophe Dubost, Pierre Genix, Shinichi Narabu, Jean-Pierre Vors
  • Publication number: 20130245127
    Abstract: A compound of formula (I) R-L-CO—X ??(I) (wherein R is a C10-24 unsaturated hydrocarbon group optionally interrupted by one or more heteroatoms or groups of heteroatoms selected from S, O, N, SO, SO2, said hydrocarbon group comprising at least 4 non-conjugated double bonds; L is a linking group forming a bridge of 1 to 5 atoms between the R group and the carbonyl CO; and X is an electron withdrawing group) for use in the treatment of rheumatoid arthritis.
    Type: Application
    Filed: March 1, 2013
    Publication date: September 19, 2013
    Applicant: Avexxin AS
    Inventors: Astrid Jullumstro Feuerherm, Berit Johansen
  • Patent number: 8530465
    Abstract: The invention provides a series of novel 1,2-disubstituted amido-anthraquinone derivatives. Further, the invention also provides the preparation method and application of said derivatives, said application comprises: said derivatives with therapeutically effective amount are prepared into pharmaceutical compositions for inhibition of cancer cell growth, further treating cancer.
    Type: Grant
    Filed: August 1, 2012
    Date of Patent: September 10, 2013
    Assignee: National Defense Medical Center
    Inventors: Hsu-Shan Huang, Chia-Chung Lee
  • Patent number: 8501971
    Abstract: The subject of the present invention is a novel process for the preparation of N-[2-n-butyl-3-{4-[(3-dibutylamino)propoxy]benzoyl}-1-benzofuran-5-yl]methanesulfonamide of formula I: and the new intermediates of the preparation process.
    Type: Grant
    Filed: May 24, 2012
    Date of Patent: August 6, 2013
    Assignee: Sanofi
    Inventors: Antal Friesz, Zsolt Dombrady, Mariann Csatarine Nagy
  • Patent number: 8404871
    Abstract: A process is provided for the synthesis of furan and related compounds by vapor phase decarbonylation of furfural and derivatives, using a palladium/alumina catalyst that has been promoted with an alkali carbonate. Catalyst lifetime is improved. The catalyst can be regenerated in situ by feeding a mixture of air and steam, with a composition of between about 2% and about 40% air, to the catalyst bed at a temperature between about 300° C. and about 500° C.
    Type: Grant
    Filed: December 8, 2009
    Date of Patent: March 26, 2013
    Assignee: E I du Pont de Nemours and Company
    Inventors: Ke Li, Ronnie Ozer
  • Patent number: 8395041
    Abstract: Disclosed is a photoelectric conversion element comprising a conductive support and provided thereon, a semiconductor layer, a charge transporting layer and an opposed electrode, the semiconductor layer comprising a semiconductor with a dye, wherein the dye is a compound represented by the following formula (1).
    Type: Grant
    Filed: April 12, 2010
    Date of Patent: March 12, 2013
    Assignee: Konica Minolta Business Technologies, Inc.
    Inventors: Hidekazu Kawasaki, Akihiko Itami, Kazuya Isobe, Hideya Miwa, Kazukuni Nishimura, Mayuko Ushiro
  • Patent number: 8383653
    Abstract: Compounds are disclosed which inhibit SIR2 base exchange more than deacetylation, thus enhancing SIR2 deacetylation activity. Methods of using the compounds for enhancing SIR2 deacetylation activity and increasing longevity of an organism are also disclosed. Methods for screening for compounds that enhance SIR2 deacetylation activity and increase longevity of an organism are additionally disclosed.
    Type: Grant
    Filed: June 30, 2004
    Date of Patent: February 26, 2013
    Assignee: Albert Einstein College of Medicine of Yeshiva University
    Inventors: Vern L. Schramm, Anthony A. Sauve
  • Patent number: 8372982
    Abstract: The present invention relates to a N-(Phenylcycloalkyl)carboxamide or N-(Benzylcycloalkyl)carboxamide or its thiocarboxamide derivative of formula (I) wherein A represents a carbo-linked, unsaturated or partially saturated, substituted or non-substituted 5-membered heterocyclyl group, T represents an oxygen or a sulphur atom, B represents a non aromatic carbocycle that can be substituted by one to four C1-C8-alkyl groups, and X, Z1, Z2 and Z3 represent various substituents; their process of preparation; the preparation of intermediate compounds; their use as fungicide active agents, particularly in the form of fungicide compositions and methods for the control of phytopathogenic fungi, notably of plants, using these compounds or compositions.
    Type: Grant
    Filed: February 16, 2010
    Date of Patent: February 12, 2013
    Assignee: Bayer Cropscience AG
    Inventors: Jurgen Benting, Peter Dahmen, Philippe Desbordes, Stephanie Gary, Marie-Claire Grosjean-Cournoyer, Philippe Rinolfi, Ulrike Wachendorff-Neumann
  • Publication number: 20130023679
    Abstract: A method of preparing furfural compounds and a mixture for preparing the same are disclosed. First, a solution is prepared by mixing an organic ammonium salt and a hydroxyl organic solvent. Then, a carbohydrate is mixed with the solution to form a mixture. The mixture is heated to a reaction temperature for conversion of the carbohydrate to produce the furfural compounds.
    Type: Application
    Filed: October 17, 2011
    Publication date: January 24, 2013
    Applicant: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE
    Inventors: Ruey-Fu Shih, Hsi-Yen Hsu, Jinn-Jong Wong
  • Publication number: 20130012610
    Abstract: Lignin polymers having distinctive properties, including a generally high molecular weight and generally homogeneous size distribution, as well as preservation of native reactive side groups, are isolated by solvent extraction of plant materials. Methods for isolation of lignin polymers, and for use of the isolated lignin polymers are disclosed. Compositions containing lignin isolated from plant materials, such as carbon fiber composites, resins, adhesive binders and coatings, polyurethane-based foams, rubbers and elastomers, plastics, films, paints, nutritional supplements, food and beverage additives are disclosed. Xylose and xylose derivatives, furfural, fermentable sugars, cellulose and hemi-cellulose products may be used directly or further processed. The lignin polymers and other plant-derived products disclosed herein may be produced in abundance at low cost, and may be used as substitutes for feedstocks originating from fossil fuel or petrochemical sources in the manufacture of various products.
    Type: Application
    Filed: September 11, 2012
    Publication date: January 10, 2013
    Applicant: VERTICHEM CORPORATION
    Inventors: Helene BELANGER, Ross L. PRESTIDGE, Tony James LOUGH, James D. WATSON
  • Patent number: 8338626
    Abstract: Method for the manufacture of 5-alkoxymethylfurfural derivatives by reacting a fructose and/or glucose-containing starting material with an alcohol in the presence of a catalytic or sub-stoechiometric amount of heterogeneous acid catalyst. The catalysts may be employed in a continuous flow fixed bed or catalytic distillation reactor. The ethers can be applied as a fuel or fuel additive.
    Type: Grant
    Filed: December 8, 2011
    Date of Patent: December 25, 2012
    Assignee: Furanix Technologies B.V.
    Inventors: Gerardus Johannes Maria Gruter, Frits Dautzenberg
  • Patent number: 8324409
    Abstract: The present disclosure provides methods to make liquid fuels from renewable, carbon neutral precursors. Specifically, methods to prepare 2,5-dimethylfuran from a source of fructose or other carbohydrates using a one-pot synthesis are provided. In some embodiments, the disclosed methods avoid the isolation of intermediates, and employ “green” reagents like formic acid and acetic acid.
    Type: Grant
    Filed: April 22, 2011
    Date of Patent: December 4, 2012
    Assignee: The Board of Trustees of the University of Illinois
    Inventors: Thomas B. Rauchfuss, Todsapon Thananatthanachon
  • Patent number: 8314260
    Abstract: Accordingly, the current invention provides a method for the manufacture of an ether or ester of 5-hydroxymethyl-furfural by reacting a hexose-containing starting material or HMF with an alcohol or an organic acid dissolved into an ionic liquid, using a metal chloride as catalyst.
    Type: Grant
    Filed: September 5, 2008
    Date of Patent: November 20, 2012
    Assignee: Furanix Technologies B.V.
    Inventors: Gerardus Johannes Maria Gruter, Leo Ernest Manzer, Ana Sofia Vagueiro De Sousa Dias, Frits Dautzenberg, Jindra Purmova
  • Patent number: 8263792
    Abstract: A method is disclosed for the acid hydrolysis of carbohydrates in or from biomass, using a solvent system including an aqueous ether, where the ether form a majority of the system, which affords high yields to the platform chemicals such as 2-furfural and 5-hydroxymethylfurfural (5-HMF). The later can also undergo a domino reaction to chemicals including levulinic acid, particularly with oxygenated anions and greater water content. A total dissolution and reaction of biomass occurs under a range of relatively mild conditions (combined Severity range ˜2.2-2.6). Lignin and lignin derived products can be easily separated by precipitation.
    Type: Grant
    Filed: September 24, 2009
    Date of Patent: September 11, 2012
    Assignee: Board of Regents, The University of Texas System
    Inventor: J. Michael Robinson
  • Patent number: 8236972
    Abstract: The instant invention involves a process for enhancing molecular mass of biomass reactants. The process comprises first forming a substituted or unsubstituted furfural from a biomass. The substituted or unsubstituted furfural is then reacted with an activated methylene compound in the presence of a catalyst and, if desired, a solvent to form a Knoevenagel product. The product may then be hydrogenated to products containing an alcohol, ether, aldehyde, or ketone functional groups or to an olefinic or aliphatic species wherein as much as all of the oxygen and/or nitrogen has been removed.
    Type: Grant
    Filed: July 29, 2008
    Date of Patent: August 7, 2012
    Assignee: Georgia Tech Research Corporation
    Inventors: Travis J. C. Hoskins, Carsten Sievers, Pradeep K. Agrawal, Christopher W. Jones
  • Publication number: 20120123085
    Abstract: Alcohols are catalytically oxidized to aldehydes, in particular to benzaldehyde and diformylfuran, which are useful as intermediates for a multiplicity of purposes. The invention also relates to the polymerization of the dialdehyde and to the decarbonylation of the dialdehyde to furan.
    Type: Application
    Filed: January 25, 2012
    Publication date: May 17, 2012
    Applicant: E.I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Vladimir Grushin, Walter Partenheimer, Leo E. Manzer
  • Patent number: 8133289
    Abstract: Method for the manufacture of 5-alkoxymethylfurfural derivatives by reacting a fructose and/or glucose-containing starting material with an alcohol in the presence of a catalytic or sub-stoechiometric amount of solid (“heterogeneous”) acid catalyst. The catalysts may be employed in a continuous flow fixed bed or catalytic distillation reactor. The ethers can be applied as a fuel or fuel additive.
    Type: Grant
    Filed: March 12, 2007
    Date of Patent: March 13, 2012
    Assignee: Furanix Technologies B.V.
    Inventors: Gerardus Johannes Maria Gruter, Frits Dautzenberg
  • Publication number: 20120059178
    Abstract: The disclosure pertains to a process for oxidation of furan aldehydes such as 5-hydroxymethyl)furfural (HMF) and derivatives thereof such as 5-(alkoxymethyl)furfural (AMF), 5-(aryloxymethyl)furfural, 5-(cycloalkoxy-methyl)furfural and 5-(alkoxycarbonyl)furfural compounds in the presence of dissolved oxygen and a Co(II), Mn(II), Ce(III) salt catalyst or mixtures thereof. The products from HMF can be selectively chosen to be predominantly 2,5-diformylfuran (DFF), particularly by inclusion of an aliphatic ketone, like methyl ethyl ketone, or can be further oxidized to 2,5-furandicarboxylic acid (FDCA) by the omission of methyl ethyl ketone and inclusion of bromide. When the reactant is an ether derivative of HMF the products are surprisingly ester derivatives where either both the ether and aldehyde functional groups have been oxidized or just the ether function group thereby producing one or both of 5-ester-furan-2-acids (i.e., 5-alkoxycarbonylfurancarboxylic acids) or 5-ester-furan aldehydes, (i.e.
    Type: Application
    Filed: May 14, 2010
    Publication date: March 8, 2012
    Applicant: ARCHER DANIELS MIDLAND COMPANY
    Inventor: Alexandra J. Sanborn
  • Publication number: 20110178102
    Abstract: Compounds are disclosed which inhibit SIR2 base exchange more than deacetylation, thus enhancing SIR2 deacetylation activity. Methods of using the compounds for enhancing SIR2 deacetylation activity and increasing longevity of an organism are also disclosed. Methods for screening for compounds that enhance SIR2 deacetylation activity and increase longevity of an organism are additionally disclosed.
    Type: Application
    Filed: June 30, 2004
    Publication date: July 21, 2011
    Applicant: ALBERT EINSTEIN COLLEGE OF MEDICINE OF YESHIVA UNIVERSITY
    Inventors: Vern L Schramm, Anthony A. Suave
  • Publication number: 20110098309
    Abstract: Disclosed are methods of inhibiting, regulating, and/or modulating the formation of soluble, globular, non-fibrillar, neurotoxic amyloid ?1-42 oligomers from amyloid ?1-42 monomers using acylhydrazide compounds. Also disclosed are methods of treating a patient suffering from diseases associated with the formation of soluble, globular, non-fibrillar, neurotoxic amyloid ?1-42 oligomers using acylhydrazide compounds.
    Type: Application
    Filed: July 11, 2008
    Publication date: April 28, 2011
    Applicant: ACUMEN PHARMACEUTICALS, INC.
    Inventors: Gary Charles Look, Lauri Schultz, Alexandre Mikhaylovich Polozov, Nikhil Bhagat, Jian Wang, David E. Zembower, William F. Goure, Todd Pray, Grant A. Krafft
  • Publication number: 20110084230
    Abstract: The present application discloses a process for preparing a compound of the general formula R1-M1-Ad.zLiX (I) by reacting a compound R1-A (III) with an element M1 in the presence of lithium salts. The application also discloses a process for preparing a compound of the general formula R1m-M3-Tm.zLiX (II) by reacting a compound R1-A (III) with an M3-containing compound in the presence of lithium salts and in the presence of an elemental metal M2. The metal M3 may be selected from Al, Mn, Cu, Zn, Sn, Ti, In, La, Ce, Nd, Y, Li, Sm, Bi, Mg, B, Si and S.
    Type: Application
    Filed: April 3, 2007
    Publication date: April 14, 2011
    Inventors: Paul Knochel, Andrei Gavryushin, Vladimir Malakhov, Arkady Krasovskiy