Reactant Is A Carboxylic Acid, Or An Amide, Anhydride, Ester, Halide, Or Salt Thereof Patents (Class 558/311)
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Patent number: 11732385Abstract: The present disclosure relates to a method that includes polymerizing a nitrile with an acrylate ester to form a copolymer, in a mixture that includes water and an alcohol (R2—OH), according to the following reaction where R1 includes at least one of a first aliphatic group or hydrogen, R2 comprises at least one of a second aliphatic group or hydrogen, 100?m?4000, and 1?n?4000. In some embodiments of the present disclosure, the mixture may be an emulsion.Type: GrantFiled: April 29, 2019Date of Patent: August 22, 2023Assignees: Alliance for Sustainable Energy, LLC, UT-Battelle, LLCInventors: Kelly Marie Meek, Todd R. Eaton, Nicholas A. Rorrer, Eric M. Karp, Amit Kumar Naskar
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Patent number: 11718714Abstract: Provided are methods of producing polyamides from beta-lactones. The polyamides include bio-based polyamides that may be obtained, either in part or completely, from renewable sources.Type: GrantFiled: March 13, 2018Date of Patent: August 8, 2023Assignee: Novomer, Inc.Inventors: Han Lee, Sadesh H. Sookraj, Alexander Tseitlin
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Patent number: 11542222Abstract: A method for preparing a dicyanoalkane may omit a filtration for a catalyst after a cyanation reaction can by carrying out the cyanation reaction in a state in which precipitation of a metal catalyst is suppressed. A method for preparing a dicyanoalkane may involve cyanating one or more aliphatic dicarboxylic acids and/or salt(s) thereof with an ammonia source in the presence of a predetermined compound and a catalyst, wherein, in the cyanation, the amount of the predetermined compound is maintained at a predetermined amount or more with respect to the catalyst.Type: GrantFiled: April 11, 2019Date of Patent: January 3, 2023Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Noriyuki Shiomi, Emi Nakano, Akifumi Iida
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Patent number: 11211570Abstract: Hole transporting material obtained through a process comprising: reacting at least one heteropoly acid containing at least one transition metal belonging to group 5 or 6 of the Periodic Table of the Elements; with an equivalent amount of at least one salt or one complex of a transition metal belonging to group 5 or 6 of the Periodic Table of the Elements with an organic anion, or with an organic ligand; in the presence of at least one organic solvent selected from alcohols, ketones, esters. Said hole transporting material can be advantageously used in the construction of photovoltaic devices (or solar devices) such as, for example, photovoltaic cells (or solar cells), photovoltaic modules (or solar modules), either on a rigid support, or on a flexible support. Furthermore, said hole transporting material can be advantageously used in the construction of Organic Light Emitting Diodes (OLEDs), or of Organic Field Effect Transistors (OFETs).Type: GrantFiled: December 22, 2017Date of Patent: December 28, 2021Assignee: ENI S.P.A.Inventors: Riccardo Po′, Alessandra Cominetti
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Patent number: 10626069Abstract: The invention pertains to a process for preparing methyl lactate including the steps of: bringing an aqueous liquid comprising lactic acid, methanol, and at least 5 wt. % of a dissolved chloride salt selected from magnesium chloride, calcium chloride, and zinc chloride to reaction conditions, thereby obtaining methyl lactate, wherein an extractant is provided to the reaction mixture before, during, and/or after formation of methyl lactate; subjecting the reaction mixture to a liquid-liquid separation step wherein an organic phase comprising methyl lactate and extractant is separated from an aqueous phase comprising dissolved chloride salt. The extractant preferably includes one or more compounds selected from C5+ ketones and C3-C10 ethers, in particular C5-C8 ketones, more in particular methyl isobutyl ketone. It has been found that the process according to the invention makes it possible to manufacture methyl lactate efficiently and in high yield.Type: GrantFiled: February 13, 2014Date of Patent: April 21, 2020Assignee: PURAC BIOCHEM B.V.Inventors: Jan Van Krieken, André Banier De Haan, Jan Van Breugel
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Patent number: 8937147Abstract: Processes that make nitrogen-containing compounds include converting succinic acid (SA) or monoammonium succinate (MAS) derived from a diammonium succinate (DAS)- or MAS-containing fermentation broth to produce such compounds including diaminobutane (DAB), succinic dinitrile (SDN), succinic amino nitrile (SAN), succinamide (DAM), and related polymers.Type: GrantFiled: May 18, 2011Date of Patent: January 20, 2015Inventors: Olan S. Fruchey, Leo E. Manzer, Dilum Dunuwila, Brian T. Keen, Brooke A. Albin, Nye A. Clinton, Bernard D. Dombek
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Publication number: 20140148607Abstract: The subject matter of the invention is a process for synthesizing ?-functionalized acids of formula R—(CH2)n—COOH in which R is COOH or NH2CH2, from a feedstock of natural origin containing hydroxylated fatty acids.Type: ApplicationFiled: July 10, 2012Publication date: May 29, 2014Applicant: ARKEMA FRANCEInventor: Jean-Luc Dubois
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Publication number: 20140100371Abstract: A process for preparing azomethines of the general formula (V) where R is an optionally substituted carbocyclic aromatic radical having 6 to 24 carbon atoms or an optionally substituted alkyl radical or an optionally substituted heteroaromatic radical having 5 to 24 carbon atoms, and R1 is an optionally substituted carbocyclic aromatic radical having 6 to 24 carbon atoms or an optionally substituted heteroaromatic radical having 5 to 24 carbon atoms, R2 is hydrogen or an optionally substituted carbocyclic aromatic radical having 6 to 24 carbon atoms or an optionally substituted alkyl radical or an optionally substituted cycloalkyl radical N or an optionally substituted heteroaromatic radical having 5 to 24 carbon atoms by reacting alpha-oxo carboxylates of the general formula (I) where n is a number in the range from 1 to 6, M(n+) is a cation, with aryl bromides of the general formula (IV) and amines of the general formula (II) via the alpha-iminocarboxylate intermediate of the general formula (III), in the pType: ApplicationFiled: November 18, 2011Publication date: April 10, 2014Applicant: Saltigo GmbHInventors: Alain Cotte, Matthias Cotta, Felix Rudolph, Bingrui Song, Lukas Goossen
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Publication number: 20130324694Abstract: Processes for producing nitrogen containing compounds include producing hexamethylenediamine (HMD), adiponitrile (ADN), adipamide (ADM) and derivatives thereof from adipic acid (AA) obtained from fermentation broths containing diammonium adipate (DAA) or monoammonium adipate (MAA).Type: ApplicationFiled: June 10, 2011Publication date: December 5, 2013Applicant: BIOAMBER S.A.S.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: 8501979Abstract: A process for the preparation of compounds containing nitrile functions and, more specifically, compounds containing two nitrile functions, such as succinonitrile and adiponitrile, is described. A process for preparing dintrile compounds obtained by reacting ammonia with an aqueous solution of a dicarboxyl compound in the presence of a silicon orthophosphate catalyst is also described.Type: GrantFiled: November 26, 2009Date of Patent: August 6, 2013Assignee: Rhodia OperationsInventors: Roland Jacquot, Philippe Marion
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Publication number: 20130172519Abstract: Processes that make nitrogen-containing compounds include converting succinic acid (SA) or monoammonium succinate (MAS) derived from a diammonium succinate (DAS)- or MAS-containing fermentation broth to produce such compounds including diaminobutane (DAB), succinic dinitrile (SDN), succinic amino nitrile (SAN), succinamide (DAM), and related polymers.Type: ApplicationFiled: May 18, 2011Publication date: July 4, 2013Applicant: BIOAMBER S.A.S.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: 8471052Abstract: A process is disclosed for producing organic nitriles such as Acetonitrile or Hydrogen Cyanide, in which yields may exceed 90%, undesirable by-products are not produced, and handling of ammonia gas is avoided. In one aspect, a process includes preparing a feed including ammonium salts and water; introducing the feed into a reactor containing a catalyst; and heating the feed in the presence of the catalyst. The catalyst may advantageously include molybdenum on a silica or silica alumina support. The feed may be ammonium acetate in water with about 50 wt % ammonium acetate and the balance water or ammonium formate in water. In another aspect, a process includes preparing a feed including ammonium hydroxide and acetic acid; introducing the feed into a reactor containing a catalyst; and heating the feed in the presence of the catalyst.Type: GrantFiled: November 20, 2009Date of Patent: June 25, 2013Assignee: Orochem Technologies Inc.Inventors: Anil Oroskar, Paul Roman Kurek, Asha Oroskar
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Publication number: 20130144028Abstract: Processes include providing a clarified diammonium succinate (DAS)- or monoammonium succinate (MAS)- containing fermentation broth; distilling the broth of 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; and converting the solid portion to produce nitrogen containing compounds such as diamino butane (DAB), succinic dinitrile (SDN), succinic amino nitrile (SAN) or succinamide (DAM) and downstream products.Type: ApplicationFiled: May 17, 2011Publication date: June 6, 2013Inventors: Olan S. Fruchey, Leo E. Manzer, Dilum Dunuwila, Brian T. Keen, Brooke A. Albin, Nye A. Clinton, Bernard D. Dombek
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Publication number: 20120329981Abstract: The invention provides a process for the preparation of valerolactone, said process comprising reacting levulinic acid with hydrogen by using a solid Ru catalyst, characterised in that the process is carried out in the presence of at least 0.08% (w/w) water relative to the amount of levulinic acid. Said process may be faster and more selective. This process advantageously allows the production of valerolactone from renewable sources. The valerolactone may be used in the preparation of methylpentenoate, adipic acid dimethylester, adipic acid, hexamethylenediamine, and polyamide 6,6 (all claimed).Type: ApplicationFiled: June 20, 2012Publication date: December 27, 2012Applicant: DSM IP ASSETS B.V.Inventors: Anna Maria Cornelia Francisca Castelijns, Michele Catherine Christianne Janssen, Henricus Wilhemus Leonardus Marie Vaessen
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Publication number: 20120323034Abstract: A method comprising an oximation step of reacting a formylalkenylcyclopropanecarboxylic acid ester represented by the formula (1): (wherein, R1 represents an alkyl group optionally having substituent(s) or halogen atom(s), and R2 represents an alkyl group optionally having substituent(s) or a benzyl group optionally having substituent(s)) and hydroxylamine in a solvent in the presence at least one compound selected from the group consisting of carboxylic acids and carboxylic acid metal salts, to produce a hydroxyiminoalkenylcyclopropanecarboxylic acid ester represented by the formula (3): (wherein, R1 and R2 are as defined above).Type: ApplicationFiled: February 25, 2011Publication date: December 20, 2012Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Kouji Yoshikawa, Toshiyuki Kiji, Jun Ohshita, Toshio Somyo, Manabu Kashiwabara, Yoko Miyanaga
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Publication number: 20120101294Abstract: Disclosed is a process for producing a (fluoroalkylthio)acetic acid ester represented by the formula (3) wherein R, R1 and R2 have the same meanings as defined below, which comprises reacting a thioglycolic acid ester represented by the formula (1) wherein R represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and R1 represents an alkyl group having 1 to 4 carbon atoms, with fluoroolefin represented by the formula (2) wherein R2 represents a fluoroalkyl group having 1 to 5 carbon atoms, in the presence of a radical generator.Type: ApplicationFiled: August 6, 2010Publication date: April 26, 2012Inventors: Masaji Hirota, Hiroyuki Miyazaki, Tadayoshi Itoh
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Publication number: 20120095230Abstract: A process for the preparation of 5-substituted 4-amino-2-methylpyrimidines of the formula (I) wherein R is CONH2 or CN, and of acid addition salts thereof, characterized in that a compound of formula H2N CH?C(R) CN (II) is reacted with acetimidic acid methyl ester or an acid addition salt thereof and that, if desired, a compound of formula (I) is transferred into an acid addition salt, and the transformation of a compound of formula (II) wherein R is CONH2 into a compound of formula (II) wherein R is CN by treatment with POCI3.Type: ApplicationFiled: April 8, 2010Publication date: April 19, 2012Inventors: Reinhard Karge, Jan Schutz
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Patent number: 8063236Abstract: A complex for transference of a nitrogen atom to an electrophilic reagent comprises a hard-hard-hard pincer ligand and an early transition metal bound to a nitride. The pincer ligand can be an OCO ligand and the transition metal can be Mo. The complex can be used to transfer the nitrogen atom bound to the metal to an electrophile in a method to produce a nitrogen containing molecule. In one novel nitrogen transfer reaction, a Mo—N triple bond is broken where the nitrogen transfers to the sp2 hybridized carbon of an acid chloride to form a nitrile.Type: GrantFiled: May 8, 2009Date of Patent: November 22, 2011Assignee: University of Florida Research Foundation, Inc.Inventors: Adam Veige, Soumya Sarkar
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Publication number: 20110144372Abstract: Disclosed is a method for producing a compound represented by Formula (4), the method including Step I of adding a solution in which hydrogen chloride is dissolved in an alcohol, to a mixture containing an organic solvent and a compound represented by Formula (1), and Step II of mixing a compound obtained in Step I, represented by Formula (3), with water.Type: ApplicationFiled: August 24, 2009Publication date: June 16, 2011Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Hajime Ishida, Massaji Hirota
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Patent number: 7915442Abstract: The present invention relates to a process for producing an aliphatic nitrile, including the step of reacting at least one compound selected from the group consisting of an aliphatic monocarboxylic acid, an aliphatic dicarboxylic acid and alkyl esters of these acids containing an alkyl group having 1 to 5 carbon atoms, with ammonia in the presence of a compound of at least one metal selected from the group consisting of zinc, cobalt, titanium and aluminum, and a sulfonic acid compound! and a process for producing an aliphatic amine, including the step of subjecting the aliphatic nitrile produced by the above process to hydrogenation reaction in the presence of a hydrogenation catalyst. There are provided an industrially advantageous process for producing an aliphatic nitrile with a high reactivity; and a process for producing an aliphatic amine using the aliphatic nitrile as a raw material.Type: GrantFiled: February 27, 2007Date of Patent: March 29, 2011Assignee: Kao CorporationInventors: Tetsuaki Fukushima, Michio Terasaka
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Publication number: 20100317822Abstract: The present invention generally relates to processes for the chemocatalytic conversion of a carbohydrate source to an adipic acid product. The present invention includes processes for the conversion of a carbohydrate source to an adipic acid product via a furanic substrate, such as 2,5-furandicarboxylic acid or derivatives thereof. The present invention also includes processes for producing an adipic acid product comprising the catalytic hydrogenation of a furanic substrate to produce a tetrahydrofuranic substrate and the catalytic hydrodeoxygenation of at least a portion of the tetrahydrofuranic substrate to an adipic acid product. The present invention also includes products produced from adipic acid product and processes for the production thereof from such adipic acid product.Type: ApplicationFiled: June 11, 2010Publication date: December 16, 2010Applicant: RENNOVIA, INC.Inventors: Thomas R. Boussie, Eric L. Dias, Zachary M. Fresco, Vincent J. Murphy
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Publication number: 20100317823Abstract: The present invention generally relates to processes for the chemocatalytic conversion of a glucose source to an adipic acid product. The present invention includes processes for the conversion of glucose to an adipic acid product via glucaric acid or derivatives thereof. The present invention also includes processes comprising catalytic oxidation of glucose to glucaric acid or derivative thereof and processes comprising the catalytic hydrodeoxygenation of glucaric acid or derivatives thereof to an adipic acid product. The present invention also includes products produced from adipic acid product and processes for the production thereof from such adipic acid product.Type: ApplicationFiled: June 11, 2010Publication date: December 16, 2010Applicant: RENNOVIA, INC.Inventors: Thomas R. Boussie, Eric L. Dias, Zachary M. Fresco, Vincent J. Murphy, James Shoemaker, Raymond Archer, Hong Jiang
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Publication number: 20100280251Abstract: Disclosed is a method for preparing a compound of Formula 1 comprising contacting a compound of Formula 2 with a metal cyanide reagent, a copper(I) salt reagent, an iodide salt reagent and at least one compound of Formula 3 wherein R1 is NHR3 or OR4; R2 is CH3 or Cl; R3 is H, C1-C4 alkyl, cyclopropyl, cyclopropylcyclopropyl, cyclopropylmethyl or methylcyclopropyl; R4 is H or C1-C4 alkyl; Y is Br or Cl; X is NR13 or O; n is 0 or 1; and R5, R6, R7, R8, R9, R10, R11, R12 and R13 are as defined in the disclosure. Also disclosed is a method for preparing a compound of Formula 2 wherein Y is Br and R1 is NHR3 comprising introducing a gas containing bromine into a liquid containing a compound of Formula 4, and further disclosed is a method for preparing a compound of Formula 5 wherein R14, R15, R16 and Z are as defined in the disclosure using a compound of Formula 1 characterized by preparing the compound of Formula 1 by the method disclosed above.Type: ApplicationFiled: December 18, 2007Publication date: November 4, 2010Applicant: E.I. Du Pont De Nemours and CompanyInventors: Joerg Bruening, Gary David Annis, Martin James Currie, Donald J. Dumas, Rafael Shapiro
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Publication number: 20100105940Abstract: Catalysts comprising: (a) a support material comprising a component selected from the group consisting of aluminum oxide, silicon dioxide, aluminum silicate, magnesium silicate, titanium dioxide, zirconium dioxide, thorium dioxide, silicon carbide, and mixtures thereof; and (b) an active material comprising a mixture of vanadium (V) and antimony (Sb) and tungsten (W) and/or molybdenum (Mo), and optionally, at least one alkali metal, wherein the vanadium, antimony, tungsten and/or molybdenum and at least one alkali metal are each present in oxidic form; wherein the support material is provided in a form selected from the group of shapes consisting of spherical or approximately spherical and having a diameter of 2 to 10 mm, tubular or rod-shaped and having a diameter of 1 to 10 mm and a length of 2 to 20 mm, granular having a maximum diameter of 2 to 20 mm, and combinations thereof; and wherein the catalyst is diluted with an inert material; along with processes for preparing such catalysts and their use in preType: ApplicationFiled: July 12, 2006Publication date: April 29, 2010Applicant: BASF AKTIENGESELLSCHAFTInventors: Sabine Huber, Randolf Hugo, Kirsten Dahmen, Thomas Preiss, Hartmut Hibst
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Patent number: 7629486Abstract: The invention relates to a method for producing amino- or hydroxybenzonitriles during which, within the scope of an ammonolysis, the corresponding amino- or hydroxybenzoic acid compounds are reacted with ammonia in the presence of a phosphate-containing supported catalyst at temperatures between 250° C. and 500° C. The production step is carried out in a reaction gas without an organic solvent followed by at least a 2-stage purification step.Type: GrantFiled: November 29, 2005Date of Patent: December 8, 2009Assignee: AlzChem Trostberg GmbHInventors: Roland Möller, Mario Gómez, Klaus Einmayr, Jens Hildebrand, Hans-Georg Erben, Hans-Peter Krimmer
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Publication number: 20090054677Abstract: The present invention relates to a process for producing an aliphatic nitrile, including the step of reacting at least one compound selected from the group consisting of an aliphatic monocarboxylic acid, an aliphatic dicarboxylic acid and alkyl esters of these acids containing an alkyl group having 1 to 5 carbon atoms, with ammonia in the presence of a compound of at least one metal selected from the group consisting of zinc, cobalt, titanium and aluminum, and a sulfonic acid compound! and a process for producing an aliphatic amine, including the step of subjecting the aliphatic nitrile produced by the above process to hydrogenation reaction in the presence of a hydrogenation catalyst. There are provided an industrially advantageous process for producing an aliphatic nitrile with a high reactivity; and a process for producing an aliphatic amine using the aliphatic nitrile as a raw material.Type: ApplicationFiled: February 27, 2007Publication date: February 26, 2009Applicant: KAO CORPORATIONInventors: Tetsuaki Fukushima, Michio Terasaka
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Patent number: 7259274Abstract: An aliphatic nitrile is prepared by a process of reacting an aliphatic carboxylic acid, an aliphatic dicarboxylic acid or an alkyl ester thereof, wherein the alkyl group has 1 to 5 carbon atoms, with ammonia in the presence of a catalyst of titanium oxide supported on solid silica.Type: GrantFiled: September 9, 2004Date of Patent: August 21, 2007Assignee: Kao CorporationInventors: Michio Terasaka, Tetsuaki Fukushima
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Patent number: 7186870Abstract: The present invention relates to processes for the preparation of any of the intermediate 1,3-substituted indenes of the formulae (Ia), (Ib) and (Ic) or a mixture thereof: wherein R1, R2, R3, R4, and R5 are defined herein. Compounds of formulae (Ia), (Ib) and (Ic) or mixtures thereof are useful in the preparation of compounds of formula (II): wherein R2, R3 and R6 are also defined herein.Type: GrantFiled: November 23, 2005Date of Patent: March 6, 2007Assignee: Pfizer IncInventors: Robert A. Singer, Jason D. Mckinley
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Patent number: 7164047Abstract: A process for preparation of cyclopropylethanol, which comprises subjecting a 3-cyclopropyl-2,3-epoxypropionic acid ester to solvolysis, treating the product of the solvolysis with an acid to obtain cyclopropylacetaldehyde, and reducing the obtained cyclopropylacetaldehyde; and a process for preparation of cyclopropylacetonitrile, which comprises subjecting a 3-cyclopropyl-2,3-epoxypropionic acid ester to solvolysis in the presence of a base, treating the product of the solvolysis with an acid to obtain cyclopropylacetaldehyde, reacting the obtained cyclopropylacetaldehyde with hydroxylamine or salts thereof to obtain cyclopropaneacetaldehyde oxime, and reacting the obtained cyclopropaneacetaldehyde oxime with acetic anhydride. According to the present invention, cyclopropylethanol and cyclopropylacetonitrile can be prepared at low costs and industrially advantageously.Type: GrantFiled: October 31, 2002Date of Patent: January 16, 2007Assignee: Kuraray Co., Ltd.Inventor: Katsuji Ujita
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Patent number: 7091372Abstract: The present invention relates to processes for the preparation of any of the intermediate 1,3-substituted indenes of the formulae (Ia), (Ib) and (Ic) or a mixture thereof: wherein R1, R2, R3, R4, and R5 are defined herein. Compounds of formulae (Ia), (Ib) and (Ic) or mixtures thereof are useful in the preparation of compounds of formula (II): wherein R2, R3 and R6 are also defined herein.Type: GrantFiled: April 17, 2002Date of Patent: August 15, 2006Assignee: Pfizer IncInventors: Robert A. Singer, Jason D. McKinley
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Patent number: 6897332Abstract: A process for cyanating an aldehyde is provided. The process comprises reacting the aldehyde with: i) a cyanide source which does not comprise a Si—CN bond or a C—(C?O)—CN moiety; and ii) a substrate susceptible to nucleophilic attack not comprising a halogen leaving group; in the presence of a chiral catalyst. Preferably, the chiral catalyst is a chiral vanadium or titanium catalyst. The cyanide source is preferably an alkali metal cyanide and the substrate susceptible to nucleophilic attack not comprising a halogen leaving group is a carboxylic anhydride.Type: GrantFiled: January 31, 2003Date of Patent: May 24, 2005Assignees: Nesmeyanov Institute of Organoelement Compounds, King's College LondonInventors: Yuri Belokon, Michael North
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Publication number: 20040063987Abstract: A process for preparing 2-cyno-2-alkoxyacetamides of the formula: 1Type: ApplicationFiled: September 30, 2003Publication date: April 1, 2004Inventors: Johannes Bartek, Rudolf Fuchs, Stefan Hildbrand
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Patent number: 6664410Abstract: A nitrile compound is prepared by treating a solid supported amide to dehydrate it and cleave it from the support in one operation. The preparation involves acetylation of the amide compound in the presence of a base at a temperature of less than 100° C.Type: GrantFiled: August 13, 2002Date of Patent: December 16, 2003Assignee: Millennium Pharmaceuticals LimitedInventors: Ryszard Kobylecki, Neal David Hone, Lloyd James Payne
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Publication number: 20030181751Abstract: The present invention relates to a novel compound 4,8-dodecadienedinitrile represented by the following formula (1): 1Type: ApplicationFiled: March 3, 2003Publication date: September 25, 2003Applicant: UBE INDUSTRIESInventors: Katsumasa Harada, Yasuhisa Fukuda, Yoshinori Yamanaka, Tadashi Murakami, Kenji Hirotsu
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Patent number: 6610874Abstract: Processes for the efficient production of chiral amino nitrites are disclosed. Generally, the processes include the esterification of the alcohol of a amino protected alcohol followed by nucleophilic substitution of the ester with a cyano group. In an exemplary embodiment the chiral amino nitrile produced is (R)-3-aminopentanenitrile.Type: GrantFiled: September 28, 2001Date of Patent: August 26, 2003Assignee: PCBU Services, Inc.Inventors: David Robert Allen, Crystal A. Achenbach-McCarthy
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Publication number: 20030144538Abstract: 1 The invention relates to a method for producing alkoxy malonic acid dinitriles of general formula (I), wherein R1 means C1-6-alkyl or halogen-substituted C1-6-alkyl. The method is characterised in that the corresponding alkoxy malonic acid diamides of general formula (II), wherein R1 has the aforementioned meaning, are converted by means of a dehydrating agent. The invention also relates to the intermediate products of general formula (III), whereby said products are formed during dehydration.Type: ApplicationFiled: October 11, 2002Publication date: July 31, 2003Inventors: Johannes Bartek, Rudolf Fuchs, Stefan Hildbrand
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Patent number: 6593486Abstract: This application relates to a process for the preparation of the cyanomethyl ester which comprises reacting 2,5-bis(2,2,2-trifluoroethoxy)benzoic acid or a salt thereof, with a haloacetonitrile of the formula XCH2CN wherein X is Cl, Br, or I.Type: GrantFiled: July 23, 2001Date of Patent: July 15, 2003Assignee: Par Pharmaceutical, Inc.Inventors: Arie L. Gutman, Genady Nisnevich, Eleonora Shkolnik, Igor Zaltzman, Boris Tishin
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Patent number: 6316627Abstract: A process for the preparation of trifluoroethoxy benzoic acid derivatives, in particular Flecainide, and their pharmaceutically acceptable salts, starting with commercially available halobenzoic acids and involving the use of simple reagents and low cost solvents, to afford high overall yield of the product. The above object is achieved in accordance with the present invention which, in one aspect thereof, provides a process for preparing a compound of formula (A): and pharmaceutically acceptable salts thereof, which process comprises the steps of: a) reacting a halobenzoic acid or a salt thereof of the formula [II ] with 2,2,2-trifluoroethanol in the presence of a strong base and a copper containing material, if desired followed by acidification to obtain a compound of formula [I] b) converting the product obtained in step a) above into the compound of formula (A) or a pharmaceutically acceptable salt thereof.Type: GrantFiled: October 21, 1999Date of Patent: November 13, 2001Assignee: Fine Tech Ltd.Inventors: Arie L. Gutman, Genady Nisnevich, Eleonora Shkolnik, Igor Zaltzman, Boris Tishin
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Patent number: 6248917Abstract: 2-Hydroxybenzonitrile is prepared by passing 2-hydroxybenzamide in the gas phase over a heterogeneous catalyst thereby effecting dehydration of the 2-hydroxybenzamide to produce 2-hydroxybenzonitrile.Type: GrantFiled: June 14, 1996Date of Patent: June 19, 2001Assignee: Huels AktiengesellschaftInventor: Wolfgang Kleemiss
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Patent number: 6046352Abstract: The invention relates to a preparation process for 4-cyano-4'-hydroxybiphenyl, the process comprising the protection of the aldehyde function of 4-bromo-benzaldehyde, the reaction of the protected 4-bromo-benzaldehyde with p-alkoxyphenyl magnesium halide, the deprotection of the formyl radical of the protected 4-alkoxy-4'-formyl-biphenyl and conversion of the formyl group into cyano and hydrolysis of the alkoxy group of the resulting 4-alkoxy 4'-cyano-biphenyl.Type: GrantFiled: August 5, 1999Date of Patent: April 4, 2000Assignee: Societe d'Expansion Scientifique ExpansiaInventors: Jean-Bernard Cazaux, Christine Le Breton
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Patent number: 6005134Abstract: The present invention provides a process for preparing a high-quality aliphatic nitrile in a high yield at a low cost without the dissolution of a catalyst in the product, which comprises reacting an aliphatic carboxylic acid, a lower alkyl ester thereof or a fatty acid glyceride with ammonia in the presence of a solid catalyst which exhibits a high activity even at a reaction temperature of as low as 300.degree. C. or below and is difficultly soluble in the reaction fluid; and a process for the preparation of amines by hydrogenating the aliphatic nitrile prepared by the above process. Namely, the present invention provides a process for the preparation of an aliphatic nitrile by reacting an aliphatic carboxylic acid, a lower alkyl ester thereof or a fatty acid glyceride with ammonia in the presence of a composite oxide catalyst comprising titanium oxide as the main component; and a process for the preparation of amines by hydrogenating the aliphatic nitrile prepared by the above process.Type: GrantFiled: May 19, 1999Date of Patent: December 21, 1999Assignee: Kao CorporationInventors: Michio Terasaka, Yasuyuki Mimura, Hiroshi Abe
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Patent number: 5965764Abstract: Process for producing a nitrile by dehydration reaction of an amide in the presence of a carboxylic acid having the same radical as the amide, or by adding urea to a carboxylic acid with the carboxylic acid either molten or dissolved in a solvent, where the amount of urea used is less than about 0.8 in molar ratio to the carboxylic acid, or when an exhaust gas distillate line connected to the reactor is kept at about 60.degree. C. or higher, or while a gas that is inert to the reaction is fed into the reaction and the produced nitrile and water are concurrently distilled out.Type: GrantFiled: August 5, 1998Date of Patent: October 12, 1999Assignee: Toray Industries, Inc.Inventors: Shotaro Matsuoka, Masaaki Suematsu, Mamoru Ishikawa
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Patent number: 5932766Abstract: The present invention discloses a process for the preparation of a compound having formula 4: ##STR1## The process comprises the step of reacting an enolate having the formula: ##STR2## with a Grignard reagent. The enolate salt is formed in situ from the reaction of a protected ester wherein M is an alkali metal. R.sub.6 and R.sub.7 are each hydrogen or are independently selected from ##STR3## wherein R.sub.a and R.sub.b are independently selected from hydrogen, lower alkyl and phenyl and R.sub.c, R.sub.d and R.sub.e are independently selected from hydrogen, lower alkyl, trifluoromethyl, alkoxy, halo and phenyl; and ##STR4## wherein the naphthyl ring is unsubstituted or substituted with one, two or three substitutents independently selected from lower alkyl, trifluoromethyl, alkoxy and halo. Alternatively, R.sub.6 is as defined above and R.sub.7 is R.sub.12 OC(O)-- wherein R.sub.12 is benzyl; or R.sub.6 and R.sub.7 taken together with the nitrogen atom to which they are bonded form ##STR5## wherein R.sub.Type: GrantFiled: May 30, 1997Date of Patent: August 3, 1999Assignee: Abbott LaboratoriesInventors: Anthony R. Haight, Timothy L. Stuk, Jerome A. Menzia
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Patent number: 5834616Abstract: The present invention relates to a process for the preparation of pentenenitriles. In this process the 3- or 4-pentenenitriles are produced by reacting 2-methylglutarimide, ethylsuccinimide, and/or their precursors, such as 4-cyanovalerimide, 2-methyl-4-cyanobutyrimide, 4-cyanovaleric acid, 2-methyl-4-cyanobutyric acid, 3-cyanovalerimide, 2-ethyl-3-cyanopropionimide, 3-cyanovaleic acid, and 2-ethyl-3-cyanopropionic acid, in the vapor phase at temperatures of 200.degree. to 600.degree. C. in the presence of an acidic solid catalyst, such as acidic molecular sieves, acidic clays, bridged or pillared clays, bulk oxides, and acidic phosphates.Type: GrantFiled: September 15, 1997Date of Patent: November 10, 1998Assignee: Rhone-Poulenc Fiber & Resin IntermediatesInventors: Anne-Marie Le Govic, Isabelle Storet
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Patent number: 5688985Abstract: A process for producing a (4S)-4-(N,N-dibenzyl)amino-5-phenyl-3-oxo-pentanenitrile derivative which comprises reacting a (2S)-2-(N,N-dibenzyl)aminophenylalanine ester derivative with acetonitrile in the presence of a lithium compound or a magnesium compound is disclosed, and a process for producing a (2S)-2-(N,N-dibenzyl)amino-5-amino-1,6-diphenyl-4-hexen-3-one derivative which comprises adding a benzylmagnesium halide or a benzyllithium to a reaction solution containing the (4S)-4-(N,N-dibenzyl)amino-5-phenyl-3-oxo-pentanenitrile derivative and reacting the derivative with the benzylmagnesium halide or the benzyllithium is also disclosed. According to these processes, optically pure (4S)-4-(N,N-dibenzyl)amino-5-phenyl-3-oxo-pentanenitrile derivative and (2S)-2-(N,N-dibenzyl)amino-5-amino-1,6-diphenyl-4-hexen-3-one derivative can be produced in a good yield on an industrial scale.Type: GrantFiled: January 23, 1996Date of Patent: November 18, 1997Assignee: Takasago International CorporationInventors: Mitsuhiko Fujihara, Kenji Asahina, Toru Watanabe, Toshiyuki Takezawa, Seiji Watanabe
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Patent number: 5659051Abstract: There is disclosed a process of producing a 2-cyano-4-oxo-4H-benzopyran compound of the general formula (2): ##STR1## wherein R.sup.1 and R.sup.2 are independently hydrogen, halogen, hydroxy, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, nitro or a group of the RCONH wherein R is C.sub.1 -C.sub.20 alkyl, phenyl, phenyl-substituted (C.sub.1 -C.sub.20) alkyl, phenyl (C.sub.1 -C.sub.20)alkoxyphenyl or (C.sub.1 -C.sub.20) alkoxyphenyl. This production process is characterized in that a carboxamide of the general formula (1): ##STR2## wherein R.sup.1 and R.sup.2 are each as defined above, is reacted with a dehydrating agent in the presence of a pyridine compound of the general formula (4): ##STR3## wherein A.sup.1 and A.sup.2 are independently hydrogen or C.sub.1 -C.sub.5 alkyl.Type: GrantFiled: July 11, 1994Date of Patent: August 19, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Takayuki Higashii, Hideki Ushio, Yukari Fujimoto, Tsutomu Matsumoto, Masayoshi Minai, Katsuichi Yasunaga, Hiroshi Sogabe, Takahiro Kotera
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Patent number: 5395974Abstract: The present invention relates to a method of reacting polyamides or mixtures thereof with ammonia to obtain a mixture of monomers. The reaction is carried out in the presence of certain Lewis Acid catalyst precursors.Type: GrantFiled: January 21, 1994Date of Patent: March 7, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventor: Ronald J. McKinney
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Patent number: 5302756Abstract: Useful monomeric products are obtained in the reaction of nylon 6,6 with ammonia. Increased yield of monomer products from nylon 6,6 is obtained from ammonolysis when a mixture with nylon 6 is employed.Type: GrantFiled: December 23, 1992Date of Patent: April 12, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventor: Ronald J. McKinney
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Patent number: 5210315Abstract: A process for producing an .alpha.-hydroxyketone represented by formula (I): ##STR1## wherein R.sup.1 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or an alkoxycarbonyl group; and R.sup.2 and R.sup.3 each represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aralkyl group, provided that they do not simultaneously represent a hydrogen atom; or a pair of R.sup.1 and R.sup.2, a pair of R.sup.1 and R.sup.3, or a pair of R.sup.2 and R.sup.3 is taken together to form a ring; and the pair of R.sup.1 and R.sup.2 and the pair of R.sup.2 and R.sup.3 may form a ring simultaneously, is disclosed, comprising reacting a compound represented by formula (II): ##STR2## wherein R.sup.1, R.sup.2, and R.sup.3 are as defined above, with an oxidizing agent in the presence of a ruthenium compound and water. .alpha.-Hydroxyketones useful as physiologically active substances are produced with good selectivity and in high yield.Type: GrantFiled: October 18, 1991Date of Patent: May 11, 1993Assignee: Takasago International CorporationInventors: Takao Saito, Hidenori Kumobayashi, Shunichi Murahashi
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Patent number: 5202455Abstract: The present invention relates to a process for the liquid-phase preparation of nitriles from aliphatic dicarboxylic acids at temperatures of about 200.degree. to 350.degree. C. using ammonia in the presence of a phosphoric acid-based catalyst, wherein an adsorbent for the catalyst is added to the reaction mixture.Type: GrantFiled: September 6, 1991Date of Patent: April 13, 1993Assignee: Huels AktiengesellschaftInventor: Karl Schmitz