From Acyclic Nitrile Patents (Class 564/130)
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Patent number: 11358927Abstract: A method of producing an N,N-disubstituted amide of the present invention is a method of reacting a nitrile with an alcohol in the presence of a catalyst, wherein the nitrile is a compound represented by R1CN (R1 represents an alkyl group having 10 or less carbon atoms or an aryl group having 10 or less carbon atoms), wherein the alcohol is a compound represented by R2OH (R2 represents an alkyl group having 10 or less carbon atoms), wherein the catalyst is a metal salt represented by MXn (M represents a metal cation having an oxidation number of n, X represents a monovalent anion including a substituted sulfonyl group represented by —S(?O)2—R3 (R3 represents a hydrocarbon group having 10 or less carbon atoms or a group in which some or all of hydrogen atoms in the hydrocarbon group are substituted with fluorine atoms), and n represents an integer of 1 to 4), a substituent bonded to a carbon atom in a carbonyl group of the N,N-disubstituted amide is R1, and two substituents bonded to nitrogen atoms in an amideType: GrantFiled: April 25, 2019Date of Patent: June 14, 2022Assignee: SHOWA DENKO K.K.Inventors: Yasuyuki Ueda, Akira Shibuya, Hideo Miyata, Hiroshi Uchida
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Patent number: 9221748Abstract: The present invention generally relates to a process for preparing 2,2-dibromomalonamide from 2,2-dibromo-3-cyanoacetamide.Type: GrantFiled: January 27, 2015Date of Patent: December 29, 2015Assignee: DOW GLOBAL TECHNOLOGIES LLCInventors: Charles D. Gartner, Dawn Carsten
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Publication number: 20150148564Abstract: The present invention generally relates to a process for preparing 2,2-dibromomalonamide from 2,2-dibromo-3-cyanoacetamide.Type: ApplicationFiled: January 27, 2015Publication date: May 28, 2015Inventors: Charles D. Gartner, Dawn Carsten
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Patent number: 8975441Abstract: The present invention generally relates to a process for preparing 2,2-dibromomalonamide from 2,2-dibromo-3-cyanoacetamide.Type: GrantFiled: November 18, 2010Date of Patent: March 10, 2015Assignee: Dow Global Technologies LLCInventors: Charles D. Gartner, Dawn Carsten
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Publication number: 20140364648Abstract: Ether-amide compounds having the formula RaRbC(OR1)—CHRc—CONR2R3 are described. Also described, are processes for the preparation and use thereof, especially as solvents, for example in phytosanitary formulations.Type: ApplicationFiled: August 26, 2014Publication date: December 11, 2014Inventors: Massimo GUGLIERI, Olivier JENTZER
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Patent number: 8853449Abstract: Process for the industrial synthesis of the compound of formula (I)Type: GrantFiled: January 4, 2012Date of Patent: October 7, 2014Assignee: Les Laboratoires ServierInventors: Samir Zard, Béatrice Sire, Mehdi Boumediene
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Patent number: 8802896Abstract: Disclosed is a polyether compound which is useful as a curing agent or the like, a curing agent using the compound and a producing method of the compound. The polyether compound of the present invention is represented by the following general formula (1). (In the formula, R1 represents a hydrogen atom or a methyl group and R2 represents a hydrogen atom or —C(?O)—C(R3)?CH2. R3 represents a hydrogen atom or a methyl group. R1, R2 and R3 may be the same as or different from each other.Type: GrantFiled: September 30, 2013Date of Patent: August 12, 2014Assignee: FUJIFILM CorporationInventors: Akihito Amao, Hirotaka Kitagawa
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Patent number: 8598385Abstract: Process for the preparation of N-vinylcarboxamides by pyrolysis of a compound of the formula CH3—CH(CN)—N(R)—CO—R1??(I), in which R and R1 are H or C1- to C6-alkyl, in the presence of solids which are doped with alkali metal or alkaline earth metal ions, under reduced pressure at a temperature of from 330 to 750° C. with elimination of hydrogen cyanide, cooling, separation and isolation of the reaction products, a solid arranged in a tubular reactor being treated at a temperature in the range from 0 to 250° C. with a solution of an alkali metal and/or alkaline earth metal base, the solution being discharged, the remaining solvent which adheres to the catalyst thus obtainable being evaporated and said catalyst then being heated to a temperature of at least 380° C. for activation.Type: GrantFiled: December 4, 2009Date of Patent: December 3, 2013Assignee: BASF SEInventors: Manfred Winter, Hagen Weigl, Andreas Kramer
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Patent number: 8586765Abstract: A process for preparing 3-amino-3-cyclobutylmethyl-2-hydroxypropionamide of the Formula I: or a salt thereof involves providing a compound of the Formula VI described herein in a solution comprising predominately dimethylsulfoxide (DMSO) and converting this compound directly to the compound of the Formula VIII described herein without working up or isolating the intermediate compound of the Formula VII described herein.Type: GrantFiled: December 17, 2008Date of Patent: November 19, 2013Assignee: Merck Sharp & Dohme Corp.Inventors: Shuan Dong, Jeonghan Park, Eugene John Vater
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Patent number: 8581002Abstract: Improved process for working up diacetone acrylamide solutions, obtained by reaction of acetone or diacetone alcohol with acrylonitrile and sulfuric acid and subsequent dilution and neutralization, in which a) the organic phase obtained subsequent to the neutralization, which comprises the crude diacetone acrylamide, is hydrolyzed by addition of an aqueous alkaline solution in order to remove acrylamide, then b) after phase separation has been carried out, the organic phase, which comprises the crude diacetone acrylamide, is neutralized by addition of an acid, and c) in succession, low-boiling-point byproducts are removed by distillation in the presence of one or more polymerization inhibitors, then t-butylacrylamide is removed by distillation and, finally, the diacetone acrylamide is isolated by product distillation, and d) the diacetone acrylamide thus obtained is converted into its final form.Type: GrantFiled: May 8, 2008Date of Patent: November 12, 2013Assignee: DSM Fine Chemicals Austria NFG GmbH & Co KgInventors: Sascha Braune, Bernhard Holub, Christoph Huber
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Patent number: 8581000Abstract: Disclosed is a process for preparing a compound of the formula wherein R1 and R1?, R2 and R2?, and R3 are as defined herein, said process comprising (I) reacting a diacid of the formula HOOC—R2—COOH with a diamine of the formula H2N—R3—NH2 to form an acid-terminated oligoamide intermediate of the formula HOOC—R2—CONH—R3—HNCO—R2?—COOH; and (II) reacting the acid-terminated oligoamide intermediate with a monoalcohol of the formula R1—OH in the presence of a tin or organic titanate catalyst, in the absence of a coupling agent, and in the absence of a solvent to form the product. Also disclosed is a composition prepared by the process.Type: GrantFiled: June 6, 2011Date of Patent: November 12, 2013Assignee: Xerox CorporationInventors: Naveen Chopra, Thomas E Enright, Michelle N Chrétien, Barkev Keoshkerian, Daryl W Vanbesien
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Patent number: 8536355Abstract: Disclosed herein is a process for producing Dialkyl substituted fatty acids amides. More particularly the present invention provides a process for producing pure form of N,N-dimethylamide of aliphatic carboxylic acids, wherein the aliphatic carboxylic acid is Octanoic Acid and Hexanoic Acid. The disclosed process comprises condensing Alkanoyl Chloride with dilute solution of Dialkylamine at a temperature of about 8 to 12° C. and isolating the crude by salting out the reaction mixture employing Sodium Chloride and distilling the same under vacuum.Type: GrantFiled: September 22, 2005Date of Patent: September 17, 2013Inventors: Ramachandran Radhakrishnan, Sisir K. Adhikari
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Publication number: 20110245539Abstract: Process for the preparation of N-vinylcarboxamides by pyrolysis of a compound of the formula CH3—CH(CN)—N(R)—CO—R1 ??(I), in which R and R1 are H or C1- to C6-alkyl, in the presence of solids which are doped with alkali metal or alkaline earth metal ions, under reduced pressure at a temperature of from 330 to 750° C. with elimination of hydrogen cyanide, cooling, separation and isolation of the reaction products, a solid arranged in a tubular reactor being treated at a temperature in the range from 0 to 250° C. with a solution of an alkali metal and/or alkaline earth metal base, the solution being discharged, the remaining solvent which adheres to the catalyst thus obtainbale being evaporated and said catalyst then being heated to a temperature of at least 380° C. for activation.Type: ApplicationFiled: December 4, 2009Publication date: October 6, 2011Applicant: BASF SEInventors: Manfred Winter, Hagen Weigl, Andreas Kramer
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Patent number: 7999129Abstract: A process for the industrial synthesis of the compound of formula (I) Application in the synthesis of agomelatine.Type: GrantFiled: December 9, 2008Date of Patent: August 16, 2011Assignee: Les Laboratories ServierInventors: Jean-Claude Souvie, Isaac Gonzalez Blanco
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Publication number: 20110123641Abstract: The present invention generally relates to a process for preparing 2,2-dibromomalonamide from 2,2-dibromo-3-cyanoacetamide.Type: ApplicationFiled: November 18, 2010Publication date: May 26, 2011Inventors: Charles D. Gartner, Dawn Carsten
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Publication number: 20110034705Abstract: A process for preparing 3-amino-3-cyclobutylmethyl-2-hydroxypropionamide of the Formula I: or a salt thereof involves providing a compound of the Formula VI described herein in a solution comprising predominately dimethylsulfoxide (DMSO) and converting this compound directly to the compound of the Formula VIII described herein without working up or isolating the intermediate compound of the Formula VII described herein.Type: ApplicationFiled: December 17, 2008Publication date: February 10, 2011Applicant: Schering-Plough CorporationInventors: Shuan Dong, Jeonghan Park, Eugene John Vater
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Publication number: 20100249449Abstract: The present invention relates to a process for preparing carboxamides by amidating nitriles in the presence of sulphuric acid, wherein the reaction is performed in a Taylor reactor. The process enables a simple and inexpensive preparation of these compounds. The present invention further provides processes for preparing (meth)acrylamides and alkyl(meth)acrylates, which comprise an inventive amidation reaction.Type: ApplicationFiled: August 15, 2008Publication date: September 30, 2010Applicant: Evonik Roehm GmbHInventors: Lorenza Sartorelli, Andreas Perl, Udo Gropp, Arndt Selbach
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Publication number: 20100217042Abstract: Improved process for working up diacetone acrylamide solutions, obtained by reaction of acetone or diacetone alcohol with acrylonitrile and sulfuric acid and subsequent dilution and neutralization, in which a) the organic phase obtained subsequent to the neutralization, which comprises the crude diacetone acrylamide, is hydrolyzed by addition of an aqueous alkaline solution in order to remove acrylamide, then b) after phase separation has been carried out, the organic phase, which comprises the crude diacetone acrylamide, is neutralized by addition of an acid, and c) in succession, low-boiling-point byproducts are removed by distillation in the presence of one or more polymerization inhibitors, then t-butylacrylamide is removed by distillation and, finally, the diacetone acrylamide is isolated by product distillation, and d) the diacetone acrylamide thus obtained is converted into its final formType: ApplicationFiled: May 8, 2008Publication date: August 26, 2010Inventors: Sascha Braune, Bernhard Holub, Christoph Huber
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Publication number: 20100087414Abstract: The invention relates to a novel method for the synthesis of N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}-N-(3,5 -difluorophenyl)methylsulfonamide.Type: ApplicationFiled: December 11, 2009Publication date: April 8, 2010Applicant: SANOFI-AVENTISInventors: Philippe BOFFELLI, Michel DELTHIL, Luc GRONDARD, Maxime LAMPILAS, Joel MALPART, Stephane MUTTI, Lahlou NAIT-BOUDA, Joerg RIEKE-ZAPP
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Patent number: 7589221Abstract: The present invention relates to a process for producing (2R)-2-propyloctanoic acid, which comprises subjecting (2R)-2-hexyloxirane to a two-carbon adding reaction with ring-opening reaction, followed by a protecting reaction of a hydroxyl group to convert it to a compound represented by formula (I): (wherein X represents an optionally protected hydroxyl group) and then subjecting the compound to a one-carbon adding reaction to convert it to (2R)-2-propyloctanamide, followed by recrystallization and hydrolysis. According to the process of the present invention, (2R)-2-propyloctanoic acid can be produced by less steps as compared with the conventional method without a dangerous reaction.Type: GrantFiled: June 9, 2004Date of Patent: September 15, 2009Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Yasumasa Hamada, Tomoyuki Hasegawa, Toshiaki Matsui, Eiji Kasamatsu
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Patent number: 7544839Abstract: Process for the industrial synthesis and new crystalline form of the compound of formula (I): Medicinal products containing the same which are useful in treating disorders of the melatoninergic system.Type: GrantFiled: April 6, 2007Date of Patent: June 9, 2009Assignee: Les Laboratoires ServierInventors: Jean-Claude Souvie, Isaac Gonzalez-Blanco, Gilles Thominot, Genevieve Chapuis, Stephane Horvath, Gerard Damien
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Publication number: 20090131719Abstract: A process for the industrial synthesis of the compound of formula (I) Application in the synthesis of agomelatine.Type: ApplicationFiled: December 9, 2008Publication date: May 21, 2009Applicant: LES LABORATOIRES SERVIERInventors: Jean-Claude Souvie, Isaac Gonzalez Blanco
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Publication number: 20080312205Abstract: The invention relates to a novel method for the synthesis of N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}-N-(3,5-difluorophenyl)methylsulfonamide.Type: ApplicationFiled: August 20, 2008Publication date: December 18, 2008Applicant: SANOFI-AVENTISInventors: Philippe BOFFELLI, Michel DELTHIL, Luc GRONDARD, Maxime LAMPILAS, Joel MALPART, Stephane MUTTI, Lahlou NAIT-BOUDA, Joerg RIEKE-ZAPP
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Patent number: 7405324Abstract: The present invention concerns a new process for synthesising aminoadamantanes of formula I in which R1 and R2 are identical or different and are H or a straight or branched alkyl group comprising from 1 to 6 carbon atoms, and addition salts thereof with inorganic or organic acids, in particular memantine hydrochloride (1-amino-3,5-dimethyladamantane hydrochloride).Type: GrantFiled: May 10, 2006Date of Patent: July 29, 2008Assignee: A.M.S.A. Anonima Materie Sintetiche E. Afini S.p.A.Inventors: Enrico Vigano′, Ernesto Landonio, Simona Lanfranconi, Renato Molteni
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Patent number: 6124501Abstract: A process for preparing lactamide with a high conversion and a high selectivity without the deterioration of a catalytic activity in a short time, which comprises subjecting lactonitrile to a hydrating reaction in the presence of (A) a catalyst including an oxide of manganese as a main component, (B) an oxidizing agent and (C) hydrogen cyanide or hydrogen cyanide and a compound represented by the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are each a hydrogen atom, a C.sub.1 to C.sub.8 alkyl group, a C.sub.1 to C.sub.8 hyroxyalkyl group, a C.sub.1 to C.sub.8 aminoalkyl group or a C.sub.1 to C.sub.8 halogenoalkyl group.Type: GrantFiled: March 3, 1999Date of Patent: September 26, 2000Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Yuichi Sugano, Takafumi Abe, Rieko Nakano
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Patent number: 6002010Abstract: A process for preparing carboxylic acid derivatives of the formula I ##STR1## where X is OR.sup.2 or NH.sub.2,R.sup.1 is C.sub.1 -C.sub.20 -alkyl, C.sub.l -C.sub.20 -hydroxyalkyl, C.sub.3 -C.sub.12 -cycloalkyl, C.sub.4 -C.sub.12 -alkylcycloalkyl, C.sub.4 -C.sub.12 -cycloalkylalkyl, C.sub.5 -C.sub.20 -alkylcycloalkylalkyl, aryl, C.sub.7 -C.sub.20 -aralkyl, C.sub.7 -C.sub.20 -alkylaryl, a heteroaliphatic or heteroaromatic ring with 5 to 8 carbon atoms andR.sup.2 is C.sub.1 -C.sub.20 -alkyl,from carbonitriles of the formula IIR.sup.1 --C.tbd.N (II),where R.sup.1 has the abovementioned meanings, and alcohols of the formula IIIR.sup.2 --OH (III),where R.sup.2 has the abovementioned meanings, at from 50 to 300.degree. C. under from 0.1 to 350 bar in the presence of a heterogeneous catalyst, wherein the reaction is carried out in liquid phase.Type: GrantFiled: November 10, 1997Date of Patent: December 14, 1999Assignee: BASF AktiengesellschaftInventor: Eberhard Fuchs
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Patent number: 5811580Abstract: Hydrocarbyl-substituted amides can be prepared in a catalyzed Ritter reaction by contacting a nitrile with a hydrocarbylating agent, in the presence of an acidified clay as the catalyst, under conditions conducive to the formation of the hydrocarbyl-substituted amide.Type: GrantFiled: December 4, 1996Date of Patent: September 22, 1998Assignee: The Lubrizol CorporationInventor: Douglas C. Rhubright
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Patent number: 5763661Abstract: A method of preparing acylated .alpha.-amino carboxylic acid amides directly from amino nitriles in high yield and purity. The method involves acylating the amino nitrile with an acyl halide under Schotten-Baumann conditions, and hydrolyzing the resulting nitrile to the amide. The resulting acylated amino carboxylic acid amide precipitates and can be isolated by filtration in high purity.Type: GrantFiled: January 17, 1997Date of Patent: June 9, 1998Assignee: Hampshire Chemical Corp.Inventor: John B. Stallman
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Patent number: 5756842Abstract: There is herein disclosed a process for preparing a lactamide by hydrating lactonitrile in the presence of a catalyst mainly comprising a manganese oxide, and a nitrogen-containing compound such as ammonia or diethylamine. According to this process, the lactamide can be obtained from lactonitrile in a high yield, while the high activity of the catalyst is maintained for a long period of time.Type: GrantFiled: October 11, 1996Date of Patent: May 26, 1998Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Fumio Tanaka, Tsumoru Morimoto, Takako Uchiyama, Takafumi Abe
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Patent number: 5712413Abstract: Hydrocarbyl-substituted amides are prepared by a process comprising contacting a nitrile with a hydrocarbylating agent, such as an alkylating agent, in the presence of a catalyst comprising a heteropolyacid or salt thereof.Type: GrantFiled: December 4, 1996Date of Patent: January 27, 1998Assignee: The Lubrizol CorporationInventors: James D. Burrington, Douglas C. Rhubright, Chester E. Ramey
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Patent number: 5648534Abstract: 1,2-di-substituted indan expressed by general formula (I) wherein X is a substituent which can be drawn out under an acidic condition to form a carbocation at 1-position of an indan skeleton, Y is a halogen atom, and X and Y can be in either cis- or trans-configuration forming either a racemic body or an optically active substance; or 1,2-di-substituted indan expressed by general formula (I') wherein X is a substituent which can be drawn out under an acidic condition to form a carbocation at 1-position of an indan skeleton, and X and OH group can be in either cis- or trans-configuration forming either a racemic body or an optically-active substance; or cis-1,2-epoxyindan expressed by general formula (VI) wherein R is phenyl or a lower alkyl group, oxazoline ring is in cis-configuration forming either a racemic body or an optically active substance is reacted, under an acidic condition, with a nitrile expressed by general formula (II) wherein R is phenyl or a lower alkyl group to produce cis-1-aminoindan-2-olType: GrantFiled: November 30, 1994Date of Patent: July 15, 1997Assignee: Ichikawa Gosei Chemical Co., Ltd.Inventors: Yoshio Igarashi, Fumihiro Asano, Makoto Shimoyamada, Masayuki Harada, Shigeru Nakano, Ryoji Iwai, Keisuke Yagami, Yuzi Konno
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Patent number: 5449808Abstract: A process which comprises contacting and catalytically reacting under essentially anhydrous conditions in the liquid phase an amide with a nitrile according to the equation:RCONH.sub.2 +R.sup.1 CN.revreaction.RCN+R.sup.1 CONH.sub.2where R and R.sup.Type: GrantFiled: March 29, 1994Date of Patent: September 12, 1995Assignee: The Standard Oil CompanyInventors: Marco Pagnotta, Mark C. Cesa, Sandra L. Denman, Robert D. Boyer, Jr.
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Patent number: 5436371Abstract: A process for preparing p-nitroaromatic amides is provided which comprises contacting a nitrile, nitrobenzene, a suitable base and water in the presence of a suitable solvent system to form a mixture, and reacting the mixture at a suitable temperature in a confined reaction zone in the presence of a controlled amount of protic material. The p-nitroaromatic amides of the invention can be reduced to p-aminoaromatic amides. In one embodiment, the p-aminoaromatic amide is further reacted with ammonia under conditions which produce the corresponding p-aminoaromatic amine and the amide corresponding to the nitrile starting material or with water in the presence of a suitable basic or acidic catalyst under conditions which produce the corresponding p-aminoaromatic amine and the acid or salt thereof corresponding to the nitrile starting material. In another embodiment, the p-aminoaromatic amine is reductively alkylated to produce alkylated p-aminoaromatic amine.Type: GrantFiled: August 29, 1994Date of Patent: July 25, 1995Assignee: Monsanto CompanyInventors: Michael K. Stern, Brian K. Cheng
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Patent number: 5387715Abstract: Alpha-hydroxy-isobutyramide is produced by continuously hydrating acetone cyanohydrin in a liquid phase in the presence of a manganese dioxide catalyst and in the presence of a particular oxide dissolved in water, oxoacid, heteropolyacid or a salt of the acids.Type: GrantFiled: February 1, 1992Date of Patent: February 7, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Minato Karasawa, Masamitsu Inomata, Hiroharu Kageyama, Kanemitsu Miyama
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Patent number: 5380946Abstract: A process for preparing p-nitroaromatic amides is provided which comprises contacting a nitrile, nitrobenzene, a suitable base and water in the presence of a suitable solvent system to form a mixture, and reacting the mixture at a suitable temperature in a confined reaction zone in the presence of a controlled amount of protic material. The p-nitroaromatic amides of the invention can be reduced to p-aminoaromatic amides. In one embodiment, the p-aminoaromatic amide is further reacted with ammonia under conditions which produce the corresponding p-aminoaromatic amine and the amide corresponding to the nitrile starting material or with water in the presence of a suitable basic or acidic catalyst under conditions which produce the corresponding p-aminoaromatic amine and the acid or salt thereof corresponding to the nitrile starting material. In another embodiment, the p-aminoaromatic amine is reductively alkylated to produce alkylated p-aminoaromatic amine.Type: GrantFiled: July 30, 1993Date of Patent: January 10, 1995Assignee: Monsanto CompanyInventors: Michael K. Stern, Brian K. M. Cheng
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Patent number: 5354891Abstract: Disclosed is a method for producing aromatic amine derivatives in a high yield at a low price, which comprises inducing an aromatic hydroxamic acid derivative to undergo a rearrangement reaction under a mild condition in the presence of a base and a nitrile or a nitrile equivalent.Type: GrantFiled: March 4, 1993Date of Patent: October 11, 1994Assignee: Fuji Photo Film Co., Ltd.Inventor: Tatsuhiko Obayashi
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Patent number: 5103055Abstract: Disclosed is a method which comprises the reaction in a reaction zone of a nitrile, RCN, with a hydroxyl compound, R'OH, in the presence of water introduced into the reaction zone in the amount of more than 0.15 mole and up to 10 moles, per mole of RCN introduced to the reaction zone, thereby producing a reaction mixture containing at least one amide selected from R--CONHR' and R--CON(R').sub.Type: GrantFiled: May 10, 1990Date of Patent: April 7, 1992Assignee: The Standard Oil CompanyInventor: Mark C. Cesa
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Patent number: 5099066Abstract: Disclosed is a method which comprises the reaction in a reaction zone of a nitrile, RCN, with a hydroxyl compound, R'OH, in the presence of a Lewis base as catalyst introduced into the reaction zone, thereby producing a reaction mixture containing at least one amide selected from R--CONHR' and R--CON(R').sub.2, whereineach of R and R' contains no acetylenic unsaturation and 1 to 30 carbon atoms,each of R and R' is independently selected from a hydrocarbyl group and a hydrocarbyl group that is substituted with a group selected from cyano, carbamoyl, hydrocarbylcarbamoyl, dihydrocarbylcarbamoyl, and hydroxyl.Type: GrantFiled: April 27, 1990Date of Patent: March 24, 1992Assignee: The Standard Oil CompanyInventor: Mark C. Cesa
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Patent number: 5087751Abstract: The present invention presents a method for preparation of S-3,4-dihydroxy butyronitrile expressed by the structural formula (II) ##STR1## characterized by causing R-3-chloro-1,2-propanediol expressed by the structural formula (I) ##STR2## to react with a cyanating agent. According to this invention, optically active 3,4-dihydroxy butyronitrile and 3,4-dihydroxy butyric acid derivatives may be manufactured economically and efficiently.Type: GrantFiled: November 9, 1990Date of Patent: February 11, 1992Assignee: Kanegafuchi Kagaku Kogyo K.K.Inventors: Kenji Inoue, Mitsunori Matsumoto, Satomi Takahashi
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Patent number: 5072024Abstract: Disclosed is a method which comprises the reaction in a reaction zone of a nitrile, RCN, with a hydroxyl compound, R'OH, in the presence of an inorganic catalyst introduced into the reaction zone, thereby producing a reaction mixture containing at least one amide selected from R--CONHR' and R--CON(R').sub.2, whereineach of R and R' contains no acetylenic unsaturation and 1 to 30 carbon atoms,each of R and R' is independently selected from a hydrocarbyl group and a hydrocarbyl group that is substituted with a group selected from cyano, carbamoyl, hydrocarbylcarbamoyl, dihydrocarbylcarbamoyl, and hydroxyl,wherein said inorganic catalyst is selected from phosphates and sulfates of Be, Ng, Al and B, and mixtures thereof.Type: GrantFiled: April 27, 1990Date of Patent: December 10, 1991Assignee: The Standard Oil CompanyInventors: Mark C. Cesa, Sandra L. Denman
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Patent number: 4950788Abstract: Acrylic acid or other unsaturated carboxylic acid is made by hydrolysing the corresponding nitrile in the presence of excess sulphuric acid to form amide sulphate, adding amide in an amount such that the total amount of amide and nitrile fed to the process is greater than 1 mole per mole sulphuric acid, hydrolysing the amide sulphate and amide to the desired acid and separating the acid from the sulphate by-products.Type: GrantFiled: February 23, 1989Date of Patent: August 21, 1990Assignee: Allied Colloids LimitedInventors: David Farrar, Peter Flesher
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Patent number: 4801748Abstract: Amide compounds are efficiently prepared directly from nitriles, amines and water, using a reaction catalyst. The invention also can applied to the manufacture of polyamides, thereby realizing a simplified and rationalized process for polyamide synthesis. The catalyst employable is at least one metallic compound selected from the group consisting of Ru- Rh-, Zn-, Ni-, Mo-, Cu-, Co-, Ti-, Cr-, Zr-, Os-, Rd-, Se-, Fe-, Pb-, Hg-, V-, Cd-, Ir- and Pt-compounds.Type: GrantFiled: March 7, 1986Date of Patent: January 31, 1989Assignee: Osaka UniversityInventors: Shunichi Murahashi, Takeshi Naota
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Patent number: 4515732Abstract: The vapor phase oxidation of acetonitrile with molecular oxygen in the presence or absence of water vapor to produce glycolonitrile or glycolamide.Type: GrantFiled: May 29, 1984Date of Patent: May 7, 1985Assignee: The Standard Oil CompanyInventors: James F. Brazdil, Jr., William A. Marritt, Michael D. Ward
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Patent number: 4446053Abstract: Disclosed are beta-amino acid derivatives which impart friction reducing properties to lubricating compositions. The additives of the invention are bifunctional carboxylic acid salts and amides derived from the basic hydrolysis of a cyanoethylated amine.Type: GrantFiled: November 4, 1982Date of Patent: May 1, 1984Assignee: Texaco Inc.Inventors: Anthony P. Skrobul, Benjamin J. Kaufman
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Patent number: 4345100Abstract: A process for the preparation of an .alpha.-ketocarboxylic acid N-tert.-butylamide of the formulaR--CO--CO--NH--C(CH.sub.3).sub.3in whichR is an aliphatic radical with up to 8 carbon atoms, a cycloalkyl radical with 3 to 6 carbon atoms, a phenyl or naphthyl radical or a heterocyclic radical,comprising reacting an acyl cyanide of the formulaR--CO--CNwith tert.-butyl methyl ether of the formula(CH.sub.3).sub.3 C--O--CH.sub.3at a temperature between about 0.degree. and 80.degree. C. in the presence of an acid which is capable of activating the ether of formula (III) under the reaction conditions to give a tert.-butyl carbonium ion, and then hydrolyzing the reaction mixture. Advantageously the acyl cyanide is pivaloyl cyanide or benzoyl cyanide and is reacted with an approximately equimolar amount of the ether in the presence of about 1.1 to 1.5 times the molar amount of concentrated sulphuric acid as the activating acid. The products are useful as intermediates in the synthesis of known herbicides.Type: GrantFiled: January 2, 1981Date of Patent: August 17, 1982Assignee: Bayer AktiengesellschaftInventors: Gerhard Bonse, Heinz U. Blank
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Patent number: 4246199Abstract: An improved process for the preparation of N-alkyl-substituted carboxylic acid amides by reaction of a component which forms a carbonium ion with a nitrile, the improvement residing in carrying out the process in the presence of an acid which is inert under distillation conditions and separating the reaction mixture by distillation.Type: GrantFiled: May 30, 1978Date of Patent: January 20, 1981Assignee: Bayer AktiengesellschaftInventors: Dieter Arlt, Franz-Gerhard Behlau