From Acyclic Nitrile Patents (Class 564/130)
  • Patent number: 11358927
    Abstract: 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 amide
    Type: Grant
    Filed: April 25, 2019
    Date of Patent: June 14, 2022
    Assignee: SHOWA DENKO K.K.
    Inventors: Yasuyuki Ueda, Akira Shibuya, Hideo Miyata, Hiroshi Uchida
  • Patent number: 9221748
    Abstract: The present invention generally relates to a process for preparing 2,2-dibromomalonamide from 2,2-dibromo-3-cyanoacetamide.
    Type: Grant
    Filed: January 27, 2015
    Date of Patent: December 29, 2015
    Assignee: DOW GLOBAL TECHNOLOGIES LLC
    Inventors: Charles D. Gartner, Dawn Carsten
  • Publication number: 20150148564
    Abstract: The present invention generally relates to a process for preparing 2,2-dibromomalonamide from 2,2-dibromo-3-cyanoacetamide.
    Type: Application
    Filed: January 27, 2015
    Publication date: May 28, 2015
    Inventors: Charles D. Gartner, Dawn Carsten
  • Patent number: 8975441
    Abstract: The present invention generally relates to a process for preparing 2,2-dibromomalonamide from 2,2-dibromo-3-cyanoacetamide.
    Type: Grant
    Filed: November 18, 2010
    Date of Patent: March 10, 2015
    Assignee: Dow Global Technologies LLC
    Inventors: Charles D. Gartner, Dawn Carsten
  • Publication number: 20140364648
    Abstract: 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: Application
    Filed: August 26, 2014
    Publication date: December 11, 2014
    Inventors: Massimo GUGLIERI, Olivier JENTZER
  • Patent number: 8853449
    Abstract: Process for the industrial synthesis of the compound of formula (I)
    Type: Grant
    Filed: January 4, 2012
    Date of Patent: October 7, 2014
    Assignee: Les Laboratoires Servier
    Inventors: Samir Zard, Béatrice Sire, Mehdi Boumediene
  • Patent number: 8802896
    Abstract: 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: Grant
    Filed: September 30, 2013
    Date of Patent: August 12, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Akihito Amao, Hirotaka Kitagawa
  • Patent number: 8598385
    Abstract: 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: Grant
    Filed: December 4, 2009
    Date of Patent: December 3, 2013
    Assignee: BASF SE
    Inventors: Manfred Winter, Hagen Weigl, Andreas Kramer
  • Patent number: 8586765
    Abstract: 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: Grant
    Filed: December 17, 2008
    Date of Patent: November 19, 2013
    Assignee: Merck Sharp & Dohme Corp.
    Inventors: Shuan Dong, Jeonghan Park, Eugene John Vater
  • Patent number: 8581002
    Abstract: 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: Grant
    Filed: May 8, 2008
    Date of Patent: November 12, 2013
    Assignee: DSM Fine Chemicals Austria NFG GmbH & Co Kg
    Inventors: Sascha Braune, Bernhard Holub, Christoph Huber
  • Patent number: 8581000
    Abstract: 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: Grant
    Filed: June 6, 2011
    Date of Patent: November 12, 2013
    Assignee: Xerox Corporation
    Inventors: Naveen Chopra, Thomas E Enright, Michelle N Chrétien, Barkev Keoshkerian, Daryl W Vanbesien
  • Patent number: 8536355
    Abstract: 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: Grant
    Filed: September 22, 2005
    Date of Patent: September 17, 2013
    Inventors: Ramachandran Radhakrishnan, Sisir K. Adhikari
  • Publication number: 20110245539
    Abstract: 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: Application
    Filed: December 4, 2009
    Publication date: October 6, 2011
    Applicant: BASF SE
    Inventors: Manfred Winter, Hagen Weigl, Andreas Kramer
  • Patent number: 7999129
    Abstract: A process for the industrial synthesis of the compound of formula (I) Application in the synthesis of agomelatine.
    Type: Grant
    Filed: December 9, 2008
    Date of Patent: August 16, 2011
    Assignee: Les Laboratories Servier
    Inventors: Jean-Claude Souvie, Isaac Gonzalez Blanco
  • Publication number: 20110123641
    Abstract: The present invention generally relates to a process for preparing 2,2-dibromomalonamide from 2,2-dibromo-3-cyanoacetamide.
    Type: Application
    Filed: November 18, 2010
    Publication date: May 26, 2011
    Inventors: Charles D. Gartner, Dawn Carsten
  • Publication number: 20110034705
    Abstract: 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: Application
    Filed: December 17, 2008
    Publication date: February 10, 2011
    Applicant: Schering-Plough Corporation
    Inventors: Shuan Dong, Jeonghan Park, Eugene John Vater
  • Publication number: 20100249449
    Abstract: 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: Application
    Filed: August 15, 2008
    Publication date: September 30, 2010
    Applicant: Evonik Roehm GmbH
    Inventors: Lorenza Sartorelli, Andreas Perl, Udo Gropp, Arndt Selbach
  • Publication number: 20100217042
    Abstract: 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: Application
    Filed: May 8, 2008
    Publication date: August 26, 2010
    Inventors: Sascha Braune, Bernhard Holub, Christoph Huber
  • Publication number: 20100087414
    Abstract: 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: Application
    Filed: December 11, 2009
    Publication date: April 8, 2010
    Applicant: SANOFI-AVENTIS
    Inventors: Philippe BOFFELLI, Michel DELTHIL, Luc GRONDARD, Maxime LAMPILAS, Joel MALPART, Stephane MUTTI, Lahlou NAIT-BOUDA, Joerg RIEKE-ZAPP
  • Patent number: 7589221
    Abstract: 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: Grant
    Filed: June 9, 2004
    Date of Patent: September 15, 2009
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Yasumasa Hamada, Tomoyuki Hasegawa, Toshiaki Matsui, Eiji Kasamatsu
  • Patent number: 7544839
    Abstract: 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: Grant
    Filed: April 6, 2007
    Date of Patent: June 9, 2009
    Assignee: Les Laboratoires Servier
    Inventors: Jean-Claude Souvie, Isaac Gonzalez-Blanco, Gilles Thominot, Genevieve Chapuis, Stephane Horvath, Gerard Damien
  • Publication number: 20090131719
    Abstract: A process for the industrial synthesis of the compound of formula (I) Application in the synthesis of agomelatine.
    Type: Application
    Filed: December 9, 2008
    Publication date: May 21, 2009
    Applicant: LES LABORATOIRES SERVIER
    Inventors: Jean-Claude Souvie, Isaac Gonzalez Blanco
  • Publication number: 20080312205
    Abstract: 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: Application
    Filed: August 20, 2008
    Publication date: December 18, 2008
    Applicant: SANOFI-AVENTIS
    Inventors: Philippe BOFFELLI, Michel DELTHIL, Luc GRONDARD, Maxime LAMPILAS, Joel MALPART, Stephane MUTTI, Lahlou NAIT-BOUDA, Joerg RIEKE-ZAPP
  • Patent number: 7405324
    Abstract: 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: Grant
    Filed: May 10, 2006
    Date of Patent: July 29, 2008
    Assignee: A.M.S.A. Anonima Materie Sintetiche E. Afini S.p.A.
    Inventors: Enrico Vigano′, Ernesto Landonio, Simona Lanfranconi, Renato Molteni
  • Patent number: 6124501
    Abstract: 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: Grant
    Filed: March 3, 1999
    Date of Patent: September 26, 2000
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Yuichi Sugano, Takafumi Abe, Rieko Nakano
  • Patent number: 6002010
    Abstract: 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: Grant
    Filed: November 10, 1997
    Date of Patent: December 14, 1999
    Assignee: BASF Aktiengesellschaft
    Inventor: Eberhard Fuchs
  • Patent number: 5811580
    Abstract: 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: Grant
    Filed: December 4, 1996
    Date of Patent: September 22, 1998
    Assignee: The Lubrizol Corporation
    Inventor: Douglas C. Rhubright
  • Patent number: 5763661
    Abstract: 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: Grant
    Filed: January 17, 1997
    Date of Patent: June 9, 1998
    Assignee: Hampshire Chemical Corp.
    Inventor: John B. Stallman
  • Patent number: 5756842
    Abstract: 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: Grant
    Filed: October 11, 1996
    Date of Patent: May 26, 1998
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Fumio Tanaka, Tsumoru Morimoto, Takako Uchiyama, Takafumi Abe
  • Patent number: 5712413
    Abstract: 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: Grant
    Filed: December 4, 1996
    Date of Patent: January 27, 1998
    Assignee: The Lubrizol Corporation
    Inventors: James D. Burrington, Douglas C. Rhubright, Chester E. Ramey
  • Patent number: 5648534
    Abstract: 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-ol
    Type: Grant
    Filed: November 30, 1994
    Date of Patent: July 15, 1997
    Assignee: Ichikawa Gosei Chemical Co., Ltd.
    Inventors: Yoshio Igarashi, Fumihiro Asano, Makoto Shimoyamada, Masayuki Harada, Shigeru Nakano, Ryoji Iwai, Keisuke Yagami, Yuzi Konno
  • Patent number: 5449808
    Abstract: 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: Grant
    Filed: March 29, 1994
    Date of Patent: September 12, 1995
    Assignee: The Standard Oil Company
    Inventors: Marco Pagnotta, Mark C. Cesa, Sandra L. Denman, Robert D. Boyer, Jr.
  • Patent number: 5436371
    Abstract: 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: Grant
    Filed: August 29, 1994
    Date of Patent: July 25, 1995
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, Brian K. Cheng
  • Patent number: 5387715
    Abstract: 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: Grant
    Filed: February 1, 1992
    Date of Patent: February 7, 1995
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Minato Karasawa, Masamitsu Inomata, Hiroharu Kageyama, Kanemitsu Miyama
  • Patent number: 5380946
    Abstract: 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: Grant
    Filed: July 30, 1993
    Date of Patent: January 10, 1995
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, Brian K. M. Cheng
  • Patent number: 5354891
    Abstract: 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: Grant
    Filed: March 4, 1993
    Date of Patent: October 11, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Tatsuhiko Obayashi
  • Patent number: 5103055
    Abstract: 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: Grant
    Filed: May 10, 1990
    Date of Patent: April 7, 1992
    Assignee: The Standard Oil Company
    Inventor: Mark C. Cesa
  • Patent number: 5099066
    Abstract: 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: Grant
    Filed: April 27, 1990
    Date of Patent: March 24, 1992
    Assignee: The Standard Oil Company
    Inventor: Mark C. Cesa
  • Patent number: 5087751
    Abstract: 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: Grant
    Filed: November 9, 1990
    Date of Patent: February 11, 1992
    Assignee: Kanegafuchi Kagaku Kogyo K.K.
    Inventors: Kenji Inoue, Mitsunori Matsumoto, Satomi Takahashi
  • Patent number: 5072024
    Abstract: 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: Grant
    Filed: April 27, 1990
    Date of Patent: December 10, 1991
    Assignee: The Standard Oil Company
    Inventors: Mark C. Cesa, Sandra L. Denman
  • Patent number: 4950788
    Abstract: 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: Grant
    Filed: February 23, 1989
    Date of Patent: August 21, 1990
    Assignee: Allied Colloids Limited
    Inventors: David Farrar, Peter Flesher
  • Patent number: 4801748
    Abstract: 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: Grant
    Filed: March 7, 1986
    Date of Patent: January 31, 1989
    Assignee: Osaka University
    Inventors: Shunichi Murahashi, Takeshi Naota
  • Patent number: 4515732
    Abstract: The vapor phase oxidation of acetonitrile with molecular oxygen in the presence or absence of water vapor to produce glycolonitrile or glycolamide.
    Type: Grant
    Filed: May 29, 1984
    Date of Patent: May 7, 1985
    Assignee: The Standard Oil Company
    Inventors: James F. Brazdil, Jr., William A. Marritt, Michael D. Ward
  • Patent number: 4446053
    Abstract: 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: Grant
    Filed: November 4, 1982
    Date of Patent: May 1, 1984
    Assignee: Texaco Inc.
    Inventors: Anthony P. Skrobul, Benjamin J. Kaufman
  • Patent number: 4345100
    Abstract: 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: Grant
    Filed: January 2, 1981
    Date of Patent: August 17, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Bonse, Heinz U. Blank
  • Patent number: 4246199
    Abstract: 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: Grant
    Filed: May 30, 1978
    Date of Patent: January 20, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dieter Arlt, Franz-Gerhard Behlau