Acid Hydrolysis Only Of Nitrile Patents (Class 564/129)
  • Patent number: 9995663
    Abstract: The present invention relates to a method for extracting acrylamide from a matrix comprising matrix components and acrylamide, comprising the steps: bringing said matrix in contact with water to obtain an aqueous extract, and, optionally, adding a base to the aqueous extract; loading a portion of the aqueous extract obtained in the previous step onto an inert support; allowing the inert support to absorb the aqueous extract; extracting acrylamide from the aqueous extract by passing a water immiscible organic solvent through the inert support; thereby obtaining an organic extract. It further relates to a method for analyzing acrylamide content in a matrix comprising matrix components and acrylamide.
    Type: Grant
    Filed: August 29, 2014
    Date of Patent: June 12, 2018
    Assignee: Biotage AB
    Inventors: Alan Edgington, Lee Williams
  • Patent number: 8759581
    Abstract: Method of preparing 1-chloroacetamido-1,3,3,5,5-pentamethylcyclohexane, an intermediate in the synthesis of 1-amino-1,3,3,5,5-pentamethylcyclohexane (Neramexane) or a pharmaceutically acceptable salt thereof, comprising step (iii): (iii) reacting 1-hydroxy-1,3,3,5,5-pentamethylcyclohexane with chloroacetonitrile in the presence of an acid, wherein 1-hydroxy-1,3,3,5,5-pentamethylcyclohexane is employed in step (iii) as obtained in the reaction of a methylmagnesium halide with 3,3,5,5-tetramethylcyclohexanone without having been subjected to a purification step.
    Type: Grant
    Filed: June 28, 2010
    Date of Patent: June 24, 2014
    Assignee: Merz Pharma GmbH & Co. KGaA
    Inventors: Herbert Koller, Michael Pyerin
  • Patent number: 8624062
    Abstract: A method for producing a phenylacetamide compound represented by formula (1): wherein Q represents a hydrogen atom or a halogen atom, R2 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R4 represents an alkyl group having 1 to 4 carbon atoms, Ar represents an unsubstituted or substituted phenyl group, R5 represents R4 when R2 is a hydrogen atom, and R5 represents a hydrogen atom when R2 is an alkyl group having 1 to 4 carbon atoms; including reacting a phenylacetamide compound represented by formula (2): wherein Q, R2 and Ar have the same meanings as defined above; with a dialkyl sulfate represented by formula (3): wherein R4 has the same meaning as defined above; in the presence of a base.
    Type: Grant
    Filed: February 12, 2010
    Date of Patent: January 7, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hajime Ishida, Masaji Hirota, Yoko Miyanaga, Yuya Mizushima
  • Publication number: 20130211140
    Abstract: The present invention relates to an apparatus for metering flowable media or gases, and to the use thereof.
    Type: Application
    Filed: March 15, 2013
    Publication date: August 15, 2013
    Inventors: Lorenza SARTORELLI, Andreas Perl, Udo Gropp, Arndt Selbach, Stefanie Sohnemann, Matthias Groemping, Norbert Mnich, Thomas Mertz
  • Publication number: 20120232155
    Abstract: The invention relates to a novel hydroxyphenyl compound, to the preparation of the compound and intermediates used therein, to the use of the compound as an antibacterial medicament and pharmaceutical compositions containing the compound.
    Type: Application
    Filed: November 11, 2009
    Publication date: September 13, 2012
    Inventors: Vincent Gerusz, Fabien Faivre, Mayalen Oxoby, Alexis Denis, Yannick Bonvin
  • Patent number: 8212065
    Abstract: A method for the production of optically active ?-alkylcarbonyl compounds with retention of the stereo information of the starting compound. The starting compound used here is a carbonyl compound which has, in the ?-position, a leaving group which is substituted by an alkyl group with inversion of the configuration. The substitution of the leaving group is effected with the use of an alkylmagnesium Grignard and a zinc (II) salt or a zinc organyl. The method permits the production of optically active ?-alkylcarbonyl compounds at very mild temperatures (for example 0° C.) with the use of starting compounds which are easy to prepare and economical and nontoxic catalysts, it also being possible to achieve a very high yield.
    Type: Grant
    Filed: September 18, 2008
    Date of Patent: July 3, 2012
    Assignee: Albert-Ludwigs-Universitat Freiburg
    Inventors: Bernhard Breit, Christopher Studte
  • Publication number: 20120130127
    Abstract: Method of preparing 1-chloroacetamido-1,3,3,5,5-pentamethylcyclohexane, an intermediate in the synthesis of 1-amino-1,3,3,5,5-pentamethylcyclohexane (Neramexane) or a pharmaceutically acceptable salt thereof, comprising step (iii): (iii) reacting 1-hydroxy-1,3,3,5,5-pentamethylcyclohexane with chloroacetonitrile in the presence of an acid, wherein 1-hydroxy-1,3,3,5,5-pentamethylcyclohexane is employed in step (iii) as obtained in the reaction of a methylmagnesium halide with 3,3,5,5-tetramethylcyclohexanone without having been subjected to a purification step.
    Type: Application
    Filed: June 28, 2010
    Publication date: May 24, 2012
    Applicant: MER PHARMA GmbH & CO. KGaA
    Inventors: Herbert Koller, Michael Pyerin
  • Publication number: 20110245494
    Abstract: The present invention includes methods/processes and intermediates for preparing compounds having structural Formula (I): wherein X is alkyl, substituted alkyl, alkenyl, substituted alkenyl, heteroalkyl, substituted heteroalkyl, heteroalkenyl, or substituted heteroalkenyl.
    Type: Application
    Filed: July 29, 2009
    Publication date: October 6, 2011
    Applicant: SENOMYX, INC.
    Inventors: Catherine Tachdjian, Donald S. Karanewsky, Xiao-Qing Tang, Qing Chen, Peter Leeming, Tayyab Rashid, Daniel Levin
  • Publication number: 20110104765
    Abstract: Provided herein are compositions including diastereomers in substantially diastereomerically pure form and enantiomers in substantially enantiomerically pure form, and processes for preparing them and converting them to metyrosine.
    Type: Application
    Filed: October 29, 2010
    Publication date: May 5, 2011
    Inventors: Kevin John HALLORAN, Alex COMELY, Zhengming CHEN, Shyam KRISHNAN
  • Publication number: 20100298603
    Abstract: Provided is a process for producing an amide (A): by hydrating a nitrile (B) at high conversion in relatively short period of time even without use of high-capacity cooling apparatuses (25, 35) and a large amount of inorganic acid (D). In the process for the present invention, a nitrile (B) is hydrated in continuous mode in the presence of an inorganic acid (D) so as to give a conversion of 80% to 98%, and the unreacted nitrile contained in the resultant hydrated reaction liquid (E) is hydrated in batch-wise mode so as to give a conversion of 99.9% or more, thereby producing an amide (A). For example, the inorganic acid (D) is sulfuric acid and the use amount thereof is 0.5 to 1-fold mol with respect to the nitrile (B), and the temperature in hydration is 40 to 70-C, and hydration is performed in continuous mode using a tubular reactor (2c), loop reactor (2d) and the like. The resultant amide (A) can be hydrolyzed to produce a thiobutanoic acid (G).
    Type: Application
    Filed: January 9, 2009
    Publication date: November 25, 2010
    Inventors: Takanori Ito, Masahiro Kinoshita
  • Patent number: 7705053
    Abstract: To provide compounds which have high angiogenesis inhibiting activity, and are useful as agents for effective treatment and prevention of diseases involving pathologic angiogenesis, for example, cancer and cancer metastasis, methods for producing the compounds, intermediate compounds useful for their production, and pharmaceutical compositions containing these compounds.
    Type: Grant
    Filed: December 27, 2004
    Date of Patent: April 27, 2010
    Assignee: Chugai Seiyaku Kabushiki Kaisha
    Inventors: Hiroshi Koyano, Atsushi Suda, Kousuke Aso, Kihito Hada, Miyuki Asai, Masami Hasegawa, Yasuko Sato
  • Patent number: 7227036
    Abstract: There is provided a process for producing an aminomethyl group-containing benzamide compound represented by the general formula (II): wherein —CONH2 and —X represent a substituent on the benzene ring and —CONH2 exists at the meta- or para-position of —CH2NH2, and X and n are as defined below, which comprises hydrating an aminomethyl group-containing benzonitrile compound represented by the general formula (I): wherein —CN and —X represent a substituent on the benzene ring and —CN exists at the meta- or para-position of —CH2NH2, X represents a chlorine atom or a fluorine atom, and n represents an integer of 0 to 4, provided that, when n is 2 or more, X may be the same or different
    Type: Grant
    Filed: May 2, 2003
    Date of Patent: June 5, 2007
    Assignee: Showa Denko K.K.
    Inventors: Yutaka Ohnishi, Hideo Miyata, Kimitaka Ohshiro
  • Patent number: 6660880
    Abstract: A process, for the preparation of an ester of 2-hydroxy-4-methylthiobutyric acid which is substantially in the monomeric form, which process, being capable of industrial application and which comprises reacting 2-hydroxy-4-methylthiobutyric acid with an alcohol in the presence of water and an acid catalyst at a temperature of from 30 to 150° C. wherein the acid is the direct product of the hydrolysis of 2-hydroxy-4-methylthiobutyronitrile.
    Type: Grant
    Filed: February 7, 2001
    Date of Patent: December 9, 2003
    Assignee: Adisseo Ireland Limited
    Inventors: Michel Garrait, Claude Casse, George Gros
  • Patent number: 6521794
    Abstract: For the production of an aromatic compound by hydrolyzing and decarboxylating a corresponding aromatic cyano compound in the presence of an acidic substance, this invention provides a method for the production of the aromaic compound, characterized by carrying out the reactions of hydrolysis and decarboxylaion in multiple steps. Particularly when the aromatic cyano compound contains a halogen, this method effectively prevents the reaction vessels from being corroded by the by-produced hydrogen halogenide and enables the target compound to be produced in a high yield.
    Type: Grant
    Filed: February 1, 2002
    Date of Patent: February 18, 2003
    Assignee: Nippon Shokubai Co., Ltd.
    Inventor: Kouichi Hirota
  • Patent number: 6492553
    Abstract: A method for preparing a N-[(aliphatic or aromatic)carbonyl)]-2-aminoacetamide compound, and for preparing a cyclized compound therefrom, as well as novel resin bound intermediate compounds that are useful for preparing such compounds.
    Type: Grant
    Filed: August 4, 1999
    Date of Patent: December 10, 2002
    Assignee: Aventis Pharamaceuticals Inc.
    Inventors: Christopher Hulme, George C. Morton, Joseph M. Salvino, Richard F. Labaudiniere, Helen J. Mason, Matthew M. Morrissette, Liang Ma, Marie-Pierre Cherrier
  • Patent number: 6482983
    Abstract: A process for obtaining an amide of the general formula R—(CO)—NH—CH2—X involves contacting a nitrile of the general formula R—CN with: a) an acid; and c) an alkoxy-containing compound comprising at least one alkoxy functionality of the general formula —OCH2—X; wherein R is hydrogen or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, or heterocyclic substituent, which substituents can be substituted or unsubstituted; wherein X is hydrogen or a radical having the general formula —CHR1R2; and wherein R1 and R2 independently or collectively represent hydrogen or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, or heterocyclic substituent, or any combination thereof, which substituents can be substituted or unsubstituted.
    Type: Grant
    Filed: July 31, 2001
    Date of Patent: November 19, 2002
    Assignee: Millennium Specialty Chemicals
    Inventors: Mikhail Yu. Lebedev, Mark B. Erman
  • Patent number: 6479695
    Abstract: A process for the preparation of 2-hydroxy-4-methylthiobutyric acid ester which comprises (a) a first step of reacting 2-hydroxy-4-methylthiobutyronitrile with sulphuric acid to produce 2-hydroxy-4-methylthiobutyramide, and (b) a second step of reacting the 2-hydroxy-4-methylthiobutyramide with an alcohol to produce a 2-hydroxy-4-methylthiobutyric acid ester, the two steps being carried out in the same reaction medium.
    Type: Grant
    Filed: December 28, 2001
    Date of Patent: November 12, 2002
    Assignee: Aventis Animal Nutrition, S.A.
    Inventors: Michel Garrait, Claude Casse, Georges Gros
  • Patent number: 6437183
    Abstract: The invention relates to the manufacture of amide compounds provided through the reaction of nitrile compounds and a sulfate compound to form the related amide compound. In a preferred embodiment a diol or a triol is employed as a solvent, thereby increasing the yield of the product.
    Type: Grant
    Filed: August 8, 2001
    Date of Patent: August 20, 2002
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Carlos Ramirez
  • Patent number: 6303817
    Abstract: The invention relates to the manufacture of amide compounds provided through the reaction of nitrile compounds and a sulfate compound to form the related amide compound. In a preferred embodiment a diol or a triol is employed as a solvent, thereby increasing the yield of the product.
    Type: Grant
    Filed: August 10, 2000
    Date of Patent: October 16, 2001
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Carlos Ramirez
  • Patent number: 6184414
    Abstract: Process for producing ammonium-2-hydroxy-4-(methylthio)-butyrate, mixtures containing the same in liquid form and their use. In order to produce ammonium-2-hydroxy-4-methylthio-n-butyrate and mixtures containing the same with a remarkable fluidity and a very low oligomer proportion by a process based on exclusively “liquid” steps, the reaction mixture is treated with a water-immiscible or partially water-miscible inert solvent, until a first organic extract and a first aqueous raffinate are obtained, and the first organic extract is decomposed into a second organic extract and a second aqueous raffinate by treating it with ammonia and phase separation. Re-extraction of MHA as MHAAS is carried out in the second aqueous raffinate, causing salt formation, and MHAAS is isolated from the second aqueous raffinate. This compound is useful as feedstuff supplement and as methionine substitute.
    Type: Grant
    Filed: January 10, 1997
    Date of Patent: February 6, 2001
    Assignee: Degussa Aktiengesellschaft
    Inventors: Helmut Suchsland, Heinz Kohl
  • 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: 5633288
    Abstract: This invention relates to a tri(lower alkoxy)benzene derivative of the general formula (I), or its salt, optical isomer or solvate, ##STR1## wherein: R.sup.1, R.sup.2 and R.sup.3 : same or different and each represents a lower alkyl group;A: a group of the formula ##STR2## and R.sup.4 and R.sup.5 : same or different and each represents a lower alkyl group, an aralkyl group or an aryl group, provided that R.sup.4 and R.sup.5 may, taken together with the adjacent nitrogen atom, form a pyrrolidinyl group, a piperidino group, a morpholino group, a thiomorpholino group, or a piperazinyl group optionally substituted by a lower alkyl group in 4-position;to pharmaceutical compositions containing the same, and to processes for their production. The compound of the invention is useful as value as a pulmonary-surfactant secretion promoting agent.
    Type: Grant
    Filed: November 22, 1995
    Date of Patent: May 27, 1997
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Hiromu Hara, Tatsuya Maruyama, Munetoshi Saito, Toshiyasu Mase
  • 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: 5414122
    Abstract: There is disclosed an efficient process for producing .alpha.-ketoacetamide of the formula: ##STR1## which is useful as an intermediate for the production of various alkoxyiminoacetamide compounds to be used for agricultural fungicides. In this process, a corresponding acid halide is condensed with isocyanide to produce the .alpha.-ketoacetamide.
    Type: Grant
    Filed: August 17, 1993
    Date of Patent: May 9, 1995
    Assignee: Shionogi & Co., Ltd.
    Inventors: Akira Murabayashi, Hideyuki Takenaka, Hiroyuki Kai
  • Patent number: 5258551
    Abstract: There is disclosed an efficient process for producing .alpha.-ketoacetamide of the formula: ##STR1## which is useful as an intermediate for the production of various alkoxyiminoacetamide compounds to be used for agricultural fungicides. In this process, a corresponding acid halide is condensed with isocyanide to produced the .alpha.-ketoacetamide.
    Type: Grant
    Filed: December 3, 1992
    Date of Patent: November 2, 1993
    Assignee: Shionogi & Co., Ltd.
    Inventors: Akira Murabayashi, Hideyuki Takenaka, Hiroyuki Kai
  • 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: 5051525
    Abstract: N-acyl-2-amino acid amides containing phosphinic esters, process for their preparation, and N-acyl-2-amino acid nitriles as precursorsPhosphorus-containing N-acyl-2-amino acid amides of the general formula (I) ##STR1## where R.sup.1 is alkyl, optionally substituted by halogen or alkoxy, or is benzyl or phenyl, each of which is optionally substituted by alkyl, alkoxy, halogen, nitro or CF.sub.3, or is cycloalkyl, andR.sup.2 is H, or alkyl, optionally substituted by halogen or alkoxy, or is (CH.sub.2).sub.n -phenyl, optionally substituted in the phenyl ring by alkyl, alkoxy, halogen, nitro or CF.sub.3, where n=0, 1, 2 or 3,are valuable intermediates for the preparation of L-phosphinothricin by enzymatic cleavage, and can be obtained from the corresponding N-acyl-2-amino acid nitrile by selective acid hydrolysis.
    Type: Grant
    Filed: February 2, 1990
    Date of Patent: September 24, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Lothar Willms
  • 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: 4851576
    Abstract: This invention relates to a process for the catalytic hydrolysis of an .alpha.-aminonitrile in the heterogeneous phase, and to polymeric resins having a catalytic activity for carrying out the present process.The process according to this invention is characterized in that said .alpha.-aminonitrile or one of the salts thereof is reacted in an aqueous medium, in the heterogeneous phase and in the presence of hydroxide ions on a polymeric resin which contains side chains carrying a carbonyl group, and which is insoluble in the aqueous basic medium.
    Type: Grant
    Filed: December 28, 1982
    Date of Patent: July 25, 1989
    Assignee: Centre National de la Recherche Scientifique (CNRS)
    Inventors: Auguste A. Commeyras, Jacques R. Taillades, Jean Brugidou, Regine Sola, Aldo Previero, Louis Mion, Robert J. Pascal, Monique Lasperas, Alain Rousset
  • Patent number: 4731447
    Abstract: A process for the preparation of piperidylidene-dihydro-dibenzo[a,d]cycloheptene or aza-derivatives thereof and intermediates in such process are disclosed.
    Type: Grant
    Filed: March 12, 1986
    Date of Patent: March 15, 1988
    Assignee: Schering Corporation
    Inventors: Doris P. Schumacher, Bruce L. Murphy, Jon E. Clark
  • Patent number: 4719303
    Abstract: A method for the preparation of substituted and unsubstituted 2-[(1-carbamoyl-1,2-dimethyl-propyl) carbamoyl]-3-quinolinecarboxylic, nicotinic and benzoic acids.
    Type: Grant
    Filed: November 21, 1983
    Date of Patent: January 12, 1988
    Assignee: American Cyanamid Company
    Inventors: William H. Gastrock, Timothy F. Mason, Gregory P. Withers
  • Patent number: 4611067
    Abstract: This invention relates to a novel process for the preparation of 3-hydroxy-3-methylglutarylcoenzyme A (HMG-CoA) reductase inhibitors which contain a 4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one moiety, such as compactin and mevinolin, by utilizing an alkyl 4-cyano-3(R)-hydroxybutanoate as a chiral synthon for the stereospecific introduction of the 4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one moiety.
    Type: Grant
    Filed: January 31, 1985
    Date of Patent: September 9, 1986
    Assignee: Merck & Co., Inc.
    Inventors: Ralph P. Volante, Thomas R. Verhoeven, Meyer Sletzinger, James M. McNamara, Thomas M. H. Liu, Edward G. Corley
  • Patent number: 4596885
    Abstract: A process for the preparation of a phenylglyocylic acid ester of the formula ##STR1## wherein R.sup.1 represents alkyl,X represents halogen, alkyl, halogenoalkyl, alkoxy or nitro, andn represents 0, 1, 2, or 3by contacting a benzoyl cyanide of the formula ##STR2## wherein X and n have the meanings stated above, in a sulphuric acid/water system in the presence of chloride ions at a temperature between 0.degree. and 70.degree. C. to form phenylglyoxylic acid amide and reacting the phenylglyoxylic acid amide without isolation with an alcohol of the formula R.sup.1 -OH, wherein R.sup.1 has the meaning stated above, optionally in the presence of a diluent, at a temperature between 40.degree. and 100.degree. C.
    Type: Grant
    Filed: February 6, 1978
    Date of Patent: June 24, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Winfried Lunkenheimer, Andreas Wittig, Wilfried Draber, Helmut Timmler
  • Patent number: 4552982
    Abstract: 9-Carbamoyl-9-(2-cyanoethyl)fluorenes are converted to 9-carbamoyl-9-(3-aminopropyl)fluorenes by catalytic hydrogenation in the presence of a strong acid.
    Type: Grant
    Filed: August 1, 1983
    Date of Patent: November 12, 1985
    Assignee: Eli Lilly and Company
    Inventors: William B. Lacefield, William Pfeifer
  • Patent number: 4524077
    Abstract: A process for the preparation of 2-hydroxy-4-methylthiobutyric acid having improved color, odor and lower viscosity. 2-hydroxy-4-methylthiobutyric acid which is also known as 2-hydroxy-4-(methylthio) butanoic acid, is hydrolyzed with sulfuric acid having an initial strength of between about 50% by weight and about 70% by weight on an organic-free basis, thereby producing an intermediate aqueous hydrolysis product solution containing 2-hydroxy-4-methylthiobutyramide. The 2-hydroxy-4-methylthiobutyramide is hydrolyzed with sulfuric acid having a strength of between about 30% by weight and about 50% by weight on an organic-free basis to produce an aqueous hydrolyzate containing 2-hydroxy-4-methylthiobutyric acid. The hydrolyzate solution is contacted with a substantially water-immiscible organic solvent in a liquid-liquid extraction system to produce an extract comprising the solvent and 2-hydroxy-4-methylthiobutyric acid transferred from the hydrolyzate. The acid product is then recovered from the extract.
    Type: Grant
    Filed: November 14, 1983
    Date of Patent: June 18, 1985
    Assignee: Monsanto Company
    Inventors: Dennis A. Ruest, Masaharu Takano, Lawrence R. Wolf
  • Patent number: 4250111
    Abstract: An improved process for catalytically hydrolyzing a nitrile to a corresponding amide which employs a reduced copper and another reduced metal catalyst. This catalyst is prepared by precipitating from an aqueous solution comprised of a mixture of a copper salt and a heavy metal salt a mixture of copper hydroxide and heavy metal hydroxide, oxidizing, heating, washing, separating and reducing under controlled conditions.
    Type: Grant
    Filed: July 12, 1976
    Date of Patent: February 10, 1981
    Assignee: Nalco Chemical Company
    Inventors: Virgil L. Seale, Louis A. Goretta