Catalytic Hydration Only Of Nitrile Patents (Class 564/126)
  • Patent number: 9718761
    Abstract: The present invention provides a method for producing ?-hydroxyisobutyric acid amide by hydration of acetone cyanohydrin under the presence of a catalyst composed mainly of manganese oxide using a reactor in which at least two reaction regions are connected in series, the method being characterized by comprising: a step (B) of cyclically supplying at least a portion of a reaction liquid withdrawn from at least one reaction region to a first reaction region (I) in the reactor; and a step (b1) of further cyclically supplying at least a portion of the reaction liquid withdrawn from at least one reaction region to at least one reaction region other than the first reaction region. The method is also characterized in that an oxidizing agent is supplied to at least one reaction region in the reactor.
    Type: Grant
    Filed: July 15, 2014
    Date of Patent: August 1, 2017
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC
    Inventors: Atsushi Kakimi, Takako Uchiyama, Hideho Matsuda, Masaki Takemoto, Katsumi Higuchi
  • Patent number: 8975440
    Abstract: The invention relates to a method for producing a carboxylic acid amide from a carbonyl compound and hydrocyanic acid, comprising the steps of A) reacting a carbonyl compound with hydrocyanic acid to produce a hydroxycarboxylic acid nitrile, B) hydrolysis of the hydroxycarboxylic acid nitrile obtained in step A) in the presence of a catalyst comprising manganese dioxide, wherein a molar excess of carbonyl compound is used in relation to the hydrocyanic acid to react the carbonyl compound with hydrocyanic acid according to step A), and the reaction mixture obtained in step A) is not purified by distillation before the hydrolysis according to step B) is carried out. The invention furthermore relates to a method for producing alkyl(meth)acrylates from polymers, moulding compounds and moulded bodies, wherein a method for producing a carboxylic acid amide from a carbonyl compound and hydrocyanic acid is carried out in accordance with the method described above.
    Type: Grant
    Filed: October 29, 2009
    Date of Patent: March 10, 2015
    Assignee: Evonik Roehm GmbH
    Inventors: Alexander May, Martin Koestner, Joerg Becker, Joerg Schallenberg, Hermann Siegert, Bernd Vogel
  • Patent number: 8889907
    Abstract: The present invention provides a method for producing an amide compound from a nitrile compound using a biocatalyst that realizes low cost, energy saving and low environmental burdens. The production method of the amide compound of the present invention is a method for producing an amide compound from a nitrile compound using a biocatalyst in a reactor, wherein the nitrile compound is reacted with the biocatalyst to produce the amide compound under such stirring conditions that the stirring power requirement is in the range of 0.08 to 0.7 kW/m3.
    Type: Grant
    Filed: March 13, 2009
    Date of Patent: November 18, 2014
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Makoto Kanou, Kiyonobu Niwa, Masahito Oda
  • Patent number: 8853450
    Abstract: A method for hydrating a nitrile derivative to generate an amide derivative is provided. The method includes mixing the nitrile derivative with a ruthenium catalyst complex in an aqueous solution to form a mixture, and reacting the nitrile derivative with water in the aqueous solution and in the presence of the ruthenium catalyst complex to form a reacted mixture comprising the amide derivative. The ruthenium catalyst complex is represented by the following structural formula: RuX2(L)n, wherein X is an anionic ligand, L is a bifunctional phosphine ligand, and n is 3 or 4.
    Type: Grant
    Filed: October 18, 2012
    Date of Patent: October 7, 2014
    Assignee: Board of Regents of the Nevada System of Higher Education, on behalf of the University of Nevada, Reno
    Inventors: Brian J. Frost, Wei-Chih Lee
  • Patent number: 8779199
    Abstract: The present invention relates to the intermediate compounds for preparation of agomelatine, as well as the preparation methods thereof The intermediate of the present invention for preparation of agomelatine is compound A as shown in the following formula. Also provided are two novel intermediate compounds. When we use these new intermediate compounds to prepare agomelatine, it is simple to manipulate, well-controlled and with high purity, without complicated operations such as rectification and column chromatography separation, and suitable for industrial production. Meanwhile, the preparation methods of the two new intermediates themselves is simple and high yield, only using the most commonly-used 7-methoxy-tetralone as original starting material and undergoing one step of reaction to obtain the intermediates, followed by one more step of converting the intermediate compounds to desired product agomelatine.
    Type: Grant
    Filed: June 8, 2011
    Date of Patent: July 15, 2014
    Assignee: Les Laboratoires Servier
    Inventors: Peng Zhang, Yu Huang, Zhedong Yuan, Hanbin Shan, Xiong Yu
  • Patent number: 8603939
    Abstract: The present provides a high-efficiency amide compound production catalyst to be used in producing an amide compound through hydration of a nitrile compound and a production method using it. The amide compound production catalyst is for producing an amide compound through reaction of a nitrile compound and water, and comprises a manganese oxide catalyst containing bismuth and further containing yttrium or vanadium. The method for producing an amide compound comprises reacting a nitrile compound and water in a liquid phase in the presence of the amide compound production catalyst.
    Type: Grant
    Filed: March 4, 2011
    Date of Patent: December 10, 2013
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takako Uchiyama, Shinyou Shirai, Yoshikazu Shima, Masaki Takemoto, Genki Nogami
  • Patent number: 8604241
    Abstract: The present invention relates to a method for synthesizing a pharmaceutically acceptable acid addition salt of (1S, 2R)-milnacipran comprising the following successive steps: (a) reaction of phenylacetonitrile and of (R)-epichlorhydrin in the presence of a base containing an alkaline metal, followed by a basic treatment, and then by an acid treatment in order to obtain a lactone; (b) reaction of said lactone with MNEt2, wherein M represents an alkaline metal, or with NHEt2 in the presence of a Lewis acid-amine complex, in order to obtain an amide-alcohol; (c) reaction of said amide-alcohol with thionyl chloride in order to obtain a chlorinated amide; (d) reaction of said chlorinated amide with a phthalimide salt in order to obtain a phthalimide derivative; (e) hydrolysis of the phthalimide group of said phthalimide derivative in order to obtain (1S, 2R)-milnacipran, and (f) salification of (1S, 2R)-milnacipran in a suitable solvent system in the presence of a pharmaceutically acceptable acid.
    Type: Grant
    Filed: January 29, 2010
    Date of Patent: December 10, 2013
    Assignee: Pierre Fabre Medicament
    Inventors: Marc Nicolas, Paul Hellier, Catherine Diard, Laurent Subra
  • Patent number: 8519187
    Abstract: The present invention relates to a process for producing organic carboxylic acid amides by nitrile hydrolysis of a nitrile compound at certain temperature and pressure in the presence of a catalyst to produce an organic carboxylic acid amide.
    Type: Grant
    Filed: December 16, 2009
    Date of Patent: August 27, 2013
    Assignee: China Petrochemical Development Corp
    Inventors: Chia Hui Shen, Chin Yi Lee, Chia Jung Tsai
  • Publication number: 20130096344
    Abstract: A method for hydrating a nitrile derivative to generate an amide derivative is provided. The method includes mixing the nitrile derivative with a ruthenium catalyst complex in an aqueous solution to form a mixture, and reacting the nitrile derivative with water in the aqueous solution and in the presence of the ruthenium catalyst complex to form a reacted mixture comprising the amide derivative. The ruthenium catalyst complex is represented by the following structural formula: RuX2(L)n, wherein X is an anionic ligand, L is a bifunctional phosphine ligand, and n is 3 or 4.
    Type: Application
    Filed: October 18, 2012
    Publication date: April 18, 2013
    Applicant: Board of Regents of the Nevada System of Higher Education, on behalf of the University of Nevada
    Inventor: Board of Regents of the Nevada System of Higher
  • Publication number: 20130041179
    Abstract: The present provides a high-efficiency amide compound production catalyst to be used in producing an amide compound through hydration of a nitrile compound and a production method using it. The amide compound production catalyst is for producing an amide compound through reaction of a nitrile compound and water, and comprises a manganese oxide catalyst containing bismuth and further containing yttrium or vanadium. The method for producing an amide compound comprises reacting a nitrile compound and water in a liquid phase in the presence of the amide compound production catalyst.
    Type: Application
    Filed: March 4, 2011
    Publication date: February 14, 2013
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Takako Uchiyama, Shinyou Shirai, Yoshikazu Shima, Masaki Takemoto, Genki Nogami
  • Patent number: 8334406
    Abstract: The present invention relates to a process for preparing carboxamides by hydrolysing carbonitriles in the presence of a catalyst comprising manganese dioxide, wherein the reaction mixture added to the catalyst comprising manganese dioxide has a pH in the range of 6.0 to 11.0 and the hydrolysis is performed in the presence of an oxidizing agent. The present invention further relates to a process for preparing alkyl (meth)acrylates, the process having a hydrolysis step according to the process described above.
    Type: Grant
    Filed: August 30, 2007
    Date of Patent: December 18, 2012
    Assignee: Evonik Roehm GmbH
    Inventors: Alexander May, Jochen Ackermann, Hermann Siegert, Bernd Vogel, Soenke Broecker
  • Patent number: 8329947
    Abstract: Process for the industrial synthesis of the compound of formula (I)
    Type: Grant
    Filed: August 3, 2009
    Date of Patent: December 11, 2012
    Assignee: Les Laboratoires Servier
    Inventors: Pascal Bontempelli, Xavier Jalenques, Jerome-Benoit Starck, Jean-Pierre Sery
  • Publication number: 20120149895
    Abstract: The present invention discloses a process for dimethylation of active methylene groups. Specifically, the invention discloses a process for preparing 3-amino-2,2-dimethylpropanamide. Compounds produced by the present dimethylation process such as 3-amino-2,2-dimethylpropanamide can be used as intermediates in the route of synthesis of therapeutic, prophylactic or diagnostic agent, for example aliskiren or cryptophycin. Particularly, the invention relates to embodiments further extending to processes for preparing pharmaceutical dosage form comprising said therapeutic, prophylactic or diagnostic agents. More specifically, the invention relates to the use of compounds produced by the present dimethylation process for the manufacture of therapeutic, prophylactic or diagnostic agents or for the manufacture of pharmaceutical dosage forms comprising said therapeutic, prophylactic or diagnostic agents.
    Type: Application
    Filed: March 30, 2010
    Publication date: June 14, 2012
    Applicant: LEK PHARMACEUTICALS D.D.
    Inventors: Branko Jenko, Anton Copar
  • Publication number: 20110060159
    Abstract: The present invention relates to a process for preparing carboxamides by hydrolysing carbonitriles in the presence of a catalyst comprising manganese dioxide, wherein the reaction mixture added to the catalyst comprising manganese dioxide has a pH in the range of 6.0 to 11.0 and the hydrolysis is performed in the presence of an oxidizing agent. The present invention further relates to a process for preparing alkyl (meth)acrylates, the process having a hydrolysis step according to the process described above.
    Type: Application
    Filed: August 30, 2007
    Publication date: March 10, 2011
    Applicant: Evonik Roehm GmbH
    Inventors: Alexander May, Jochen Ackermann, Hermann Siegert, Bernd Vogel, Soenke Broecker
  • Publication number: 20110021819
    Abstract: The present invention provides a method for producing an amide compound from a nitrile compound using a biocatalyst that realizes low cost, energy saving and low environmental burdens. The production method of the amide compound of the present invention is a method for producing an amide compound from a nitrile compound using a biocatalyst in a reactor, wherein the nitrile compound is reacted with the biocatalyst to produce the amide compound under such stirring conditions that the stirring power requirement is in the range of 0.08 to 0.7 kW/m3.
    Type: Application
    Filed: March 13, 2009
    Publication date: January 27, 2011
    Applicant: Dia-Nitrix Co., Ltd.
    Inventors: Makoto Kanou, Kiyonobu Niwa, Masahito Oda
  • Publication number: 20100331574
    Abstract: An object of the present invention is to provide a hydroxyapatite with silver supported on the surface thereof, a new compound useful as a catalyst for the reaction of producing an amide compound by hydration of the corresponding nitrile compound. The hydroxyapatite with silver supported on the surface thereof according to the present invention is obtained by supporting zero-valent Ag on the surface of a hydroxyapatite. Also provided are a hydroxyapatite with silver supported on the surface thereof used as a catalyst, and a method for producing an amide compound, comprising producing the amide compound by hydration of the corresponding nitrile compound in the presence of a hydroxyapatite with silver supported on the surface thereof having zero-valent Ag supported on the surface of the hydroxyapatite.
    Type: Application
    Filed: March 3, 2009
    Publication date: December 30, 2010
    Inventors: Kiyotomi Kaneda, Noritsugu Yamasaki
  • Publication number: 20100197965
    Abstract: This process is carried out in the presence of a solid catalyst comprising an active phase. The catalyst is formulated and the conversion is carried out in a medium essentially free of strong mineral acid.
    Type: Application
    Filed: July 30, 2008
    Publication date: August 5, 2010
    Applicant: ADISSEO IRELAND LIMITED
    Inventors: Virginie Belliere-Baca, Jean-Claude Kiefer, Jean-Christophe Rossi
  • Patent number: 7714166
    Abstract: A process for producing carnitinamide which is an intermediate for production of L-carnitine is provided, which can hydrate carnitine nitrile to form carnitinamide with high selectivity, whereby highly-purified carnitinamide excellent as a substrate for stereoselective hydrolysis by optical resolution or a microorganism is produced in high yield. The process comprises hydrating carnitine nitrile to form carnitinamide using a catalyst containing a manganese oxide, and thus carnitinamide substantially free from by-produced carnitine is produced in high yield, so that carnitinamide of extremely high purity can be obtained through simple and easy crystallization operation.
    Type: Grant
    Filed: August 24, 2006
    Date of Patent: May 11, 2010
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Genki Nogami, Hideo Ikarashi, Shinyo Gayama
  • Patent number: 7704917
    Abstract: A process for producing a catalyst for cyanhydrin hydration, which comprises a manganese oxide as a main component and is excellent in both physical strength and reaction activity, is provided, as well as a catalyst for cyanhydrin hydration obtained by the production process. Specifically, a process for producing a catalyst which is useful for cyanhydrin hydration and contains a manganese oxide as a main component, potassium, and one or more elements selected from the group consisting of bismuth, vanadium and tin, in which the above compounds are mixed together in an aqueous system; the resulting slurry precipitate is subjected to solid-liquid separation; and the resulting hydrous cake is dried in at least two separate stages comprising a predrying and a main drying, is provided, as well as a catalyst for cyanhydrin hydration obtained by the production process.
    Type: Grant
    Filed: July 6, 2006
    Date of Patent: April 27, 2010
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Hideho Matsuda, Takako Uchiyama, Yoshikazu Shima, Masaki Takemoto
  • Publication number: 20100094050
    Abstract: A method is provided of using a highly impact-resistant and corrosion-resistant alloy material for an apparatus for use in hydration of 2-hydroxy-4-methylthiobutanenitrile to obtain 2-hydroxy-4-methylthiobutanamide, the material being readily fabricated for an apparatus with a complicated structure and being composed of an alloy which contains 16.0 to 22.0% by weight of a Cr element, 16.0 to 22.0% by weight of a Mo element, 1.0 to 2.5% by weight of a Ta element and a Ni element as the rest, or an alloy which contains 26.0 to 32.0% by weight of a Mo element and a Ni element as the rest.
    Type: Application
    Filed: October 9, 2009
    Publication date: April 15, 2010
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Kazuo FUJITA, Kozo ONISHI
  • Patent number: 7358393
    Abstract: The invention relates to ?-alanine amides of general formula (I), wherein: R1 represents hydrogen or C1-6 alkyl that is optionally substituted by hydroxy, amino, carboxy, carbamoyl, methylmercapto, guanidino, optionally substituted aryl or heteroaryl, and; R2 represents hydrogen or R1 and R2, together, form a group of formula —(CH2)n—, wherein n is 3 or 4. Said ?-alanine amides are produced without using an amino protective group by reacting the corresponding amine with a cyanoacetic ester in order to form an acetamide and by effecting a subsequent catalytic hydrogenation. The method is suited, in particular, for producing carcinine (?-alanyl-histamine, R?1 =imidazol-4-ylmethyl, R2=H), a naturally occurring pseudo dipeptide, which is used as an active ingredient having an antioxidative effect in medicaments and cosmetics.
    Type: Grant
    Filed: September 4, 2002
    Date of Patent: April 15, 2008
    Assignee: Lonza Ltd.
    Inventors: Paul Hanselmann, Stefan Hildbrand
  • 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: 6472561
    Abstract: Stable highly active supported copper based catalysts of copper oxide or elemental copper crystallites supported on mechanically stable aluminum oxide are disclosed. These catalysts are characterized by high surface area, small copper crystallite size, and high metal loading. The average crystallite size of the copper compound is from about 20 to about 300 Å, the copper loading is from about 10 to about 35 weight percent, the average particle diameter is from about 0.1 mm to about 10 mm, and the total surface area is from about 20 to about 400 square meters per gram. The catalysts are useful for hydration of nitrites to amides, especially hydration of acrylonitrile to acrylamide. The catalysts are distinguished by high mechanical stability, extended lifetime, and excellent resistance to hydration and copper leaching.
    Type: Grant
    Filed: September 28, 2001
    Date of Patent: October 29, 2002
    Assignee: Cytec Technology Corp
    Inventors: Mark Donal Ryan, John Bradley Roucis, James Donald Carruthers
  • Publication number: 20020028836
    Abstract: Compounds of formula I: 1
    Type: Application
    Filed: February 5, 2001
    Publication date: March 7, 2002
    Inventors: Robert J. Altenbach, Hao Bai, Jorge D. Brioni, William A. Carroll, Murali Gopalakrishnan, Robert J. Gregg, Mark W. Holladay, Peggy P. Huang, John F. Kincaid, Michael E. Kort, Philip R. Kym, John K. Lynch, Arturo Perez-Medrano, Henry Q. Zhang
  • Patent number: 6133478
    Abstract: A platinum complex useful as a catalyst for converting nitrites into amides comprises a platinum complex of dialkyl phosphine of stoichiometric formula: PtX(R.sub.2 POHOPR.sub.2)(PR.sub.2 OH) where R is an alkyl, alicyclic, chiral, alkylaryl group or substituted alkyl, alicyclic, chiral, alkaryl group or the two R groups attached to one phosphorous atom can form a heterocyclic ring with the phosphorous atom and X is H or a halide. The conversion takes place under reflux conditions to give a high yield of the amide.
    Type: Grant
    Filed: June 7, 1999
    Date of Patent: October 17, 2000
    Inventors: Adrian W Parkins, Talit Ghaffar
  • 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: 6100427
    Abstract: A process for producing an amide and/or acid from a nitrile comprises introducing a nitrile, as a first reactant, and a hydration compound, as a second reactant which is capable of reacting with the nitrile to convert it to its corresponding amide thus hydrating the nitrile and/or to convert it to its corresponding acid, into a treatment zone. The nitrile is subjected to catalytic distillation in the treatment zone in the presence of the hydration compound, to hydrate at least some of the nitrile to the corresponding amide and/or to form its corresponding acid. The amide and/or acid is withdrawn from the treatment zone.
    Type: Grant
    Filed: October 30, 1998
    Date of Patent: August 8, 2000
    Assignee: Catalytic Distillation Technologies
    Inventors: Barend Christiaan Buurman Bezuidenhout, Zamile Denga, Rian Steyn, Petrus Johannes Steynberg, Nicolaus Ladislaus Stark
  • 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: 5932756
    Abstract: A platinum complex useful as a catalyst for converting nitriles into amides comprises a platinum complex of dialkyl phosphine of stoichiometric formula: PtX(R.sub.2 POHOPR.sub.2)(PR.sub.2 OH) were R is an alkyl, alicyclic, chiral, alkylaryl group or substituted alkyl, alicyclic, chiral, alkaryl group or the two R groups attached to one phosphorus atom can form a heterocyclic ring with the phosphorus atom and X is H or a halide. The conversion takes place under reflux conditions to give a high yield of the amide.
    Type: Grant
    Filed: September 10, 1997
    Date of Patent: August 3, 1999
    Inventors: Adrian W Parkins, Talit Ghaffar
  • Patent number: 5922912
    Abstract: A method is disclosed for the concentration of an aqueous acrylamide solution prepared by hydration of acrylonitrile or an aqueous acrylamide solution substantially free of acrylonitrile. The method makes use of a concentration apparatus at least a part of whose solution-contacting section is made of a copper-containing material. The concentration is conducted while introducing an oxygen-containing gas into the apparatus. Use of this method can prevent formation, adhering, accumulation and the like of popcorn polymers inside the concentration apparatus upon concentration of the aqueous acrylamide solution, and can also produce high-quality acrylamide.
    Type: Grant
    Filed: April 7, 1997
    Date of Patent: July 13, 1999
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Yoshihiko Kambara, Mutsuo Matsumura, Michiaki Umeno, Yoshikazu Uehara, Koichi Asao
  • Patent number: 5900507
    Abstract: The present invention relates to a process for the preparation of 1-amino-1-methyl-3(4)-aminomethyl cyclohexane (AMCA) bya) catalytically hydrogenating 1-formamido-1-methyl-3(4)-cyano cyclohexane (FMC) in a first reaction stage to form 1-formamido-1-methyl-3(4)-aminomethyl cyclohexane (FMA), 1-amino-1-methyl-3(4)-formamidomethyl cyclohexane (AMF), 1-formamido-1-methyl-3(4)-formamidomethyl cyclohexane (FMF) and/or AMCA, andb) reacting FMA, AMF and/or FMF in a second reaction stage with an alkaline compound to from AMCA and a formic acid derivative, andc) separating the reaction mixture obtained in step b) into components by fractional distillation and/or by crystallization and filtration.The present invention is also relates to carrying the hydrogenation reaction of step a) in the presence of a formulating agent to form 1-formamido-1-methyl-3(4)-formamidomethyl cyclohexane (FMF).
    Type: Grant
    Filed: March 11, 1998
    Date of Patent: May 4, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Konrad Fischer, Oswald Wilmes, Dieter Arlt, Carl Casser, Peter Maas, Pierre Woestenborghs, Theo Van Der Knaap, Raf Reintjens
  • Patent number: 5866611
    Abstract: Compounds of formula I, and their pharmaceutically acceptable salts, ##STR1## in which R.sup.1 and R.sup.2 are hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, phenylalkyl or alkenyl; or NR.sup.1 R.sup.2 is a heterocyclic group; A is trimethylene optionally substituted by alkyl and the phenyl ring is optionally substituted by substituents such as halogeno, alkenyl, amino, cyano, ureido, alkyl, carbamoylalkyl, alkanoylamino, alkoxycarbonyl, N-alkyl-alkanoylamino, alkanoyl and amines thereof; are inhibitors of squalene synthese and hence useful in treating diseases in which a lowering of cholesterol is desirable. As well as the use of these compounds in medicine, novel compounds, processes for their preparation and pharmaceutical compositions are also referred to.
    Type: Grant
    Filed: May 19, 1994
    Date of Patent: February 2, 1999
    Assignee: Zeneca Limited
    Inventors: George Robert Brown, Murdoch Allan Eakin, Peter John Harrison, deceased, Keith Blakeney Mallion
  • 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: 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: 5534655
    Abstract: A process for preparing acrylamide is disclosed herein which comprises subjecting acrylonitrile to a hydration reaction in the presence of a copper-based catalyst, said process comprising the step of allowing a compound having an active methylene group and an acidic group in one molecule or a salt of the compound, for example, malonic acid, cyanoacetic acid or its salt to be present in a reaction system. According to the hydration reaction, it is possible to inhibit the secondary formation of impurities which cannot be heretofore removed, without any deterioration of a catalyst activity, and acrylamide can be obtained which is useful as a material for the manufacture of a high-molecular weight flocculant having a sufficiently large molecular weight and a good water solubility.
    Type: Grant
    Filed: February 23, 1995
    Date of Patent: July 9, 1996
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Yoshihiko Kambara, Yoshikazu Uehara, Takeya Abe, Koichi Asao
  • Patent number: 5476883
    Abstract: This invention provides a process for the preparation of acrylamide. Acrylonitrile is treated through at least two purification steps in which acrylonitrile is brought into contact with a strongly-acidic cation exchange resin and then with a resin having primary and/or secondary amino groups or with activated carbon. The resulting acrylonitrile is subjected to hydration in the presence of a copper-base catalyst. The process of this invention can provide high-quality acrylamide even when acrylonitrile of ordinary quality is used, and permits preparation of a polyacrylamide suitable for use in the production of a coagulant having good water solubility or the like.
    Type: Grant
    Filed: July 13, 1994
    Date of Patent: December 19, 1995
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Takeya Abe, Yoshihiko Kambara
  • Patent number: 5463123
    Abstract: There is disclosed a process for producing .alpha.-hydroxyisobutyramide by hydration reaction of acetone cyanohydrin in the presence of a catalyst consisting essentially of manganese dioxide which process comprises pretreating the catalyst with a reducing agent. The above process is capable of eliminating the catalyst clogging trouble due to the deposition of the by-produced oxamide and thus proceeding with long-term reaction with the stabilized catalyst performance.
    Type: Grant
    Filed: October 12, 1993
    Date of Patent: October 31, 1995
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takako Uchiyama, Hirofumi Higuchi
  • 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: 5276185
    Abstract: Amides are produced by reacting nitriles with water in a liquid phase in the presence of a manganese oxide containing an element selected from Groups IIIA, IVA, VA, IIIB, IVB, VB , VIB and VIII of the Periodic Table.
    Type: Grant
    Filed: December 24, 1992
    Date of Patent: January 4, 1994
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Minato Karasawa, Masamitsu Inomata, Hiroharu Kageyama, Masahiro Tokumitsu, Sinji Tokunoh, Kanemitsu Miyama
  • Patent number: 5175366
    Abstract: A process for preparing an amide by hydrating a cyanohydrin with a denatured manganese dioxide catalyst. The catalyst is prepared by reacting an aqueous permanganate solution and an aqueous manganese (II) compound solution in an acidic aqueous solution at a temperature of 70.degree. C. to 150.degree. C.
    Type: Grant
    Filed: August 14, 1991
    Date of Patent: December 29, 1992
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Shuji Ebata, Hiroyuki Hirayama, Hirofumi Higuchi, Koichi Kida
  • Patent number: 5087750
    Abstract: A process for producing .alpha.-hydroisobutyric acid amide by a hydration reaction of acetonecyanohydrin in the presence of a catalyst containing manganese dioxide as a main component, and also in the presence of an oxidizing agent. In accordance with the process, the service life of the catalyst is increased, and the .alpha.-hydroxyisobutyric acid amide is produced in a high yield.
    Type: Grant
    Filed: September 24, 1990
    Date of Patent: February 11, 1992
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Akitomo Uda, Shuji Ebata, Hirofumi Higuchi
  • 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: 4987256
    Abstract: Process for production of .alpha.-hydroxycarboxylic acid amide of the general formula (A), comprising hydrating cyanhydrin of the general formula (B) by the use of a modified manganese dioxide catalyst containing one or more of zirconium, vanadium, and tin, and an alkali metal element. ##STR1## wherein all the symbols are as defined in the appended claims.
    Type: Grant
    Filed: July 9, 1990
    Date of Patent: January 22, 1991
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Shuji Ebata, Hiroyuki Hirayama, Takako Uchiyama
  • Patent number: 4950801
    Abstract: Disclosed is a process for producing .alpha.-hydroxy-carboxylic acid amide represented by the formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are as defined in the specification, by a catalytic hydration reaction of cyanohydrin represented by the formula (II): ##STR2## which comprises using a modified manganese dioxide containing one or more of an alkali metal element and an alkaline earth element in an amount of 0.05 to 0.5 based on the manganese element in terms of atomic ratio.
    Type: Grant
    Filed: December 26, 1989
    Date of Patent: August 21, 1990
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Shuji Ebata, Hiroyuki Hirayama, Hirofumi Higuchi, Toshio Kondo, Koichi Kida
  • 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