Catalytic Hydration Only Of Nitrile Patents (Class 564/126)
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Patent number: 9718761Abstract: 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method being characterized by comprising: a step (B) of cyclically supplying at least a portion of a reaction liquid withdrawn from at least one reaction region to a first reaction region (I) in the reactor; and a step (b1) of further cyclically supplying at least a portion of the reaction liquid withdrawn from at least one reaction region to at least one reaction region other than the first reaction region.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: GrantFiled: July 15, 2014Date of Patent: August 1, 2017Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INCInventors: Atsushi Kakimi, Takako Uchiyama, Hideho Matsuda, Masaki Takemoto, Katsumi Higuchi
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Patent number: 8975440Abstract: 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: GrantFiled: October 29, 2009Date of Patent: March 10, 2015Assignee: Evonik Roehm GmbHInventors: Alexander May, Martin Koestner, Joerg Becker, Joerg Schallenberg, Hermann Siegert, Bernd Vogel
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Patent number: 8889907Abstract: 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: GrantFiled: March 13, 2009Date of Patent: November 18, 2014Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Makoto Kanou, Kiyonobu Niwa, Masahito Oda
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Patent number: 8853450Abstract: 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: GrantFiled: October 18, 2012Date of Patent: October 7, 2014Assignee: Board of Regents of the Nevada System of Higher Education, on behalf of the University of Nevada, RenoInventors: Brian J. Frost, Wei-Chih Lee
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Patent number: 8779199Abstract: 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: GrantFiled: June 8, 2011Date of Patent: July 15, 2014Assignee: Les Laboratoires ServierInventors: Peng Zhang, Yu Huang, Zhedong Yuan, Hanbin Shan, Xiong Yu
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Patent number: 8603939Abstract: 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: GrantFiled: March 4, 2011Date of Patent: December 10, 2013Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takako Uchiyama, Shinyou Shirai, Yoshikazu Shima, Masaki Takemoto, Genki Nogami
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Patent number: 8604241Abstract: 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: GrantFiled: January 29, 2010Date of Patent: December 10, 2013Assignee: Pierre Fabre MedicamentInventors: Marc Nicolas, Paul Hellier, Catherine Diard, Laurent Subra
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Patent number: 8519187Abstract: 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: GrantFiled: December 16, 2009Date of Patent: August 27, 2013Assignee: China Petrochemical Development CorpInventors: Chia Hui Shen, Chin Yi Lee, Chia Jung Tsai
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Publication number: 20130096344Abstract: 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: ApplicationFiled: October 18, 2012Publication date: April 18, 2013Applicant: Board of Regents of the Nevada System of Higher Education, on behalf of the University of NevadaInventor: Board of Regents of the Nevada System of Higher
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Publication number: 20130041179Abstract: 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: ApplicationFiled: March 4, 2011Publication date: February 14, 2013Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Takako Uchiyama, Shinyou Shirai, Yoshikazu Shima, Masaki Takemoto, Genki Nogami
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Patent number: 8334406Abstract: 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: GrantFiled: August 30, 2007Date of Patent: December 18, 2012Assignee: Evonik Roehm GmbHInventors: Alexander May, Jochen Ackermann, Hermann Siegert, Bernd Vogel, Soenke Broecker
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Patent number: 8329947Abstract: Process for the industrial synthesis of the compound of formula (I)Type: GrantFiled: August 3, 2009Date of Patent: December 11, 2012Assignee: Les Laboratoires ServierInventors: Pascal Bontempelli, Xavier Jalenques, Jerome-Benoit Starck, Jean-Pierre Sery
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Publication number: 20120149895Abstract: 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: ApplicationFiled: March 30, 2010Publication date: June 14, 2012Applicant: LEK PHARMACEUTICALS D.D.Inventors: Branko Jenko, Anton Copar
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Publication number: 20110060159Abstract: 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: ApplicationFiled: August 30, 2007Publication date: March 10, 2011Applicant: Evonik Roehm GmbHInventors: Alexander May, Jochen Ackermann, Hermann Siegert, Bernd Vogel, Soenke Broecker
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Publication number: 20110021819Abstract: 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: ApplicationFiled: March 13, 2009Publication date: January 27, 2011Applicant: Dia-Nitrix Co., Ltd.Inventors: Makoto Kanou, Kiyonobu Niwa, Masahito Oda
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Publication number: 20100331574Abstract: 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: ApplicationFiled: March 3, 2009Publication date: December 30, 2010Inventors: Kiyotomi Kaneda, Noritsugu Yamasaki
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Publication number: 20100197965Abstract: 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: ApplicationFiled: July 30, 2008Publication date: August 5, 2010Applicant: ADISSEO IRELAND LIMITEDInventors: Virginie Belliere-Baca, Jean-Claude Kiefer, Jean-Christophe Rossi
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Patent number: 7714166Abstract: 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: GrantFiled: August 24, 2006Date of Patent: May 11, 2010Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Genki Nogami, Hideo Ikarashi, Shinyo Gayama
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Patent number: 7704917Abstract: 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: GrantFiled: July 6, 2006Date of Patent: April 27, 2010Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Hideho Matsuda, Takako Uchiyama, Yoshikazu Shima, Masaki Takemoto
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Publication number: 20100094050Abstract: 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: ApplicationFiled: October 9, 2009Publication date: April 15, 2010Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Kazuo FUJITA, Kozo ONISHI
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Patent number: 7358393Abstract: 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: GrantFiled: September 4, 2002Date of Patent: April 15, 2008Assignee: Lonza Ltd.Inventors: Paul Hanselmann, Stefan Hildbrand
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Patent number: 7227036Abstract: 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 differentType: GrantFiled: May 2, 2003Date of Patent: June 5, 2007Assignee: Showa Denko K.K.Inventors: Yutaka Ohnishi, Hideo Miyata, Kimitaka Ohshiro
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Patent number: 6472561Abstract: 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: GrantFiled: September 28, 2001Date of Patent: October 29, 2002Assignee: Cytec Technology CorpInventors: Mark Donal Ryan, John Bradley Roucis, James Donald Carruthers
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Publication number: 20020028836Abstract: Compounds of formula I: 1Type: ApplicationFiled: February 5, 2001Publication date: March 7, 2002Inventors: 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
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Patent number: 6133478Abstract: 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: GrantFiled: June 7, 1999Date of Patent: October 17, 2000Inventors: Adrian W Parkins, Talit Ghaffar
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Patent number: 6124501Abstract: A process for preparing lactamide with a high conversion and a high selectivity without the deterioration of a catalytic activity in a short time, which comprises subjecting lactonitrile to a hydrating reaction in the presence of (A) a catalyst including an oxide of manganese as a main component, (B) an oxidizing agent and (C) hydrogen cyanide or hydrogen cyanide and a compound represented by the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are each a hydrogen atom, a C.sub.1 to C.sub.8 alkyl group, a C.sub.1 to C.sub.8 hyroxyalkyl group, a C.sub.1 to C.sub.8 aminoalkyl group or a C.sub.1 to C.sub.8 halogenoalkyl group.Type: GrantFiled: March 3, 1999Date of Patent: September 26, 2000Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Yuichi Sugano, Takafumi Abe, Rieko Nakano
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Patent number: 6100427Abstract: 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: GrantFiled: October 30, 1998Date of Patent: August 8, 2000Assignee: Catalytic Distillation TechnologiesInventors: Barend Christiaan Buurman Bezuidenhout, Zamile Denga, Rian Steyn, Petrus Johannes Steynberg, Nicolaus Ladislaus Stark
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Patent number: 6002010Abstract: A process for preparing carboxylic acid derivatives of the formula I ##STR1## where X is OR.sup.2 or NH.sub.2,R.sup.1 is C.sub.1 -C.sub.20 -alkyl, C.sub.l -C.sub.20 -hydroxyalkyl, C.sub.3 -C.sub.12 -cycloalkyl, C.sub.4 -C.sub.12 -alkylcycloalkyl, C.sub.4 -C.sub.12 -cycloalkylalkyl, C.sub.5 -C.sub.20 -alkylcycloalkylalkyl, aryl, C.sub.7 -C.sub.20 -aralkyl, C.sub.7 -C.sub.20 -alkylaryl, a heteroaliphatic or heteroaromatic ring with 5 to 8 carbon atoms andR.sup.2 is C.sub.1 -C.sub.20 -alkyl,from carbonitriles of the formula IIR.sup.1 --C.tbd.N (II),where R.sup.1 has the abovementioned meanings, and alcohols of the formula IIIR.sup.2 --OH (III),where R.sup.2 has the abovementioned meanings, at from 50 to 300.degree. C. under from 0.1 to 350 bar in the presence of a heterogeneous catalyst, wherein the reaction is carried out in liquid phase.Type: GrantFiled: November 10, 1997Date of Patent: December 14, 1999Assignee: BASF AktiengesellschaftInventor: Eberhard Fuchs
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Patent number: 5932756Abstract: 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: GrantFiled: September 10, 1997Date of Patent: August 3, 1999Inventors: Adrian W Parkins, Talit Ghaffar
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Patent number: 5922912Abstract: 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: GrantFiled: April 7, 1997Date of Patent: July 13, 1999Assignee: Mitsui Chemicals, Inc.Inventors: Yoshihiko Kambara, Mutsuo Matsumura, Michiaki Umeno, Yoshikazu Uehara, Koichi Asao
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Patent number: 5900507Abstract: 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: GrantFiled: March 11, 1998Date of Patent: May 4, 1999Assignee: Bayer AktiengesellschaftInventors: Konrad Fischer, Oswald Wilmes, Dieter Arlt, Carl Casser, Peter Maas, Pierre Woestenborghs, Theo Van Der Knaap, Raf Reintjens
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Patent number: 5866611Abstract: 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: GrantFiled: May 19, 1994Date of Patent: February 2, 1999Assignee: Zeneca LimitedInventors: George Robert Brown, Murdoch Allan Eakin, Peter John Harrison, deceased, Keith Blakeney Mallion
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Patent number: 5811580Abstract: Hydrocarbyl-substituted amides can be prepared in a catalyzed Ritter reaction by contacting a nitrile with a hydrocarbylating agent, in the presence of an acidified clay as the catalyst, under conditions conducive to the formation of the hydrocarbyl-substituted amide.Type: GrantFiled: December 4, 1996Date of Patent: September 22, 1998Assignee: The Lubrizol CorporationInventor: Douglas C. Rhubright
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Patent number: 5763661Abstract: A method of preparing acylated .alpha.-amino carboxylic acid amides directly from amino nitriles in high yield and purity. The method involves acylating the amino nitrile with an acyl halide under Schotten-Baumann conditions, and hydrolyzing the resulting nitrile to the amide. The resulting acylated amino carboxylic acid amide precipitates and can be isolated by filtration in high purity.Type: GrantFiled: January 17, 1997Date of Patent: June 9, 1998Assignee: Hampshire Chemical Corp.Inventor: John B. Stallman
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Patent number: 5756842Abstract: There is herein disclosed a process for preparing a lactamide by hydrating lactonitrile in the presence of a catalyst mainly comprising a manganese oxide, and a nitrogen-containing compound such as ammonia or diethylamine. According to this process, the lactamide can be obtained from lactonitrile in a high yield, while the high activity of the catalyst is maintained for a long period of time.Type: GrantFiled: October 11, 1996Date of Patent: May 26, 1998Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Fumio Tanaka, Tsumoru Morimoto, Takako Uchiyama, Takafumi Abe
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Patent number: 5712413Abstract: Hydrocarbyl-substituted amides are prepared by a process comprising contacting a nitrile with a hydrocarbylating agent, such as an alkylating agent, in the presence of a catalyst comprising a heteropolyacid or salt thereof.Type: GrantFiled: December 4, 1996Date of Patent: January 27, 1998Assignee: The Lubrizol CorporationInventors: James D. Burrington, Douglas C. Rhubright, Chester E. Ramey
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Patent number: 5633288Abstract: 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: GrantFiled: November 22, 1995Date of Patent: May 27, 1997Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Hiromu Hara, Tatsuya Maruyama, Munetoshi Saito, Toshiyasu Mase
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Patent number: 5534655Abstract: 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: GrantFiled: February 23, 1995Date of Patent: July 9, 1996Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Yoshihiko Kambara, Yoshikazu Uehara, Takeya Abe, Koichi Asao
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Patent number: 5476883Abstract: 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: GrantFiled: July 13, 1994Date of Patent: December 19, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Takeya Abe, Yoshihiko Kambara
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Patent number: 5463123Abstract: 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: GrantFiled: October 12, 1993Date of Patent: October 31, 1995Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takako Uchiyama, Hirofumi Higuchi
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Patent number: 5436371Abstract: A process for preparing p-nitroaromatic amides is provided which comprises contacting a nitrile, nitrobenzene, a suitable base and water in the presence of a suitable solvent system to form a mixture, and reacting the mixture at a suitable temperature in a confined reaction zone in the presence of a controlled amount of protic material. The p-nitroaromatic amides of the invention can be reduced to p-aminoaromatic amides. In one embodiment, the p-aminoaromatic amide is further reacted with ammonia under conditions which produce the corresponding p-aminoaromatic amine and the amide corresponding to the nitrile starting material or with water in the presence of a suitable basic or acidic catalyst under conditions which produce the corresponding p-aminoaromatic amine and the acid or salt thereof corresponding to the nitrile starting material. In another embodiment, the p-aminoaromatic amine is reductively alkylated to produce alkylated p-aminoaromatic amine.Type: GrantFiled: August 29, 1994Date of Patent: July 25, 1995Assignee: Monsanto CompanyInventors: Michael K. Stern, Brian K. Cheng
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Patent number: 5387715Abstract: Alpha-hydroxy-isobutyramide is produced by continuously hydrating acetone cyanohydrin in a liquid phase in the presence of a manganese dioxide catalyst and in the presence of a particular oxide dissolved in water, oxoacid, heteropolyacid or a salt of the acids.Type: GrantFiled: February 1, 1992Date of Patent: February 7, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Minato Karasawa, Masamitsu Inomata, Hiroharu Kageyama, Kanemitsu Miyama
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Patent number: 5380946Abstract: A process for preparing p-nitroaromatic amides is provided which comprises contacting a nitrile, nitrobenzene, a suitable base and water in the presence of a suitable solvent system to form a mixture, and reacting the mixture at a suitable temperature in a confined reaction zone in the presence of a controlled amount of protic material. The p-nitroaromatic amides of the invention can be reduced to p-aminoaromatic amides. In one embodiment, the p-aminoaromatic amide is further reacted with ammonia under conditions which produce the corresponding p-aminoaromatic amine and the amide corresponding to the nitrile starting material or with water in the presence of a suitable basic or acidic catalyst under conditions which produce the corresponding p-aminoaromatic amine and the acid or salt thereof corresponding to the nitrile starting material. In another embodiment, the p-aminoaromatic amine is reductively alkylated to produce alkylated p-aminoaromatic amine.Type: GrantFiled: July 30, 1993Date of Patent: January 10, 1995Assignee: Monsanto CompanyInventors: Michael K. Stern, Brian K. M. Cheng
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Patent number: 5276185Abstract: 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: GrantFiled: December 24, 1992Date of Patent: January 4, 1994Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Minato Karasawa, Masamitsu Inomata, Hiroharu Kageyama, Masahiro Tokumitsu, Sinji Tokunoh, Kanemitsu Miyama
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Patent number: 5175366Abstract: 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: GrantFiled: August 14, 1991Date of Patent: December 29, 1992Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Shuji Ebata, Hiroyuki Hirayama, Hirofumi Higuchi, Koichi Kida
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Patent number: 5087750Abstract: 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: GrantFiled: September 24, 1990Date of Patent: February 11, 1992Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Akitomo Uda, Shuji Ebata, Hirofumi Higuchi
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Patent number: 5087751Abstract: The present invention presents a method for preparation of S-3,4-dihydroxy butyronitrile expressed by the structural formula (II) ##STR1## characterized by causing R-3-chloro-1,2-propanediol expressed by the structural formula (I) ##STR2## to react with a cyanating agent. According to this invention, optically active 3,4-dihydroxy butyronitrile and 3,4-dihydroxy butyric acid derivatives may be manufactured economically and efficiently.Type: GrantFiled: November 9, 1990Date of Patent: February 11, 1992Assignee: Kanegafuchi Kagaku Kogyo K.K.Inventors: Kenji Inoue, Mitsunori Matsumoto, Satomi Takahashi
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Patent number: 4987256Abstract: 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: GrantFiled: July 9, 1990Date of Patent: January 22, 1991Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Shuji Ebata, Hiroyuki Hirayama, Takako Uchiyama
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Patent number: 4950801Abstract: 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: GrantFiled: December 26, 1989Date of Patent: August 21, 1990Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Shuji Ebata, Hiroyuki Hirayama, Hirofumi Higuchi, Toshio Kondo, Koichi Kida
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Patent number: 4851576Abstract: 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: GrantFiled: December 28, 1982Date of Patent: July 25, 1989Assignee: 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