Directly From A -coo- Containing Compound (e.g., From Methyl Acrylate, Etc.) Patents (Class 548/554)
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Patent number: 5478950Abstract: The invention relates to a process for producing pyrrolidone and N-alkyl pyrrolidones from saturated or unsaturated 1,4-dicarboxylic acids or their anhydrides, hydrogen, and a primary amine, characterized in that the dicarboxylic acid or its anhydride is allowed to react in an appropriate reactor with hydrogen or ammonia via a first catalyst bed and the unisolated intermediate product is subsequently reacted with the primary amine or ammonia directly via a second, downstream catalyst bed.Type: GrantFiled: August 8, 1994Date of Patent: December 26, 1995Assignee: Akzo Nobel N.V.Inventors: Manfred Bergfeld, Gunter Wiesgickl
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Patent number: 5434273Abstract: The preparation of N-substituted 2-pyrrolidones (I) by the reaction of maleic acid, fumaric acid, or succinic acid or functional derivatives of these acids (compounds II) with a primary amine (III) or by the reaction of amides or imides derived from II and III under hydrogenating conditions in a synthesis stage followed by isolation, by distillation, of I and other volatile components from the resulting reaction mixture, in which the residues present following distillation are subjected to further hydrogenation treatment and the compound (I) thus formed is isolated by distillation.Type: GrantFiled: February 4, 1994Date of Patent: July 18, 1995Assignee: BASF AktiengesellschaftInventors: Hans-Juergen Weyer, Rolf Fischer
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Patent number: 5393888Abstract: This invention relates to a liquid phase process for producing 2-pyrrolidone in high yield and selectivity in the absence of catalyst and extraneous solvents which involves contacting ammonia with butyrolactone in a molar ratio of from 0.5:1 to 0.85:1 at high temperature and pressure sufficient to maintain the liquid phase.Type: GrantFiled: March 2, 1994Date of Patent: February 28, 1995Assignee: ISP Investments Inc.Inventors: Francis B. Minnock, Paul D. Taylor
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Patent number: 5298628Abstract: Stereoselective process for the production of (4R)- or (4S)-4-aryl-2-pyrrolidinones as well as intermediate products and the stereoselective process for the production of the optically active intermediate compounds.Type: GrantFiled: July 1, 1992Date of Patent: March 29, 1994Assignee: Schering AktiengesellschaftInventors: Johann H. Mulzer, Ralf H. Zuhse
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Patent number: 5276165Abstract: A process for the preparation of N-substituted lactams of the formula I ##STR1## where Z is C.sub.2 - to C.sub.10 -alkylene, C.sub.7 - to C.sub.12 -aralkylene, phenylene or naphthylene, andR.sup.1 is C.sub.1 - to C.sub.20 -alkyl, C.sub.6 - to C.sub.10 -aryl or C.sub.7 - to C.sub.12 -aralkyl,by hydrogenating a compound of the formula II ##STR2## where W is C.sub.2 - to C.sub.10 -alkylene, C.sub.2 - to C.sub.10 -alkenylene, C.sub.7 - to C.sub.12 -aralkylene, phenylene or naphthylene, andX and Y together form an oxa or imido bridge of the formula ##STR3## or alternatively are identical or different and are hydroxyl, C.sub.1 - to C.sub.20 -alkoxy, C.sub.6 - to C.sub.10 -aryloxy or C.sub.7 - to C.sub.12 -aralkoxy, and, if X and Y are different, Y, in addition to the abovementioned meanings, may also be hydrogen,at superatmospheric pressure and at elevated temperature in the presence of a catalyst and in the presence of an amine, which comprises using a secondary and/or tertiary amine of the formula IIINH.sub.n R.Type: GrantFiled: November 25, 1992Date of Patent: January 4, 1994Assignee: BASF AktiengesellschaftInventors: Hans-Juergen Weyer, Rolf Fischer
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Patent number: 5157127Abstract: A process for the preparation of N-substituted pyrrolidones by the catalytic hydrogenation of maleic anhydride, maleic acid and/or fumaric acid in the presence of a primary amine and a solvent, at elevated temperature and pressure, wherein a catalyst is used which contains cobalt and at least one of the elements manganese, copper, phosphorus, molybdenum and/or sodium.Type: GrantFiled: June 4, 1991Date of Patent: October 20, 1992Inventors: Hans-Juergen Weyer, Rolf Fischer, Wolfgang Harder
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Patent number: 5142066Abstract: A stereoselective process for the preparation of the compounds of formula ##STR1## wherein R, R.sub.1, R.sub.2, a and b have the meanings reported in the specification, is described.The compounds of formula I have a remarkable central analgesic activity and they are useful in the pharmaceutical field.Type: GrantFiled: March 20, 1991Date of Patent: August 25, 1992Assignee: Zambon Group S.p.AInventors: Mauro Napoletano, Gian C. Grancini, Carlo Veneziani, Dario Chiarino
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Patent number: 5101045Abstract: A process for the preparation of N-substituted pyrrolidones by catalytic hydrogenation of maleic anhydride, maleic acid and/or fumaric acid in the presence of ammonia uses at least stoichiometric amounts of a primary alcohol or of an aldehyde and uses a catalyst which comprises cobalt and at least one of the elements manganese, copper, phosphorus, molybdenum and/or sodium.Type: GrantFiled: June 4, 1991Date of Patent: March 31, 1992Assignee: BASF AktiengesellschaftInventors: Ulrich Koehler, Hardo Siegel
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Patent number: 5091567Abstract: The instant invention concerns a novel process for the preparation of 1-aminomethyl-1-cyclohexaneacetic acid (gabapentin), a known compound useful for treating certain cerebral diseases such as epilepsy and dizziness.Type: GrantFiled: August 21, 1990Date of Patent: February 25, 1992Assignee: Godecke AktiengesellschaftInventors: Wolfram Geibel, Johannes Hartenstein, Wolfgang Herrmann, Joachim Witzke
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Patent number: 4904804Abstract: Process is disclosed for the one reaction step preparation of 2-pyrrolidone by contacting with hydrogen, ammonia, at least one diluent and a catalyst consisting essentially of palladium on alumina; wherein the molar ratio of ammonia to succinic acid on succinic anhydride is about 1:1 to about 10:1.Type: GrantFiled: April 22, 1988Date of Patent: February 27, 1990Assignee: Phillips Petroleum CompanyInventor: Michael S. Matson
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Patent number: 4885371Abstract: The present invention relates to a process for the selective preparation of an N-alkyl lactam having minimal coloration by reacting the corresponding lactone with an alkyl amine in the presence of a catalytic amount of an ammonium, alkali metal or alkaline earth metal borohydride.Type: GrantFiled: June 22, 1989Date of Patent: December 5, 1989Assignee: GAF Chemicals CorporationInventors: David J. Tracy, Mohamed M. Hashem
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Patent number: 4824967Abstract: This invention relates to an improved process for reacting butyrolactone and ammonia which comprises conducting the reaction in the vapor phase in the presence of a magnesium silicate catalyst to selectively produce 2-pyrrolidone in higher yield and purity.Type: GrantFiled: June 27, 1988Date of Patent: April 25, 1989Assignee: GAF CorporationInventors: Kou-Chang Liu, Paul D. Taylor
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Patent number: 4814464Abstract: An improved process for making N-alkylpyrrolidones from a maleic derivative or a succinic derivative which involves catalytically reducing the maleic derivative with hydrogen to succinic anhydride, if the maleic derivative is the starting point, converting succinic anhydride to a N-alkylsuccinimide by ammonolysis-alkylation with a C.sub.1 and C.sub.4 alkanol and ammonia, and catalytically reducing the resulting N-alkylsuccinimide to the N-alkylpyrrolidone.Type: GrantFiled: March 30, 1987Date of Patent: March 21, 1989Assignee: Amoco CorporationInventor: Robert J. Olsen
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Patent number: 4780547Abstract: C.sub.1 -- to C.sub.6 -N-alkylpyrrolidones are produced from succinic anhydride and C.sub.1 -- to C.sub.6 -N-alkylamines or C.sub.1 -- to C.sub.6 --N-alkylsuccinimides. They are hydrogenated in the presence of a Ni hydrogenation catalyst containing from about 0.1-3% of one or several alkaline earth oxides and/or iron oxide and/or chromium oxide, at temperatures of from about 180.degree.-250.degree. C. and under pressures of at least about 100 bar. Preferably, a Ni catalyst is utilized which contains a total of 1.5-2% alkaline earth oxides, iron oxide and chromium oxide.Type: GrantFiled: July 6, 1987Date of Patent: October 25, 1988Assignee: Huels AktiengesellschaftInventors: Manfred zur Hausen, Werner Otte
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Patent number: 4647661Abstract: A method of preparing .omega.-lactams, in particular caprolactam, comprising: a step of premixing cycloaliphatic acids having the formula ##STR1## where n=3-13, with a dehydrating agent; the first step of reaction with a nitrosating agent; the second step of reaction with the addition of a very small amount of water corresponding to a molar ratio U=H.sub.2 O/SO.sub.3 within the 0.1 to 0.9 range; and the step of reclaiming the unreacted cycloaliphatic acid. The method affords improved output from the lactamization reaction and reduced byproducts.Type: GrantFiled: March 27, 1986Date of Patent: March 3, 1987Assignee: Chimica del Friuli S.p.A.Inventors: Paolo Senni, Leandro Zuliani, Sergio Ferruzzi
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Patent number: 4560760Abstract: Disclosed is a process for preparing a lactam which consists essentially in the reductive amination in the gas phase of an oxoalkane carboxylic acid having the formula ##STR1## or an alkyl ester thereof, wherein R is an alkyl group having from 1 to 4 carbon atoms and n varies from 2 to 3, and wherein the reaction is carried out:A. in an atmosphere of hydrogen, andB. in the presence of a gas phase reactant selected from the group consisting of gaseous ammonia and a vaporized primary amine, andC. in the presence of a hydrogenation catalyst promoted with an alkali metal.The alkali metal particularly preferred as a promoter is sodium.Type: GrantFiled: August 31, 1984Date of Patent: December 24, 1985Assignee: Stamicarbon B.V.Inventors: Roland E. van der Stoel, Marcel A. R. Bosma, Petrus H. J. Janssen, Cornelis G. M. van de Moesdijk
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Patent number: 4515803Abstract: Compounds of the formula I ##STR1## in which n denotes 0-3,R.sup.1 and R.sup.1' are the same or different and denote hydrogen, alkyl or alkenyl, phenyl or benzyl, each substituted as desired;R.sup.2 denotes hydrogen, alkyl or alkenyl;R.sup.3 denotes hydrogen, alkyl, hydroxyalkyl, alkoxyalkyl or aminoalkyl, alkanoylaminoalkyl, guanidinoalkyl, imidazolylalkyl, indolylalkyl, mercaptoalkyl or alkylthioalkyl, phenylalkyl, hydroxyphenylalkyl, phenoxyalkyl or phenylthioalkyl, or R.sup.2 and R.sup.3, together with the C and N atoms carrying them, denote a saturated or unsaturated 4- to 8-membered monocyclic or 8- to 10-membered bicyclic isocycle or heterocycle, optionally monosubstituted or disubstituted by hydroxyl, alkoxy having 1 to 3 C atoms or alkyl,R.sup.4 denotes hydrogen, alkyl, alkenyl, alkadienyl, alkinyl, alkeninyl or alkadiinyl, cycloalkyl, phenyl, benzyl, phenethyl or phenylpropyl, each of which can be optionally monosubstituted or disubstituted;R.sup.5 denotes hydrogen or alkyl, hydroxyl or alkoxy andR.Type: GrantFiled: September 1, 1982Date of Patent: May 7, 1985Assignee: Hoechst AktiengesellschafatInventors: Rainer Henning, Hansjorg Urbach, Rolf Geiger, Volker Teetz, Bernward Scholkens
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Patent number: 4420620Abstract: 2-pyrrolidone and N-substituted 2-pyrrolidones such as N-methyl 2-pyrrolidone and N-(beta-hydroxyethyl)-2-pyrrolidone are prepared by the catalyzed reaction of methyl 4-oxobutyrate with ammonia or a primary amine and hydrogen.Type: GrantFiled: November 27, 1981Date of Patent: December 13, 1983Assignee: National Distillers and Chemical CorporationInventor: Jawad H. Murib