Directly From A -coo- Containing Compound (e.g., From Methyl Acrylate, Etc.) Patents (Class 548/554)
  • Patent number: 5478950
    Abstract: 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: Grant
    Filed: August 8, 1994
    Date of Patent: December 26, 1995
    Assignee: Akzo Nobel N.V.
    Inventors: Manfred Bergfeld, Gunter Wiesgickl
  • Patent number: 5434273
    Abstract: 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: Grant
    Filed: February 4, 1994
    Date of Patent: July 18, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Juergen Weyer, Rolf Fischer
  • Patent number: 5393888
    Abstract: 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: Grant
    Filed: March 2, 1994
    Date of Patent: February 28, 1995
    Assignee: ISP Investments Inc.
    Inventors: Francis B. Minnock, Paul D. Taylor
  • Patent number: 5298628
    Abstract: 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: Grant
    Filed: July 1, 1992
    Date of Patent: March 29, 1994
    Assignee: Schering Aktiengesellschaft
    Inventors: Johann H. Mulzer, Ralf H. Zuhse
  • Patent number: 5276165
    Abstract: 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: Grant
    Filed: November 25, 1992
    Date of Patent: January 4, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Juergen Weyer, Rolf Fischer
  • Patent number: 5157127
    Abstract: 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: Grant
    Filed: June 4, 1991
    Date of Patent: October 20, 1992
    Inventors: Hans-Juergen Weyer, Rolf Fischer, Wolfgang Harder
  • Patent number: 5142066
    Abstract: 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: Grant
    Filed: March 20, 1991
    Date of Patent: August 25, 1992
    Assignee: Zambon Group S.p.A
    Inventors: Mauro Napoletano, Gian C. Grancini, Carlo Veneziani, Dario Chiarino
  • Patent number: 5101045
    Abstract: 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: Grant
    Filed: June 4, 1991
    Date of Patent: March 31, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Koehler, Hardo Siegel
  • Patent number: 5091567
    Abstract: 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: Grant
    Filed: August 21, 1990
    Date of Patent: February 25, 1992
    Assignee: Godecke Aktiengesellschaft
    Inventors: Wolfram Geibel, Johannes Hartenstein, Wolfgang Herrmann, Joachim Witzke
  • Patent number: 4904804
    Abstract: 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: Grant
    Filed: April 22, 1988
    Date of Patent: February 27, 1990
    Assignee: Phillips Petroleum Company
    Inventor: Michael S. Matson
  • Patent number: 4885371
    Abstract: 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: Grant
    Filed: June 22, 1989
    Date of Patent: December 5, 1989
    Assignee: GAF Chemicals Corporation
    Inventors: David J. Tracy, Mohamed M. Hashem
  • Patent number: 4824967
    Abstract: 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: Grant
    Filed: June 27, 1988
    Date of Patent: April 25, 1989
    Assignee: GAF Corporation
    Inventors: Kou-Chang Liu, Paul D. Taylor
  • Patent number: 4814464
    Abstract: 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: Grant
    Filed: March 30, 1987
    Date of Patent: March 21, 1989
    Assignee: Amoco Corporation
    Inventor: Robert J. Olsen
  • Patent number: 4780547
    Abstract: 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: Grant
    Filed: July 6, 1987
    Date of Patent: October 25, 1988
    Assignee: Huels Aktiengesellschaft
    Inventors: Manfred zur Hausen, Werner Otte
  • Patent number: 4647661
    Abstract: 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: Grant
    Filed: March 27, 1986
    Date of Patent: March 3, 1987
    Assignee: Chimica del Friuli S.p.A.
    Inventors: Paolo Senni, Leandro Zuliani, Sergio Ferruzzi
  • Patent number: 4560760
    Abstract: 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: Grant
    Filed: August 31, 1984
    Date of Patent: December 24, 1985
    Assignee: Stamicarbon B.V.
    Inventors: Roland E. van der Stoel, Marcel A. R. Bosma, Petrus H. J. Janssen, Cornelis G. M. van de Moesdijk
  • Patent number: 4515803
    Abstract: 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: Grant
    Filed: September 1, 1982
    Date of Patent: May 7, 1985
    Assignee: Hoechst Aktiengesellschafat
    Inventors: Rainer Henning, Hansjorg Urbach, Rolf Geiger, Volker Teetz, Bernward Scholkens
  • Patent number: 4420620
    Abstract: 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: Grant
    Filed: November 27, 1981
    Date of Patent: December 13, 1983
    Assignee: National Distillers and Chemical Corporation
    Inventor: Jawad H. Murib