Forming Amine Group Directly By Reduction Patents (Class 564/489)
  • Patent number: 6420613
    Abstract: A method of preparing a reduced product by efficiently reducing an unsaturated organic compound by using, as a reducing agent, a trichlorosilane which is industrially cheaply available and is easy to handle, and a reducing agent therefor. A reduced product of an unsaturated organic compound is obtained by mixing the unsaturated organic compound and a trichlorosilane together to reduce the unsaturated organic compound in the presence of a compound that forms a silicon complex having five coordinations upon acting on the trichlorosilane such as an N-formylated product of a secondary amine having not less than 3 carbon atoms. The invention further provides a reducing agent comprising a particular silicon complex.
    Type: Grant
    Filed: December 11, 2000
    Date of Patent: July 16, 2002
    Assignee: Tokuyama Corporation
    Inventors: Fumiaki Iwasaki, Yoshihiro Matsumura, Osamu Onomura, Kenji Tanaka
  • Publication number: 20020049258
    Abstract: The present invention provides a method of recovering a polyamine compound and/or a polyol compound useful for starting materials of polyurethane resin in an industrially advantageous manner by first dissolving the polyurethane resin such as polyurethane foams discharged in a large amount as industrial wastes in a solubilizing agent containing a polyamine compound, a low molecular glycol or an amino alcohol, hydrolyzing the resulting solution with liquid water at 200 to 320° C., then recovering the polyamino compound and/or polyol compound thus formed.
    Type: Application
    Filed: October 1, 1999
    Publication date: April 25, 2002
    Inventors: KATSUHISA KODAMA, KOUICHI MURAYAMA, TAKASHI KUMAKI
  • Publication number: 20010047116
    Abstract: A method of increasing enantioselectivity in a reduction reaction of a prochiral substrate with a borane reagent including a borohydride species (for example, a borohydride stabilized borane-tetrahydrofuran complex) catalyzed by a chiral catalyst includes the step of maintaining the concentration of borohydride species in the borane reagent below approximately 0.005 M during the reduction of the prochiral substrate. A method of increasing enantioselectivity in a reduction reaction of a prochiral substrate with a borane reagent including a borohydride species that is catalyzed by a chiral catalyst includes the step of reducing the detrimental effect the borohydride species has on enantioselectivity by adding a Lewis acid. For example, the prochiral substrate can be a ketone and the chiral catalyst can be a chiral oxazaborolidine.
    Type: Application
    Filed: January 26, 2001
    Publication date: November 29, 2001
    Applicant: Mine Safety Appliances Company
    Inventors: Karl Matos, Joseph A. Corella, Elizabeth R. Burkhardt, Shawn M. Nettles
  • Patent number: 6307103
    Abstract: An improved process for the preparation of a 1,1,1-trifluoro-2-aminoalkane of formula I wherein R1 represents an optionally substituted alkyl group; which comprises hydrogenating the corresponding oxime of formula II wherein R1 has the meaning given above and the winding line indicates that the hydroxy group may be in the (E)- or (Z)-position with respect to the trifluoromethyl group, in the presence of Raney nickel and a diluent; the improvement wherein is, that said reaction is carried out in a diluent selected from an alkanol, a cyclic ether and an aromatic hydrocarbon.
    Type: Grant
    Filed: March 28, 2000
    Date of Patent: October 23, 2001
    Assignee: American Cyanamid Company
    Inventors: Hans-Peter Niedermann, Dieter Gutheil
  • Patent number: 6265616
    Abstract: The invention provides a process for preparing trifluoroisopropylamine. Trifluoroisopropylamine is produced by reducing trifluoroacetone oxime with hydrogen, in the vapor phase, in the presence of a reduction catalyst. Trifluoroisopropylamine is useful intermediate in the preparation of fluorinated pharmaceutical compounds such as antihypertensives.
    Type: Grant
    Filed: January 27, 2000
    Date of Patent: July 24, 2001
    Assignee: Honeywell International Inc.
    Inventor: Michael Van Der Puy
  • Publication number: 20010005764
    Abstract: The present invention relates to a process for the preparation of 2-aminomethyl-1,5-pentanediamine by simultaneously reacting 2,4-dicyano-1-butene, hydrogen and ammonia in one step without isolation of 2-amino-methyl-1,5-pentanedinitrile; the products are useful as an intermediate in the production of coating compositions, surfactants, detergents and as a component of epoxide compositions.
    Type: Application
    Filed: February 1, 2000
    Publication date: June 28, 2001
    Inventors: Konrad Fischer, Frank Richter, Anatoly Bazanov, Alexandre Timofeev, Natalja Zubritskaya, Galina Smirnova
  • Patent number: 5986139
    Abstract: A process for the preparation of primary or secondary amines by hydrogenation of imines with hydrogen at elevated pressure and in the presence of a dinuclear Ir(III) complex having ditertiary diphosphine ligands, halide bridges, halide and hydride ligands, or an Ir(III) halide complex salt containing ditertiary diphosphine ligands, as catalyst, wherein the catalyst corresponds to formula I or Ia or to mixtures of at least two compounds of formula I, at least two compounds of formulae I and Ia, or at least two compounds of formula Ia[(DIP)IrX.sub.q Y.sub.r ].sub.2 (I),[(DIP)X.sub.4 ].sup..crclbar. Me.sup..sym. (Ia),whereinDIP is the ditertiary diphosphine ligand of a ferrocenyldiphosphine the phosphine groups of which are either bonded directly or via a bridge group --CR.sub.v R.sub.w -- to the ortho positions of a cyclopentadienyl ring or are each bonded to a cyclopentadienyl ring of a ferrocenyl, so that a 5-, 6- or 7-membered ring is formed together with the Ir atom;R.sub.v and R.sub.
    Type: Grant
    Filed: January 26, 1998
    Date of Patent: November 16, 1999
    Assignee: Novartis Crop Protection, Inc.
    Inventors: Rafael Sablong, John Anthony Osborn, Felix Spindler
  • Patent number: 5922917
    Abstract: A process for the preparation of 2-amino-1,3-propanediol comprising the catalytic hydrogenation of 1,3-dihydroxyacetone oxime in the presence of rhodium supported on alumina is described.
    Type: Grant
    Filed: September 19, 1996
    Date of Patent: July 13, 1999
    Assignee: Bracco International B.V.
    Inventors: Antonio Nardi, Marco Villa
  • Patent number: 5919961
    Abstract: Chiral compounds of the formula I ##STR1## where the variables are as described in the specification.
    Type: Grant
    Filed: May 30, 1997
    Date of Patent: July 6, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Rainer Sturmer, Jun Okuda, Kurt Ritter
  • Patent number: 5847110
    Abstract: The invention relates to methods of reducing Schiff bases and making chelator conjugates by treating with borane-pyridine complex.
    Type: Grant
    Filed: August 15, 1997
    Date of Patent: December 8, 1998
    Assignee: Biomedical Frontiers, Inc.
    Inventors: Paul R. Dragsten, Gregory J. Hansen
  • Patent number: 5801280
    Abstract: A process for preparing an optically active alcohol by reacting a prochiral ketone corresponding to the optically active alcohol and an acid with a mixture of (1) a boron-containing compound selected from the group consisting of i) a borane compound which is obtained from an optically active .beta.-aminoalcohol and a boron hydride; or obtained from the optically active .beta.-aminoalcohol, a metal borohydride and an acid and ii) an optically active oxazaborolidine and (2) a metal borohydride; and a process for preparing an optically active amine by reacting an oxime derivative and an acid with a mixture of (1) a boron-containing compound selected from the group consisting of i) a borane compound which is obtained from an optically active .beta.-aminoalcohol and a boron hydride, or obtained from said optically active .beta.-aminoalcohol, a metal borohydride and an acid and ii) an optically active oxazaborolidine, and (2) a metal borohydride.
    Type: Grant
    Filed: April 5, 1996
    Date of Patent: September 1, 1998
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yukio Yoneyoshi, Naoto Konya, Gohfu Suzukamo, Masashi Kamitamari, Takashi Miyawaki
  • Patent number: 5693865
    Abstract: Fluorinated alkene compounds useful for and methods of controlling nematodes, insects, and acarids that prey on agricultural crops. Polar compounds, for example, 3,4,4-trifluoro-3-butene-1-amine or 3,4,4-trifluoro-3-butenoic acid, are particularly useful for systemic control of pests. Novel method and intermediates for the preparation of 3,4,4-trifluoro-3-butene-1-amine are also provided.
    Type: Grant
    Filed: December 11, 1996
    Date of Patent: December 2, 1997
    Assignee: Monsanto Company
    Inventor: Peter Gerrard Ruminski
  • Patent number: 5686616
    Abstract: A novel process for preparing an optically active amine by asymmetric hydrogenation of an imine compound, such as an imine compound prepared by condensing benzylamine and acetophenone, in the presence of a catalytic amount of an iridium-optically active phosphine complex and benzylamine or a benzylamine derivative. The present invention provides an optically active amine of high optical purity.
    Type: Grant
    Filed: March 14, 1996
    Date of Patent: November 11, 1997
    Assignee: Takasago International Corporation
    Inventors: Kazuhide Tani, Tsuneaki Yamagata, Yasutaka Kataoka, Hidenori Kumobayashi
  • Patent number: 5648544
    Abstract: A process for the preparation of 2-aminoalkane-1,3-diols by a single step reduction of alkyl 2-oximino-3-oxoalkanoates. The reduction is carried out in the presence of at least one hydride, in a solvent, under inert atmosphere and at a controlled initial temperature.Synthetic yields are markedly improved.
    Type: Grant
    Filed: November 29, 1995
    Date of Patent: July 15, 1997
    Assignee: L'Oreal
    Inventors: Didier Semeria, Michel Philippe
  • Patent number: 5587494
    Abstract: Sphingolipids are involved in the structure of biological membranes. There is a link between sphingolipids and signal transduction. The invention relates to the stereospecific syntheses of dihidrosphingosines using certain chiral epoxides.
    Type: Grant
    Filed: April 5, 1993
    Date of Patent: December 24, 1996
    Assignee: The Board of Governors for Higher Education, State of Rhode Island and Providence Plantations
    Inventors: Raymond P. Panzica, Hussein I. El Subbagh, Elie Abushanab
  • Patent number: 5504253
    Abstract: A method of making (R)-N- 1-(3-methoxyphenyl)ethyl!-3-(2-chlorobenzene)propanamine which involves reducing the appropriate amidyl or iminyl precursor with an appropriate reducing agent. The appropriate amidyl or iminyl precursor is made from a synthesis involving the use of (R)-3-methoxy-.alpha.-methylbenzylamine. A method of condensing a nitrile with a primary or secondary amine to form an imine involves the reaction of a nitrile with diisobutylaluminum hydride; and then reacting the resultant compound with a primary or secondary amine to form the imine. The process is especially useful for producing enantiomerically pure chiral imines, and, ultimately, amines. Typical such imines have the formula: ##STR1## wherein R, R.sub.1, R.sub.2 and R.sub.3 are independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, aryl and aralkyl.
    Type: Grant
    Filed: July 15, 1994
    Date of Patent: April 2, 1996
    Assignee: NPS Pharmaceuticals, Inc.
    Inventors: Bradford C. VanWagenen, Thomas E. D'Ambra
  • Patent number: 5488166
    Abstract: Provided by the present invention is a process for the biocatalytic synthesis of optically pure sphingosines from achiral starting material. The stereoisomers of sphingosine are prepared from chiral arene diols using stereospecific reaction techniques to obtain the desired sphingosine or derivative thereof.
    Type: Grant
    Filed: January 23, 1995
    Date of Patent: January 30, 1996
    Assignee: Virginia Tech Intellectual Properties, Inc.
    Inventor: Tomas Hudlicky
  • Patent number: 5488167
    Abstract: Provided by the present invention is a process for the biocatalytic synthesis of optically pure sphingosines from achiral starting material. The stereoisomers of sphingosine are prepared from chiral arene diols using stereospecific reaction techniques to obtain the desired sphingosine or derivative thereof.
    Type: Grant
    Filed: February 21, 1995
    Date of Patent: January 30, 1996
    Assignee: Virginia Tech Intellectual Properties, Inc.
    Inventor: Tomas Hudlicky
  • Patent number: 5442118
    Abstract: A method for the enantioselective reduction of an .alpha.-iminoketone to an .alpha.-aminoalcohol is disclosed. The method utilizes a borane reducing agent as the reducing agent and a chiral 1,3,2-oxazaborole as the catalyst. The method is applied to the synthesis of R-albuterol from methyl 5-acetylsalicylate in high yield and high optical purity.
    Type: Grant
    Filed: April 22, 1994
    Date of Patent: August 15, 1995
    Assignee: Sepracor, Inc.
    Inventors: Yun Gao, Yaping Hong, Charles M. Zepp
  • Patent number: 5382729
    Abstract: Compounds of formula I ##STR1## wherein R.sub.1 denotes identical or different radicals and is linear or branched C.sub.1 -C.sub.12 alkyl, unsubstituted C.sub.5 -C.sub.6 cycloalkyl or C.sub.5 -C.sub.6 cycloalkyl which is substituted by C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, or is phenyl or benzyl, or both substituents R.sub.1 of a group (R.sub.1).sub.2 P are o,o-diphenylene, R.sub.2 is hydrogen, linear or branched C.sub.1 -C.sub.12 alkyl, phenyl or benzyl, R.sub.3 is C.sub.1 -C.sub.12 alkylene, R.sub.4 is C.sub.2 -C.sub.18 alkylene, phenylene or benzylene, and R.sub.5 is C.sub.1 -C.sub.6 alkyl or phenyl, can be applied to solid carriers, such as silica gel or aerosils, and complexed with rhodium or iridium compounds. These materials are heterogeneous and separable catalysts for the assymetrical hydrogenation of prochiral compounds containing carbon double bonds or carbon/hetero atom double bonds, for example ketones and imines.
    Type: Grant
    Filed: February 16, 1994
    Date of Patent: January 17, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Benoit Pugin, Felix Spindler, Manfred Muller
  • Patent number: 5334764
    Abstract: Amines such as methyl amine are reacted with materials such as reducing sugars in hydroxy solvents such as methanol to prepare N-alkyl polyhydroxy amines. Accordingly, glucose is reacted with methyl amine and the resulting adduct is hydrogenated to yield N-methylglucamine. The N-alkyl polyhydroxyamines can be subsequently reacted with fatty esters to provide polyhydroxy fatty acid amides useful as detersive surfactants. Thus, detersive surfactants are available from non-petrochemical precursors such as sugars and sugar sources such as corn syrup, and fatty acid esters derivable from various fats and oils.
    Type: Grant
    Filed: May 6, 1993
    Date of Patent: August 2, 1994
    Assignee: The Procter & Gamble Company
    Inventors: Jeffrey J. Scheibel, Daniel S. Connor, Robert E. Shumate, James B. St. Laurent
  • Patent number: 5296633
    Abstract: The methylated tertiary amines are selectively prepared by reacting a primary or secondary amine, or a nitrile or aminonitrile, including an aminoalcohol, etheramine, a polyamine or fatty polyamine or amidoamine, or amidopolyamine or dinitrile, with hexamethylenetetramine ("HMTA"), under hydrogen pressure at a temperature no greater than about 160.degree. C. and in the presence of a catalytically effective amount of a hydrogenation catalyst, e.g., nickel deposited onto appropriate support substrate therefor.
    Type: Grant
    Filed: December 30, 1992
    Date of Patent: March 22, 1994
    Inventor: Stephane Fouquay
  • Patent number: 5283364
    Abstract: Polyamines containing primary amino groups are made by hydrolyzing an isocyanate with water in the presence of a solvent which is a carboxylic acid amide. The solvent must be used in a quantity of at least 10% by weight solvent based on 100% by weight of isocyanate. The weight ratio of solvent to water must be from 3 to 200. A homogeneous phase is maintained during the hydrolysis which is carried out at temperatures of from 20.degree. to 210.degree. C. A not incorporable basic and/or metal catalyst particularly alkali metal hydroxides may be employed. The polyamines produced by this process are particularly useful for the production of polyurethanes.
    Type: Grant
    Filed: January 15, 1993
    Date of Patent: February 1, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Werner Rasshofer, Klaus Konig, Hans-Joachim Meiners, Gerhard Grogler
  • Patent number: 5200561
    Abstract: Disclosed is a process for producing an optically active amine represented by the formula (IV) ##STR1## wherein R.sub.7 and R.sub.8 each denote an alkyl group, aryl group or aralkyl group, providing that they do not denote the same group at the same time, and * indicates an asymmetric carbon atom, which comprises reacting an asymmetric reducing agent obtained from (1) an optically active amine derivative represented by the formula (I) ##STR2## wherein R.sub.1 denotes an alkyl group, aryl group or aralkyl group; R.sub.2 denotes a hydrogen atom, alkyl group or aralkyl group; R.sub.3 denotes an aryl group or a substituent represented by the formula (II) ##STR3## wherein R.sub.4 and R.sub.5 each denote a hydrogen atom, aryl group or aralkyl group, and * is as defined above, (2) a metal borohydride and (3) sulfuric acid, with either the syn-isomer or the anti-isomer of an oxime derivative represented by the formula (III) or with a mixture rich in either one of the two isomers ##STR4## wherein R.sub.
    Type: Grant
    Filed: October 7, 1991
    Date of Patent: April 6, 1993
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Naoto Konya, Yukio Yoneyoshi, Yoji Sakito, Shinji Nishii, Gohfu Suzukamo, Hiroko Sakane
  • Patent number: 5196601
    Abstract: Disclosed herein is a process for producing an alcohol or an amine by reducing a compound having a formyl, keto, nitro, oxirane, ester, nitrile, amide or halogenated carboxyl group with an alkali metal boro-hydride in the presence of a compound having a hydroxyl group and ether linkage. According to the present invention, a functional group having a great steric hindrance can be reduced, and a corresponding alcohol or amine can efficiently be produced under very mild conditions on an industrial scale.
    Type: Grant
    Filed: June 17, 1992
    Date of Patent: March 23, 1993
    Assignee: Kao Corporation
    Inventors: Tomohito Kitsuki, Yoshiaki Fujikura
  • Patent number: 5166443
    Abstract: A process for the preparation of a 2,2-disubstituted pentane-1,5-diamine of the formula I ##STR1## where R.sup.1 and R.sup.2, independently of one another, are C.sub.1 - to C.sub.10 -alkyl or C.sub.2 - to C.sub.10 -alkenyl or together are a C.sub.4 - to C.sub.7 -alkylene chain which is unsubstituted or monosubstituted to pentasubstituted by C.sub.1 - to C.sub.4 -alkyl, from a 2,2-disubstituted 4-cyanobutanal of the formula II ##STR2## where R.sup.1 and R.sup.2 are as defined above, comprises, in two spatially separate reaction spaces,a) reacting the 4-cyanobutanal of the formula II, in a first reaction space, with excess ammonia on an acidic heterogeneous catalyst at from 20.degree. to 150.degree. C.
    Type: Grant
    Filed: March 17, 1991
    Date of Patent: November 24, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Claus-Ulrich Priester, Tom Witzel, Gerhard Koppenhoefer, Ludwig Schuster
  • Patent number: 5145998
    Abstract: A method for producing an optically active amine which is an important compound as a resolving agent for medicines, agricultural chemicals, intermediates thereof, etc is disclosed.
    Type: Grant
    Filed: October 2, 1990
    Date of Patent: September 8, 1992
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yoji Sakito, Gohfu Suzukamo, Yukio Yoneyoshi
  • Patent number: 5124484
    Abstract: A process for the preparation of a polyisobutene amine, in particularly a polyisobutene amine of formula (I): ##STR1## comprises reacting a carbonyl funtionalized polyisobutene [PIB]--(CO)R and an amine H.sub.2 NR.sup.1 and hydrogenating the product of the reaction between said carbonyll functionalized polyisobutene and said amine, where PIB is a polyisobutenyl group,R=H, methyl or vinyl,R.sup.1 =C.sub.1 -C.sub.20 alkyl group or --(CHR.sup.2).sub.n [X(CH.sub.2).sub.m ].sub.p X.sup.1 R.sup.3R.sup.2 =H or methyln=an integer of 1-4m=an integer of 2-4p=0, or an integer of 1-10R.sup.3 =H or C.sub.1 -C.sub.10 alkylXm X.sup.1 =O or NR.sup.4R.sup.4 =H, C.sub.1 -C.sub.10 alkyl group, or [(CH.sub.2).sub.q X.sup.2 R.sup.5 ]q=an integer of 2-4R.sup.5 is H, C.sub.1 -C.sub.10 alkyl groupX.sup.2 is 0 or NHeach of X and X.sup.1 may be the same or may be different and when p>1 each of the repeating units [X(CH.sub.2).sub.m ] may be the same or may be different.Polyamines or alcoholamines are preferred amines.
    Type: Grant
    Filed: November 19, 1991
    Date of Patent: June 23, 1992
    Assignee: BP Chemicals (Additives) Limited
    Inventors: Simon C. Brown, Michael J. Clarke
  • Patent number: 5105014
    Abstract: The present invention relates to an improved method of forming vicinal diamines. The method according to the present invention has the advantage of being highly stereoselective, capable of forming a wide variety of diamines including racemic and enantiomeric forms, and employing readily available starting and reaction materials.In particular the present invention relates to a method of forming vicinal diamines from a bis-imine precursor using nucleophilic additions of organometallic reagents.
    Type: Grant
    Filed: August 6, 1991
    Date of Patent: April 14, 1992
    Assignee: Mallinckrodt Medical, Inc.
    Inventor: William L. Neumann
  • Patent number: 5053545
    Abstract: A method of preparing an amino alcohol of the formula ##STR1## where R.sub.1 is H, lower alkyl or R.sub.2, R.sub.2 is R.sub.3 CHOH in which R.sub.3 is H, alkyl or aryl. R.sub.3 preferably is hydrogen, lower alkyl or monocyclic aryl such as phenyl. The inventive method involves the reaction of halonitroalcohol with hydrogen in the presence of methanol, a suitable buffering agent such as ammonia, and a hydrogenation catalyst to form amino alcohol salt, neutralizing the amino alcohol salt, and recovering the resultant amino alcohol.
    Type: Grant
    Filed: August 7, 1990
    Date of Patent: October 1, 1991
    Assignee: Angus Chemical Company
    Inventors: Thomas H. Marman, Vincent Nocito
  • Patent number: 5023379
    Abstract: A process for the production of hydroxyamines of the formula IR.sup.1 --CH(OH)--CH(NHR.sup.3)--R.sup.2 (I)whereinR.sup.1 and R.sup.2 independently of one another are H or CH.sub.2 OH andR.sup.3 is H, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -hydroxyalkyl comprising reacting an oxo compound with an amine and reducing the resultant ketimine with a reducing agent.
    Type: Grant
    Filed: March 12, 1990
    Date of Patent: June 11, 1991
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Ernst Felder, Michael Romer, Hans Bardonner, Hartmut Hartner, Wolfgang Fruhstorfer
  • Patent number: 5012000
    Abstract: A method for the preparation of chiral 2-amino-1,3-diols is disclosed. The method involves four steps including performance of an aldol condensation with a chiral oxazolidinone on an aldehyde, treating the aldol condensation product with an alkali metal azide, treating the product with a borohydride reagent and reducing the azide to an amine.
    Type: Grant
    Filed: October 30, 1989
    Date of Patent: April 30, 1991
    Assignee: Eastman Kodak Company
    Inventors: Carl R. Illig, Alexander L. Weis
  • Patent number: 4931595
    Abstract: Polyamines containing primary amino groups are prepared in a single stage process by hydrolyzing an isocyanate in the presence of a catalyst incorporable through an NCO reactive group and a water-miscible aprotic-dipolar solvent. This hydrolysis is carried out at from 20.degree. to 210.degree. C. with the reactants being in substantially homogeneous phase. The isocyanate starting material has an NCO content of from 0.5 to 40% by weight. The catalyst is used in a quantity of at least 0.0001% by weight, based on 100% by weight of isocyanate compound. The water-miscible solvent is used in a quantity of at least 10% by weight, based on 100% by weight of isocyanate compound. The polyamines thus produced are particularly useful in the production of polyurethanes.
    Type: Grant
    Filed: August 2, 1989
    Date of Patent: June 5, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventor: Werner Rasshofer
  • Patent number: 4792631
    Abstract: Di-tert.-butylethylenediamine is prepared by reacting tert.-butylamine with glyoxal to form di-tert.-butylglyoxaldiimine and water and subsequently hydrogenating the diimine by(a) carrying out the reaction of tert.-butylamine with glyoxal in the presence of a hydrocarbon phase,(b) separating the hydrocarbon with the reaction product from water, and(c) catalytically hydrogenating the reaction product in the hydrocarbon phase.
    Type: Grant
    Filed: January 28, 1987
    Date of Patent: December 20, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Herbert Mueller, Walter Mesch
  • Patent number: 4705898
    Abstract: A two-step process for the preparation of secondary amines in good yield from olefins, carbon monoxide, hydrogen and primary amines is described. The intermediate imine may be isolated in good yield as well.
    Type: Grant
    Filed: April 4, 1986
    Date of Patent: November 10, 1987
    Assignee: Texaco Inc.
    Inventors: Edward E. McEntire, John F. Knifton
  • Patent number: 4658066
    Abstract: Novel diamines of the formula ##STR1## are described, in which R.sub.1 is C.sub.1-12 -alkyl, R.sub.2 is H or C.sub.1-12 -alkyl, R.sub.3 is C.sub.1-12 -alkyl, cycloalkyl having 4-12 ring C atoms, C.sub.7-8 -aralkyl, substituted or unsubstituted aryl or, if R.sub.4 =H, is also --CH.dbd.CH--alkyl or --C(alkyl).dbd.CH-- alkyl each having 1-4 C atoms in the alkyl groups, and R.sub.4 is H, C.sub.1-12 -alkyl, cycloalkyl having 4-12 ring C atoms, C.sub.7-8 -aralkyl or substituted or unsubstituted aryl, or R.sub.1 and R.sub.2 and/or R.sub.3 and R.sub.4 together are C.sub.3-11 -alkylene. The diamines (I) are valuable intermediates and are suitable especially for the preparation of transparent crosslinkable polyamides.
    Type: Grant
    Filed: August 7, 1985
    Date of Patent: April 14, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Dieter Reinehr, Josef Pfeifer
  • Patent number: 4535154
    Abstract: A method for the reduction of nitrogen compounds containing an N--N or N.dbd.N bond, which are soluble in water or lower alcohols, particularly nitrosamines, hydrazines, nitramines, azo- and azoxy-compounds, to the corresponding amines; comprising contacting the nitrogen compounds with a hydroxide solution and a nickel-aluminum alloy in the absence of a hydrogen atmosphere, at room temperature and at atmospheric pressure, for a sufficient time to produce the corresponding amine in a single step.
    Type: Grant
    Filed: July 13, 1983
    Date of Patent: August 13, 1985
    Assignee: United States of America
    Inventors: Larry K. Keefer, George Lunn
  • Patent number: 4525590
    Abstract: The invention relates to an improved process for the production of polyamines containing urethane and/or urea and/or biuret and/or isocyanurate groups and, preferably, also alkylene ether, carbonate and/or acetal groups by the alkaline hydrolysis of corresponding compounds containing terminal aliphatic and/or aromatic isocyanate groups.To this end, the compounds containing terminal NCO-groups, preferably NCO-preadducts, are converted by means of selected bases into the carbamates and neutralized by introduction into equivalent quantities of acid or by the simultaneous introduction of the components in equivalent quantities into a reaction vessel, after which the polyamines are directly isolated by methods known per se.The invention also relates to the use of the polyamines obtained by the process for the production of polyurethanes.
    Type: Grant
    Filed: July 15, 1982
    Date of Patent: June 25, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Werner Rasshofer, Klaus Konig, Holger Meyborg, Walter Meckel, Armin Zenner
  • Patent number: 4331557
    Abstract: A ruthenium-containing catalyst is regenerated after use for an organic chemical treatment, e.g., hydrogenation, dehydrogenation, isomerization, disproportionation, hydrocracking, etc., at an elevated temperature and at a considerably reduced pressure of the order of about 600 mm Hg and much lower of the order of about 0.001 mm Hg.
    Type: Grant
    Filed: May 22, 1980
    Date of Patent: May 25, 1982
    Assignee: Phillips Petroleum Company
    Inventor: Charles A. Drake
  • Patent number: 4264776
    Abstract: Tertiary amines such as alkyl or benzyl amines are catalytically oxidized by oxygen over an activated carbon catalyst to selectively produce secondary amines.
    Type: Grant
    Filed: January 2, 1976
    Date of Patent: April 28, 1981
    Assignee: Monsanto Company
    Inventors: Arnold Hershman, Donald J. Bauer
  • Patent number: 4248801
    Abstract: Tertiary monomethylamines having long chain alkyl groups are advantageously prepared from unsaturated aliphatic nitriles under a low pressure at a high yield by the steps of:(a) reducing the nitriles with hydrogen in the presence of a nickel hydrogenation catalyst at 200.degree. through 230.degree. C. and under a hydrogen pressure of 0 through 10 kg/cm.sup.2 G, while the formed ammonia is removed;(b) reacting the resultant amines with a hydroxymethylation agent in the presence of the nickel catalyst at 150.degree. through 180.degree. C., while hydrogen is passed through the reaction zone under 0.3 through 7 kg/cm.sup.2 G and the formed water is removed, and;(c) reducing the resultant tertiary amines with hydrogen in the presence of the nickel catalyst at 175.degree. through 210.degree. C. and under a hydrogen pressure of 5 through 10 kg/cm.sup.2 G.
    Type: Grant
    Filed: July 3, 1979
    Date of Patent: February 3, 1981
    Assignee: The Lion Fat & Oil Co., Ltd.
    Inventors: Susumu Tomidokoro, Michito Sato, Daini Saika