Of Aldehyde Or Ketone Containing Compound Patents (Class 564/446)
  • Patent number: 6194615
    Abstract: The present invention relates to the composition, process of preparation, and use of novel derivatives prepared from 1,5-bis-(4′-carbomethoxyphenyl)-1,4-pentadien-3-one. These novel compositions can act as crosslinkers with polyfunctional monomeric, oligomeric, and/or polymeric anhydrides, esters, carboxylic acids, isocyantes, epoxies, carbonates, acetoacetates, and alkoxylated melamines.
    Type: Grant
    Filed: June 17, 1999
    Date of Patent: February 27, 2001
    Assignee: Eastman Chemical Company
    Inventors: Philip Conrad Heidt, Matthew Lynn Elliott
  • Patent number: 6187957
    Abstract: Amines are prepared by reacting primary or secondary alcohols, aldehydes or ketones with nitrogen compounds selected from the group consisting of ammonia and primary and secondary amines at elevated temperatures and superatmospheric pressures in the presence of hydrogen and of a catalyst containing copper and oxygen-containing compounds of titanium by a process in which the catalyst is used in the form of moldings which have been prepared with the addition of metallic copper powder.
    Type: Grant
    Filed: December 14, 1999
    Date of Patent: February 13, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerald Meyer, Frank Funke, Gerhard Schulz, Detlef Kratz, Marc Walter, Michael Hesse
  • Patent number: 6107522
    Abstract: Cyclopropylamine is prepared from butyrolactone by a process comprising:(a) reacting butyrolactone with hydrogen chloride, thereby yielding chlorobutyric acid, (b) esterifying said chlorobutyric acid with a primary or secondary alcohol having 4-8 carbon atoms, (c) cyclizing the ester with an alkali metal alcoholate of a primary alcohol having 1-3 carbon atoms to give a mixture of cyclopropanecarboxylic acid esters, (d) converting the cyclopropanecarboxylic acid ester mixture into cyclopropanecarboxylic acid amide by reacting the ester mixture with ammonia, and (e) reacting said cyclopropanecarboxylic acid amide with hypohalite ion in a basic medium, thereby forming cyclopropylamine.
    Type: Grant
    Filed: July 9, 1999
    Date of Patent: August 22, 2000
    Assignee: Degussa-Huels Aktiengesellschaft
    Inventors: Wolfgang Kleemiss, Marcel Feld, Manfred Kaufhold
  • Patent number: 6100430
    Abstract: An alicyclic polyamine of the formula (1) ##STR1## wherein Y.sub.1 represents a saturated aliphatic hydrocarbon group and R.sub.1 through R.sub.4 are the same or different and each represents hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or an aralkyl group. The alicyclic polyamine can be obtained by subjecting a 3-formylcycloalkanone or 3-formylcycloalkenone to reductive amination reaction.
    Type: Grant
    Filed: September 10, 1998
    Date of Patent: August 8, 2000
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Kenichi Yamamoto, Kazuyuki Matsuoka, Hiroshi Yagihara
  • Patent number: 6046360
    Abstract: The present invention relates to a process for preparing 4-substituted cis-cyclohexylamines of high cis-selectivity by reductive amination of cyclohexanones which are substituted in position 4 by an organic radical.
    Type: Grant
    Filed: March 17, 1999
    Date of Patent: April 4, 2000
    Assignee: Hoechst Schering AgrEvo GmbH
    Inventors: Dieter Bernd Reuschling, Adolf Heinz Linkies
  • Patent number: 6011179
    Abstract: A process for the production of primary and/or secondary amines from imines or nitriles, comprising an aminating hydrogenation of imine or of nitrile with hydrogen in the presence of ammonia, of a hydrogenation catalyst based on cobalt, nickel, ruthenium or mixtures of these metals and of a base, at a temperature within the range of 50.degree. C. to 200.degree. C. and at a pressure within the range of 0.3 to 30 MPa. The yield of amine is increased by the use of a quaternary ammonium hydroxide as base. Preferably a tetraalkylammonium hydroxide is used in a quantity of from 0.01 to 100 mMol per mol of amine or of nitrile. The process is suitable in particular for the production of isophoronediamine from isophorone nitrile imine.
    Type: Grant
    Filed: October 30, 1998
    Date of Patent: January 4, 2000
    Assignee: Degussa-Huls AG
    Inventors: Thomas Haas, Karl Ludwig Weber, Klaus Stadtmuller, Willi Hofen, Rudolf Vanheertum
  • Patent number: 5986141
    Abstract: Disclosed is a process for the preparation of cyclopropanemethylamine (CPMA) from cyclopropanecarboxaldehyde (CPCA), ammonia and hydrogen by a two-step process wherein CPCA is contacted with ammonia to form an imine followed by the hydrogenation of the imine in the presence of a nickel or cobalt catalyst to obtain CPMA in high yields and high selectivity.
    Type: Grant
    Filed: September 29, 1998
    Date of Patent: November 16, 1999
    Assignee: Eastman Chemical Company
    Inventor: Shaowo Liang
  • Patent number: 5817698
    Abstract: A method of treatment of a condition or disease related to the accumulation of calcium in the brain cells of a mammal which comprises administering to a subject in need thereof an effective amount of a compound of formula (I), wherein X is O, S, C.dbd.O or a bond; p and q are independently 0-4; R.sup.1 and R.sup.2 are each independently selected from the group consisting of hydrogen, C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl or C.sub.3-6 cycloalkylC.sub.1-4 alkyl; n is 1, 2, 3 or 4; and Ar is phenyl optionally substituted by 1 to 3 substituents selected from; halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-2 alkylenedioxy, trifluoromethyl, trifluoromethoxy, CN, NO.sub.2, amino, mono- or di- alkylamino and Ph(Alk.sup.1).sub.r Y(Alk.sup.2).sub.s -- where Ph is optionally substituted phenyl, Y is a bond, oxygen or a carbonyl group, Alk.sup.1 and Alk.sup.2 are independently C.sub.1-4 alkyl which may be straight or branched and r and s are independently 0 or 1, provided that the length of (Alk.sup.1).sub.r Y(Alk.sup.
    Type: Grant
    Filed: September 20, 1996
    Date of Patent: October 6, 1998
    Assignee: SmithKline Beecham plc
    Inventors: Thomas Henry Brown, John David Harling, Barry Sidney Orlek
  • Patent number: 5756845
    Abstract: A process for the preparation of 3-aminomethyl-3,5,5-trimethylcyclohexylamine from 3-cyano-3,5,5-trimethylcyclohexanone which requires three spatially separated reaction spaces, in order to carry out the following three steps in sequence:a) reacting the 3-cyano-3,5,5-trimethylcyclohexanone with excess ammonia on acidic metal-oxide catalysts in a first reaction space at from 20.degree. to 150.degree. C. and from 50 to 300 bar,b) hydrogenating the resultant reaction products using hydrogen in a second reaction space in the presence of excess ammonia and preferably liquid ammonia on hydrogenation catalysts, optionally using basic components or on neutral or basic supports at from 50.degree. to 100.degree. C. and at from 50 to 300 bar, andc) hydrogenating the resultant reaction products in the presence of hydrogen and also ammonia in a third reaction space on hydrogenation catalysts, optionally using basic components or on neutral or basic supports at from 110.degree. to 160.degree. C. and at from 150 to 300 bar.
    Type: Grant
    Filed: February 28, 1996
    Date of Patent: May 26, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Guido Voit, Tom Witzel, Boris Breitscheidel, Wolfgang Harder, Hermann Luyken, Axel Paul, Karl-Heinz Ross, Peter Wahl
  • Patent number: 5705699
    Abstract: 3-Aminomethyl-3,5,5-trimethylcyclohexylamine is prepared by reacting 3-cyano-3,5,5-trimethylcyclohexanone with 3-aminomethyl-3,5,5-trimethylcyclohexylamine and subsequently or simultaneously adding ammonia under a hydrogen pressure of from 50 to 300 bar in the presence of a hydrogenation catalyst at from 20.degree. to 150.degree. C., by a process in which the reaction is carried out without removing the water of reaction.
    Type: Grant
    Filed: February 28, 1995
    Date of Patent: January 6, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Tom Witzel, Guido Voit
  • Patent number: 5589596
    Abstract: A process is disclosed for producing an amine by carrying out a reductive amination of a cyclic ketone or by carrying out a reduction of an imino derivative of a cyclic ketone to the corresponding amine which process is characterized in using a cobalt catalyst containing a carbonate of an alkaline earth metal and/or lanthanum oxide.
    Type: Grant
    Filed: February 8, 1994
    Date of Patent: December 31, 1996
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Atsushi Furutani, Takuo Hibi, Michio Yamamoto, Kazuyuki Tanaka, Kazuhiro Tada, Masami Fukao, Gohfu Suzukamo
  • Patent number: 5583260
    Abstract: A method of controlling the cis/trans isomer ratio in the preparation of isophoronediamine by the aminating hydrogenation of isophoronenitrile in the presence of ammonia, H.sub.2 and a catalyst. The reaction takes place in two temperature steps, initially at 10.degree. to 90.degree. C. and then at above 90.degree. to 150.degree. C. with a temperature difference of at least 30.degree. C. between the two steps, the contact time being shorter in the first step than in the second. The cis/trans ratio is increased by lowering the temperature of the first step.
    Type: Grant
    Filed: December 22, 1994
    Date of Patent: December 10, 1996
    Assignee: Degussa Aktiengesellschaft
    Inventors: Thomas Haas, Dietrich Arntz, Dieter Most
  • Patent number: 5504254
    Abstract: A process is disclosed for the continuous preparation of 3-aminomethyl-3,5,5-trimethylcyclohexylamine (isophoronediamine) in high yield and high purity from 3-cyano-3,5,5-trimethylcyclohexanone (isophoronenitrile) by aminating hydrogenation with hydrogen and ammonia in the presence of a fixed bed catalyst. The aminating hydrogenation is carried out by allowing a mixture of isophoronenitrile, ammonia and a C.sub.1 -C.sub.3 -alcohol, in the presence of hydrogen, to trickle over a trickle bed reactor provided with a Co and/or Ru fixed bed catalyst, at 3 to 8 MPa and at a temperature of 40.degree. to 150.degree. C., preferably 90 to 130.degree. C., and working up the reaction mixture by distillation. Preferably, a high-boiling by-product fraction, containing a bicyclic amidine, is added to the mixture to be hydrogenated, thereby appreciably increasing the yield.
    Type: Grant
    Filed: December 22, 1994
    Date of Patent: April 2, 1996
    Assignee: Degussa Aktiengesellschaft
    Inventors: Thomas Haas, Dietrich Arntz, Dieter Most
  • Patent number: 5491264
    Abstract: Isophorone diamine is prepared from isophorone nitrile by imination using a supported heteropoly acid catalyst to form the ketimine followed by the reduction of the ketimine to form the diamine.
    Type: Grant
    Filed: September 12, 1994
    Date of Patent: February 13, 1996
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Frank E. Herkes, Kostantinos Kourtakis
  • Patent number: 5434309
    Abstract: A process for preparing a controlled functional density poly(secondary amine) comprising:(a) contacting a polymer containing olefinic unsaturation with carbon monoxide in hydrogen under hydroformylation conditions in the presence of a hydroformylation catalyst to produce a controlled functional density polyaldehyde containing reactive carbon-carbon double bonds, and (b) contacting the polyaldehyde with hydrogen and a primary amine under reductive amination conditions in the presence of a ruthenium-containing imine hydrogenation catalyst or (b.sup.1) contacting the polyaldehyde with a sterically hindered aliphatic or cycloaliphatic primary amine or an aromatic primary amine under reductive amination conditions in the presence of an alkali metal borohydride to produce poly(secondary amine) having a substantially equivalent ratio of secondary amine groups to reactive carbon-carbon double bonds as the ratio of aldehyde groups to reactive carbon-carbon double bonds in the polyaldehyde.
    Type: Grant
    Filed: April 28, 1994
    Date of Patent: July 18, 1995
    Assignee: Monsanto Company
    Inventors: Martin P. McGrath, Samuel J. Tremont
  • Patent number: 5406000
    Abstract: A method is disclosed for the selective preparation of 3-aminomethyl-3,5,5-trialkylcyclohexylamine by preparing dried 3-cyano-3,5,5-trialkylcyclohexylimine from the reaction of 3-cyano-3,5,5-trialkylcyclohexanone with ammonia in the presence of a drying agent in an amount at least sufficient to retain the water present or generated during the imine-forming reaction, and hydrogenating the dried 3-cyano-3,5,5-trialkylcyclohexylimine in the presence of a cobalt-containing catalyst at elevated temperature and pressure.
    Type: Grant
    Filed: January 12, 1993
    Date of Patent: April 11, 1995
    Assignee: Elf/Atochem North America, Inc.
    Inventor: Christian Forquy
  • Patent number: 5403959
    Abstract: A process for the preparation of 8-N,N-dialkylaminotricyclo[5.2.1.0.sup.2,6 ]decane by reaction of tricyclo[5.2.1.0.sup.2,6 ]decan-8(9)-one with an amine of the formula HNR.sub.1 R.sub.2, where R.sub.1 and R.sub.2 are each an alkyl radical having 1 to 6 carbon atoms, in the presence of hydrogen and a platinum-containing supported catalyst, preferably at elevated pressure and elevated temperature.
    Type: Grant
    Filed: April 12, 1994
    Date of Patent: April 4, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Claus Kniep, Detlef Kampmann, Juger Weber
  • Patent number: 5395972
    Abstract: Amines are produced in high yield by the process which comprises allowing a cyclic ketone to react with ammonia in the presence of active carbon to produce imino derivatives and then, allowing the imino derivatives to react with hydrogen in the presence of a hydrogenating catalyst.
    Type: Grant
    Filed: February 8, 1994
    Date of Patent: March 7, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Atsushi Furutani, Takuo Hibi, Michio Yamamoto, Gohfu Suzukamo
  • Patent number: 5371292
    Abstract: A process for the preparation of 3-aminomethyl-3,5,5-trimethyl-cyclohexylamine from 3-cyano-3,5,5-trimethyl-cyclohexanone, wherein the following stages are carried out in discrete reaction chambers:a) the 3-cyano-3,5,5-trimethyl-cyclohexanone is reacted in a first reaction chamber with excess ammonia over an acidic metal oxide catalyst at a temperature of from 20.degree. to 150.degree. C. and a pressure of from 15 to 500 bar, andb) in a second reaction chamber, the reaction product from stage a) is hydrogenated with hydrogen at a temperature of from 60.degree. to 150.degree. C. and a pressure of from 50 to 300 bar in the presence of excess ammonia over a catalyst containing cobalt, nickel, ruthenium, and/or some other noble metal, which catalyst optionally contains a basic component or is supported by neutral or basic supporting material.
    Type: Grant
    Filed: July 15, 1993
    Date of Patent: December 6, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Claus-Ulrich Priester, Tom Witzel, Gerhard Koppenhoefer, Wolfgang Harder
  • Patent number: 5344990
    Abstract: Intermediates and a process for their preparation are disclosed which are useful for the preparation of a renin inhibiting compound of the formula: ##STR1## wherein R is a nitrogen-containing heterocycle which is bonded via a nitrogen atom to the sulfonyl group, R.sub.6 is hydrogen, alkoxy, halogen or loweralkyl, R.sub.7 is loweralkyl having 2 to 7 carbon atoms, and R.sub.8 is loweralkyl, cycloalkyl, or aryl or a pharmaceutically acceptable acid addition salt thereof.
    Type: Grant
    Filed: October 5, 1993
    Date of Patent: September 6, 1994
    Assignee: Abbott Laboratories
    Inventors: William R. Baker, Stephen L. Condon
  • Patent number: 5344983
    Abstract: Process for preparing a pentane-1,5-diamine of the formula ##STR1## where R.sup.1 represents a variety of organic radicals including alkyl which can bear substituents such as hydroxyl, halogen, alkoxy, carbalkoxy, carboxyl, alkylamino, cycloalkyl or aryl, andR.sup.2 and R.sup.3 independently of one another, represent hydrogen or have the same meanings as R.sup.1 or together are a C.sub.4 -C.sub.7 -alkylene chain which is unsubstituted or substituted by one to five C.sub.1 -C.sub.4 -alkyl groups,which comprises:(a) reacting a .gamma.-cyanoketone of the formula ##STR2## where R.sup.1, R.sup.2 and R.sup.3 have the meanings given above, with excess ammonia in a first reaction space on an acidic heterogeneous catalyst at 20.degree.-150.degree. C. and 15-500 bar, and(b) hydrogenating the resulting reaction product in a second separate reaction space in the presence of excess ammonia on a cobalt, nickel or noble metal catalyst at 50.degree.-180.degree. C. and 30-500 bar.
    Type: Grant
    Filed: August 26, 1992
    Date of Patent: September 6, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Tom Witzel, Eberhard Fuchs, Franz Merger, Claus-Ulrich Priester
  • Patent number: 5322965
    Abstract: Optionally substituted cyclohexylamine and optionally substituted dicyclohexylamine can be obtained by catalytic hydrogenation of optionally substituted aniline, a catalyst being employed which contains ruthenium, palladium or a mixture of both metals, which are applied to a support of niobic acid or tantalic acid or a mixture of both. The catalyst contains the noble metal(s) in a total amount from 0.05 to 5% by weight, relative to the total weight of the catalyst. In the case of the use of both noble metals, their weight ratio to one another is 1:9-9:1.
    Type: Grant
    Filed: August 27, 1993
    Date of Patent: June 21, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Immel, Gerhard Darsow, Helmut Waldmann, Gerd-Michael Petruck
  • Patent number: 5286906
    Abstract: A process for the preparation of a 3-aminomethyl-3,5,5-trialkylcyclohexylamine, which comprises hydrogenating 3-cyano-3,5,5-trialkylcyclohexylamine in the presence of ammonia and a ruthenium-cobalt catalyst.
    Type: Grant
    Filed: September 25, 1992
    Date of Patent: February 15, 1994
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Yoshinori Hara, Haruhiko Kusaka, Masamichi Onuki, Sugio Nishimura
  • Patent number: 5283366
    Abstract: The reductive amination of 1,3,3-trimethyl-5-oxocyclohexane carbonitrile (IPN) with ammonia and hydrogen in the presence of nickel- or cobalt Raney catalysts to 3-aminomethyl-3, 5,5-trimethyl-cyclohexyl amine is achieved in a single stage with a good yield and requires no pressure distillation if a co-catalyst selected from the group consisting of salts of nickel, cobalt, yttrium, lanthanum and cerium is used in an amount of 0.01 to 0.5 mole per mole Raney catalyst.
    Type: Grant
    Filed: February 25, 1993
    Date of Patent: February 1, 1994
    Assignee: Degussa AG
    Inventors: Klaus Huthmacher, Hermann Schmitt
  • Patent number: 5276198
    Abstract: A process for producing 2-methyl-1,3-cyclohexanedione which comprises subjecting 1,3-cyclohexanedione, formaldehyde and a dialkylamine to Mannich reaction to obtain a 2-dialkylaminomethyl-1,3-cyclohexanedione, and subjecting the 2-dialkylaminomethyl to hydrogenolysis, and a process for producing 2-methylresorcinol which comprises aromatizing 2-methyl-1,3-cyclohexanedione obtained. According to these processes, it is possible to produce high-purity 2-methylresorcinol and 2-methyl-1,3-cyclohexanedione commercially easily and advantageously.
    Type: Grant
    Filed: August 21, 1992
    Date of Patent: January 4, 1994
    Assignees: Sumitomo Chemical Company, Limited, Sumika Fine Chemicals Co., Ltd.
    Inventors: Toshio Nakamatsu, Yasuhiro Nishida, Norio Kometani
  • Patent number: 5270471
    Abstract: A branched chain polyalkylene polyamine ("PAPA") having plural amine groups, including a secondary amine group intermediate terminal primary amine groups one of which is hindered, and having at least two carbon atoms between each group, is selectively reductively alkylated with a ketone. The reaction provides a convenient method for selectively reductively alkylating a PAPA having a hindered primary amine group, the method comprising contacting the PAPA with hydrogen and the ketone in the presence of a catalytically effective amount of a Group VIII metal on a catalyst support, at a pressure in the range from about 500-1000 psi and a temperature in the range from about 50.degree. C. to about 200.degree. C. for a period of time sufficient to preferentially alkylate the unhindered amine primary terminal amine group. The alkylation proceeds essentially without alkylating either the sterically hindered terminal primary amine group or the intermediate unhindered secondary amine group.
    Type: Grant
    Filed: October 27, 1992
    Date of Patent: December 14, 1993
    Assignee: The B. F. Goodrich Company
    Inventors: John T. Lai, Pyong-Nae Son
  • Patent number: 5239120
    Abstract: A process for the preparation of a 2-(3-aminopropyl)-cycloalkylamine of the general formula I ##STR1## in which the subscript n is an integer from 1 to 4, from a 2-(2-cyanoethyl)-cycloalkanone of the general formula II ##STR2## in which the subscript n has the meaning stated, wherein the following stages are carried out in discrete reaction chambers:a) the 2-(2-cyanoethyl)-cycloalkanone of formula II is reacted in a first reaction chamber with excess ammonia over an acidic heterogeneous catalyst at a temperature from 20.degree. to 150.degree. C. and a pressure of from 15 to 500 bar, andb) in a second reaction chamber, the reaction product from stage a) is hydrogenated at a temperature of from 60.degree. to 150.degree. C. and a pressure of from 50 to 300 bar in the presence of excess ammonia over a catalyst containing cobalt, nickel, ruthenium, and/or some other noble metal, which catalyst optionally contains a basic component or is supported on neutral or basic supporting material.
    Type: Grant
    Filed: March 27, 1991
    Date of Patent: August 24, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Claus-Ulrich Priester, Gerhard Koppenhoefer, Wolfgang Harder, Tom Witzel, Helmut Lermer, Ulrich Koehler
  • Patent number: 5225597
    Abstract: A continuous method of preparing N-monoalkyl alkylenediamines, uncontaminated by the N,N'-dialkyl alkylenediamine, is based on the observation that the disubstituted material selectively precipitates from aqueous media. A scheme is presented where an aqueous alkylenediamine is reacted with a suitable carbonyl component and hydrogen over a supported platinum catalyst. Where the alkylenediamine forms an azeotrope with water it can be conveniently recycled to the reactor.
    Type: Grant
    Filed: March 13, 1992
    Date of Patent: July 6, 1993
    Assignee: UOP
    Inventor: Paul R. Kurek
  • 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: 5105013
    Abstract: A process for the preparation of permethylated amines, particularly pentamethyldiethylenetriamine, by the reductive methylation of diethylenetriamine in the presence of hydrogen, a nickel-containing catalyst, aqueous formaldehyde and methanol, comprising feeding continuously the formalehyde to the reaction system in two phases. In the first phase, a sufficient amount of formaldehyde to mono-methylate the primary amine groups present, is fed to the reaction system at a high flow rate, and thereafter the flow rate of the formaldehyde is substantially reduced, for the reductive methylation of the secondary amine groups. By this method the production of by-products is substantially reduced and preparation times are significantly shorter in comparison to processes where the formaldehyde flow rate remains constantly high for the entirety of the reaction.
    Type: Grant
    Filed: December 19, 1988
    Date of Patent: April 14, 1992
    Assignee: The Dow Chemical Company
    Inventors: Maarten Tanis, Govind Rauniyar
  • Patent number: 5055618
    Abstract: The object of this invention is the preparation of .alpha.,.omega.-diamines from .alpha., .omega.-dialdehydes in a method which comprises the reaction of a starting mixture of said dialdehyde, a primary amine, and water to form a reaction mixture, followed by treatment of said reaction mixture with excess ammonia and hydrogen in the presence of a hydrogenation catalyst to produce a final mixture.
    Type: Grant
    Filed: May 21, 1990
    Date of Patent: October 8, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Detlef Kampmann, Jurgen Weber, Claus Kniep
  • Patent number: 5041675
    Abstract: This invention relates to a process for preparing 3(4),8(9)-bis(aminomethyl)tricyclo[5.2.1.0.sup.2,6 ]decane. The starting material for the synthesis of this compound is dicyclopentadiene, which is hydroformylated in the presence of a rhodium compound and subjected to reductive amination without the hydroformylation catalyst being separated from the reaction mixture.
    Type: Grant
    Filed: August 17, 1990
    Date of Patent: August 20, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rainer Lukas, Klaus Mathieu, Franz Thonnessen, Georg Dambkes, Hanswilhelm Bach
  • Patent number: 4996316
    Abstract: A process for the preparation of tertiary N,N-dimethylamines by the reaction of primary amines, formaldehyde, and hydrogen under pressure and at elevated temperature in the presence of a nickel-containing hydrogenation catalyst in the liquid phase. The hydrogenation catalyst is suspended in a solvent, the nickel concentration is 0.1 to 10% by weight, based on the primary amine. The starting materials are separate from each other, brought to 80.degree. to 150.degree. C. and 1 to 15 MPa and fed into the catalyst suspension simultaneously with stirring and reacted in one step to form the tertiary N,N-dimethylamines.
    Type: Grant
    Filed: December 24, 1988
    Date of Patent: February 26, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jurgen Weber, Detlef Kampmann, Claus Kniep
  • Patent number: 4954654
    Abstract: A process for the preparation of secondary and tertiary amines such as dimethylcyclohexylamine, comprising reacting an amine of the formula ##STR1## wherein R.sub.1 is an organic group and R.sub.2 is an organic group or hydrogen atom, with a ketone such as cyclohexanone in the liquid phase in the presence of an unsupported metallic copper catalyst under hydrogenating conditions. The process further includes providing an acid such as acetic acid as a condensation promoter, permitting the metallic copper catalyst to separate out by gravitation over a period of time, removing post-reaction material from contact with the catalyst, separating the post-reaction material into fractions, as by distillation, and recycling unreacted starting material for further reaction.
    Type: Grant
    Filed: August 29, 1988
    Date of Patent: September 4, 1990
    Assignee: Phillips Petroleum Company
    Inventor: Howard F. Efner
  • Patent number: 4929741
    Abstract: Propiolophenone derivatives of the formula ##STR1## wherein R.sup.6 is hydrogen, lower alkyl or a group of the formula ##STR2## as well as corresponding hydroxy compounds of the formula ##STR3## wherein R.sup.6' is hydrogen, lower alkyl, a group of formula (a), (b), (c), (d) or (e) or a group of the formula--C(R.sup.14)(R.sup.15)OR.sup.16' (f'):exhibit mucosa-protective and/or gastric acid secretion-inhibiting properties, such that they can be used for the control or prevention of illnesses of the gastrointestinal tract, especially against gastric ulcers and/or duodenal ulcers.
    Type: Grant
    Filed: March 17, 1988
    Date of Patent: May 29, 1990
    Assignee: Hoffman-La Roche Inc.
    Inventors: Albert Fischli, Eva-Maria Gutknecht, Daniel Obrecht
  • Patent number: 4902832
    Abstract: A compound of the formula: ##STR1## wherein R.sub.1 is a hydrogen atom, a fluorine atom or a methyl group and R.sub.2 is as C.sub.1 -C.sub.3 alkyl group, a C.sub.1 -C.sub.5 alkoxy group, a chloro(C.sub.2 -C.sub.4)alkoxy group, a dichloro(C.sub.2 -C.sub.4)alkoxy group, a cyclo(C.sub.3 -C.sub.7)alkoxy group, a phenoxy group, a C.sub.1 -C.sub.5 alkylthio group or a di(C.sub.1 -C.sub.5)alkylamino group, which is useful as a herbicide.
    Type: Grant
    Filed: January 10, 1986
    Date of Patent: February 20, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toru Haga, Eiki Nagano, Ryo Yoshida, Shunichi Hashimoto
  • Patent number: 4806690
    Abstract: A method for producing amines, the method comprising contacting at reactive conditions at least one alcohol, aldehyde or ketone, or a mixture thereof, with an aminating agent in the presence of a catalyst, is improved by employing as the catalyst a composition comprising cobalt, copper, and a third component selected from a group consisting of iron, zinc, zirconium and mixtures thereof.
    Type: Grant
    Filed: May 13, 1985
    Date of Patent: February 21, 1989
    Assignee: The Dow Chemical Company
    Inventor: Robert G. Bowman
  • Patent number: 4772750
    Abstract: A method for producing amines, the method comprising contacting at reactive conditions at least one alcohol, aldehyde or ketone, or a mixture thereof, with an aminating agent in the presence of a cobalt/copper catalyst, is improved by employing as the catalyst a composition comprising cobalt and copper, the catalyst being prepared by the molten salt impregnation technique.
    Type: Grant
    Filed: October 3, 1986
    Date of Patent: September 20, 1988
    Assignee: The Dow Chemical Company
    Inventor: Clarence E. Habermann
  • Patent number: 4757144
    Abstract: A tertiary amine is effectively prepared by reacting a primary or secondary amine with formaldehyde in the presence of a palladium or platinum catalyst at a hydrogen pressure of 3 to 50 kg/cm2 (gauge pressure) at a temperature of 80.degree. to 180.degree. C., by controlling the addition of formaldehyde to the starting amine.
    Type: Grant
    Filed: September 30, 1986
    Date of Patent: July 12, 1988
    Assignee: Kao Corporation
    Inventors: Kazuhiko Okabe, Yukinaga Yokota, Kazuhito Matsutani, Tatuhiro Imanaka
  • Patent number: 4730075
    Abstract: A process for the production of (1) an ether or (2) a second amine comprises reacting an activated olefin with respectively an alcohol or first amine in the presence of a catalyst which is either (a) an amidine or (b) a Lewis base and epoxide. The same catalyst may also be used to carry out the reverse reaction in which an activated olefin and an alcohol or first amine are produced from the appropriate ether or second amine.
    Type: Grant
    Filed: June 20, 1986
    Date of Patent: March 8, 1988
    Assignee: BP Chemicals Limited
    Inventor: Michael J. Green
  • Patent number: 4719046
    Abstract: The present invention relates to compounds of formula (I)ArCH.sub.2 R.sup.1 (I)or a monomethyl or a monoethyl ether thereof (the compound of formula (I) including these ethers may contain no more than 30 carbon atoms in total); ethers, esters thereof; acid addition salts thereof; wherein Ar is a chrysene or substituted chrysene ring system; R.sup.1 contains not more than eight carbon atoms and is a group ##STR1## wherein m is 0 or 1;R.sup.5 is hydrogen;R.sup.6 and R.sup.7 are the same or different and each is hydrogen or C.sub.1-3 alkyl optionally substituted by hydroxy;R.sup.8 and R.sup.9 are the same or different and each is hydrogen or C.sub.1-3 alkyl, ##STR2## is a five- or six-membered saturated carbocyclic ring; R.sup.10 is hydrogen, methyl or hydroxymethyl;R.sup.11, R.sup.12 and R.sup.13 are the same or different and each is hydrogen or methyl;R.sup.14 is hydrogen, methyl, hydroxy, or hydroxymethyl.
    Type: Grant
    Filed: October 18, 1984
    Date of Patent: January 12, 1988
    Assignee: Burroughs Wellcome Co.
    Inventor: Kenneth W. Bair
  • Patent number: 4665174
    Abstract: A process for preparing cyclopentenone derivatives of the formula: ##STR1## wherein R.sup.1 is hydrogen, lower alkyl or lower alkenyl, R.sup.2 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, cycloalkyl, substituted or unsubstituted aryl or substituted or unsubstituted ar(lower)alkyl and A is the residue of a nucleophilic agent from which a hydrogen atom is excluded, which comprises reacting a 3-hydroxy-4-cyclopentenone compound of the formula: ##STR2## wherein R.sup.1 and R.sup.2 are each as defined above with a nucleophilic agent of the formulaA--H (III)wherein A is as defined above.The cyclopentenone derivatives of the formula (I) are useful as pharmaceuticals, agricultural chemicals, perfumes and as intermediates for the preparation of agricultural chemicals, pharmaceuticals and perfumes.
    Type: Grant
    Filed: May 11, 1982
    Date of Patent: May 12, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masayoshi Minai, Tadashi Katsura
  • Patent number: 4543411
    Abstract: Secondary and tertiary amines are selectively prepared by a process comprising reacting an olefin, a nitrogen-containing compound and synthesis gas in the presence of a catalyst system comprising a ruthenium-containing compound mixed with a quaternary onium salt, optionally in the presence of a solvent, heating the resultant mixture to a temperature of at least 100.degree. C. and a pressure of at least 100 psi until there is substantial formation of the desired tertiary amine and separating the desired amine by a phase separation technique.
    Type: Grant
    Filed: November 10, 1983
    Date of Patent: September 24, 1985
    Assignee: Texaco Inc.
    Inventors: John F. Knifton, David C. Alexander
  • Patent number: 4521624
    Abstract: Process for preparing cyclic amines by the reductive amination of saturated cyclic ketones. For example, cyclohexanone is reductively aminated to obtain N,N-dimethylcyclohexylamine.
    Type: Grant
    Filed: April 16, 1984
    Date of Patent: June 4, 1985
    Assignee: Ethyl Corporation
    Inventor: Philip F. Jackisch
  • Patent number: 4487966
    Abstract: 3-Aminomethyl-1-(3-aminopropyl-1-methyl)-4-methylcyclohexane and a process for the preparation of this new compound, which uses limonene and/or monohydroformylation products of limonene as starting substances and proceeds via a dihydroformylation product of limonene. The new compound is useful as a corrosion inhibitor, as a crosslinking agent for epoxide resins and as a chain lengthening agent for NCO prepolymers.
    Type: Grant
    Filed: July 15, 1983
    Date of Patent: December 11, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Paul Fiedler, Rudolf Braden
  • Patent number: 4480137
    Abstract: Described is a carbonylation process using novel homogeneous trihydrocarbyl silyl-substituted alkyl diaryl phosphine transition metal complexes of the general formula:[(Ar.sub.2 PQ).sub.y SiR.sub.4 --y].sub.g (MX.sub.n).sub.swherein Ar is a C.sub.6 to C.sub.10 aromatic hydrocarbyl radical, Q is a C.sub.1 to C.sub.30 saturated straight chain divalent radical, R is a C.sub.1 to C.sub.10 hydrocarbyl, wherein Ar, Q and R, can be substituted or unsubstituted, y is 1 to 4, g times y is 1 to 6, M is a transition metal selected from the group consisting of Group VIII transition metals, X is an anion or organic ligand excluding halogen satisfying the valence and coordination sites of the metal, n is 2 to 6 and s is 1 to 3, are disclosed. These materials exhibit high thermal stability and are superior catalysts for the selective hydroformylation of olefins, particularly in the presence of excess quantities of ligand of the formula:(Ar.sub.2 PQ).sub.y SiR.sub.4 -.sub.ywherein Ar, Q, R, and y are as previously defined.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: October 30, 1984
    Assignee: Exxon Research & Engineering Company
    Inventors: Alexis A. Oswald, Torris G. Jermansen, Andrew A. Westner, I-Der Huang
  • Patent number: 4442286
    Abstract: This invention relates to the preparation of amines by the reduction of imines with phosphorous acid, preferably under basic conditions.
    Type: Grant
    Filed: October 15, 1976
    Date of Patent: April 10, 1984
    Assignee: Petrolite Corporation
    Inventor: Derek Redmore
  • Patent number: 4434299
    Abstract: A process for the preparation of aniline by reaction of alicyclic alcohols or ketones with ammonia in the presence of a crystalline silicate catalyst having the structure of ZSM-5. Especially preferred alicyclic charge stocks are the mononuclear naphthenic type compounds such as cyclohexanol and cyclohexanone or mixtures thereof.
    Type: Grant
    Filed: November 12, 1982
    Date of Patent: February 28, 1984
    Assignee: Mobil Oil Corporation
    Inventors: Clarence D. Chang, William H. Lang
  • Patent number: 4429157
    Abstract: Primary amines and/or diamines can be prepared from oxo compounds, optionally containing additional reducible groups, by a process comprising:(1) reacting the oxo compound with ammonia in the presence of an imine-forming catalyst, preferably an ion exchanger loaded with ammonia ions, at a temperature of 10.degree. to 120.degree. C. and a pressure of 1 to 300 bar, whereby a Schiff base is formed; and(2) reducing the Schiff base by reaction with ammonia and hydrogen in the presence of a hydrogenation catalyst.
    Type: Grant
    Filed: June 10, 1981
    Date of Patent: January 31, 1984
    Inventors: Josef Disteldorf, Werner Hubel, Lothar Broschinski
  • Patent number: 4317932
    Abstract: A process for forming amines by contacting, in a liquid media, an olefinic compound, carbon monoxide, water, and ammonia in the presence of a rhodium atom containing compound selected from metallic rhodium, rhodium salts, rhodium oxides, and rhodium carbonyls and ligands thereof at a temperature of from 50.degree. to 250.degree. C. and at a pressure of from about 10 to about 300 atmospheres.
    Type: Grant
    Filed: February 22, 1980
    Date of Patent: March 2, 1982
    Assignee: W. R. Grace & Co.
    Inventor: Felek Jachimowicz