By Reductive Amination Patents (Class 564/397)
  • 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: 6072085
    Abstract: The method of the present invention provides a simple general route to a wide range of secondary amines.
    Type: Grant
    Filed: September 30, 1997
    Date of Patent: June 6, 2000
    Assignee: Massachusetts Institute of Technology
    Inventors: Xavier Verdaguer, Udo E. W. Lange, Stephen L. Buchwald
  • Patent number: 5977411
    Abstract: This invention provides a method for preparing 4-ADPA by charging nitrobenzene into a reaction zone under hydrogen pressure in the presence of a strong organic base and a catalyst for hydrogenation. The method provides the convenience and economy of a one-step process, while producing improved yields and selectivities. The invention further provides for various embodiments of the foregoing which are suitable for the production of 4-ADPA, and the hydrogenation or reductive alkylation to produce PPD. Important to the invention are the molar ratios of aniline to nitrobenzene and nitrobenzene to the strong organic base and the choice and use of hydrogenation catalyst.
    Type: Grant
    Filed: June 10, 1997
    Date of Patent: November 2, 1999
    Assignee: Flexsys America L.P.
    Inventor: Antonio L. DeVera
  • Patent number: 5973205
    Abstract: A process for preparing a compound of formula (I) or an addition salt thereof and/or a solvate thereof: ##STR1## wherein R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are each independently C.sub.1-4 alkoxy and R.sup.3 is C.sub.1-6 alkyl, which process comprises reacting an arylamine of formula (II): ##STR2## wherein R.sup.4 and R.sup.5 are as defined in relation to formula (I) with a .beta.-aminoaldehyde of formula (III): ##STR3## wherein R.sup.1, R.sup.2 and R.sup.3 are as defined in relation to formula (I); and thereafter reducing the intermediate so formed and, optionally, forming an addition salt of the compound of formula (I) and/or a solvate thereof.
    Type: Grant
    Filed: April 23, 1998
    Date of Patent: October 26, 1999
    Assignee: SmithKline Beecham plc
    Inventors: Thomas Weir Ramsay, Robin Patrick Attrill
  • Patent number: 5885538
    Abstract: The present invention provides a method and composition regeneration of an aminal that has previously been reacted with a sulfide selected from hydrogen sulfide and mercaptans. The method includes contacting a scavenging mixture which includes an aminal, and an oxidation catalyst with a gas such as air, oxygen enriched air, oxygen, ozone enriched air and ozone. The composition includes an aminal, and an oxidation catalyst. The method and composition are useful for the regeneration of an aminal base sulfur scavenging compound.
    Type: Grant
    Filed: July 2, 1997
    Date of Patent: March 23, 1999
    Assignee: Quaker Chemical Corporation
    Inventors: Edward A. Trauffer, Muge Caglar
  • Patent number: 5861535
    Abstract: Tertiary aminoaryl compounds, such as N,N'dialkylaminoaryl compounds, are prepared using successive reductive steps without isolation therebetween, at high temperature and pressure. A nitroaryl compound is reduced using a ketone as both solvent and reactant in a reductive environment, and the resulting intermediate is further reacted with an aldehyde in the same reaction mixture without isolation to provide the second substituent on the amino group.
    Type: Grant
    Filed: September 23, 1997
    Date of Patent: January 19, 1999
    Assignee: Eastman Kodak Company
    Inventor: Victor L. Mylroie
  • Patent number: 5817876
    Abstract: Preparation of an N-alkyl-arylamine of the formula ##STR1## in which Ar represents an aryl radical which is optionally monosubstituted or polysubstituted by at least one of halogen and in each case optionally substituted alkyl, alkoxy or alkoxycarbonyl,R.sup.1 represents hydrogen or alkyl andR.sup.2 represents in each case optionally substituted alkyl or aryl, or, together with R.sup.1, represents alkanediyl,by reacting a nitroarene of the formulaAr--NO.sub.2 (II)with a carbonyl compound of the formulaR.sup.1 --CO--R.sup.2 (III)in the presence of hydrogen and in the presence of a catalyst at a temperature between 0.degree. C. and 200.degree. C.
    Type: Grant
    Filed: September 22, 1994
    Date of Patent: October 6, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Fritz Maurer, Lothar Rohe, Hans-Joachim Knops
  • 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: 5719298
    Abstract: A method of producing a pantothenic acid derivative of formula (I): ##STR1## wherein each of R.sup.1 and R.sup.2 is different, and is a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, or a phenyl group; or a straight chain aliphatic hydrocarbon group having 5 to 10 carbon atoms, is provided, including methods of producing the starting materials for producing the same and novel amine derivative that can be used for the production of the pantothenic acid derivative.
    Type: Grant
    Filed: May 22, 1995
    Date of Patent: February 17, 1998
    Assignee: Fujirebio Inc.
    Inventors: Hiroshi Ikawa, Hajime Matsumoto
  • Patent number: 5654483
    Abstract: A process for producing an alkoxy-substituted tri-phenylamine comprising reacting an alkoxy-substituted cyclohexanone with a diphenylamine or an aniline, while forming said cyclohexanone in the same system from an alkoxy-substituted phenol by using said phenol as a hydrogen acceptor, in the presence of a hydrogen transfer catalyst and a catalytic amount of the alkoxy-substituted cyclohexanone corresponding to the alkoxy-substituted phenol used for the reaction, or after converting partially the alkoxy-substituted phenol to a catalytic amount of the alkoxy-substituted cyclohexanone under a hydrogen pressure in the presence of a hydrogen transfer catalyst, wherein a surface-supported catalyst is used as the hydrogen transfer catalyst.
    Type: Grant
    Filed: December 19, 1995
    Date of Patent: August 5, 1997
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Chiyuki Kikuchi, Hiroshi Naruse, Masaru Wada, Teruyuki Nagata
  • Patent number: 5633407
    Abstract: A process for preparing substituted aromatic azo compounds is provided which comprises contacting a nucleophilic compound and an azo containing compound in the presence of a suitable solvent system, and reacting the nucleophilic compound and the azo containing compound in the presence of a suitable base and a controlled amount of protic material at a temperature of about 10.degree. C. to about 150.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1. In another embodiment, the substituted aromatic azo compounds are further reacted with a nucleophilic compound in the presence of a suitable solvent system, a suitable base and a controlled amount of protic material at a temperature of about 70.degree. C. to about 200.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1 to produce a substituted aromatic amine.
    Type: Grant
    Filed: May 18, 1995
    Date of Patent: May 27, 1997
    Assignee: Flexsys America L. P.
    Inventors: Michael K. Stern, Brian K-M Cheng
  • Patent number: 5618979
    Abstract: A process for preparing substituted aromatic amines which comprises contacting a nucleophilic compound and a substituted aromatic azo compound in the presence of a suitable solvent system, and reacting the nucleophilic compound and the substituted aromatic azo compound in the presence of a suitable base and a controlled amount of protic material at a temperature of about 70.degree. C. to about 200.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1. In another embodiment, the substituted aromatic amines of the invention are reductively alkylated to produce alkylated diamines or substituted derivatives thereof.
    Type: Grant
    Filed: May 18, 1995
    Date of Patent: April 8, 1997
    Assignee: Flexsys America L. P.
    Inventors: Michael K. Stern, Brian K-M Cheng
  • Patent number: 5616799
    Abstract: A process for the preparation of glycoloylanilide of the formula (G) ##STR1## is recited that involves reacting a nitrobenzene with hydrogen and, if desired, with a carbonyl compound, in the presence of a noble metal catalyst and a solvent, reacting the compound produced with chloroacetyl chloride, reacting the resulting product with a benzyl alcohol and with a base, or reacting the resulting compound with an O-benzylglycoloyl chloride, and debenzylating the resulting benzylglycoloylanilide product by reacting with hydrogen in the presence of a noble metal catalyst. The invention also relates to a process for the preparation of O-benzylglycoloylanilide.
    Type: Grant
    Filed: April 17, 1995
    Date of Patent: April 1, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Siegfried Planker, Theodor Papenfuhs
  • Patent number: 5608111
    Abstract: A method of producing 4-ADPA is disclosed wherein aniline or substituted aniline derivatives and nitrobenzene are reacted under suitable conditions to produce 4-nitrodiphenylamine or substituted derivatives thereof and/or 4-nitrosodiphenylamine or substituted derivatives thereof and/or their salts, either or both of which are subsequently reduced to produce 4-ADPA or substituted derivatives thereof. The 4-ADPA or substituted derivatives thereof can be reductively alkylated to produce p-phenylenediamine products or substituted derivatives thereof which are useful as antiozonants.
    Type: Grant
    Filed: May 5, 1995
    Date of Patent: March 4, 1997
    Assignee: Flexsys America L. P.
    Inventors: Michael K. Stern, James M. Allman, James K. Bashkin, Roger K. Rains
  • Patent number: 5545751
    Abstract: A process for the preparation of 4-methoxy-2,2',6-trimethyldiphenylamine, which comprises heating and reacting 2,6-dimethylcyclohexanone and 2-methyl-4-methoxyaniline in the presence of a dehydrogenation catalyst while removing the resultant hydrogen and water from the reaction system.
    Type: Grant
    Filed: December 14, 1994
    Date of Patent: August 13, 1996
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Chiyuki Kusuda, Masayuki Furuya, Masaru Wada, Yoshihiro Irizato, Hiroshi Naruse, Teruyuki Nagata
  • Patent number: 5536878
    Abstract: Disclosed are (1) a method for preparing an aromatic secondary amino compound which comprises reacting an N-cyclohexylideneamino compound in the presence of a hydrogen moving catalyst and a hydrogen acceptor by the use of a sulfur-free polar solvent and/or a cocatalyst, and (2) a method for preparing an aromatic secondary amino compound which comprises reacting cyclohexanone or a nucleus-substituted cyclohexanone, an amine and a nitro compound corresponding to the amine in a sulfur-free polar solvent in the presence of a hydrogen moving catalyst, a cocatalyst being added or not added. In a further aspect, a method is provided for the preparation of aminodiphenylamine by reacting phenylenediamine and cyclohexanone in the presence of a hydrogen transfer catalyst in a sulfur-free polar solvent while using nitroaniline as a hydrogen acceptor.
    Type: Grant
    Filed: December 2, 1994
    Date of Patent: July 16, 1996
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Teruyuki Nagata, Chiyuki Kusuda, Masaru Wada, Kenichi Satou, Masae Uchida
  • Patent number: 5453541
    Abstract: A method of producing 4-ADPA is disclosed wherein aniline or substituted aniline derivatives and nitrobenzene are reacted under suitable conditions to produce 4-nitrodiphenylamine or substituted derivatives thereof and/or 4-nitrosodiphenylamine or substituted derivatives thereof and/or their salts, either or both of which are subsequently reduced to produce 4-ADPA or substituted derivatives thereof. The 4-ADPA or substituted derivatives thereof can be reductively alkylated to produce p-phenylenediamine products or substituted derivatives thereof which are useful as antiozonants.
    Type: Grant
    Filed: December 6, 1993
    Date of Patent: September 26, 1995
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, James K. Bashkin
  • Patent number: 5449829
    Abstract: A diphenylamine with both the phenyl groups being substituted is prepared by reacting a phenol with ammonia in the presence of a hydrogen transfer catalyst and a cyclohexanone; or by converting a portion of the phenol to the cyclohexanone in the presence of a hydrogen transfer catalyst and under hydrogen pressure and then reacting the remaining portion of the phenol with ammonia in the presence of the cyclohexanone so converted and the hydrogen transfer catalyst. The diphenylamine can be obtained very efficiently.
    Type: Grant
    Filed: June 15, 1994
    Date of Patent: September 12, 1995
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Chiyuki Kusuda, Masaru Wada, Teruyuki Nagata
  • Patent number: 5442114
    Abstract: There is disclosed a process for producing an aromatic amide compound of the general formula (4), including the steps of subjecting an o-nitrophenol compound of the general formula (1) to catalytic reduction in acetone or an aromatic hydrocarbon solvent under the presence of a nickel catalyst to give an o-aminophenol compound of the general formula (2); and (b) subjecting the o-aminophenol compound of the general formula (2) to condensation with an acid chloride compound having a sulfur content of 0.5% or less, based on the weight of the acid chloride compound, of the general formula (3) in acetone or an aromatic hydrocarbon solvent under an atmosphere of an inert gas having an oxygen concentration of 1% or less. The acid chloride compound having a sulfur content of 0.5% or less, based on the weight of the acid chloride compound, of the general formula (3) may be obtained by allowing a carboxylic acid compound of the general formula (5) to react with thionyl chloride and by concentrating the reaction mixture.
    Type: Grant
    Filed: January 18, 1994
    Date of Patent: August 15, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kan Takamine, Michio Yamato, Akira Murakami, Tooru Tokumaru, Yoshinori Nakayama, Motoo Hazama
  • Patent number: 5436371
    Abstract: A process for preparing p-nitroaromatic amides is provided which comprises contacting a nitrile, nitrobenzene, a suitable base and water in the presence of a suitable solvent system to form a mixture, and reacting the mixture at a suitable temperature in a confined reaction zone in the presence of a controlled amount of protic material. The p-nitroaromatic amides of the invention can be reduced to p-aminoaromatic amides. In one embodiment, the p-aminoaromatic amide is further reacted with ammonia under conditions which produce the corresponding p-aminoaromatic amine and the amide corresponding to the nitrile starting material or with water in the presence of a suitable basic or acidic catalyst under conditions which produce the corresponding p-aminoaromatic amine and the acid or salt thereof corresponding to the nitrile starting material. In another embodiment, the p-aminoaromatic amine is reductively alkylated to produce alkylated p-aminoaromatic amine.
    Type: Grant
    Filed: August 29, 1994
    Date of Patent: July 25, 1995
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, Brian K. Cheng
  • Patent number: 5382690
    Abstract: Disclosed are(1) a method for preparing an aromatic secondary amino compound which comprises reacting an N-cyclohexylideneamino compound in the presence of a hydrogen moving catalyst and a hydrogen acceptor by the use of a sulfur-free polar solvent and/or a cocatalyst, and(2) a method for preparing an aromatic secondary amino compound which comprises reacting cyclohexanone or a nucleus-substituted cyclohexanone, an amine and a nitro compound corresponding to the amine in a sulfur-free polar solvent in the presence of a hydrogen moving catalyst, a cocatalyst being added or not added.
    Type: Grant
    Filed: August 2, 1993
    Date of Patent: January 17, 1995
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Teruyuki Nagata, Chiyuki Kusuda, Masaru Wada, Kenichi Satou
  • Patent number: 5380946
    Abstract: A process for preparing p-nitroaromatic amides is provided which comprises contacting a nitrile, nitrobenzene, a suitable base and water in the presence of a suitable solvent system to form a mixture, and reacting the mixture at a suitable temperature in a confined reaction zone in the presence of a controlled amount of protic material. The p-nitroaromatic amides of the invention can be reduced to p-aminoaromatic amides. In one embodiment, the p-aminoaromatic amide is further reacted with ammonia under conditions which produce the corresponding p-aminoaromatic amine and the amide corresponding to the nitrile starting material or with water in the presence of a suitable basic or acidic catalyst under conditions which produce the corresponding p-aminoaromatic amine and the acid or salt thereof corresponding to the nitrile starting material. In another embodiment, the p-aminoaromatic amine is reductively alkylated to produce alkylated p-aminoaromatic amine.
    Type: Grant
    Filed: July 30, 1993
    Date of Patent: January 10, 1995
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, Brian K. M. Cheng
  • Patent number: 5344987
    Abstract: Optionally substituted diphenylamines can be obtained by reacting optionally substituted anilines with optionally substituted cyclohexanones over a supported catalyst at 200.degree.-450.degree. C. and 0.1-20 bar, the supported catalyst containing one or more metals having a dehydrogenating action selected from the group Ru, Pd, Os, Ir, Pt, Fe, Co, Ni, Re, Mn, Cu, Ag, Cr and Ce.
    Type: Grant
    Filed: July 16, 1993
    Date of Patent: September 6, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Immel, Gerhard Darsow, Hans-Josef Buysch
  • Patent number: 5276193
    Abstract: A process for preparing an N-alkyl-substituted aminophenol is disclosed, comprising continuously feeding an aldehyde or a ketone to a reaction system containing an organic solvent, a catalyst for reduction, hydrogen, and an aminophenol to conduct a reductive alkylation reaction, wherein said reductive alkylation reaction is carried out while continuously adding an organic carboxylic acid into the reaction system. The process attains a high yield even when the catalyst is repeatedly used and does not cause corrosion of equipment.
    Type: Grant
    Filed: August 1, 1990
    Date of Patent: January 4, 1994
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Hiroshi Maki, Michihiro Kawasaki, Hiroshi Shimizu, Yoshiaki Ito
  • Patent number: 5252737
    Abstract: A process for preparing N-aliphatic substituted p-phenylenediamine intermediates is provided which comprises contacting an aliphatic amine or substituted aliphatic amine derivative and nitrobenzene in the presence of a suitable solvent system, and reacting the aliphatic amine or substituted aliphatic amine derivative and nitrobenzene in the presence of a suitable base and a controlled amount of protic material at a suitable temperature in a confined reaction zone. In one embodiment, the N-aliphatic substituted p-phenylenediamine intermediates are reduced to N-aliphatic substituted p-phenylenediamines and the N-aliphatic substituted p-phenylenediamines can be reductively alkylated to N'-alkylated, N-aliphatic substituted p-phenylenediamines. In another embodiment of the invention, N-aliphatic substituted p-phenylenediamine intermediates are reductively alkylated to N'-alkylated, N-aliphatic substituted p-phenylenediamines.
    Type: Grant
    Filed: May 22, 1992
    Date of Patent: October 12, 1993
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, Brian K. Cheng
  • Patent number: 5231217
    Abstract: The present invention is directed to a novel solvent-free process for preparing amine terminated compounds by reacting a polyfunctional acetoacetic acid ester with either ammonia or an organic compound which contains one or more primary amino groups in the presence of an acidic catalyst selected from the group consisting of (i) boron trifluoride etherate and (ii) organic acids having pKa values of from 0.1 to 0.8.
    Type: Grant
    Filed: March 20, 1991
    Date of Patent: July 27, 1993
    Assignee: Miles Inc.
    Inventors: Robert P. Yeater, Robson Mafoti, Josef Sanders
  • Patent number: 5202485
    Abstract: A process for preparing an N-alkylaminophenol is disclosed, comprising subjecting an aminophenol to reductive alkylation with an aldehyde or a ketone in the presence of an organic solvent and hydrogen, wherein the reductive alkylation is carried out at a temperature of from 20.degree. to 70.degree. C. in the further presence of a catalyst for reduction comprising platinum and at least one metal element selected from metal elements belonging to the IB group, IIB group, IVB group, VB group, and VIB group of the Periodic Table, supported on activated carbon, or comprising palladium and at least one metal element selected from metal elements belonging to the IB group, IIB group, IVB group, VB group and VIB group of the Periodic Table, supported on activated carbon.
    Type: Grant
    Filed: April 29, 1991
    Date of Patent: April 13, 1993
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Hiroshi Maki, Michihiro Kawasaki, Horishi Shimizu, Yoshiaki Ito
  • Patent number: 5117063
    Abstract: A method of producing 4-ADPA is disclosed wherein aniline and nitrobenzene are reacted under suitable conditions to produce 4-nitrodiphenylamine and/or 4-nitrosodiphenylamine and/or their salts, either or both of which are subsequently reduced to produce 4-ADPA. The 4-ADPA can be reductively alkylated to produce p-phenylenediamine products which are useful as antiozonants.
    Type: Grant
    Filed: June 21, 1991
    Date of Patent: May 26, 1992
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, James K. Bashkin
  • 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: 5066824
    Abstract: The present invention is directed to a process for preparing amine terminated compounds by reacting a polyfunctional acetoacetic acid ester with either ammonia or an organic compound which contains one or more primary amino groups in the presence of a solvent and an acidic catalyst selected from the group consisting of (i) boron trifuloride etherate and (ii) organic acids having pKa values of from 0.1 to 0.8 with the proviso that if the primary amino group containing compound contains no aromatically bound amino groups, the pKa of said organic acid is from 0.1 to less than 0.7.
    Type: Grant
    Filed: August 3, 1990
    Date of Patent: November 19, 1991
    Assignee: Mobay Corporation
    Inventors: Robson Mafoti, Josef Sanders
  • Patent number: 5053540
    Abstract: The present invention relates to a process for the preparation of a p-aminodiphenylamine comprising reacting N-phenylquinoneimine of the formula: ##STR1## with ammonia, ammonium hydroxide or mixtures thereof, wherein the molar ratio of N-phenylquinoneimine to NH.sub.3 in the reaction mixture ranges from about 1:1 to 1:80.
    Type: Grant
    Filed: March 8, 1990
    Date of Patent: October 1, 1991
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Kirkwood S. Cottman
  • Patent number: 5011996
    Abstract: Reaction products of oxo compounds and amines or ammonia, in which at least one substituent is aromatic and monosubstituted to trisubstituted by halogen, can be catalytically hydrogenated to the respective amines, the halogen essentially being completely retained if an Ni-containing or Co-containing catalyst is employed and the reaction is carried out in the presence of organic sulphur compounds.
    Type: Grant
    Filed: July 5, 1989
    Date of Patent: April 30, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfgang Kiel, Heinz Ziemann
  • Patent number: 4992587
    Abstract: Process for preparing a ruthenium promoted, halogen-containing, nickel and/or cobalt catalyst includes impregnating, in one or more steps, a porous metal oxide support with a nickel compound and/or a cobalt compound, and a ruthenium compound to form a catalyst intermediate; reducing the nickel compound and/or cobalt compound, and ruthenium compound, in one or more steps, to the respective metal by reacting the catalyst intermediate with hydrogen gas at an elevated temperature sufficient to reduce the respective compounds to the metal; and introducing halogen by adding a halide compound at any stage in the process. Catalyst prepared by the above process and use thereof.
    Type: Grant
    Filed: June 2, 1989
    Date of Patent: February 12, 1991
    Assignee: Berol Kemi AB
    Inventor: Juhan Koll
  • Patent number: 4968843
    Abstract: The present invention relates to a process for the preparation of a N-substituted phenylenediamine of the formula: ##STR1## comprising reacting N-phenylquinoneimine of the formula: ##STR2## with a primary amine of the formula:R--NH.sub.2 (III),wherein the molar ratio of II to III in the reaction mixture ranges from about 1:1 to 1:10; and wherein R is selected from the group of radicals consisting of alkyls having 1 to 20 carbon atoms, cycloalkyls having 6 to 8 carbon atoms and radicals of the structural formula: ##STR3## wherein R.sup.2 may be the same or different and is independently selected from the group of radicals consisting of hydrogen and an alkyl having 1 carbon atom, R.sup.3 is selected from the group of radicals consisting of an alkyl having 1 to 12 carbon atoms and n is an integer of from 0 to 6. The present process is characterized by its excellent yields of high purity N-substituted phenylenediamines.
    Type: Grant
    Filed: March 8, 1990
    Date of Patent: November 6, 1990
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Kirkwood S. Cottman
  • Patent number: 4967004
    Abstract: A process for producing an N,N-diethylaminophenol is disclosed, comprising subjecting an aminophenol to reductive alkylation with acetaldehyde in the presence of a solvent, a catalyst, and hydrogen is disclosed, in which the reaction mixture from which the catalyst has been removed is subjected to distillation while maintaining the temperature of the bottom at 160.degree. C. or lower to substantially remove the unreacted acetaldehyde and the solvent, the residual bottom is distilled while maintaining the temperature of the bottom at 200.degree. C. or lower to recover a crude N,N-diethylaminophenol as a distillate, and the recovered crude N,N-diethylaminophenol is contacted with a solvent to which at least one of acid sulfites and dithionites has been added, said solvent being substantially incompatible with the N,N-diethylaminophenol, in an inert gas atmosphere, followed by precipitating and recovering the N,N-diethylaminophenol by cooling.
    Type: Grant
    Filed: April 8, 1988
    Date of Patent: October 30, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroshi Maki, Shigeru Sasaki
  • Patent number: 4952731
    Abstract: Diphenylamines or N,N'-diphenyl-phenylenediamines can be obtained by heat-reacting an aniline or a phenylenediamine with preferably an excess of a phenol in an amount of 4 to 20 moles per mole of the aniline or phenylenediamine in th presence of a hydrogen transfer catalyst and a cyclohexanone corresponding to said phenol.The excess phenol used in the reaction undergoes reduction in the reaction system to form a cyclohexanone, which in turn reacts with the aniline or phenylenediamine to form a Schiff base and is thus consumed. The Schiff base forms the intended product by means of a dehydrogenation reaction, and the hydrogen evolved at this time reduces the phenol to form a cyclohexanone.The phenol present in excess thus becomes in the system a solvent, a starting material for the cyclohexanone, and an acceptor of the hydrogen that forms as a by-product at the time of formation of the intended product.
    Type: Grant
    Filed: August 15, 1988
    Date of Patent: August 28, 1990
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Teruyuki Nagata, Akihiro Tamaki, Nobuyuki Kajimoto, Masaru Wada
  • Patent number: 4804783
    Abstract: Diphenylamines or N,N'-diphenyl-phenylenediamines can be obtained by heat-reacting an aniline or a phenylenediamine with preferably an excess of a phenol in an amount of 4 to 20 moles per mole of the aniline or phenylenediamine in the presence of a hydrogen transfer catalyst and a cyclohexanone corresponding to said phenol.The excess phenol used in the reaction undergoes reduction in the reaction system to form a cyclohexanone, which in turn reacts with the aniline or phenylenediamine to form a Schiff base and is thus consumed. The Schiff base forms the intended product by means of a dehydrogenation reaction, and the hydrogen evolved at this time reduces the phenol to form a cyclohexanone.The phenol present in excess thus becomes in the system a solvent, a starting material for the cyclohexanone, and an acceptor of the hydrogen that forms as a by-product at the time of formation of the intended product.
    Type: Grant
    Filed: July 31, 1987
    Date of Patent: February 14, 1989
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Teruyuki Nagata, Akihiro Tamaki, Nobuyuki Kajimoto, Masaru Wada
  • Patent number: 4713488
    Abstract: Cycloalkyl aminophenol derivatives are produced by reacting o-, m- or p-aminophenol with a cycloalkanone having 5 to 12 carbon atoms in the presence of a reducing agent and preferably with the addition of an acid.
    Type: Grant
    Filed: October 11, 1985
    Date of Patent: December 15, 1987
    Assignee: Kanzaki Paper Manufacturing Co., Ltd.
    Inventors: Masayuki Omatsu, Naoki Yonese, Mitsuru Kondo
  • Patent number: 4621158
    Abstract: A method for making amines by reacting alcohols and/or aldehydes with primary and/or secondary amines or with ammonia in the presence of a catalyst at elevated temperature, and optionally at elevated pressure, in the liquid phase, the catalyst being an unsupported catalyst consisting of a combination of copper and tin compounds.
    Type: Grant
    Filed: August 21, 1985
    Date of Patent: November 4, 1986
    Assignee: Schering Aktiengesellschaft
    Inventors: Hans-Juergen Hubert, Klaus D. Tillmetz
  • Patent number: 4539403
    Abstract: There is disclosed a process for the preparation of a 2-alkyl-4-amino-5-aminomethylpyrimidine, which comprises subjecting a 2-alkyl-4-amino-5-formylpyrimidine to catalytic reaction with hydrogen and ammonia in the presence of a reduction catalyst.According to the process of this invention, the desired product can be obtained in much higher yield as compared with the processes known to the art.
    Type: Grant
    Filed: January 26, 1983
    Date of Patent: September 3, 1985
    Assignee: UBE Industries, Ltd.
    Inventors: Kozo Fujii, Keigo Nishihira, Hiroyuki Sawada, Shuji Tanaka, Mamoru Nakai, Hiroshi Yoshida, Teruhiko Inoue, Kiyosi Oomori
  • Patent number: 4536577
    Abstract: Disclosed is a process for preparing 2-alkyl-4-amino-5-aminomethylpyrimidine comprising (i) a first step of reacting 2-alkyl-4-amino-5-formylpyrimidine with ammonia in an inert solvent in the presence of at least one compound selected from heteropolyacids, isopolyacids, oxyacids and salts thereof containing molybdenum or tungsten, and (ii) a second step of reacting the reaction product in the first step catalytically with ammonia and hydrogen in an inert solvent in the presence of a reducing catalyst together with or without a hydroxide of an alkali metal or alkaline earth metal.
    Type: Grant
    Filed: March 26, 1984
    Date of Patent: August 20, 1985
    Assignee: Ube Industries, Ltd.
    Inventors: Hiroshi Yoshida, Sadao Niida
  • Patent number: 4506039
    Abstract: Polymer-containing polyether polyamines containing terminal aromatically-bound amino groups are produced by in situ polymerization of a polyether polyamine with an olefinically unsaturated monomer. The polyether polyamine starting material must have terminal aromatic amino groups, a molecular weight of from 800 to 10,000 and an aromatic amino group content of from 0.3 to 16 wt. %. Suitable olefinically unsaturated monomers include .alpha.,.beta.-unsaturated nitriles, aromatic vinyl compounds, .alpha.,.beta.-unsaturated carboxylic acids and esters thereof, vinyl esters, vinyl halides, vinylidene halides, .alpha.,.beta.-unsaturated carboxylic acid amides and aminoalkyl esters of unsaturated carboxylic acids. Acrylonitrile/styrene mixtures are preferred monomers. The starting materials are employed in quantities such that the product modified polyether polyamine contains from 1 to 60 wt. % polymer or graft-polymer. The product polyamines are particularly useful in the production of polyurethanes.
    Type: Grant
    Filed: December 20, 1982
    Date of Patent: March 19, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Balle, Werner Rasshofer, Winfried Schoberth
  • 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: 4304939
    Abstract: The desired compounds, namely, N-phenyl-N'-alkylphenylenediamines, are prepared by the reductive alkylation of a nitrogen-containing diphenylamine and a ketone in the presence of hydrogen and a hydrogenation catalyst. The desired product may be obtained in a more economical way when effecting the process in a continuous manner by utilizing an organic solvent for the reaction which comprises an ether compound such as a monoether of a dihydric alcohol, a diether of a dihydric alcohol, or a cyclic diether.
    Type: Grant
    Filed: November 2, 1978
    Date of Patent: December 8, 1981
    Assignee: UOP Inc.
    Inventor: Ted Symon
  • Patent number: 4299984
    Abstract: The present invention relates to novel biologically active tricyclic compounds of the general formula: ##STR1## and salts thereof, in whichR.sub.1 and R.sub.2 stand for hydrogen, alkyl or alkenyl, an optionally substituted aralkyl group or an acyl group orR.sub.1 +R.sub.2 together with the nitrogen atom represent a heterocyclic 5- or 6-membered ring, andX and Y stand for hydrogen, hydroxy, halogen, alkyl or alkoxy of 1-6 carbon atoms, nitro, trifluoromethyl or an acyloxy group,which compounds have valuable biological activities, particularly anorectic activity.
    Type: Grant
    Filed: December 30, 1977
    Date of Patent: November 10, 1981
    Assignee: Akzona Incorporated
    Inventors: Colin L. Hewett, David S. Savage