By Reductive Amination Patents (Class 564/397)
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Patent number: 6187957Abstract: 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: GrantFiled: December 14, 1999Date of Patent: February 13, 2001Assignee: BASF AktiengesellschaftInventors: Gerald Meyer, Frank Funke, Gerhard Schulz, Detlef Kratz, Marc Walter, Michael Hesse
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Patent number: 6072085Abstract: The method of the present invention provides a simple general route to a wide range of secondary amines.Type: GrantFiled: September 30, 1997Date of Patent: June 6, 2000Assignee: Massachusetts Institute of TechnologyInventors: Xavier Verdaguer, Udo E. W. Lange, Stephen L. Buchwald
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Patent number: 5977411Abstract: 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: GrantFiled: June 10, 1997Date of Patent: November 2, 1999Assignee: Flexsys America L.P.Inventor: Antonio L. DeVera
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Patent number: 5973205Abstract: 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: GrantFiled: April 23, 1998Date of Patent: October 26, 1999Assignee: SmithKline Beecham plcInventors: Thomas Weir Ramsay, Robin Patrick Attrill
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Patent number: 5885538Abstract: 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: GrantFiled: July 2, 1997Date of Patent: March 23, 1999Assignee: Quaker Chemical CorporationInventors: Edward A. Trauffer, Muge Caglar
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Patent number: 5861535Abstract: 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: GrantFiled: September 23, 1997Date of Patent: January 19, 1999Assignee: Eastman Kodak CompanyInventor: Victor L. Mylroie
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Patent number: 5817876Abstract: 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: GrantFiled: September 22, 1994Date of Patent: October 6, 1998Assignee: Bayer AktiengesellschaftInventors: Fritz Maurer, Lothar Rohe, Hans-Joachim Knops
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Patent number: 5817698Abstract: 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: GrantFiled: September 20, 1996Date of Patent: October 6, 1998Assignee: SmithKline Beecham plcInventors: Thomas Henry Brown, John David Harling, Barry Sidney Orlek
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Patent number: 5719298Abstract: 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: GrantFiled: May 22, 1995Date of Patent: February 17, 1998Assignee: Fujirebio Inc.Inventors: Hiroshi Ikawa, Hajime Matsumoto
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Patent number: 5654483Abstract: 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: GrantFiled: December 19, 1995Date of Patent: August 5, 1997Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Chiyuki Kikuchi, Hiroshi Naruse, Masaru Wada, Teruyuki Nagata
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Patent number: 5633407Abstract: 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: GrantFiled: May 18, 1995Date of Patent: May 27, 1997Assignee: Flexsys America L. P.Inventors: Michael K. Stern, Brian K-M Cheng
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Patent number: 5618979Abstract: 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: GrantFiled: May 18, 1995Date of Patent: April 8, 1997Assignee: Flexsys America L. P.Inventors: Michael K. Stern, Brian K-M Cheng
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Patent number: 5616799Abstract: 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: GrantFiled: April 17, 1995Date of Patent: April 1, 1997Assignee: Hoechst AktiengesellschaftInventors: Siegfried Planker, Theodor Papenfuhs
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Patent number: 5608111Abstract: 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: GrantFiled: May 5, 1995Date of Patent: March 4, 1997Assignee: Flexsys America L. P.Inventors: Michael K. Stern, James M. Allman, James K. Bashkin, Roger K. Rains
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Patent number: 5545751Abstract: 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: GrantFiled: December 14, 1994Date of Patent: August 13, 1996Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Chiyuki Kusuda, Masayuki Furuya, Masaru Wada, Yoshihiro Irizato, Hiroshi Naruse, Teruyuki Nagata
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Patent number: 5536878Abstract: 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: GrantFiled: December 2, 1994Date of Patent: July 16, 1996Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Teruyuki Nagata, Chiyuki Kusuda, Masaru Wada, Kenichi Satou, Masae Uchida
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Patent number: 5453541Abstract: 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: GrantFiled: December 6, 1993Date of Patent: September 26, 1995Assignee: Monsanto CompanyInventors: Michael K. Stern, James K. Bashkin
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Patent number: 5449829Abstract: 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: GrantFiled: June 15, 1994Date of Patent: September 12, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Chiyuki Kusuda, Masaru Wada, Teruyuki Nagata
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Patent number: 5442114Abstract: 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: GrantFiled: January 18, 1994Date of Patent: August 15, 1995Assignee: Sumitomo Chemical Company, LimitedInventors: Kan Takamine, Michio Yamato, Akira Murakami, Tooru Tokumaru, Yoshinori Nakayama, Motoo Hazama
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Patent number: 5436371Abstract: 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: GrantFiled: August 29, 1994Date of Patent: July 25, 1995Assignee: Monsanto CompanyInventors: Michael K. Stern, Brian K. Cheng
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Patent number: 5382690Abstract: 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: GrantFiled: August 2, 1993Date of Patent: January 17, 1995Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Teruyuki Nagata, Chiyuki Kusuda, Masaru Wada, Kenichi Satou
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Patent number: 5380946Abstract: 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: GrantFiled: July 30, 1993Date of Patent: January 10, 1995Assignee: Monsanto CompanyInventors: Michael K. Stern, Brian K. M. Cheng
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Patent number: 5344987Abstract: 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: GrantFiled: July 16, 1993Date of Patent: September 6, 1994Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Gerhard Darsow, Hans-Josef Buysch
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Patent number: 5276193Abstract: 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: GrantFiled: August 1, 1990Date of Patent: January 4, 1994Assignee: Sumitomo Chemical Co., Ltd.Inventors: Hiroshi Maki, Michihiro Kawasaki, Hiroshi Shimizu, Yoshiaki Ito
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Patent number: 5252737Abstract: 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: GrantFiled: May 22, 1992Date of Patent: October 12, 1993Assignee: Monsanto CompanyInventors: Michael K. Stern, Brian K. Cheng
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Patent number: 5231217Abstract: 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: GrantFiled: March 20, 1991Date of Patent: July 27, 1993Assignee: Miles Inc.Inventors: Robert P. Yeater, Robson Mafoti, Josef Sanders
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Patent number: 5202485Abstract: 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: GrantFiled: April 29, 1991Date of Patent: April 13, 1993Assignee: Sumitomo Chemical Co., Ltd.Inventors: Hiroshi Maki, Michihiro Kawasaki, Horishi Shimizu, Yoshiaki Ito
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Patent number: 5117063Abstract: 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: GrantFiled: June 21, 1991Date of Patent: May 26, 1992Assignee: Monsanto CompanyInventors: Michael K. Stern, James K. Bashkin
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Patent number: 5105013Abstract: 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: GrantFiled: December 19, 1988Date of Patent: April 14, 1992Assignee: The Dow Chemical CompanyInventors: Maarten Tanis, Govind Rauniyar
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Patent number: 5066824Abstract: 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: GrantFiled: August 3, 1990Date of Patent: November 19, 1991Assignee: Mobay CorporationInventors: Robson Mafoti, Josef Sanders
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Patent number: 5053540Abstract: 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: GrantFiled: March 8, 1990Date of Patent: October 1, 1991Assignee: The Goodyear Tire & Rubber CompanyInventor: Kirkwood S. Cottman
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Patent number: 5011996Abstract: 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: GrantFiled: July 5, 1989Date of Patent: April 30, 1991Assignee: Bayer AktiengesellschaftInventors: Wolfgang Kiel, Heinz Ziemann
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Patent number: 4992587Abstract: 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: GrantFiled: June 2, 1989Date of Patent: February 12, 1991Assignee: Berol Kemi ABInventor: Juhan Koll
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Patent number: 4968843Abstract: 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: GrantFiled: March 8, 1990Date of Patent: November 6, 1990Assignee: The Goodyear Tire & Rubber CompanyInventor: Kirkwood S. Cottman
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Patent number: 4967004Abstract: 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: GrantFiled: April 8, 1988Date of Patent: October 30, 1990Assignee: Sumitomo Chemical Company, LimitedInventors: Hiroshi Maki, Shigeru Sasaki
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Patent number: 4952731Abstract: 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: GrantFiled: August 15, 1988Date of Patent: August 28, 1990Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Teruyuki Nagata, Akihiro Tamaki, Nobuyuki Kajimoto, Masaru Wada
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Patent number: 4804783Abstract: 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: GrantFiled: July 31, 1987Date of Patent: February 14, 1989Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Teruyuki Nagata, Akihiro Tamaki, Nobuyuki Kajimoto, Masaru Wada
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Patent number: 4713488Abstract: 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: GrantFiled: October 11, 1985Date of Patent: December 15, 1987Assignee: Kanzaki Paper Manufacturing Co., Ltd.Inventors: Masayuki Omatsu, Naoki Yonese, Mitsuru Kondo
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Patent number: 4621158Abstract: 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: GrantFiled: August 21, 1985Date of Patent: November 4, 1986Assignee: Schering AktiengesellschaftInventors: Hans-Juergen Hubert, Klaus D. Tillmetz
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Patent number: 4539403Abstract: 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: GrantFiled: January 26, 1983Date of Patent: September 3, 1985Assignee: UBE Industries, Ltd.Inventors: Kozo Fujii, Keigo Nishihira, Hiroyuki Sawada, Shuji Tanaka, Mamoru Nakai, Hiroshi Yoshida, Teruhiko Inoue, Kiyosi Oomori
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Patent number: 4536577Abstract: 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: GrantFiled: March 26, 1984Date of Patent: August 20, 1985Assignee: Ube Industries, Ltd.Inventors: Hiroshi Yoshida, Sadao Niida
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Patent number: 4506039Abstract: 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: GrantFiled: December 20, 1982Date of Patent: March 19, 1985Assignee: Bayer AktiengesellschaftInventors: Gerhard Balle, Werner Rasshofer, Winfried Schoberth
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Patent number: 4434299Abstract: 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: GrantFiled: November 12, 1982Date of Patent: February 28, 1984Assignee: Mobil Oil CorporationInventors: Clarence D. Chang, William H. Lang
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Patent number: 4429157Abstract: 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: GrantFiled: June 10, 1981Date of Patent: January 31, 1984Inventors: Josef Disteldorf, Werner Hubel, Lothar Broschinski
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Patent number: 4304939Abstract: 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: GrantFiled: November 2, 1978Date of Patent: December 8, 1981Assignee: UOP Inc.Inventor: Ted Symon
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Patent number: 4299984Abstract: 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: GrantFiled: December 30, 1977Date of Patent: November 10, 1981Assignee: Akzona IncorporatedInventors: Colin L. Hewett, David S. Savage