Of Aldehyde Containing Compound Patents (Class 564/473)
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Patent number: 6013681Abstract: A liquid amine compound which can be applied to various uses such as emulsification for bitumens since it has as high surface activity as those of solid amines and is more excellent in workability as compared with the solid amines, and an emulsifier for bitumens produced by using the amine compound. Furthermore, a process for producing an emulsifier a bituminous emulsion by reacting an aliphatic amine having at least one hydrocarbon group having not less than 8 carbon atoms with a carbonyl compound and adding an acid thereto to adjust the pH of the amine compound so as to be not more than 5, and a process for producing a bituminous emulsion composition by using the amine compound.Type: GrantFiled: February 17, 1998Date of Patent: January 11, 2000Assignee: Kao CorporationInventors: Katsuhiko Asamori, Ryoichi Tamaki, Hitoshi Funada, Takao Taniguchi, Francisco Castaneda Juarez, Cesar Alvarez Ortiz, Alvaro Gutierrez Muniz, Humberto Ramirez Hernandez
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Patent number: 5998669Abstract: The present invention relates to a process of making 2-amino-1,3-propanediol by reacting 1,3-dihyrdroxyacetone dimer with an amine compound.Type: GrantFiled: September 17, 1998Date of Patent: December 7, 1999Assignee: Abbott LaboratoriesInventors: Russell C. Klix, Deborah A. Davis, Owen J. Goodmonson
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Patent number: 5973208Abstract: A process for producing diamines by reacting a dialdehyde with ammonia and hydrogen in the presence of a hydrogenation catalyst to produce the corresponding diamine, where a solvent comprising an alcohol is used in the reaction and the concentration of water in the reaction mixture is 5 to 15% by weight.Type: GrantFiled: May 14, 1998Date of Patent: October 26, 1999Assignee: Kuraray Co., Ltd.Inventors: Katsushi Nagareda, Yoshihiro Tokuda, Shigeaki Suzuki
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Patent number: 5886227Abstract: Disclosed is an improved process for the catalytic hydrogenation of cyanopropionaldehyde alkyl acetals (CPAA) to form the aminobutyraldehyde alkyl acetals. The basic process comprises hydrogenating the cyanopropionaldehyde alkyl acetals by contacting said cyanopropionaldehyde alkyl acetals with hydrogen in the presence of a nickel or cobalt catalyst under conditions for reducing the nitrile group to the primary amine. The improvement resides in effecting the hydrogenation of a cyanopropionitrile dialkyl acetal feedstock containing contaminating levels of cyanopropionaldehyde in the presence of a secondary alkanol or water.Type: GrantFiled: October 28, 1997Date of Patent: March 23, 1999Assignee: Air Products and Chemicals, Inc.Inventors: Gamini Ananda Vedage, Kathryn Sue Hayes
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Patent number: 5808160Abstract: Hydroxyalkyl-substituted aminoalkynes of the general formula I ##STR1## where at least one of the substituents R.sup.1, R.sup.4 or R.sup.5 is hydroxyalkyl are prepared in a reaction with heterogeneous catalysis.Type: GrantFiled: April 25, 1997Date of Patent: September 15, 1998Assignee: BASF AktiengesellschaftInventors: Thomas Ruhl, Thomas Preiss, Jochem Henkelmann
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Patent number: 5773658Abstract: A process for the preparation of N-methylalkylamines of the formula CH.sub.3 --NH--CH.sub.2 --R in which R is an aliphatic radical having 1 to 3 carbon atoms, by reacting an aldehyde of the formula R--CHO with an amine of the formula R'--NH.sub.2 to give a Schiff base, removing the water of reaction, and reacting the Schiff base with methylamine and hydrogen in the presence of a hydrogenation catalyst.Type: GrantFiled: June 3, 1993Date of Patent: June 30, 1998Assignee: Hoechst AktiengesellschaftInventors: Jurgen Weber, Detlef Kampmann, Detlef Deymann, Claus Kniep
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Patent number: 5756306Abstract: A process for producing an .alpha.-hydroxy acid or an .alpha.-hydroxyamide which comprises treating an aldehyde and prussic acid or an .alpha.-hydroxynitrile with a microorganism having nitrilase or nitrile hydratase activity in an aqueous medium and maintaining the aldehyde concentration and/or the .alpha.-hydroxynitrile concentration in the reaction mixture within a predetermined range. Also disclosed is a process for producing an .alpha.-hydroxy acid or an .alpha.-hydroxyamide from an aldehyde and prussic acid with a microorganism in an aqueous medium, which comprises maintaining the cyanogen concentration in the reaction mixture within a predetermined range and supplying the aldehyde to the reaction mixture at a predetermined ratio to the prussic acid.Type: GrantFiled: November 8, 1996Date of Patent: May 26, 1998Assignee: Nitto Chemical Industry Co., Ltd.Inventors: Yasumasa Yamaguchi, Masahiro Ushigome, Takeshi Kato
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Patent number: 5756769Abstract: A method for producing a propargylamine compound represented by the general formula (I): ##STR1## which comprises reacting a propargyl compound represented by the general formula (II): ##STR2## with an aromatic aldehyde represented by the general formula (III):ArCHO (III)and ammonia to obtain an imine compound represented by the general formula (IV): ##STR3## and hydrolyzing the resultant imine compound. It is to provide a method for producing a propargylamine compound from a propargyl compound by a simple operation without using a special facility, using ammonia as a reaction reagent, without producing a dipropatygylamine compound and a tripropargylamine compound as by-products.Type: GrantFiled: May 30, 1997Date of Patent: May 26, 1998Assignee: Sumitomo Chemical Company, Ltd.Inventors: Shinzo Seko, Akihiko Nakamura, Motoo Hazama
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Patent number: 5756558Abstract: A method for preparing a polyurethane foam which comprises reacting an organic polyisocyanate and a polyol in the presence of a blowing agent, a cell stabilizer and a catalyst composition comprising a compound having the following formula I: ##STR1## where R.sup.1 is hydrogen or a linear or branched C1-C4 alkyl or a C1-C4 hydroxyalkyl group;R.sup.2 and R.sup.3 independently are hydrogen, hydroxy, a linear or branched C1-C4 alkyl or a linear or branched C1-C4 hydroxyalkyl group; andR.sup.4 is a linear or branched C1-C10 hydroxyalkyl group.Type: GrantFiled: July 3, 1996Date of Patent: May 26, 1998Assignee: Air Products and Chemicals, Inc.Inventors: Ann Coates Lescher Savoca, Richard Paul Underwood, Richard Van Court Carr, James Stephen Emerick
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Patent number: 5744630Abstract: The present invention has for its object to provide an efficient and economical method for producing an 3-amino-2-hydroxy-1-propanol derivative and an oxazolidinone derivative derived therefrom, both of which are of use as intermediates for the production of drugs including HIV protease inhibitors.The invention relates to a method for producing an 3-amino-2-hydroxy-1-propanol derivative of general formula (2) ##STR1## (wherein R.sup.1 represents alkyl, aralkyl or aryl; R.sup.2 and R.sup.3 independently represent hydrogen or an amino-protecting group, provided, however, that both R.sup.2 and R.sup.3 are not concurrently hydrogen) and an oxazolidinone derivative derived therefrom.Type: GrantFiled: July 18, 1995Date of Patent: April 28, 1998Assignee: Kaneka CorporationInventors: Kenji Inoue, Hiroshi Awaji, Satomi Takahashi
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Patent number: 5744644Abstract: It has been found that certain polyhydroxyalkylamines have a particularly good solubility in water, alcohols and in mixtures of water and alcohols. The concentrated solutions described consist essentially of water, alcohols, preferably C.sub.1 -C.sub.3 -alcohols, or water/alcohol mixtures as solvent and at least one dialkylaminopropylglucamine of the formula 1 belowZ--NH--CH.sub.2 CH.sub.2 CH.sub.2 --NR.sup.1 R.sup.2 ( 1)where R.sup.1 and R.sup.2 are identical or different and are C.sub.1 -C.sub.4 -alkyl or hydroxyalkyl having from 2 to 4 carbon atoms and Z is a linear polyhydroxyhydrocarbon radical having at least three OH groups which may, if desired, be alkoxylated, The concentrated solutions are particularly useful for preparing the corresponding polyhydroxyalkylcarboxamides.Type: GrantFiled: May 23, 1996Date of Patent: April 28, 1998Assignee: Hoechst AktiengesellschaftInventor: Bernd Papenfuhs
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Patent number: 5646235Abstract: A method is provided for the preparation of tertiary polyamines by alkylating a polyamine having at least two primary amino groups without the use of excess solvent. More particularly, a tertiary amine is produced by reductively alkylating a polyamine with a carbonyl compound, such as formaldehyde, in a reaction zone while in the presence of a hydrogenation catalyst and hydrogen under reductive conditions. The carbonyl compound is continuously supplied to the reaction zone.Type: GrantFiled: June 18, 1996Date of Patent: July 8, 1997Assignee: Huntsman Petrochemical CorporationInventors: Robert LeRoy Zimmerman, Wheeler Conrad Crawford, Rodney Frederick Lloyd
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Patent number: 5631405Abstract: The present invention relates to a method of forming a 1,3-diamino-3-substituted-2-propanol chemical intermediate from which various chemicals, such as selected protease-inhibitors and other drugs, as well as polymers, can be synthesized.This method includes contacting a nitromethyl amino acid compound with at least one reducing agent to form the 1,3-diamino-3-substituted-2-propanol chemical intermediate.Type: GrantFiled: June 7, 1995Date of Patent: May 20, 1997Assignee: Pharm-Eco Laboratories, IncorporatedInventors: Biman Pal, Siya Ram, Bing Cai, Yesh P. Sachdeva, Jaechul Shim, Salah A. Zahr, Emile Al-Farhan, Richard L. Gabriel
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Patent number: 5475141Abstract: Process for preparing primary amines from aldehydes by mixing an aldehyde with a diluent, where in the case of an alcohol or of water as diluent the mixing temperature is at most 5.degree. C. to prevent the formation of the hemiacetal or the aldehyde hydrate, and bringing the mixture into contact with a mixture of ammonia, hydrogen and hydrogenation catalyst, whereby the formation of an imine is prevented, at temperatures of from 60.degree. to 180.degree. C. and pressures of from 20 to 60 bar, at least 15 mol of ammonia being used per mol of aldehyde group, and also an apparatus for carrying out the process.Type: GrantFiled: June 3, 1994Date of Patent: December 12, 1995Assignee: Chemie Linz GmbHInventors: Carlo Kos, Friedrich Hebesberger, Eduard Artner, Engelbert Kloimstein, Robert Haar, Ernst Lust
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Patent number: 5457233Abstract: A process for the preparation of amines of formula ##STR1## wherein the variables are defined as in the claims, which comprises reacting 1 molar equivalent of an amine of formula ##STR2## with 0.8 to 1.5 molar equivalents of an aldehyde of formulaR--CHO (3)and 0.8 to 2 molar equivalents of formic acid, in aqueous medium, and adjusting the pH by addition of a mineral acid such that, at the conclusion of the reaction, the pH is in the range from 3 to 7. The compounds obtainable by the process are useful intermediates for the synthesis of dyeing assistants.Type: GrantFiled: November 28, 1994Date of Patent: October 10, 1995Assignee: Ciba-Geigy CorporationInventor: Philippe Ouziel
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Patent number: 5434309Abstract: 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: GrantFiled: April 28, 1994Date of Patent: July 18, 1995Assignee: Monsanto CompanyInventors: Martin P. McGrath, Samuel J. Tremont
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Patent number: 5331101Abstract: A process for preparing amines or imines which comprises contacting an alcohol, aldehyde, or ketone with an aminating agent in the presence of a catalyst under reaction conditions sufficient to form an amine or imine, wherein the catalyst comprises a homogeneous mixture of (a) 10-90 mole percent cobalt or an insoluble salt thereof, (b) 9-89 mole percent copper or an insoluble salt thereof, and (c) 1-20 mole percent of a metal or insoluble salt of a metal selected from the group consisting of a Lanthanum series metal, thorium, uranium, scandium, titanium, and yttrium is described. A process which employs zirconium as component (c) and which is supported on a carrier material, wherein the carrier material has been neutralized with a base, is also disclosed.Type: GrantFiled: January 5, 1990Date of Patent: July 19, 1994Assignee: The Dow Chemical CompanyInventor: Clarence E. Habermann
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Patent number: 5239120Abstract: 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: GrantFiled: March 27, 1991Date of Patent: August 24, 1993Assignee: BASF AktiengesellschaftInventors: Franz Merger, Claus-Ulrich Priester, Gerhard Koppenhoefer, Wolfgang Harder, Tom Witzel, Helmut Lermer, Ulrich Koehler
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Patent number: 5225597Abstract: 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: GrantFiled: March 13, 1992Date of Patent: July 6, 1993Assignee: UOPInventor: Paul R. Kurek
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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: 5196601Abstract: Disclosed herein is a process for producing an alcohol or an amine by reducing a compound having a formyl, keto, nitro, oxirane, ester, nitrile, amide or halogenated carboxyl group with an alkali metal boro-hydride in the presence of a compound having a hydroxyl group and ether linkage. According to the present invention, a functional group having a great steric hindrance can be reduced, and a corresponding alcohol or amine can efficiently be produced under very mild conditions on an industrial scale.Type: GrantFiled: June 17, 1992Date of Patent: March 23, 1993Assignee: Kao CorporationInventors: Tomohito Kitsuki, Yoshiaki Fujikura
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Patent number: 5166443Abstract: 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: GrantFiled: March 17, 1991Date of Patent: November 24, 1992Assignee: BASF AktiengesellschaftInventors: Franz Merger, Claus-Ulrich Priester, Tom Witzel, Gerhard Koppenhoefer, Ludwig Schuster
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Patent number: 5166433Abstract: Catalysts whose active material contains, in addition to from 20 to 85% by weight, calculated as ZrO.sub.2, of oxygen-containing zirconium compounds, from 1 to 30% by weight, calculated as CuO, of oxygen-containing compounds of copper and from 1 to 40% by weight each, calculated as CoO or NiO, respectively, of oxygen-containing compounds of cobalt and of nickel are used for the amination of alcohols under hydrogenating conditions.Type: GrantFiled: January 7, 1991Date of Patent: November 24, 1992Assignee: BASF AktiengesellschaftInventors: Matthias Irgang, Juergen Schossig, Wolfgang Schroeder, Siegfried Winderl
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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: 5099070Abstract: A process for producing neopentyldiamine is provided. This process entails contacting a feedstream containing neopentanolamine with ammonia and hydrogen in the presence of a support nickel catalyst under amination conditions.Type: GrantFiled: December 7, 1990Date of Patent: March 24, 1992Assignee: Eastman Kodak CompanyInventors: Garrett C. Luce, Anthony W. McCollum
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Patent number: 5091585Abstract: A method for continuous production of tertiary aliphatic methyl amines, particularly fatty aliphatic methyl amines such as di-hydrogenated tallow methyl amine from fatty alkyl amines, such as di-hydrogenated tallow amine over a nickel catalyst has been discovered. The reaction gives high selectivity of tertiary methyl amine over the coproduced secondary amines. The reaction may be conducted continuously in the presence of hydrogen and a formaldehyde source. The formaldehyde source may be selected from the group consisting of formaldehyde alone, formalin, a solution of mixed formaldehyde and paraformaldehyde in methanol and water, trioxane and mixtures thereof. The nickel catalyst may be promoted with copper and/or chromium, in one embodiment.Type: GrantFiled: December 21, 1990Date of Patent: February 25, 1992Assignee: Texaco Chemical CompanyInventors: Wei-Yang Su, Robert L. Zimmerman
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Patent number: 5055618Abstract: 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: GrantFiled: May 21, 1990Date of Patent: October 8, 1991Assignee: Hoechst AktiengesellschaftInventors: Detlef Kampmann, Jurgen Weber, Claus Kniep
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Patent number: 5023379Abstract: A process for the production of hydroxyamines of the formula IR.sup.1 --CH(OH)--CH(NHR.sup.3)--R.sup.2 (I)whereinR.sup.1 and R.sup.2 independently of one another are H or CH.sub.2 OH andR.sup.3 is H, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -hydroxyalkyl comprising reacting an oxo compound with an amine and reducing the resultant ketimine with a reducing agent.Type: GrantFiled: March 12, 1990Date of Patent: June 11, 1991Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Ernst Felder, Michael Romer, Hans Bardonner, Hartmut Hartner, Wolfgang Fruhstorfer
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Patent number: 4996316Abstract: 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: GrantFiled: December 24, 1988Date of Patent: February 26, 1991Assignee: Hoechst AktiengesellschaftInventors: Jurgen Weber, Detlef Kampmann, Claus Kniep
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Patent number: 4994620Abstract: Alkylamines such as methylamine and dimethylamine react with alcohols and aldehydes at 150.degree.-275.degree. C. in the presence of hydrogen and a catalyst initially consisting essentially of (1) a copper compound selected from copper carbonate, copper oxide, copper hydroxide or mixtures thereof, (2) a zinc compound selected from zinc carbonate, zinc oxide, zinc hydroxide or mixtures thereof and (3) a metal compound selected from carbonates, oxides and hydroxides of a Group IIA metal and mixtures thereof at least one of said copper compound and zinc compound being a carbonate. Conversions and yields are high and the amount of heavy by-product is low.Type: GrantFiled: May 19, 1988Date of Patent: February 19, 1991Assignee: Ethyl CorporationInventors: Pak Y. Fong, Kim R. Smith, Joe D. Sauer
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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: 4983736Abstract: This invention relates to a process for making amines by condensing an amino compound in the presence of a metallic polyphosphate condensation catalyst having a condensed structure. This invention also relates to an alkyleneamines producers composition rich in triethylenetetramine (TETA), tetraethylenepentamine (TEPA) and pentatethylenehexamine (PEHA).Type: GrantFiled: August 8, 1989Date of Patent: January 8, 1991Assignee: Union Carbide Chemicals and Plastic Company Inc.Inventors: Arthur R. Doumaux, Jr., David J. Schreck
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Patent number: 4952734Abstract: A process for the preparation of methylamines by the reaction of amines, formaldehyde and hydrogen as starting materials on a fixed-bed catalyst in the liquid phase under pressure and preferably at elevated temperature. The starting materials contain a reduced percentage of water. They are heated to a predetermined temperature apart from each other, and then mixed with each other in the presence of the fixed-bed catalyst.Type: GrantFiled: June 23, 1988Date of Patent: August 28, 1990Assignee: Hoechst AG Werk RuhrchemieInventors: Jurgen Weber, Detlef Kampmann, Claus Kniep
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Patent number: 4940818Abstract: A process for the preparation of 2,2'-oxybis[N,N-dimethylethanamine] by reaction of 2,2'oxybisethanamine, hydrogen and formaldehyde having a reduced percentage of water on conventional fixed-bed hydrogenation catalysts. The reactants, especially the amine and formaldehyde, are heated to a predetermined temperature separate from each other, and then mixed with each other in the presence of the fixed-bed catalyst.Type: GrantFiled: June 23, 1988Date of Patent: July 10, 1990Assignee: Hoechst AktiengesellschaftInventors: Jurgen Weber, Detlef Kampmann, Franz Thonnessen, Claus Kniep
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Patent number: 4855505Abstract: The invention relates to a ruthenium promoted nickel and/or cobalt dehydrogenation-hydrogenation catalyst. The ruthenium on the catalyst is applied from a solution containing a ruthenium halide compound. The catalyst use in organic reactions and a process performed in its presence are also described. Preferably, the catalyst is used to aminate alkylene oxides, alcohols, phenols, alkanolamines, aldehydes, and ketones.Type: GrantFiled: December 8, 1986Date of Patent: August 8, 1989Assignee: Berol Kemi ABInventor: Juhan Koll
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Patent number: 4806690Abstract: 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: GrantFiled: May 13, 1985Date of Patent: February 21, 1989Assignee: The Dow Chemical CompanyInventor: Robert G. Bowman
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Patent number: 4792622Abstract: A secondary amine is effectively prepared by reacting an alcohol or an aldehyde with a primary amine in the presence of a catalyst of copper, nickel and a metal element belonging to the platinum group VIII at a pressure of the atmospheric pressure to 5 kg/cm.sup.2 G at a temperature of 150.degree. to 250.degree. C., while water produced in the reaction is being removed out, and separating the resulting secondary amine from the product mixture.Type: GrantFiled: November 21, 1986Date of Patent: December 20, 1988Assignee: Kao CorporationInventors: Yukinaga Yokota, Yuzi Sawamoto, Hideki Taniguchi, Kazuhiko Okabe
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Patent number: 4792631Abstract: Di-tert.-butylethylenediamine is prepared by reacting tert.-butylamine with glyoxal to form di-tert.-butylglyoxaldiimine and water and subsequently hydrogenating the diimine by(a) carrying out the reaction of tert.-butylamine with glyoxal in the presence of a hydrocarbon phase,(b) separating the hydrocarbon with the reaction product from water, and(c) catalytically hydrogenating the reaction product in the hydrocarbon phase.Type: GrantFiled: January 28, 1987Date of Patent: December 20, 1988Assignee: BASF AktiengesellschaftInventors: Herbert Mueller, Walter Mesch
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Patent number: 4772750Abstract: 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: GrantFiled: October 3, 1986Date of Patent: September 20, 1988Assignee: The Dow Chemical CompanyInventor: Clarence E. Habermann
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Patent number: 4757144Abstract: 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: GrantFiled: September 30, 1986Date of Patent: July 12, 1988Assignee: Kao CorporationInventors: Kazuhiko Okabe, Yukinaga Yokota, Kazuhito Matsutani, Tatuhiro Imanaka
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Patent number: 4683336Abstract: Amines are produced by reacting an aliphatic alcohol and/or an aliphatic aldehyde with an aminating agent in the presence of a catalyst containing copper carbonate and nickel carbonate and/or cobalt carbonate.Type: GrantFiled: December 13, 1985Date of Patent: July 28, 1987Assignee: Sherex Chemical Company Inc.Inventor: Clarence W. Blackhurst
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Patent number: 4665234Abstract: A novel class of severely sterically hindered secondary aminoether alcohols of the general formula: ##STR1## are prepared wherein R.sub.1 and R.sub.2 are each selected from the group consisting of alkyl and hydroxylalkyl radicals R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are each selected from the group consisting of hydrogen, alkyl and hydroxyalkyl radicals, with the proviso that at least one of R.sub.4 or R.sub.5 bonded to the carbon atom directly bonded to the nitrogen atom is an alkyl or hydroxyalkyl radical when R.sub.3 is hydrogen, x and y are each positive integers ranging from 2-4 and z is a positive integer ranging from 1-4. The compounds are useful in the selective removal of H.sub.2 S from mixtures containing H.sub.2 S and CO.sub.2.Type: GrantFiled: August 15, 1983Date of Patent: May 12, 1987Assignee: Exxon Research and Engineering CompanyInventor: Eugene L. Stogryn
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Patent number: 4665195Abstract: Disclosed is a process for producing di-amino-polyalkenyl ethers by reacting (a) one or more acyclic or heterocyclic amino compounds with (b) one or more polyalkenyl ether glycols or polyalkenyl amino ether alcohols, in the presence of a hydrogenation catalyst, at elevated temperatures and pressures.Type: GrantFiled: December 23, 1983Date of Patent: May 12, 1987Assignee: Exxon Research and Engineering CompanyInventors: Eugene L. Stogryn, W.S. Winston Ho, Angelo A. Montagna
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Patent number: 4638091Abstract: A method for the preparation of a fluorinated amine of the formula: ##STR1## wherein X represents hydrogen or fluorine, R represents hydrogen, lower alkyl, difluoromethyl or trifluoromethyl and each of R.sup.1 and R.sup.2, independently, represents hydrogen or lower alkyl, which comprises reacting a carbonyl compound of the formula:XCF.sub.2 CORat an elevated temperature with a nitrogenous base of the formula: ##STR2## and hydrogen in the presence of a hydrogenation catalyst.Type: GrantFiled: February 11, 1985Date of Patent: January 20, 1987Assignee: Imperial Chemical Industries PLCInventor: Roy D. Bowden
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Patent number: 4625063Abstract: A tertiary amine of a high purity is prepared from an alcohol or an aldehyde and a primary or second amine at a low temperature, using a catalyst of copper, nickel and an element belonging to the VIII platinum group such as platinum, palladium, ruthenium and rhodium, while removing out water formed by the reaction.Type: GrantFiled: June 6, 1985Date of Patent: November 25, 1986Assignee: Kao CorporationInventors: Yukinaga Yokota, Yuji Sawamoto, Hideki Taniguchi, Kazuhiko Okabe
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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: 4543411Abstract: 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: GrantFiled: November 10, 1983Date of Patent: September 24, 1985Assignee: Texaco Inc.Inventors: John F. Knifton, David C. Alexander
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Patent number: 4540821Abstract: A process for the manufacture of aminopolyols and polyaminopolyols by continuous reductive amination of sugars in aqueous solution is described. Syrups such as corn syrups may be used directly for this process. It has been found that the lower the mol ratio of NH.sub.3 to the sugar, with a ratio of 1 as the lower limit, the higher is the degree of nitrogen incorporation into the sugar. It is essential that the streams of ammonia and aqueous sugar solution be pumped to the reaction zone separately.Type: GrantFiled: January 26, 1981Date of Patent: September 10, 1985Assignee: Texaco Inc.Inventors: John M. Larkin, Ernest L. Yeakey, Lewis W. Watts, Jr.
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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