Of Nitro Or Nitroso Patents (Class 564/416)
-
Patent number: 6140538Abstract: A process for preparing an optionally substituted 4-aminodiphenylamine comprising reacting an optionally substituted aniline and an optionally substituted nitrobenzene in the presence of water and a base while controlling the water content so as to ensure a molar ratio of water to the base charged of not less than about 4:1 at the start of the coupling reaction and not less than about 0.6:1 at the end of the coupling reaction to produce 4-nitrodiphenylamine and/or 4-nitrosodiphenylamine and/or salts thereof. The coupling reaction is followed by a hydrogenation reaction where the coupling reaction product is hydrogenated in the presence of a hydrogenation catalyst and added water so as to ensure a molar ratio of total water to base of at least about 4:1 at the end of hydrogenation. Aqueous and organic phases are obtained and the optionally substituted 4-aminodiphenylamine recovered from the organic phase.Type: GrantFiled: February 3, 1999Date of Patent: October 31, 2000Assignee: Flexsys America L.P.Inventors: Roger Keranen Rains, Ralph Albert Genetti, Edward Albert Lambers, Antonius Johannes van Hengstum
-
Patent number: 6087480Abstract: Preparation of sparingly soluble aromatic amines by catalytic hydrogenation of the corresponding aromatic nitro compounds in the presence of hydrogen, a solvent and a catalyst having a particle size of not less than 0.5 mm, wherein the aromatic nitro compound selected is a compound whose corresponding amine is soluble to an extent of not more than 50% by weight in the solvent used under the reaction conditions of the hydrogenation, and also their use for preparing azo compounds.Type: GrantFiled: December 16, 1998Date of Patent: July 11, 2000Assignee: Ciba Specialty Chemcals CorporationInventor: Bernd Lamatsch
-
Patent number: 6069278Abstract: This invention relates the novel diamines, the polyimide oligomers and the polyimides derived therefrom and to the method of preparing the diamines, oligomers and the polyimides. The thermoplastic polyimides derived from the aromatic diamines of this invention are characterized as having a high glass transition temperature, good mechanical properties and improved processability in the manufacture of adhesives, electronic and composite materials for use in the automotive and aerospace industry. The distinction of the novel aromatic diamines of this invention is the 2,2',6,6'-substituted biphenyl radicals which exhibit noncoplanar conformation that enhances the solubility of the diamine as well as the processability of the polyimides, while retaining a relatively high glass transition temperature and improved mechanical properties at useful temperature ranges.Type: GrantFiled: November 23, 1999Date of Patent: May 30, 2000Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventor: Chun-Hua K. Chuang
-
Patent number: 6054617Abstract: The invention concerns a process for the reduction of nitro groups to amino groups, characterized that a nitro compound is reacted with hydrogen in the presence of an aqueous solution of a water-soluble metal catalyst of the formula M (L).sub.n (Y).sub.m wherein M is ruthenium, rhodium, nickel, or palladium; L, is a water soluble ligand; Y is a further ligand or an alkaline earth ion; n is 1, 2, 3, or 4; and m is 0, 1, or 2.Type: GrantFiled: May 22, 1998Date of Patent: April 25, 2000Assignee: Clariant GmbHInventors: Helmut Bahrmann, Boy Cornils, Andreas Dierdorf, Steffen Haber
-
Patent number: 6034276Abstract: Disclosed is an improved process for preparing 1-chloro-2,4-diaminobenzene by the selective hydrogenation of 1-chloro-2,4-dinitro-benzene wherein the hydrogenation is carried out in the presence of a modified Raney nickel catalyst containing about 70 to 95 weight percent nickel, about 4 to 10 weight percent aluminum, about 0.1 to 4 weight percent molybdenum, and from 0 to about 20 weight percent cobalt. The 1-chloro-2,4-diaminobenzene is useful as an intermediate for disperse dyes and for color photography.Type: GrantFiled: March 22, 1999Date of Patent: March 7, 2000Assignee: Eastman Chemical CompanyInventors: Robert Joseph Maleski, Edward Tipton Mullins
-
Patent number: 6011178Abstract: 2-Amino-4,5,3',4'-tetramethoxybenzophenone of the formula: ##STR1## is prepared by mononitration of 3,3',4,4'-tetramethyoxybenzophenone using nitric acid in the presence of acetic acid, and subsequent reduction of the nitro group. The compound is an intermediate in the synthesis of active ingredients against rheumatoid arthritis.Type: GrantFiled: March 12, 1999Date of Patent: January 4, 2000Assignee: Lonza, Ltd.Inventors: Oleg Werbitzky, Walter Brieden, Etienne Heinzmann
-
Patent number: 5994584Abstract: 4-Aminodiphenylamines are prepared by hydrogenating nitrosobenzene or mixtures of nitrosobenzene and nitrobenzene with hydrogen in the presence of fluorides and heterogeneous catalysts in inert aprotic solvents at temperatures from 0 to 200.degree. C. and pressures from 0.1 to 150 bar.Type: GrantFiled: March 8, 1999Date of Patent: November 30, 1999Assignee: Bayer AktiengesellschaftInventors: Pieter Ooms, Henrey Giera
-
Patent number: 5932768Abstract: 4-aminodiphenylamines are prepared by hydrogenating nitrosobenzene or mixtures of nitrosobenzene and nitrobenzene with hydrogen in the presence of bases containing hydroxide, oxide and/or alkoxide groups and heterogeneous catalysts in inert aprotic solvents at temperatures of from 0 to 200.degree. C. and at pressures of from 0.1 to 150 bar.Type: GrantFiled: July 30, 1998Date of Patent: August 3, 1999Assignee: Bayer AGInventors: Pieter Ooms, Ulrich Notheis, Christian Laue
-
Patent number: 5925791Abstract: 4-aminodiphenylamines are produced by hydrogenating nitrobenzene with hydrogen in the presence of bases containing hydroxide and/or oxide groups and heterogeneous catalysts and in the presence of inert aprotic solvents at temperatures of 0 to 200.degree. C. and pressures of 0.1 to 150 bars.Type: GrantFiled: February 27, 1998Date of Patent: July 20, 1999Assignee: Bayer AGInventors: Hans-Josef Buysch, Christian Laue, Heinrich Konigshofen, Ulrich Notheis, Pieter Ooms, Ursula Pentling
-
Patent number: 5907061Abstract: A group of benzamide compounds are disclosed which are useful for treating neurodegenerative disorders. Methods for making these compounds are provided. These materials are formed into pharmaceutical compositions for oral or intravenous administration to patients suffering from conditions such as Parkinson's disease which can exhibit themselves as progressive loss of central nervous system function. The compounds can arrest or slow the progressive loss of function.Type: GrantFiled: July 3, 1997Date of Patent: May 25, 1999Assignee: Centaur Pharmaceuticals, Inc.Inventors: William Flitter, William Garland, Richard Paylor, Allan Wilcox
-
Patent number: 5861533Abstract: A process for nitrosating C-H-acidic compounds. The process substantially avoids producing polluted wastewater.Type: GrantFiled: June 5, 1997Date of Patent: January 19, 1999Assignee: Huels AktiengesellschaftInventors: Frank Bauer, Marcel Feld
-
Patent number: 5859299Abstract: A process is provided for the production of nitrobenzamides or aminobenzamides having the formula: ##STR1## in which n is 1 or 2, preferably 1, X is an amino or nitro group and R is hydrogen, unsubstituted alkyl or alkyl substituted by halogen, C.sub.1 -C.sub.4 -alkoxy, phenyl, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, a mono- or di-C.sub.1 -C.sub.4 alkylated amino group or by --SO.sub.3 M in which M is hydrogen, an alkali metal atom, ammonium or a cation formed from an amine, which process comprises reacting a nitrobenzoyl chloride having the formula: ##STR2## in which n has its previous significance, with an aqueous solution of an amine having the formula NH.sub.2 --R in which R has its previous significance, in the presence of an inert organic solvent, to produce a compound having the formula: ##STR3## in which n and R have their previous significance; and finally optionally reducing the nitro group(s) to amino group(s).Type: GrantFiled: August 15, 1997Date of Patent: January 12, 1999Assignee: Ciba Specialty Chemicals CorporationInventor: Dieter Meier
-
Patent number: 5629449Abstract: Disclosed is a method of making 3,5-diaminobenzotrifluoride from 4-chloro-3,5-dinitrobenzotrifluoride. A solution of 4-chloro-3,5-dinitrobenzotrifluoride in an alcohol is prepared. Separately, a slurry is prepared of a palladium catalyst on a suitable substrate, at least one equivalent of magnesium oxide per equivalent of 4-chloro-3,5-dinitrobenzotrifluoride, sufficient hydrogen-donating reducing agent to reduce the 4-chloro-3,5-dinitrobenzotrifluoride to 3,5-diaminobenzotrifluoride, and an amount of alcohol sufficient to make the slurry stirrable. The solution is added to the slurry with stirring at a rate that does not exceed the reaction rate of the 4-chloro-3,5-dinitrobenzotrifluoride so that no unreacted 4-chloro-3,5-dinitrobenzotrifluoride accumulates in the slurry. The reaction mixture is heated at about 75.degree. to about 100.degree. C.Type: GrantFiled: August 17, 1992Date of Patent: May 13, 1997Assignee: Occidental Chemical CorporationInventor: David E. Albright, Jr.
-
Patent number: 5608112Abstract: Nitrogen-containing substituents of aliphatic or aromatic compounds can be reduced by treatment with a reagent comprising (i) at least one complex of a transition metal of group 4 or 5 with a multidentate or unidentate organic or inorganic ligand and (ii) a reducing agent. The reaction is conducted optionally in the presence of an aliphatic or aromatic amine, and/or in the presence of an inert organic solvent.Type: GrantFiled: July 10, 1995Date of Patent: March 4, 1997Assignee: The Trustees of Princeton UniversityInventor: Jeffrey Schwartz
-
Patent number: 5563296Abstract: Aromatic diamines and polyamines are produced by a continuous process for the catalytic hydrogenation of the corresponding dinitro and polynitro compounds at elevated temperature. Heat removed from the reaction mixture may be used to produce steam with an overpressure of .gtoreq.2 bar.Type: GrantFiled: June 30, 1994Date of Patent: October 8, 1996Assignee: Bayer AktiengesellschaftInventors: Uwe J. Zarnack, Fritz Pohl, Dieter Grenner, Hartmut Hetzel, Helmut Judat
-
Patent number: 5484953Abstract: Novel o-phenylenediamines of the formula containing fluoroalkyl(ene) groups ##STR1## in which the symbols used have the meaning given in the description, processes for their preparation and their use as intermediates.Type: GrantFiled: June 3, 1994Date of Patent: January 16, 1996Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Bernd Baasner, Folker Lieb
-
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
-
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
-
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
-
Patent number: 5364968Abstract: There is provided o-nitrophenyl cyclopropyl ketone, a key intermediate in the manufacture of the crop-selective, herbicidal agent 1-{[o-(cyclopropylcarbonyl)phenyl]sulfamoyl}-3-(4,6-dimethoxy-2-pyrimidiny l)urea and a method for the preparation of said ketone from dihydro-3-acetyl-2(3H)-furanone and o-nitrobenzoyl halide.Type: GrantFiled: December 2, 1993Date of Patent: November 15, 1994Assignee: American Cyanamid CompanyInventors: Marco P. Burello, Jeffrey G. Stack, David A. Cortes
-
Patent number: 5347052Abstract: 3,5-Diaminobenzotrifluoride can be produced, in a single step, by reacting 4-chloro-3,5-dinitrobenzotrifluoride, in methanol, with hydrogen gas, in the presence of magnesium oxide, and in the presence of a catalyst comprising palladium on a carbon support.Type: GrantFiled: April 15, 1991Date of Patent: September 13, 1994Assignee: Occidental Chemical CorporationInventor: David E. Albright, Jr.
-
Patent number: 5336808Abstract: 3,5-Diaminobenzotrifluoride is prepared by reaction of 4-chloro-3,5-dinitrobenzotrifluoride with sodium formate in acetic acid, in the presence of sodium acetate and palladium on charcoal.Type: GrantFiled: December 10, 1990Date of Patent: August 9, 1994Assignee: Occidental Chemical CorporationInventors: Ramesh Krishnamurti, Mahendra K. Dosi, Henry C. Lin
-
Patent number: 5279714Abstract: A process for the preparation of a compound of Formula A: ##STR1## wherein X.sup.1 and X.sup.2 are independently selected from H or any substituent which does not interfere with the electrochemical reductive fluorination; andZ.sup.1 and Z.sup.2 are each independently selected from H or an electron donating group;which comprises electrochemical reductive fluorination of a compound of Formula B: ##STR2## wherein X.sup.1, X.sup.2, Z.sup.1 and Z.sup.2 are as defined above in a mixture of anhydrous hydrogen fluoride and an alkali metal fluoride.The 4-fluoroanilines find use as intermediates in the manufacture of a wide range of agrochemicals, dyestuffs and pharmaceuticals.Type: GrantFiled: March 18, 1992Date of Patent: January 18, 1994Assignee: Imperial Chemical Industries PLCInventors: John S. Moilliet, Ian K. Jones
-
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
-
Patent number: 5220020Abstract: A process is provided whereby organic carbonyl substrates, including esters, lactones, ketones, amides and imides are reduced in a reaction with a silane reducing reagent and a catalyst. Exemplary catalysts include metal alkoxides and metal aryloxides.Type: GrantFiled: November 14, 1991Date of Patent: June 15, 1993Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Alberto Gutierrez, Scott C. Berk, Kristina A. Kreutzer
-
Patent number: 5216138Abstract: There are described water soluble azo compounds conforming to the formula (1)D--N.dbd.N--K (1)where D is a radical of the formula (2), (2a) or (2b) ##STR1##where Y is a substituent which is eliminable by alkali to form a vinyl group, Y.sup.2 has one of the meanings of Y or is hydroxyl, X is chlorine or bromine, and R is hydrogen, lower alkyl, phenyl or halogen, and K is a radical of a singly couplable coupling component which may additionally contain an azo group, or the radical of a doubly couplable coupling component.The compounds of the formula (1) have fiber-reactive properties and are very highly suitable for use as dyes for dyeing hydroxy- and/or carboxamido-containing material, in particular fiber material, for example cellulose-fiber materials, wool and synthetic polyamide fibers, in strong, fast shades.There are also described novel starting compounds of the formulae (7), (7a) and (7b) ##STR2##where Y.sup.2, X and R are each as defined above, x is zero or 2 and W is nitro or amino.Type: GrantFiled: November 27, 1991Date of Patent: June 1, 1993Assignee: Hoechst AktiengesellschaftInventor: Jorg Dannheim
-
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
-
Patent number: 5126485Abstract: A process for the hydrogenation of halogenonitro-aromatic compounds wherein said compounds are contacted with a nickel-, cobalt- or iron-based catalyst, preferably Raney nickel, and hydrogen in the presence of a sulfur-containing compound. Preferably, the sulfur-containing compound is a sulfoxide or sulfone, and the molar ratio of the sulfur-containing compound to the catalyst ranges from about 1:1 to 10:1.Type: GrantFiled: July 20, 1990Date of Patent: June 30, 1992Assignee: Rhone-Poulenc ChimieInventors: Rosemarie Bailliard, Georges Cordier, Jean-Michel Grosselin, Bernard Langlois, Laurent Gilbert, Gerard Forat
-
Patent number: 5113025Abstract: A process for selective reduction is provided wherein an organic compound containing a reducible group such as acid, acid chloride, ester, aldehyde, ketone, epoxide, amide, oxime, imine, nitrile, or the like, is reacted with a tertiary amine alane such that an alcohol or an amine is produced, substantially without reduction of another group in the molecule such as a halogen-containing functionality, nitro group, or double bond.Type: GrantFiled: March 5, 1991Date of Patent: May 12, 1992Assignee: Ethyl CorporationInventors: Won S. Park, Everett M. Marlett
-
Patent number: 5099067Abstract: The present invention relates to a method of converting .beta.-nitro compounds, specifically alcohols, into the corresponding hydroxy amines with retention of configuration by the use of ammonium formate.Type: GrantFiled: August 15, 1991Date of Patent: March 24, 1992Assignee: Northwestern UniversityInventors: Anthony G. M. Barrett, Christopher D. Spilling
-
Patent number: 5087755Abstract: A process for producing an aromatic amine under moderate conditions is provided wherein a catalyst higher in activity than conventional catalysts is used. Reduction of an aromatic nitro compound under a CO/H.sub.2 O system is conducted using a rhodium compound catalyst in the presence of an aqueous alkali solution such as aqueous sodium hydroxide solution. Alternatively, an aromatic nitro compound is reduced under a CO/H.sub.2 O system using a rhodium compound or a ruthenium compound catalyst in the presence of the aqueous alkali solution and additionally at least one compound of amine compounds, diamine compounds, phosphine compounds, phosphite compounds, and diphosphine compounds.Type: GrantFiled: November 15, 1989Date of Patent: February 11, 1992Assignee: Sumitomo Chemical Company, LimitedInventors: Kotohiro Nomura, Masaru Ishino
-
Patent number: 5041672Abstract: A process for producing p-phenylenediamine or a derivative thereof which comprises reducing p-nitroaniline or a derivative thereof by hydrazine in the presence of an aromatic quinone compound or an aromatic dihydroxy compound.Type: GrantFiled: October 16, 1990Date of Patent: August 20, 1991Assignee: Nippon Kayaku Kabushiki KaishaInventor: Tsukasa Ishikura
-
Patent number: 4960936Abstract: The catalytic hydrogenation of halogenated nitro aromatics using Raney nickel in the presence of a formamidine salt as dehalogenation inhibitor affords halogenated aromatic primary amines in high yields and high chemical purity within short reaction times even at elevated temperatures.Type: GrantFiled: December 19, 1988Date of Patent: October 2, 1990Assignee: Ciba-Geigy CorporationInventors: Peter Baumeister, Wilfried Scherrer
-
Patent number: 4885388Abstract: New 2-methyl-4-fluoro-phenols and process for their preparation from 2-methyl-4-fluoro-phenol.Type: GrantFiled: September 12, 1988Date of Patent: December 5, 1989Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Reiner Fischer
-
Patent number: 4870209Abstract: A process for the purification of crude 4-aminophenol which was prepared by the catalytic hydrogenation of nitrobenzene in aqueous sulfuric acid is described involving: adjusting the pH of an aqueous solution of crude 4-aminophenol to pH 4.0-5.0 at a temperature between 75.degree. C. and 85.degree. C.; mixing the aforesaid solution with toluene as the solvent, in order to extract various impurities and the dissolved nitrobenzene starting material; adjusting the pH of the resultant solution as required to maintain it at pH 4.0-5.0; allowing the resultant mixture to settle thereby forming a top organic layer and a bottom aqueous raffinate layer which raffinate contains 4-aminophenol and the by-product material, ortho-aminophenol; separating the two layers and repeatedly extracting the raffinate layer which toluene at pH 4.0-5.0 at a temperature of 75.degree.-85.degree. C.Type: GrantFiled: April 29, 1987Date of Patent: September 26, 1989Assignee: Noramco, Inc.Inventors: James T. F. Kao, Dwight E. Raff, II
-
Patent number: 4831193Abstract: This invention relates to a novel process for preparing 3-amino-2-methylbenzotrifluoride from benzotrifluoride. The process comprises nitrating benzotrifluoride to form 3-nitrobenzotrifluoride, reacting this compound with trimethyl sulphoxonium halide to form 3-nitro-2-methylbenzotrifluoride and reducing the nitro group to an amino group.Type: GrantFiled: June 19, 1987Date of Patent: May 16, 1989Assignee: Schering CorporationInventors: Joseph F. Lamendola, Dhiru Vashi, Robert G. Tyson
-
Patent number: 4792625Abstract: The invention provides a process for reducing substantially water insoluble organic compounds containing reducible groups comprising contacting these compounds with an aqueous solution of a formic acid salt in the presence of a hydrogenation catalyst and in the substantial absence of a phase transfer catalyst.Type: GrantFiled: July 9, 1987Date of Patent: December 20, 1988Assignee: Yissum Research Development CompanyInventors: Harold Wiener, Shmuel Vandel, Yoel Sasson
-
Patent number: 4751328Abstract: Aminobenzylamines are produced by catalytically reducing o-, m- or p-nitrobenzaldoxime in an organic solvent in the presence of a compound selected from the group consisting of (a) boric acid, phosphoric acid and/or anhydrides thereof, (b) CO.sub.2 gas and (c) an organic acid. The starting material, nitrobenzaldoxime is produced by reaction of the corresponding nitrobenzaldehyde with hydroxylamine.Type: GrantFiled: November 24, 1986Date of Patent: June 14, 1988Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Keizaburo Yamaguchi, Kenichi Sugimoto, Yoshimitsu Tanabe, Midori Yamazaki, Akihiro Yamaguchi
-
Patent number: 4723040Abstract: A process for preparing an N-mono-substituted-p-phenylenediamine by reacting the corresponding p-nitroso-N-mono-substituted aniline compound with a primary or secondary alcohol in the presence of a base.Type: GrantFiled: December 19, 1986Date of Patent: February 2, 1988Assignee: Uniroyal Chemical Company, Inc.Inventor: Wadim Batorewicz
-
Patent number: 4713439Abstract: A novel series of polymers and copolymers based on a polyimide backbone with the incorporation of carbonate moieties along the backbone. The process for preparing these polymers and copolymers is also disclosed as is a novel series of dinitrodiphenyl carbonates and diaminodiphenyl carbonates. The novel polymers and copolymers exhibit high temperature capability and because of the carbonate unit, many exhibit a high degree of order and/or crystallinity.Type: GrantFiled: February 27, 1986Date of Patent: December 15, 1987Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: Terry L. St. Clair, Shubha Maudgal, J. Richard Pratt
-
Patent number: 4675445Abstract: A process for eliminating N-nitrosamines, particularly N,N-dialkyl-N-nitrosamines and N-alkyl-N-aryl-N-nitrosamines from N-nitrosamine containing compositions through the addition of organic carboxylic acid halides. The process eliminates N-nitroso compounds without rearrangement to C-nitroso compounds.Type: GrantFiled: November 12, 1985Date of Patent: June 23, 1987Assignee: BASF CorporationInventors: Pauls Davis, Donald C. Mente
-
Patent number: 4625062Abstract: 4-Alkoxyanilines are obtained industrially advantageously by catalytically hydrogenating a nitrobenzene in the presence of a noble metal catalyst in a mixed solvent containing a lower aliphatic alcohol, sulfuric acid, and water or a lower aliphatic carboxylic acid or both to induce hydrogenation and a Bamberger-type rearrangement reaction. The mixed solvent contains at least 10 moles, preferably 30 to 60 moles, of the lower aliphatic alcohol per mole of the nitrobenzene, 1 to 10 moles, preferably 2 to 7 moles, of sulfuric acid per mole of the nitrobenzene, and 2 to 30% by weight, preferably 3 to 10% by weight, of water, the lower aliphatic carboxylic acid or both.Type: GrantFiled: November 27, 1984Date of Patent: November 25, 1986Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Teruyuki Nagata, Akihiro Tamaki, Hiroki Ohnishi, Hideki Mizuta
-
Patent number: 4537713Abstract: The invention concerns a process for the reduction of groups containing unsaturated C,C--, C,N--,N,N--,N,O-- bonds, especially of NO.sub.2 --,NO--,NOH--,NR--,CN--,N.sub.3 --,N.sub.2 -groups or C.dbd.C or C-halogen- or acyl groups with hydrogen on MPc or with a suitable reduction agent on [MPc].sup..crclbar., whereby a platinum metal-phthalocyanine is used as the catalyst. It is possible that by the reversible change (control) of the oxidation phase z of the platinum metal from z.gtoreq.2 to z.ltoreq.1 using the same MPc complex, basically different reductions can be selectively catalysed.Thus the invention concerns a process for selective reduction using platinum metal-phthalocyanine catalysts with reaction specificity in three different reaction patterns.The inventive process is suitable, especially for the synthesis of .alpha.-phenylalkylamines, benzylalkylamines, N-alkyl-amino carboxylic acids, .alpha.Type: GrantFiled: May 19, 1982Date of Patent: August 27, 1985Inventor: Heiner Eckert
-
Patent number: 4535154Abstract: A method for the reduction of nitrogen compounds containing an N--N or N.dbd.N bond, which are soluble in water or lower alcohols, particularly nitrosamines, hydrazines, nitramines, azo- and azoxy-compounds, to the corresponding amines; comprising contacting the nitrogen compounds with a hydroxide solution and a nickel-aluminum alloy in the absence of a hydrogen atmosphere, at room temperature and at atmospheric pressure, for a sufficient time to produce the corresponding amine in a single step.Type: GrantFiled: July 13, 1983Date of Patent: August 13, 1985Assignee: United States of AmericaInventors: Larry K. Keefer, George Lunn
-
Patent number: 4506098Abstract: A process for the preparation of 2,6-dialkylaniline which comprises the reaction of a 1-nitroalkene with a 1,3-alkadiene to form a dialkyl nitrocyclohexene adduct and subsequent reaction of the resulting adduct with hydrogen in the presence of a hydrogenation catalyst to form the corresponding dialkylcyclohexyl amine, followed by dehydrogenation with aqueous ammonia in the presence of a dehydrogenation catalyst.Type: GrantFiled: July 6, 1981Date of Patent: March 19, 1985Assignee: Chevron Research CompanyInventor: Shigeto Suzuki
-
Patent number: 4496764Abstract: A process for the preparation of 4-amino-3-methyl-phenol from 4-nitroso-3-methyl-phenol, which comprises contacting said 4-nitroso-3-methyl-phenol with iron in an acid aqueous medium at a temperature of 20.degree. to 100.degree. C. said medium having pH in the range from 2 to 6.5.Type: GrantFiled: January 14, 1983Date of Patent: January 29, 1985Assignee: Bayer AktiengesellschaftInventors: Guido Skipka, Hans-Ulrich Alles, Gert Randau, Manfred Niese
-
Patent number: 4448994Abstract: Alkali metal salts of C-nitrosoarylamines may be readily reduced in aqueous solution by a reducing sugar. The reaction affords the corresponding aminoarylamine in good yield with little, if any, byproduct formation and affords a method of preparing aminoarylamines without isolation of the C-nitrosoarylamine.Type: GrantFiled: September 16, 1983Date of Patent: May 15, 1984Assignee: UOP Inc.Inventor: Paul R. Kurek
-
Patent number: 4404401Abstract: An improved process for the preparation of para-amino diphenylamine in which para-nitroso-diphenylhydroxylamine is catalytically hydrogenated in the presence of an organic solvent and one or more metal components selected from the group consisting of ruthenium, rhodium, palladium, osmium, iridium, and platinum, and their sulfidic compounds, at temperatures from 20.degree. to 200.degree. C., is disclosed. The improvement comprises utilizing as the organic solvent one or more members of the group consisting of aniline and aniline derivatives containing ring-alkyl groups, N-alkyl groups, or a combination thereof, wherein the ring-alkyl groups contain a total of 1 to 6 carbon atoms and the N-alkyl groups contain from 1 to 6 carbon atoms.Type: GrantFiled: February 23, 1979Date of Patent: September 13, 1983Assignee: Akzona IncorporatedInventors: Hans G. Zengel, Manfred Bergfeld
-
Patent number: 4372893Abstract: Selective reduction of compounds containing reducible nitro-, nitroso-, nitrilo-, oximes or double bonds is effected by the use of a metal macrocyclic compound in prereduced form, such as a metal phthalocyanine or a metal porphyrin.Type: GrantFiled: October 6, 1980Date of Patent: February 8, 1983Inventor: Heiner Eckert
-
Patent number: 4348335Abstract: Polynitrated diaryl compounds of the formula given in the description are reduced with 1-2 mols of sulphides, or compounds which donate sulphide ions, per mol of nitro group in the presence of 0.5-10 mols of ammonia per mol of starting compound at 30.degree.-110.degree. C. to give nitroamino-diaryl compounds, for example 4,4'-dinitro-dibenzyl-2,2'-disulphonic acid is reduced to 4-nitro-4'-amino-stilbene-2,2'-disulphonic acid.Type: GrantFiled: April 14, 1980Date of Patent: September 7, 1982Assignee: Bayer AktiengesellschaftInventors: Karl Linhart, Dieter Pawellek, Harald Gleinig