Of Nitro Or Nitroso Patents (Class 564/416)
  • Patent number: 6140538
    Abstract: 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: Grant
    Filed: February 3, 1999
    Date of Patent: October 31, 2000
    Assignee: Flexsys America L.P.
    Inventors: Roger Keranen Rains, Ralph Albert Genetti, Edward Albert Lambers, Antonius Johannes van Hengstum
  • Patent number: 6087480
    Abstract: 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: Grant
    Filed: December 16, 1998
    Date of Patent: July 11, 2000
    Assignee: Ciba Specialty Chemcals Corporation
    Inventor: Bernd Lamatsch
  • Patent number: 6069278
    Abstract: 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: Grant
    Filed: November 23, 1999
    Date of Patent: May 30, 2000
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventor: Chun-Hua K. Chuang
  • Patent number: 6054617
    Abstract: 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: Grant
    Filed: May 22, 1998
    Date of Patent: April 25, 2000
    Assignee: Clariant GmbH
    Inventors: Helmut Bahrmann, Boy Cornils, Andreas Dierdorf, Steffen Haber
  • Patent number: 6034276
    Abstract: 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: Grant
    Filed: March 22, 1999
    Date of Patent: March 7, 2000
    Assignee: Eastman Chemical Company
    Inventors: Robert Joseph Maleski, Edward Tipton Mullins
  • Patent number: 6011178
    Abstract: 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: Grant
    Filed: March 12, 1999
    Date of Patent: January 4, 2000
    Assignee: Lonza, Ltd.
    Inventors: Oleg Werbitzky, Walter Brieden, Etienne Heinzmann
  • Patent number: 5994584
    Abstract: 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: Grant
    Filed: March 8, 1999
    Date of Patent: November 30, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Pieter Ooms, Henrey Giera
  • Patent number: 5932768
    Abstract: 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: Grant
    Filed: July 30, 1998
    Date of Patent: August 3, 1999
    Assignee: Bayer AG
    Inventors: Pieter Ooms, Ulrich Notheis, Christian Laue
  • Patent number: 5925791
    Abstract: 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: Grant
    Filed: February 27, 1998
    Date of Patent: July 20, 1999
    Assignee: Bayer AG
    Inventors: Hans-Josef Buysch, Christian Laue, Heinrich Konigshofen, Ulrich Notheis, Pieter Ooms, Ursula Pentling
  • Patent number: 5907061
    Abstract: 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: Grant
    Filed: July 3, 1997
    Date of Patent: May 25, 1999
    Assignee: Centaur Pharmaceuticals, Inc.
    Inventors: William Flitter, William Garland, Richard Paylor, Allan Wilcox
  • Patent number: 5861533
    Abstract: A process for nitrosating C-H-acidic compounds. The process substantially avoids producing polluted wastewater.
    Type: Grant
    Filed: June 5, 1997
    Date of Patent: January 19, 1999
    Assignee: Huels Aktiengesellschaft
    Inventors: Frank Bauer, Marcel Feld
  • Patent number: 5859299
    Abstract: 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: Grant
    Filed: August 15, 1997
    Date of Patent: January 12, 1999
    Assignee: Ciba Specialty Chemicals Corporation
    Inventor: Dieter Meier
  • Patent number: 5629449
    Abstract: 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: Grant
    Filed: August 17, 1992
    Date of Patent: May 13, 1997
    Assignee: Occidental Chemical Corporation
    Inventor: David E. Albright, Jr.
  • Patent number: 5608112
    Abstract: 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: Grant
    Filed: July 10, 1995
    Date of Patent: March 4, 1997
    Assignee: The Trustees of Princeton University
    Inventor: Jeffrey Schwartz
  • Patent number: 5563296
    Abstract: 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: Grant
    Filed: June 30, 1994
    Date of Patent: October 8, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Uwe J. Zarnack, Fritz Pohl, Dieter Grenner, Hartmut Hetzel, Helmut Judat
  • Patent number: 5484953
    Abstract: 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: Grant
    Filed: June 3, 1994
    Date of Patent: January 16, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albrecht Marhold, Bernd Baasner, Folker Lieb
  • Patent number: 5442114
    Abstract: There is disclosed a process for producing an aromatic amide compound of the general formula (4), including the steps of subjecting an o-nitrophenol compound of the general formula (1) to catalytic reduction in acetone or an aromatic hydrocarbon solvent under the presence of a nickel catalyst to give an o-aminophenol compound of the general formula (2); and (b) subjecting the o-aminophenol compound of the general formula (2) to condensation with an acid chloride compound having a sulfur content of 0.5% or less, based on the weight of the acid chloride compound, of the general formula (3) in acetone or an aromatic hydrocarbon solvent under an atmosphere of an inert gas having an oxygen concentration of 1% or less. The acid chloride compound having a sulfur content of 0.5% or less, based on the weight of the acid chloride compound, of the general formula (3) may be obtained by allowing a carboxylic acid compound of the general formula (5) to react with thionyl chloride and by concentrating the reaction mixture.
    Type: Grant
    Filed: January 18, 1994
    Date of Patent: August 15, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kan Takamine, Michio Yamato, Akira Murakami, Tooru Tokumaru, Yoshinori Nakayama, Motoo Hazama
  • Patent number: 5436371
    Abstract: A process for preparing p-nitroaromatic amides is provided which comprises contacting a nitrile, nitrobenzene, a suitable base and water in the presence of a suitable solvent system to form a mixture, and reacting the mixture at a suitable temperature in a confined reaction zone in the presence of a controlled amount of protic material. The p-nitroaromatic amides of the invention can be reduced to p-aminoaromatic amides. In one embodiment, the p-aminoaromatic amide is further reacted with ammonia under conditions which produce the corresponding p-aminoaromatic amine and the amide corresponding to the nitrile starting material or with water in the presence of a suitable basic or acidic catalyst under conditions which produce the corresponding p-aminoaromatic amine and the acid or salt thereof corresponding to the nitrile starting material. In another embodiment, the p-aminoaromatic amine is reductively alkylated to produce alkylated p-aminoaromatic amine.
    Type: Grant
    Filed: August 29, 1994
    Date of Patent: July 25, 1995
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, Brian K. Cheng
  • Patent number: 5380946
    Abstract: A process for preparing p-nitroaromatic amides is provided which comprises contacting a nitrile, nitrobenzene, a suitable base and water in the presence of a suitable solvent system to form a mixture, and reacting the mixture at a suitable temperature in a confined reaction zone in the presence of a controlled amount of protic material. The p-nitroaromatic amides of the invention can be reduced to p-aminoaromatic amides. In one embodiment, the p-aminoaromatic amide is further reacted with ammonia under conditions which produce the corresponding p-aminoaromatic amine and the amide corresponding to the nitrile starting material or with water in the presence of a suitable basic or acidic catalyst under conditions which produce the corresponding p-aminoaromatic amine and the acid or salt thereof corresponding to the nitrile starting material. In another embodiment, the p-aminoaromatic amine is reductively alkylated to produce alkylated p-aminoaromatic amine.
    Type: Grant
    Filed: July 30, 1993
    Date of Patent: January 10, 1995
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, Brian K. M. Cheng
  • Patent number: 5364968
    Abstract: 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: Grant
    Filed: December 2, 1993
    Date of Patent: November 15, 1994
    Assignee: American Cyanamid Company
    Inventors: Marco P. Burello, Jeffrey G. Stack, David A. Cortes
  • Patent number: 5347052
    Abstract: 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: Grant
    Filed: April 15, 1991
    Date of Patent: September 13, 1994
    Assignee: Occidental Chemical Corporation
    Inventor: David E. Albright, Jr.
  • Patent number: 5336808
    Abstract: 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: Grant
    Filed: December 10, 1990
    Date of Patent: August 9, 1994
    Assignee: Occidental Chemical Corporation
    Inventors: Ramesh Krishnamurti, Mahendra K. Dosi, Henry C. Lin
  • Patent number: 5279714
    Abstract: 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: Grant
    Filed: March 18, 1992
    Date of Patent: January 18, 1994
    Assignee: Imperial Chemical Industries PLC
    Inventors: John S. Moilliet, Ian K. Jones
  • Patent number: 5252737
    Abstract: A process for preparing N-aliphatic substituted p-phenylenediamine intermediates is provided which comprises contacting an aliphatic amine or substituted aliphatic amine derivative and nitrobenzene in the presence of a suitable solvent system, and reacting the aliphatic amine or substituted aliphatic amine derivative and nitrobenzene in the presence of a suitable base and a controlled amount of protic material at a suitable temperature in a confined reaction zone. In one embodiment, the N-aliphatic substituted p-phenylenediamine intermediates are reduced to N-aliphatic substituted p-phenylenediamines and the N-aliphatic substituted p-phenylenediamines can be reductively alkylated to N'-alkylated, N-aliphatic substituted p-phenylenediamines. In another embodiment of the invention, N-aliphatic substituted p-phenylenediamine intermediates are reductively alkylated to N'-alkylated, N-aliphatic substituted p-phenylenediamines.
    Type: Grant
    Filed: May 22, 1992
    Date of Patent: October 12, 1993
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, Brian K. Cheng
  • Patent number: 5220020
    Abstract: 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: Grant
    Filed: November 14, 1991
    Date of Patent: June 15, 1993
    Assignee: Massachusetts Institute of Technology
    Inventors: Stephen L. Buchwald, Alberto Gutierrez, Scott C. Berk, Kristina A. Kreutzer
  • Patent number: 5216138
    Abstract: 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: Grant
    Filed: November 27, 1991
    Date of Patent: June 1, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Jorg Dannheim
  • Patent number: 5196601
    Abstract: 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: Grant
    Filed: June 17, 1992
    Date of Patent: March 23, 1993
    Assignee: Kao Corporation
    Inventors: Tomohito Kitsuki, Yoshiaki Fujikura
  • Patent number: 5126485
    Abstract: 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: Grant
    Filed: July 20, 1990
    Date of Patent: June 30, 1992
    Assignee: Rhone-Poulenc Chimie
    Inventors: Rosemarie Bailliard, Georges Cordier, Jean-Michel Grosselin, Bernard Langlois, Laurent Gilbert, Gerard Forat
  • Patent number: 5113025
    Abstract: 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: Grant
    Filed: March 5, 1991
    Date of Patent: May 12, 1992
    Assignee: Ethyl Corporation
    Inventors: Won S. Park, Everett M. Marlett
  • Patent number: 5099067
    Abstract: 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: Grant
    Filed: August 15, 1991
    Date of Patent: March 24, 1992
    Assignee: Northwestern University
    Inventors: Anthony G. M. Barrett, Christopher D. Spilling
  • Patent number: 5087755
    Abstract: 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: Grant
    Filed: November 15, 1989
    Date of Patent: February 11, 1992
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kotohiro Nomura, Masaru Ishino
  • Patent number: 5041672
    Abstract: 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: Grant
    Filed: October 16, 1990
    Date of Patent: August 20, 1991
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventor: Tsukasa Ishikura
  • Patent number: 4960936
    Abstract: 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: Grant
    Filed: December 19, 1988
    Date of Patent: October 2, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Baumeister, Wilfried Scherrer
  • Patent number: 4885388
    Abstract: New 2-methyl-4-fluoro-phenols and process for their preparation from 2-methyl-4-fluoro-phenol.
    Type: Grant
    Filed: September 12, 1988
    Date of Patent: December 5, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albrecht Marhold, Reiner Fischer
  • Patent number: 4870209
    Abstract: 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: Grant
    Filed: April 29, 1987
    Date of Patent: September 26, 1989
    Assignee: Noramco, Inc.
    Inventors: James T. F. Kao, Dwight E. Raff, II
  • Patent number: 4831193
    Abstract: 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: Grant
    Filed: June 19, 1987
    Date of Patent: May 16, 1989
    Assignee: Schering Corporation
    Inventors: Joseph F. Lamendola, Dhiru Vashi, Robert G. Tyson
  • Patent number: 4792625
    Abstract: 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: Grant
    Filed: July 9, 1987
    Date of Patent: December 20, 1988
    Assignee: Yissum Research Development Company
    Inventors: Harold Wiener, Shmuel Vandel, Yoel Sasson
  • Patent number: 4751328
    Abstract: 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: Grant
    Filed: November 24, 1986
    Date of Patent: June 14, 1988
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Keizaburo Yamaguchi, Kenichi Sugimoto, Yoshimitsu Tanabe, Midori Yamazaki, Akihiro Yamaguchi
  • Patent number: 4723040
    Abstract: 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: Grant
    Filed: December 19, 1986
    Date of Patent: February 2, 1988
    Assignee: Uniroyal Chemical Company, Inc.
    Inventor: Wadim Batorewicz
  • Patent number: 4713439
    Abstract: 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: Grant
    Filed: February 27, 1986
    Date of Patent: December 15, 1987
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Terry L. St. Clair, Shubha Maudgal, J. Richard Pratt
  • Patent number: 4675445
    Abstract: 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: Grant
    Filed: November 12, 1985
    Date of Patent: June 23, 1987
    Assignee: BASF Corporation
    Inventors: Pauls Davis, Donald C. Mente
  • Patent number: 4625062
    Abstract: 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: Grant
    Filed: November 27, 1984
    Date of Patent: November 25, 1986
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Teruyuki Nagata, Akihiro Tamaki, Hiroki Ohnishi, Hideki Mizuta
  • Patent number: 4537713
    Abstract: 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: Grant
    Filed: May 19, 1982
    Date of Patent: August 27, 1985
    Inventor: Heiner Eckert
  • Patent number: 4535154
    Abstract: 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: Grant
    Filed: July 13, 1983
    Date of Patent: August 13, 1985
    Assignee: United States of America
    Inventors: Larry K. Keefer, George Lunn
  • Patent number: 4506098
    Abstract: 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: Grant
    Filed: July 6, 1981
    Date of Patent: March 19, 1985
    Assignee: Chevron Research Company
    Inventor: Shigeto Suzuki
  • Patent number: 4496764
    Abstract: 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: Grant
    Filed: January 14, 1983
    Date of Patent: January 29, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Guido Skipka, Hans-Ulrich Alles, Gert Randau, Manfred Niese
  • Patent number: 4448994
    Abstract: 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: Grant
    Filed: September 16, 1983
    Date of Patent: May 15, 1984
    Assignee: UOP Inc.
    Inventor: Paul R. Kurek
  • Patent number: 4404401
    Abstract: 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: Grant
    Filed: February 23, 1979
    Date of Patent: September 13, 1983
    Assignee: Akzona Incorporated
    Inventors: Hans G. Zengel, Manfred Bergfeld
  • Patent number: 4372893
    Abstract: 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: Grant
    Filed: October 6, 1980
    Date of Patent: February 8, 1983
    Inventor: Heiner Eckert
  • Patent number: 4348335
    Abstract: 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: Grant
    Filed: April 14, 1980
    Date of Patent: September 7, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl Linhart, Dieter Pawellek, Harald Gleinig