Group Viii Noble Metal Containing Catalyst Utilized Patents (Class 564/423)
  • Patent number: 5498794
    Abstract: The invention relates to a process for preparing fluoroanilines of the formula (I)F.sub.n ArNH.sub.2 (I)in which n is 1, 2, 3 or 4, Ar is phenyl, naphthyl or pyridyl, and the remaining substituents on the Ar radical are identical or different and are, independently of each other, hydrogen, halogen, (C.sub.1 -C.sub.1)-alkyl, phenyl, NR.sub.2, OR, CN, CHO, or COR, where R is hydrogen or (C.sub.1 -C.sub.6)-alkyl, wherein fluoronitrobenzenes of the formula (II)X.sub.m F.sub.n ArNO.sub.2 (II)in which n, Ar and the remaining substituents on the Ar radical have the abovementioned meaning, X is chlorine or bromine and m is 1, 2, 3 or 4, are reacted with hydrogen in the presence of a palladium catalyst, of an amine which is not soluble in water and which also does not form water-soluble hydrohalides, and, where appropriate, of an inert solvent.
    Type: Grant
    Filed: February 9, 1995
    Date of Patent: March 12, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Thomas Schach, Theodor Papenfuhs
  • Patent number: 5463129
    Abstract: The present invention relates to a method of cleaving arylethers such as arylethers represented by the formula: ##STR1## wherein R is hydrogen, C.sub.1 -C.sub.6 alkyl, cycloalkyl, phenyl, substituted phenyl or CH.dbd.CH.sub.2 ; each A is independently NO.sub.2, hydroxy, halo, or methoxy; n is an integer from 0 to 5; and x is 1 or 2, comprising contacting the arylether with an amide hydrohalide salt under conditions sufficient to cleave the ether group(s) of the arylether and form a phenol or substituted phenol. The present invention also relates to a method of preparing 4,6-diaminoresorcinol, which is a monomer used for making polybenzoxazoles (PBO).
    Type: Grant
    Filed: December 23, 1993
    Date of Patent: October 31, 1995
    Assignee: The Dow Chemical Company
    Inventors: Zenon Lysenko, Richard G. Pews
  • Patent number: 5453541
    Abstract: A method of producing 4-ADPA is disclosed wherein aniline or substituted aniline derivatives and nitrobenzene are reacted under suitable conditions to produce 4-nitrodiphenylamine or substituted derivatives thereof and/or 4-nitrosodiphenylamine or substituted derivatives thereof and/or their salts, either or both of which are subsequently reduced to produce 4-ADPA or substituted derivatives thereof. The 4-ADPA or substituted derivatives thereof can be reductively alkylated to produce p-phenylenediamine products or substituted derivatives thereof which are useful as antiozonants.
    Type: Grant
    Filed: December 6, 1993
    Date of Patent: September 26, 1995
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, James K. Bashkin
  • Patent number: 5451702
    Abstract: A process for preparing substituted aromatic amines is provided which comprises contacting a nucleophilic compound and an azo containing compound in the presence of a suitable solvent system, reacting the nucleophilic compound and the azo containing compound in the presence of a suitable base and a controlled amount of protic material at a temperature of about 10.degree. C. to about 150.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1 and reducing the product of the reaction of the nucleophilic compound and the azo containing compound under conditions which produce the substituted aromatic amine. In another embodiment, the substituted aromatic amines of the invention are reductively alkylated to produce alkylated diamines or substituted derivatives thereof.
    Type: Grant
    Filed: April 26, 1993
    Date of Patent: September 19, 1995
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, Brian K-M Cheng
  • 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: 5434308
    Abstract: A method of dehydrogenating 3-amino-2-cyclohexene-1-one with a supported palladium or palladium-platinum catalyst in a solvent in the presence of base to produce 3-aminophenol and its use directly without purification to produce 3,4'-oxydianiline.
    Type: Grant
    Filed: January 18, 1994
    Date of Patent: July 18, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Stephen E. Jacobson
  • Patent number: 5430189
    Abstract: An arylisonitrosoalkanone is hydrogenated in the presence of a noble metal catalyst and a weak carboxylic acid to form an arylalkanolamine which is then hydrogenated in the presence of a strong mineral acid and the transition metal catalyst to form an arylalkylamine. When the arylisonitrosoalkanone is an isonitrosoacetophenone, the isonitrosoacetophenone is prepared by one of two methods.In the first method, a substituted or an unsubstituted isonitrosoacetophenone is prepared from a corresponding substituted or unsubstituted acetophenone by oxidizing the acetophenone to form a substituted or an unsubstituted phenylglyoxalacetal in a reactor, hydrolyzing the phenylglyoxal acetal in the same reactor to form a corresponding substituted or unsubstituted phenylglyoxal, and condensing the phenylglyoxal with hydroxylamine or a salt thereof in the same reactor to form the substituted or unsubstituted isonitrosoacetophenone.
    Type: Grant
    Filed: January 19, 1994
    Date of Patent: July 4, 1995
    Assignee: Hoechst Celanese Corporation
    Inventors: Joseph A. McDonough, Ahmed M. Tafesh, Olan S. Fruchey
  • Patent number: 5420354
    Abstract: A process of preparing para phenylenediamines, such as, p-aminodiphenylamine. The process involves contacting nitrobenzene or a substituted derivative thereof with hydrogen and an amine, such as aniline, in the presence of a hydrogenation catalyst, a hydrogenation inhibitor, and an acid cocatalyst under reaction conditions.
    Type: Grant
    Filed: October 6, 1994
    Date of Patent: May 30, 1995
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: Russell E. Malz, Gerard V. Smith, Mark P. Ferrandino, Ruozhi Song
  • Patent number: 5414130
    Abstract: A method of producing 4,6-diaminoresorcinol comprisinga) reducing a dinitroarylether of the formula: ##STR1## wherein R is hydrogen, C.sub.1 -C.sub.6 alkyl, cycloalkyl or CH.dbd.CH.sub.2, R' is hydrogen or CH.sub.2 --R, each A is independently Cl, Br, or I, and n is 0, 1 or 2; to form a diaminoarylether, andb) cleaving the ether group(s) from the diaminoarylether under conditions such that 4,6-diaminoresorcinol is formed as a salt or other stabilized form thereof.
    Type: Grant
    Filed: December 23, 1993
    Date of Patent: May 9, 1995
    Assignee: The Dow Chemical Company
    Inventors: Zenon Lysenko, Richard G. Pews, Paul Vosejpka
  • Patent number: 5410085
    Abstract: Chlorine-substituted aromatic amines are prepared by the hydrogenation of chlorine-substituted aromatic nitro compounds in the presence of a catalyst containing platinum and nickel and/or cobalt on an activated charcoal support, the platinum having been simultaneously deposited and reduced on the activated charcoal support in the preparation of the catalyst. Such catalysts are furthermore prepared, as are catalysts containing noble metals on an activated charcoal support, it also being possible for the latter to be used for the reduction of nitronaphthalenes or nitrotoluenes.
    Type: Grant
    Filed: October 20, 1993
    Date of Patent: April 25, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Udo Birkenstock, Walter Kipshagen, Herbert Schmidt, Thomas-Jorn Schulz, Eberhard Zirngiebl
  • Patent number: 5410083
    Abstract: The invention relates to a novel process for preparing 4,6-diaminoresorcinol, a precursor to polybenzoxazole, from resorcinol according to the following scheme. ##STR1## Resorcinol (I) is reacted with a di-tert-alkylating reagent to form a 4,6,-di-tert-alkylresorcinol (II), which is then halogenated to form a 2-halo-4,6-di-tert-alkylresorcinol (III). The 2-halo-4,6-di-tert-alkylresorcinol is nitrated in one of two ways to form a 2-halo-4,6-dinitroresorcinol (IV), which is then hydrogenated to from the 4,6-diaminoresorcinol.The invention also relates to a novel chemical composition-2-halo-4,6-di-tert-alkylresorcinol (III )--and a process for preparing same.
    Type: Grant
    Filed: October 15, 1993
    Date of Patent: April 25, 1995
    Assignee: The Dow Chemical Company
    Inventor: Bassam S. Nader
  • Patent number: 5399768
    Abstract: The present invention relates to a method of preparing 4,6-diaminoresorcinol from 1,2-dichloro-3,5-dinitrobenzene comprising the steps of:(a) contacting 1,2-dichloro-3,5-dinitrobenzene with a hydroperoxide in the presence of anhydrous base to form 2,3-dichloro-4,6-dinitrophenol;(b) contacting 2,3-dichloro-4,6-dinitrophenol with a hydroxy-containing compound to form 2-chloro-4,6-dinitroresorcinol; and(c) converting 2-chloro-4,6-dinitroresorcinol to 4,6-diaminoresorcinol, which is isolated as a salt or other stabilized form thereof,
    Type: Grant
    Filed: December 23, 1993
    Date of Patent: March 21, 1995
    Assignee: The Dow Chemical Company
    Inventors: Zenon Lysenko, Richard G. Pews
  • Patent number: 5382729
    Abstract: Compounds of formula I ##STR1## wherein R.sub.1 denotes identical or different radicals and is linear or branched C.sub.1 -C.sub.12 alkyl, unsubstituted C.sub.5 -C.sub.6 cycloalkyl or C.sub.5 -C.sub.6 cycloalkyl which is substituted by C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, or is phenyl or benzyl, or both substituents R.sub.1 of a group (R.sub.1).sub.2 P are o,o-diphenylene, R.sub.2 is hydrogen, linear or branched C.sub.1 -C.sub.12 alkyl, phenyl or benzyl, R.sub.3 is C.sub.1 -C.sub.12 alkylene, R.sub.4 is C.sub.2 -C.sub.18 alkylene, phenylene or benzylene, and R.sub.5 is C.sub.1 -C.sub.6 alkyl or phenyl, can be applied to solid carriers, such as silica gel or aerosils, and complexed with rhodium or iridium compounds. These materials are heterogeneous and separable catalysts for the assymetrical hydrogenation of prochiral compounds containing carbon double bonds or carbon/hetero atom double bonds, for example ketones and imines.
    Type: Grant
    Filed: February 16, 1994
    Date of Patent: January 17, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Benoit Pugin, Felix Spindler, Manfred Muller
  • Patent number: 5360932
    Abstract: An aromatic diamino-diol (such as 4,6-diaminoresorcinol) is made by reducing an aromatic halo-dinitro-diol (such as 2-halo-4,6-dinitroresorcinol) with molecular hydrogen in an aqueous mixture containing a noble metal hydrogenation catalyst, an aqueous solvent and about 2 moles of hydrogen halide per mole of aromatic halo-dinitro-diol, plus an additional quantity sufficient to provide a 0.75 to 4 molar solution of the hydrogen halide.
    Type: Grant
    Filed: January 11, 1993
    Date of Patent: November 1, 1994
    Assignee: The Dow Chemical Company
    Inventor: Patrick J. McGrath
  • 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: 5304525
    Abstract: A process for the preparation of aniline by hydrogenation of nitrobenzene in the gas phase in the presence of a catalyst containing a noble metal is described. The process can be carried out in an improved manner if the catalyst employed is palladium on graphite or petrol coke, as the support, containing 0.001-1% by weight of Pd, based on the total weight of the catalyst, it being possible for the catalyst also to contain, in addition to the Pd, 0.001-0.5% by weight of Ir and/or 0.001-0.3% by weight of Rh, all figures being based on the total weight of the catalyst.
    Type: Grant
    Filed: April 21, 1993
    Date of Patent: April 19, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Immel, Helmut Waldmann, Rudolf Braden, Christian Frohlich, Gerhard Friedhofen, Wilfried Niemeier
  • Patent number: 5283365
    Abstract: A process for the continuous preparation of aniline by hydrogenating nitrobenzene is disclosed which comprises the steps of suspending, in an aniline solvent, a catalyst of palladium or palladium-platinum which is deposited on a lipophilic carbon having an oil absorbency of at least 100, adding a zinc compound and an alkali metal carbonate or a zinc compound and an alkali metal bicarbonate as promotors to the reaction system, and carrying out reaction at a temperature of from 150 to 250.degree. C. substantially in the absence of water while aniline and water formed in said reaction are continuously distilled off as vapor from the reaction product, and the concentration of nitrobenzene in the reaction solution is maintained at 0.01% by weight or less.
    Type: Grant
    Filed: June 10, 1992
    Date of Patent: February 1, 1994
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Teruyuki Nagata, Katsuji Watanabe, Yoshitsugu Kono, Akihiro Tamaki, Takashi Kobayashi
  • 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: 5166435
    Abstract: The present invention relates to a process for the preparation of organic hydroxylamines as a result of the corresponding nitroderivative being hydrogenated in the presence of an inert solvent, a platinum catalyst, a nitrogen-containing base (in an amount of less than 10% by weight calculated on the amount of nitro derivative) and a tri- or pentavalent organic phosphorus compound. It has been found that if only use is made of the nitrogen-containing base or the phosphorus compound the yields of isolated hydroxyl amine are significantly reduced in comparison with those obtained with the present process.
    Type: Grant
    Filed: March 24, 1988
    Date of Patent: November 24, 1992
    Assignee: Akzo N.V.
    Inventors: Ashutosh H. Sharma, Peter Hope
  • Patent number: 5144076
    Abstract: 3,5-Diaminobenzotrifluoride can be produced, in a single step, by reacting 4-chloro-3,5-dinitro benzotrifluoride in a suitable solvent, with hydrogen gas, in the presence of a catalyst comprising palladium on a suitable carrier, and in the presence of a suitable base.
    Type: Grant
    Filed: October 1, 1991
    Date of Patent: September 1, 1992
    Assignee: Occidental Chemical Corporation
    Inventors: Ramesh Krishnamurti, Lawrence B. Fertel, Henry C. Lin, Mahendra K. Dosi
  • Patent number: 5117063
    Abstract: A method of producing 4-ADPA is disclosed wherein aniline and nitrobenzene are reacted under suitable conditions to produce 4-nitrodiphenylamine and/or 4-nitrosodiphenylamine and/or their salts, either or both of which are subsequently reduced to produce 4-ADPA. The 4-ADPA can be reductively alkylated to produce p-phenylenediamine products which are useful as antiozonants.
    Type: Grant
    Filed: June 21, 1991
    Date of Patent: May 26, 1992
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, James K. Bashkin
  • Patent number: 5105012
    Abstract: There is provided an improved process for the reduction of optionally substituted dinitrobenzenes to the corresponding nitroanilines with high yields which comprises contacting the dinitrobenzene with hydrogen in an acidic medium in the presence of a catalytic amount of a combination of a noble metal hydrogenation catalyst, and iron or an iron salt. Isomer specific reductions may be achieved with those compounds containing suitable directing substituents.The 2-halo-5-nitroanilines which may be produced in this process may be converted via a multi-step synthesis to useful 1-aryl-4-substituted 1,4-dihydro-5H-tetrazol-5-one herbicides.
    Type: Grant
    Filed: October 11, 1990
    Date of Patent: April 14, 1992
    Assignee: FMC Corporation
    Inventor: George Theodoridis
  • Patent number: 5081303
    Abstract: A two-stage process for the co-production of aniline and m-phenylenediamine where, in the first stage, benzene, nitric acid, and sulfuric acid are reacted in a liquid phase to produce in greater amounts nitrobenzene (approximately 70%) and m-dinitrobenzene (approximately 30%), and in lesser or trace amounts o-dinitrobenzene and p-dinitrobenzene, and water; and in the second stage the products of the first stage are reacted with hydrogen in the liquid phase to produce aniline (approximately 70%) and m-phenylenediamine (approximately 30%) in greater amounts, and o-phenylenediamine and p-phenylenediamine in lesser amounts, and water. The reaction products are separated by distillation.
    Type: Grant
    Filed: April 21, 1989
    Date of Patent: January 14, 1992
    Assignee: First Chemical Corporation
    Inventors: Harold Greenfield, Arthur C. Bayer, Earl G. Alley
  • Patent number: 5077436
    Abstract: Bis(3-nitrophenoxy) derivatives of aromatic or bridged aromatic hydrocarbons are derived from m-dinitrobenzene and dihydroxy derivatives of said hydrocarbons and certain substituted derivatives thereof by a condensation reaction in dipolar aprotic solvents in the presence of bases. The bis(3-nitrophenoxy) derivatives and derivatives obtained are successively reduced to afford bis-(3-aminophenoxy)derivatives. This is a new method for reacting the dihydroxy-derivatives with m-dinitrobenzene, and hence can prepare novel bis(3-aminophenoxy) derivatives such as 4,4'-bis(3-amino-phenoxy)biphenyl, 1-[4-(3-aminophenoxy)phenyl]-1,3,3-trimethyl-6-(3-aminophenoxy)indan, 6,6'-bis(3-aminophenoxy)3,3,3',3'-tetramethyl-1,1'spirobiindan, and methyl substituted 2,2'-bis[4-(3-aminophenoxy)phenyl]propane.
    Type: Grant
    Filed: February 21, 1986
    Date of Patent: December 31, 1991
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Yukihiro Yoshikawa, Keizaburo Yamaguchi, Kenichi Sugimoto, Yoshimitsu Tanabe, Akihiro Yamaguchi
  • Patent number: 5037994
    Abstract: A regioselective nitration process for diphenyl compounds which can be carried out at about ambient temperature in which each ring of the diphenyl compound is selectively nitrated in the para position to form the corresponding di(4-nitrophenyl) compound. Such compounds as diphenyl carbonate, 2,2-diphenylpropane, 2,2-diphenylhexafluoropropane, diphenyl sulfide, diphenyl ketone, diphenyl sulfone, and the like can be converted to an isomeric mixture containing an enhanced amount of the corresponding di(4-nitrophenyl) compound, which mixture may be reduced or purified and reduced to the di(4-aminophenyl) analogues for use in the manufacture of polyamides, polyimides, and polyamide-imides.
    Type: Grant
    Filed: February 8, 1990
    Date of Patent: August 6, 1991
    Assignee: Amoco Corporation
    Inventors: Allen B. Mossman, Weilong L. Chiang
  • Patent number: 5008456
    Abstract: Diamino compounds, dinitro compounds, diol compounds and a process for preparing the diamino compounds which are useful as materials of poly-imide compounds for obtaining aligning films having high pretilt angles in liquid crystal display elements are provided.The diamino compounds are represented by the general formula: ##STR1## wherein R.sub.1 -R.sub.6 are a hydrogen atom or an alkyl group having 1 to 22 carbon atoms, respectively, and R.sub.7 -R.sub.12 are a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, F or Cl respectively.
    Type: Grant
    Filed: November 8, 1989
    Date of Patent: April 16, 1991
    Assignee: Chisso Corporation
    Inventors: Shizuo Murata, Minoru Nakayama, Kenji Furukawa, Ryuji Kobayashi
  • Patent number: 4929757
    Abstract: 3-Aminophenyl 2-hydroxyethyl sulphone (I) can be prepared in a high yield and purity by treating 2-chloro-5-nitrophenyl 2-hydroxyethyl sulphone (II) or 4-chloro-3-nitrophenyl 2-hydroxyethyl sulphone (III) with hydrogen in the presence of hydrogenation catalysts in an aqueous or aqueous organic medium. (II) is obtained by reducing 2-chloro-5-nitrobenzenesulphochloride with sodium sulphite and subsequently reacting the product with ethylene oxide.
    Type: Grant
    Filed: June 17, 1988
    Date of Patent: May 29, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventor: Karl-Josef Herd
  • Patent number: 4760187
    Abstract: A process for reducing chloronitrobenzenes to the corresponding chloroanilines using a combination ruthenium-platinum catalyst is disclosed. The ratio of ruthenium to platinum in the catalyst is from 75:1 to 30:1. The pressure used is from 200 to 800 psi with from 400 to 600 psi being the preferred range. The temperature used is from 70.degree. to 160.degree. C. with from 110.degree. to 150.degree. C. being the preferred range.
    Type: Grant
    Filed: June 17, 1987
    Date of Patent: July 26, 1988
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: John R. Kosak
  • 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: 4723030
    Abstract: A method is provided for enhancing the production rate of arylhydroxylamines by moderated catalytic hydrogenation reactions. Small quantities of acid introduced to the reaction medium doubles the hydrogenation rate of nitroaromatic compounds without a significant loss in selectivity to arylhydroxylamines.
    Type: Grant
    Filed: August 5, 1985
    Date of Patent: February 2, 1988
    Assignee: General Electric Company
    Inventor: Gary C. Davis
  • Patent number: 4714689
    Abstract: Catalysts for the gas-phase reduction of aromatic nitro compounds to aromatic amines are regenerated by treatment of the catalyst, at elevated temperature, with a gas mixture which contains oxygen, inorganic and/or organic amines and/or nitrogen oxides and, where appropiate, steam.
    Type: Grant
    Filed: August 7, 1986
    Date of Patent: December 22, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunter Stammann, Zoltan Kricsfalussy, Helmut Waldmann, Joachim Schneider, Harald Medem
  • Patent number: 4612394
    Abstract: A process for producing aminophenyl-.beta.-hydroxyethylsulfone of the formula (I), ##STR1## which comprises the following steps: (1) condensing nitrohalobenzene with mercaptoethanol in the presence of an alkali hydroxide and at least one reaction medium selected from N-alkyl-substituted amides and sulfoxides to produce mononitrophenyl-.beta.-hydroxyethylsulfide of the formula (II): ##STR2## (2) oxidizing the mononitrophenyl-.beta.-hydroxyethylsulfide (II) to produce mononitrophenyl-.beta.-hydroxyethylsulfone of the formula (III): ##STR3## and (3) reducing the mononitrophenyl-.beta.-hydroxyethylsulfone to produce the aminophenyl-.beta.-hydroxyethylsulfone of the formula (I). This compound is useful as an intermediate for aminophenyl-.beta.-sulfatoethylsulfone represented by the following formula: ##STR4## which is an important intermediate for vinyl sulfone type reactive dyes largely used for dyeing cellulose fiber materials.
    Type: Grant
    Filed: March 21, 1983
    Date of Patent: September 16, 1986
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Norio Kotera, Kazuhiro Tada, Shinzaburo Masaki, Kunihisa Goto, Tatsuo Kaneoya
  • Patent number: 4551551
    Abstract: Bis(aminophenyl) ethers are prepared by effecting condensation reaction of an (N-acetyl)aminophenol or the corresponding sodium or potassium (N-acetyl)aminophenate with a halonitrobenzene under condensation reaction conditions to form an (N-acetyl)aminophenylnitrophenyl ether and hydrogenating the nitro group thereof under nitro- group hydrogenation conditions to form an (N-acetyl)bis(aminophenyl) ether. The latter compound is hydrolyzed with aqueous mineral acid under acid hydrolysis conditions to form an acidic aqueous dispersion of the bis(aminophenyl) ether product, which can readily be recovered from the disperson. Final bis(aminophenyl) ether products thus prepared are typically of high purity and excellent color properties, i.e., substantially colorless.
    Type: Grant
    Filed: September 27, 1982
    Date of Patent: November 5, 1985
    Assignee: Mallinckrodt, Inc.
    Inventor: Ervin B. Inskip
  • Patent number: 4539428
    Abstract: Diaminodiphenyl ethers (DADPE's) are prepared by refluxing sodium or potassium aminophenate with chloronitrobenzene in dimethylformamide. The reaction mixture is hydrogenated directly without isolating the resulting intermediate product, aminophenyl-nitrophenyl ether, to form the corresponding DADPE, e.g., oxydianiline (ODA). The DADPE is crystallized from the hydrogenated reaction mixture in the presence of an aliphatic alcohol, which may be added to the reaction mixture prior to, during, or after hydrogenation. The resulting crystallized DADPE is typically of high purity and excellent color.
    Type: Grant
    Filed: May 10, 1982
    Date of Patent: September 3, 1985
    Assignee: Mallinckrodt, Inc.
    Inventors: Philip H. Merrell, Michael F. Ellis
  • Patent number: 4532351
    Abstract: Supported catalysts comprised of one or more metals of Group VIII, optionally one or more metals from Group IB and IIA, aluminum and silicate are used for hydrogenating hydrogenatable organic compounds. The catalysts can be produced by coprecipitating metal ions from Group VIII, optionally metal ions from Groups IB and IIA, aluminum ions, and silicate ions, in the presence of solid porous particles.
    Type: Grant
    Filed: June 16, 1982
    Date of Patent: July 30, 1985
    Assignee: Exxon Research and Engineering Co.
    Inventors: Allan E. Barnett, Albert P. Halluin
  • Patent number: 4522931
    Abstract: A method for the preparation of catalysts, particularly suitable for the hydrogenation of organic compounds, according to which method a catalytic element, preferably selected from the VIII Group elements, is supported on the outer surface of an adsorbent carbon, said method being characterized by the fact that:(a) said carbon containing an amount of ash lower than 1% by weight, is suspended in water;(b) a liquid immiscible with water is added to the suspension obtained according to (a), the volume of said immiscible liquid being substantially equal to or lower than the volume of the carrier's pores;(c) an aqueous solution, containing a compound of the catalytic element, is brought into contact with the suspension obtained according to (b).
    Type: Grant
    Filed: September 9, 1983
    Date of Patent: June 11, 1985
    Assignee: Montepolimeri S.p.A
    Inventors: Giuseppe Gubitosa, Antonio Berton, Nicola Pernicone, Graziano Vidotto
  • Patent number: 4482742
    Abstract: 3,3'-diamino diphenylsulfones are prepared by catalytically reducing and dehalogenating, in the presence of a reduction catalyst and a dehydrohalogenation agent, a diphenylsulfone compound of the general formula ##STR1## in which X is a halogen atom and Y is hydrogen or a halogen atom.
    Type: Grant
    Filed: April 12, 1983
    Date of Patent: November 13, 1984
    Assignee: Mitsui Toatsu Chemicals Inc.
    Inventors: Keizaburo Yamaguchi, Kenichi Sugimoto, Yoshimitsu Tanabe
  • Patent number: 4474987
    Abstract: A process for preparing an N,N-disubstituted p-phenylenediamine of the formula ##STR1## wherein R.sup.1 is alkyl of 1-6 C atoms, R.sup.2 is alkyl of 1-6 C atoms or alkyl of 1-6 C atoms which is substituted by OH, lower alkoxy, a sulfo group or an alkylsulfonamido group and R.sup.3 is hydrogen or lower alkylor an acid addition salt thereof,comprises adding an alkyl nitrite, as a nitrosation agent,to an aqueous, acid suspension of the corresponding aniline derivative of the formula ##STR2## thereby forming the corresponding N,N-disubstituted p-nitroso-aniline, and subsequently hydrogenating the latter without isolation thereof from the reaction mixture.
    Type: Grant
    Filed: April 5, 1982
    Date of Patent: October 2, 1984
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Bruno Wollemann, Hartmut Hartner, Hans Bardonner
  • Patent number: 4474989
    Abstract: A process for preparing dinitrobenzophenones which comprises reacting benzene with ethylene in the presence of an alkylation catalyst to obtain an alkylation product containing unreacted benzene, ethylbenzene, polyethylbenzenes, 1,1-diphenylethane and heavier products, separating benzene, ethylbenzene and polyethylbenzenes from said alkylation product, recovering from the remainder of said alkylation product a fraction whose boiling points fall within the temperature range of about 260.degree. to about 290.degree. C., reacting said fraction with nitric acid at a temperature within the range of about 130.degree. to about 210.degree. C., wherein the molar ratio of nitric acid to said fraction is in the range of about 3:1 to about 8:1, and thereafter reacting the total resulting reaction product with nitric acid in oleum to obtain a nitration product predominating in dinitrobenzophenones.
    Type: Grant
    Filed: July 1, 1982
    Date of Patent: October 2, 1984
    Assignee: Gulf Research & Development Company
    Inventors: Anatoli Onopchenko, Edward T. Sabourin, Charles M. Selwitz
  • Patent number: 4422954
    Abstract: This invention is a method to restore the metal content of a supported noble metal hydrogenation catalyst comprising adding the appropriate amount of a noble metal salt of a weak acid to a fluid feed passing across the catalyst.
    Type: Grant
    Filed: March 31, 1982
    Date of Patent: December 27, 1983
    Assignee: Allied Corporation
    Inventor: Jan F. Van Peppen
  • Patent number: 4415754
    Abstract: Aniline can be prepared by catalytic hydrogenation of nitrobenzene containing polynitrophenol impurities. The polynitrophenol impurities are converted to tars, and can be separated and disposed of.
    Type: Grant
    Filed: January 17, 1983
    Date of Patent: November 15, 1983
    Assignee: E. I. Du Pont de Nemours & Co.
    Inventor: Frederick R. Lawrence
  • Patent number: 4400538
    Abstract: The instant invention is directed to a process for the production of an aromatic amino compound of the formula: ##STR1## wherein R is an alkyl substituent of from 1 to about 18 carbon atoms,m is an integer of from 1 to 3, andn is an integer of from 0 to 5,comprising subjecting a nitro compound of the formula: ##STR2## wherein R, m, and n are as defined above, to gaseous hydrogen in the presence of a catalyst, the improvement wherein said catalyst is an activated noble metal in the form of a screen or other coherent body.
    Type: Grant
    Filed: June 11, 1981
    Date of Patent: August 23, 1983
    Assignee: Mobay Chemical Corporation
    Inventors: David H. Chadwick, Thomas E. Boyd
  • Patent number: 4323708
    Abstract: A method for preparing 2,4-diaminophenol or 2,4-diaminophenol dihydrochloride comprising hydrogenation of 2,4-dinitrophenol on a membrane catalyst made of an alloy consisting of 90 to 98% by mass of palladium, 2 to 10% by mass of rhodium or ruthenium. Said hydrogenation of 2,4-dinitrophenol is effected by hydrogen diffusing through said membrane catalyst. The starting 2,4-dinitrophenol is used in a medium of water or a 4--37% aqueous solution of hydrochloric acid at a concentration of 2,4-dinitrophenol in said medium ranging from 2 to 50% by mass. The hydrogenation is effected at a temperature within the range of from 50.degree. to 150.degree. C. under a pressure of from 1 to 60 atm.
    Type: Grant
    Filed: April 14, 1980
    Date of Patent: April 6, 1982
    Inventors: Alexandr P. Mischenko, Vladimir M. Gryaznov, Igor G. Gakh, Iraida L. Parbuzina, Evgeny M. Savitsky, Viktoria P. Polyakova, Natalia R. Roshan
  • Patent number: 4322556
    Abstract: Aniline may be prepared by reaction of nitrobenzene and vinylcyclohexene at 170.degree. C.-300.degree. C., typically 200.degree. C., in the presence of a homogeneous catalyst typified by IrCl(CO)(Ph.sub.3 P).sub.2.
    Type: Grant
    Filed: September 26, 1980
    Date of Patent: March 30, 1982
    Assignee: Texaco Inc.
    Inventors: John A. Patterson, Wheeler C. Crawford, James R. Wilson
  • Patent number: 4320021
    Abstract: Amino phenols of the general formula ##STR1## wherein R is a substantially saturated, hydrocarbon-based group of at least about 30 aliphatic carbon atoms, a, b and c are, for example, each 1, 2 or 3, and Ar is an aromatic moiety such as a benzene nucleus, naphthalene nucleus or linked benzene nuclei, are useful additives for fuels and lubricants. These amino phenols can be conveniently prepared by nitrating an appropriate hydroxy aromatic compound and reducing the nitro groups to amino groups. Typically such amino phenols are formed by nitration and reduction of alkyl phenols having an alkyl or alkenyl group of at least about 50 carbon atoms.
    Type: Grant
    Filed: April 13, 1981
    Date of Patent: March 16, 1982
    Assignee: The Lubrizol Corporation
    Inventor: Richard M. Lange
  • Patent number: 4320020
    Abstract: Amino phenols of the general formula ##STR1## wherein R is a substantially saturated hydrocarbyl substituent having an average of from about 30 to about 750 aliphatic carbon atoms; R' is a substituent selected from the group consisting of lower alkyl, lower alkoxyl, nitro, and halo; and z is 0 or 1, are useful as additives for fuels and lubricants. These amino phenols can be conveniently prepared by nitrating an appropriate hydroxy aromatic compound and reducing the nitro groups to amino groups.
    Type: Grant
    Filed: April 1, 1981
    Date of Patent: March 16, 1982
    Assignee: The Lubrizol Corporation
    Inventor: Richard M. Lange
  • Patent number: 4313018
    Abstract: Anthranilic acid has been anchored to polystyrene, and rhodium, palladium, platinum and ruthenium complexes of this modified polystyrene have been prepared. These catalysts will reduce a variety of olefinic and aromatic hydrocarbons, and also nitrile, nitro and carbonyl functional groups, said carbonyl groups being present in either ketones or aldehydes.
    Type: Grant
    Filed: April 7, 1978
    Date of Patent: January 26, 1982
    Assignee: Western Kentucky University
    Inventors: Norman L. Holy, William A. Logan, Karl D. Stein
  • Patent number: 4313002
    Abstract: A method of preparing p-aminodiphenylamines from diphenylamines is described whereby neither the N-nitrosodiphenylamine or the p-nitrosodiphenylamine need be isolated. The method rests on the discovery that alkali metal salts of p-nitrosodiphenylamines are soluble in non-aqueous organic solvent systems consisting of certain aromatic hydrocarbons and saturated aliphatic alcohols, and that such salts can be readily hydrogenated in their non-aqueous solution to the corresponding p-aminodiphenylamine.
    Type: Grant
    Filed: October 29, 1980
    Date of Patent: January 26, 1982
    Assignee: UOP Inc.
    Inventors: Ted Symon, Paul R. Kurek, Michael D. Tufano
  • Patent number: 4300010
    Abstract: This invention provides a process for selective conversion of vinylcyclohexene to ethylbenzene in the presence of a palladium on nonacidic zeolite catalyst.In the catalyst preparation, the catalyst is calcined first in air and then in a hydrocarbon type environment. Without the two step calcination procedure, the catalyst has a lower level of activity and selectivity.
    Type: Grant
    Filed: April 29, 1980
    Date of Patent: November 10, 1981
    Assignee: El Paso Products Company
    Inventor: John L. Cihonski
  • Patent number: 4261926
    Abstract: N-alkylated aromatic amines are produced by reductively alkylating an aromatic amine with pressurized hydrogen in the presence of a ketone, a noble metal catalyst and a promoter acid having a pKa between 0.3 and 1.5.
    Type: Grant
    Filed: November 19, 1979
    Date of Patent: April 14, 1981
    Assignee: American Cyanamid Company
    Inventors: Lawrence J. Ross, Stephen D. Levy