Preparing Compound Which Contains Hydroxy, Bonded Directly To Carbon, Or Ether Patents (Class 564/418)
  • 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: 4590263
    Abstract: Novel diazonium salts which possess excellent photo speed, good thermal stability, exceptional resistance to discoloration in the D.sub.min areas, rapid development, and allow a wide range of azo dye colors are provided. The diazonium salts are of the following formula: ##STR1## wherein R.sub.1 is tertiary butyl or tertiary amyl; Y is hydrogen, alkyl, hydroxyalkyl, cyanoalkyl, cycloalkyl, aralkyl, alkoxy, aryloxy, aralkoxy, aralkylthio, arylthio, alkylthio, halogen, allyl, allyloxy, allylthio, cyanoalkoxy, hydroxyalkoxy, methoxyalkoxy, trifluoroalkyl, alkylacetylamino, morpholino, or dialkyl carbonamido;R.sub.2 and R.sub.3 are the same or different, and are alkyl, aralkyl, allyl, cyanoalkyl, hydroxyalkyl, hydrogen, acyl, cycloalkyl, beta-chloroalkyl, branched alkyl, or a structure wherein R.sub.2 and R.sub.3 may be linked together to form a heterocyclic structure; andX is an anion.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: May 20, 1986
    Assignee: James River Graphics, Inc.
    Inventors: Robert C. Desjarlais, Everett W. Bennett
  • Patent number: 4588410
    Abstract: 2-hydroxy-4-aminobenzene are disclosed, useful as oxidative hair coloring substances. These are of the formula ##STR1## wherein R is hydrogen, methyl or hydroxyethel.
    Type: Grant
    Filed: July 18, 1983
    Date of Patent: May 13, 1986
    Assignee: Wella Aktiengesellschaft
    Inventors: Eugen Konrad, Hans-Jurgen Braun, Herbert Mager
  • Patent number: 4571437
    Abstract: A process for preparing unsubstituted and alkyl substituted p-aminophenols. A charge mixture is prepared comprising an unsubstituted or alkyl substituted nitrobenzene, a highly dissociated acid, a catalyst containing platinum and a divalent sulfur compound in which sulfur is bonded to two other moieties, the sulfur compound being present in a proportion of between about 0.1 and about 100 moles per gram-atom of platinum. The mixture comprises an organic phase containing the substrate and an aqueous phase containing the acid. Hydrogen is introduced into the mixture at a pressure of 0-50 psig while the mixture is agitated at a temperature of 70.degree. C. to 100.degree. C., thereby causing the substrate to be reduced to phenylhydroxylamine or an alkyl substituted phenylhydroxylamine. The hydroxylamine is rearranged in the presence of acid to the substituted or unsubstituted p-aminophenol, which is recovered from the aqueous phase.
    Type: Grant
    Filed: July 25, 1983
    Date of Patent: February 18, 1986
    Assignee: Mallinckrodt, Inc.
    Inventors: Douglas C. Caskey, Douglas W. Chapman
  • 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: 4506100
    Abstract: Novel polyimides, optionally end-capped with polymerizable or inert groups, and the polyamic acid or ester intermediates thereof are prepared by reacting a tetracarboxylic acid compound (e.g. pyromellitic dianhydride or 3,3',4,4'-benzophenone tetracarboxylic acid dianhydride or its methyl diester) with diamines having the general formula ##STR1## wherein Z is oxygen or sulfur, X and/or Y are carbonyl or carbinol groups, the amine groups may be in the 2-, 3-, and/or 4-position, and isomerism is present when X and/or Y is a carbinol group. The polyimides may be end-capped by reaction, during or after their formation, with polymerizable groups such as 3-aminophenyl acetylene or 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride. The diamines are novel classes of amines when Z is sulfur and X and/or Y are carbonyl or carbinol groups and when Z is oxygen and X, Y, or X and Y are carbinol groups.
    Type: Grant
    Filed: August 4, 1982
    Date of Patent: March 19, 1985
    Assignee: National Starch and Chemical Corporation
    Inventors: Jules E. Schoenberg, Stephen P. Anderson
  • 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: 4415753
    Abstract: A process for the production of unsubstituted and lower alkyl substituted p-aminophenols. A charge mixture is prepared comprising an unsubstituted or lower alkyl substituted nitrobenzene substrate, a platinum catalyst and a sulfur compound. The sulfur compound may be a divalent sulfur compound in which sulfur is bonded to two other moieties or a compound reducible to such sulfur compound under catalytic hydrogenation conditions. Hydrogen is introduced into the mixture while it is agitated at a temperature of 0.degree.-40.degree. C., thereby reducing the substrate to an unsubstituted or alkyl substituted phenylhydroxylamine. The hydroxylamine is thereafter heated to a temperature of at least 70.degree. C. and agitated at at least 70.degree. C. in the presence of a highly dissociated acid, thereby effecting rearrangement of the hydroxylamine to the corresponding p-aminophenol.
    Type: Grant
    Filed: January 29, 1982
    Date of Patent: November 15, 1983
    Assignee: Mallinckrodt, Inc.
    Inventors: Douglas C. Caskey, Douglas W. Chapman
  • Patent number: 4329503
    Abstract: The process of reducing 2,4-dinitrophenol to 2-amino-4-nitrophenol by reduction with a hydrosulfide in aqueous alkaline solution at temperatures from 20.degree.-100.degree. C. is improved by maintaining the pH at 7 to 9.5 during the reduction.
    Type: Grant
    Filed: January 19, 1981
    Date of Patent: May 11, 1982
    Assignee: Cassella Aktiengesellschaft
    Inventors: Wolfgang Bauer, Klaus Kuhlein
  • Patent number: 4326081
    Abstract: Hydrogenation of mononitroaromatic compounds, particularly nitrobenzene, nitrotoluene and their monochloro and monohydroxy ring substitution products, using hydrogen sulfide as reducing agent and a titanium dioxide catalyst at 200.degree.-400.degree. C. and atmospheric pressure.
    Type: Grant
    Filed: February 23, 1981
    Date of Patent: April 20, 1982
    Assignee: Allied Corporation
    Inventors: Charles T. Ratcliffe, Stuart L. Soled, Anthony J. Signorelli, Irving L. Mador
  • 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: 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: 4307249
    Abstract: An improved process for preparing p-aminophenol by the catalytic hydrogenation of nitrobenzene in an aqueous acidic reaction medium containing a dimethylalkylamine oxide whereby the hydrogenation rate is increased and the selectivity of the reaction for p-aminophenol is improved.
    Type: Grant
    Filed: January 7, 1981
    Date of Patent: December 22, 1981
    Assignee: Mallinckrodt, Inc.
    Inventor: Edward L. Derrenbacker
  • Patent number: 4287365
    Abstract: A particularly active Raney nickel catalyst is provided with a high-iron content, containing about 10 to 30% by weight of iron relative to the sum of the active metals nickel and iron. The catalyst can be prepared by treating aluminum/nickel/iron alloys which contain (1) 21 to 49.5% by weight of nickel, (2) 3 to 16.5% by weight of iron and (3) aluminum to make up to 100%, with an inorganic or organic base and separating the catalyst from the reaction mixture. According to the invention, said particularly active Raney nickel catalysts are used for the hydrogenation of organic compounds.
    Type: Grant
    Filed: June 11, 1979
    Date of Patent: September 1, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Joachim Becker, Walter Schmidt
  • Patent number: 4264529
    Abstract: This invention relates to the field of organic chemistry, and more particularly, to a method for the preparation of p-aminophenol.
    Type: Grant
    Filed: March 24, 1980
    Date of Patent: April 28, 1981
    Assignee: Mallinckrodt, Inc.
    Inventor: Thomas J. Dunn
  • Patent number: 4264525
    Abstract: A stepwise reduction and acetylation process for the production of pure N-acetyl-p-aminophenol (APAP) from p-nitrophenol in an aqueous system that avoids the need for strong acids or excess acetic anhydride.
    Type: Grant
    Filed: July 2, 1979
    Date of Patent: April 28, 1981
    Assignee: Penick Corporation
    Inventor: John Huber, Jr.
  • Patent number: 4264526
    Abstract: A process for the direct production of aminophenol and N-acetyl-p-aminophenol from nitrophenols using a borate ion additive during hydrogenation to eliminate undesirable by-products and color formation.
    Type: Grant
    Filed: July 2, 1979
    Date of Patent: April 28, 1981
    Assignee: Penick Corporation
    Inventors: Donald C. Ruopp, Mark A. Thorn
  • Patent number: 4260558
    Abstract: An improvement in the process for the preparation of an aromatic hydroxy compounds by reacting an aromatic nitroso compound of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 independently represent hydrogen, a lower alkyl radical, halogen, a carboxyl or sulfo group or the corresponding alkali metal salt thereof orR.sup.1, R.sup.2 or R.sup.3 individually represent an optionally substituted aromatic ring formed by linking two adjacent radicals,with hydrazine, the improvement residing in reacting the aromatic nitroso compound with the hydrazine in approximately equivalent amounts in an aqueous medium at temperatures from 10.degree. to 50.degree. C., in the absence of a catalyst the aromatic nitroso compound being initially introduced into a reaction chamber and the hydrazine being added thereto.
    Type: Grant
    Filed: October 23, 1978
    Date of Patent: April 7, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventor: Theodor Pfister
  • Patent number: 4252824
    Abstract: New compounds of the formula ##STR1## are disclosed wherein R.sub.1 =H, linear or branched alkyl-radical with from 1 to 6 carbon atoms, cycloalkyl radical with from 3 to 6 carbon atoms, alkylphenyl radical where the phenyl group may be in turn substituted with a hydroxy or methoxy group;R.sub.2 =hydroxy, hydromethylR.sub.3 =H, alkyl with 1-4 carbon atoms, formyl, carboalkyl where the alkyl groups have 1-3 carbon atoms, carbomido group simple or mono- or di-substituted on the nitrogen atom with alkyl radicals containing 1-3 carbon atoms.The new compounds are useful in the treatment of bronchial affections. They are endowed with unique properties in that they provide the desired bronchial dilation effect without any concomitant cardiac stimulation.
    Type: Grant
    Filed: November 10, 1976
    Date of Patent: February 24, 1981
    Assignee: Valeas S.R.L., Industria Chimica e Farmaceutica
    Inventors: Virgilio Bernareggi, Giuseppe Crespi, Giuseppe Bugada