Patents Examined by Harry B. Shubin
  • 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: 4543425
    Abstract: 1,3-diamino-4-(2',2',2'-trifluoroethoxy)-benzene, as well as its acid addition salts, are used as new compounds to serve as coupler substance in hair dyeing compositions and yields with known developer substances 1,4-diaminobenzene and 2,5-diaminobenzylalcohol to stable blue tones without any red fraction. Moreover, the new compounds lead to exceptional black tones and ash tones.
    Type: Grant
    Filed: August 5, 1983
    Date of Patent: September 24, 1985
    Assignee: Wella AG
    Inventors: Eugen Konrad, Hans J. Braun, Herbert Mager, Friedrich Noser, Max Bracher
  • Patent number: 4539430
    Abstract: Method for the preparation of ethylenediamine dinitrate. Ethylenediamine dinitrate, a useful explosive, may readily be prepared by solvent extraction of nitrate ion from an acidic aqueous solution thereof using a high-molecular-weight, water-insoluble amine dissolved in an organic solvent, and reacting the resulting organic solution with ethylenediamine. The process of the instant invention avoids the use of concentrated nitric acid, as is currently practiced, resulting in a synthesis which is far less hazardous especially for large quantities of the explosive, and more efficient.
    Type: Grant
    Filed: May 17, 1984
    Date of Patent: September 3, 1985
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventor: Kien-yin Lee
  • Patent number: 4539429
    Abstract: Novel lower-alkyl 2-(hydroxyphenylamino)phenyl ketones, useful as inhibitors of lipoxygenase activity, are of the formula ##STR1## wherein R is hydrogen, lower-alkyl, lower-alkoxy or halo; R' is hydrogen or lower-alkyl; R" is hydrogen, lower-alkyl or halo; and Alk is lower-alkyl. The compounds are prepared by de-etherification of the corresponding alkyl or benzyl ethers which are in turn prepared by reacting a 2-(alkoxy- or benzyloxyphenylamino)benzoic acid with an alkyllithium.
    Type: Grant
    Filed: July 11, 1983
    Date of Patent: September 3, 1985
    Assignee: Sterling Drug Inc.
    Inventor: Denis M. Bailey
  • Patent number: 4537992
    Abstract: A method for removal of nitrosoamine impurities from herbicides comprising contacting a nitrosoamine containing herbicide homogeneously with 0.001% to 1.0% of a compound having the formula: ##STR1## where X equals chlorine or bromine,R.sup.1 equals lower alkyl, anda equals zero or 1; provided that when a equals 1, then:R equals X.sub.n H.sub.(3-n) C(CH.sub.2).sub.p --, or ##STR2## or R.sup.2 COX, where R.sup.2 is selected from alkylene, alkenylene, alkynylene groups having 1 to 5 carbon atoms,n equals 1 to 3, andp equals zero, 1 or 2; and provided that when a equals zero, then:R equals aminophenyl,for a sufficient length of time to remove at least a substantial amount of the nitrosoamine.
    Type: Grant
    Filed: February 9, 1984
    Date of Patent: August 27, 1985
    Assignee: Agan Chemical Manufacturers, Ltd.
    Inventors: Michael Pikarski, Julian Gabe, Edmund Dykman
  • Patent number: 4536602
    Abstract: The present invention involves the catalytic amination of olefins with ammonia, a primary amine, or a secondary amine using a perfluorinated organic acid catalyst.
    Type: Grant
    Filed: June 1, 1984
    Date of Patent: August 20, 1985
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Michael Deeba
  • Patent number: 4532353
    Abstract: This invention pertains to two substituted benzotrifluoride compounds useful as chemical intermediates for a new class of 2-haloacetanilide herbicides and a process for making these intermediates. The process generally involves nitration and reduction of the corresponding benzotrifluoride compound.
    Type: Grant
    Filed: June 16, 1983
    Date of Patent: July 30, 1985
    Assignee: Monsanto Co.
    Inventors: John P. Chupp, Audrey Y. Ku, Thomas E. Neumann, Thomas E. Nickson
  • Patent number: 4532352
    Abstract: A process is disclosed for the separation of p-fluoroaniline from a mixture, containing aniline and p-fluoroaniline, by contacting the mixture with a mineral acid in the presence of an organic solvent. The corresponding salt of p-fluoro-aniline is insoluble and can easily be isolated by conventional means such as filtration. If desired, the isolated salt can be converted to p-fluoroaniline by reaction with a base.
    Type: Grant
    Filed: October 24, 1983
    Date of Patent: July 30, 1985
    Assignee: Mallinckrodt, Inc.
    Inventor: Jerry R. Patton
  • Patent number: 4518804
    Abstract: Novel N-aroyl N'-phenyl urea compounds having halogen substituents in the 2- and 5-position of the phenyl radical possess exceptional insecticidal activity.
    Type: Grant
    Filed: August 3, 1983
    Date of Patent: May 21, 1985
    Assignee: The Dow Chemical Company
    Inventors: Raymond H. Rigterink, Barat Bisabri-Ershadi
  • Patent number: 4514574
    Abstract: Separate isomers via supercritical gas extraction.
    Type: Grant
    Filed: January 9, 1984
    Date of Patent: April 30, 1985
    Assignee: The Dow Chemical Company
    Inventors: Kimio Inoue, Gale G. Hoyer, Stanley I. Bates
  • Patent number: 4508922
    Abstract: Process for the manufacture of an optionally halogenated aniline of the formula: ##STR1## in which Y=halogen, R=H, alkyl (C.sub.1 -C.sub.4) or alkoxy (C.sub.1 -C.sub.4) and n=0 to 5.Halogenobenzenes of the formula: ##STR2## in which Y, R and n are as above and X=halogen, are subjected to ammonolysis with aqueous ammonia solution, in the presence of copper and 8-hydroxyquinoline.The process can be used, in particular, for the preparation of 3,5-dichloroaniline.
    Type: Grant
    Filed: June 28, 1983
    Date of Patent: April 2, 1985
    Assignee: Rhone-Poulenc Agrochimie
    Inventor: Serge Ratton