Formation Of Azo Group By Oxidative Coupling Patents (Class 534/578)
  • Patent number: 10131638
    Abstract: A synthesis for an azo intermediate, 5,5?-azobis(4-chloropyrimidine) is disclosed. 5,5?-azobis(4-chloropyrimidine) is a relatively stable azo compound in that decomposition does not occur until about 194° C. 5,5?-azobis(4-chloropyrimidine) is a product of oxidative dimerization of 5-amino-4-pyrimidine, which a water soluble compound. The azo intermediate is formed in an aqueous solution, but the azo intermediate is substantially insoluble in water; and as it forms it separates producing a reaction mixture that is a slurry. The azo intermediate is isolated by filtration. The azo intermediate is marginally soluble in acetone. The yield is at least 18%, and the oxidizing agent (bleach) is inexpensive, reaction conditions do not require extreme heat or cold, which taken together make the azo intermediate suitable for scaling up.
    Type: Grant
    Filed: March 12, 2018
    Date of Patent: November 20, 2018
    Assignee: The United States of America as Represented by the Secretary of the Navy
    Inventors: Patrick A. Caruana, Alfred G. Stern, Alex J. Zaita, Thao Vo
  • Publication number: 20090215999
    Abstract: Thermally stable functionalized organosilicon compounds containing at least one activated azo group, of formula (I): [(G0)3SiO1/2]m[(G0)2SiO2/2]n[G0SiO3/2]o[SiO4/2]p[(G2)a(G1)a?(Z-CO—HN?NH—CO-A)SiO(3-a-a?)/2] are synthesized from at least one hydrazino precursor (II) (—HN—NH—) of the compound (I), oxidizing the precursor (II) into an azo group for the compound (I), employing an oxidizing system including at least one oxidizing agent (Ox) and at least one base (B), such oxidizing being carried out in a two-phase aqueous/organic medium and such that the pH of the aqueous phase ranges from 3 to 11.
    Type: Application
    Filed: May 17, 2006
    Publication date: August 27, 2009
    Applicant: RHODIA CHIMIE
    Inventor: Sebastien Sterin
  • Publication number: 20040132982
    Abstract: The present invention relates to a process for the preparation of aromatic azo-compounds, in particular 3,3′-azo-bis(6-hydroxybenzoic acid) (olsalazine) and its salts and derivatives.
    Type: Application
    Filed: September 17, 2003
    Publication date: July 8, 2004
    Applicant: Generics [UK] Limited
    Inventors: Vinayak G. Gore, Manoj M. Ghadge, Vishakha R. Shembekar, R. Venkat Raman
  • Patent number: 5760192
    Abstract: An azodinitrile composition comprising a mixture of at least six different azodinitriles of formula I ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are each independently acyclic aliphatic hydrocarbon radicals of 1-9 carbon atoms, said mixture having a freezing point of a maximum of 25.degree. C. and a process for its preparation are disclosed.
    Type: Grant
    Filed: June 28, 1996
    Date of Patent: June 2, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Ernest Byron Wysong
  • Patent number: 5606034
    Abstract: The invention discloses a process for the preparation of azo dyes using an aminodiphenylamine as diazo component. The process comprises reacting the amine, an alkali metal nitrite and a mineral acid continuously in the temperature range from 35.degree. to 65.degree. C. to give the diazo compound, using a 3 to 15% excess of alkali metal nitrite, and thereafter coupling the diazo compound to a coupling component. Azo dyes of superior quality constancy and in high yield are obtained by the novel process.
    Type: Grant
    Filed: February 16, 1995
    Date of Patent: February 25, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Horst Langfeld, Karl-Friedrich Haarburger, Herbert Mauser
  • Patent number: 5288908
    Abstract: Compounds of the formula ##STR1## in which X represents hydrogen, --NO.sub.2 or --NH.sub.2 and Y represents --CH.sub.3, --COOH, --CONH.sub.2, --NH.sub.2 or --N.dbd.N--Z, in which the group --Z is ##STR2## with the proviso that if Y represents the group --N.dbd.N--Z, X is only --NO.sub.2, and if Y represents the group --CH.sub.3, X is only hydrogen, are described. A compound of the formula ##STR3## the preparation of which in a multi-stage process, in which the compounds of the general formula (I) are also obtained, is described, is preferred.The resulting 3,4'-diamino compound is suitable for the preparation of polycondensates and shaped articles, films and fibers of high heat resistance.
    Type: Grant
    Filed: July 19, 1993
    Date of Patent: February 22, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jurgen Lau, Gunter Siegemund, Freimund Rohrscheid
  • Patent number: 4962040
    Abstract: 2-Hydrazono-4,6-dinitrobenzthiazolones of the formula ##STR1## in which X.sub.1 represents hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -hydroxyalkyl, C.sub.1 -C.sub.4 -sulphoalkyl or C.sub.1 -C.sub.4 -sulphatoalkyl, andX.sub.2 represents hydrogen or --SO.sub.2 X.sub.3, whereX.sub.3 may represent hydrogen, C.sub.1 -C.sub.8 -alkyl or optionally substituted aryl andX.sub.1 also represents a double bond between the cyclic nitrogen atom and the carbon atom 2 according to the formula II below: ##STR2## where X.sub.2 has the meaning specified under the above formula. These hydrazones may be employed in the preparation of azo dyestuffs and as color formers for detecting of biological substances, and in the determination of H.sub.2 O.sub.2.
    Type: Grant
    Filed: August 10, 1989
    Date of Patent: October 9, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Herbert Hugl, Aloysius Engel, Klaus Wehling
  • Patent number: 4889846
    Abstract: The invention concerns azo compounds of formula ##STR1## or a salt thereof, in which formula R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, and R.sup.6 are each independently hydrogen or lower alkyl, R.sup.7 and R.sup.8 are each independently alkyl of 1 to 7 carbon atom or cycloalkyl of 5 to 7 carbon atoms optionally substituted by lower alkyl which possess anti-inflammatory activity.
    Type: Grant
    Filed: April 15, 1988
    Date of Patent: December 26, 1989
    Assignee: John Wyeth & Brother Limited
    Inventor: Roger Crossley
  • Patent number: 4837308
    Abstract: A universally usable process for preparing azo dyestuffs by oxidative coupling consists in carrying out the oxidation in the presence of redox mediators with a standard potential of 0.2-1.5 volts and, if appropriate, an additional oxidizing agent with a standard potential of 0.25-2.5 volts, wherein the sum of the oxidation equivalents should be at least 4. The preferred redox mediator is iodine. The process is particularly suitable for the preparation of heteroaromatic azo dyestuffs using an aniline coupling component.
    Type: Grant
    Filed: January 12, 1988
    Date of Patent: June 6, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventor: Rainer Gerlach
  • Patent number: 4612368
    Abstract: A process for the preparation of 2,2'-azobis(2-methylbutanenitrile) in high yield, good quality and filtering and drying characteristics by reacting 2-amino-2-methylbutanenitrile with a metal hypochorite in the presence of water and a mixture of surface active compounds at a temperature of about -10.degree. C. to about 30.degree. C. and recovering the 2,2'-azobis(2-methylbutanenitrile) from the reaction mixture.
    Type: Grant
    Filed: June 3, 1981
    Date of Patent: September 16, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Earl P. Moore, Jr.