Patents by Inventor Hughie R. Frick

Hughie R. Frick has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 5264646
    Abstract: A process for preparing a vinylically-unsaturated product compound comprises reacting a halogenated organic compound with a hydrolytically-stable, vinylically-unsaturated precursor compound in the presence of (a) a homogeneous zerovalent palladium catalyst complex, (b) an organic hydrogen halide acceptor and (c) a diluent, wherein the diluent is water or an aqueous solution containing up to 95% by volume of an organic solvent. The halogenated organic compound is selected from aryl halides, benzyl halides or vinylic halides. The hydrolytically-stable, vinylically-unsaturated precursor compound is selected from organosilicon compounds, hydrocarbon compounds or compounds containing at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom or a combination thereof.
    Type: Grant
    Filed: March 28, 1991
    Date of Patent: November 23, 1993
    Assignee: The Dow Chemical Company
    Inventors: Robert A. DeVries, Gregory F. Schmidt, Hughie R.* Frick, Bonnie Frick
  • Patent number: 5243068
    Abstract: A process for preparing a vinylically-unsaturated product compound comprises reacting a halogenated organic compound with a hydrolytically-stable, vinylically-unsaturated precursor compound in the presence of (a) a homogeneous zerovalent palladium catalyst complex, (b) an inorganic hydrogen halide acceptor and (c) a diluent, wherein the diluent is water or an aqueous solution containing up to 95% by volume of an organic solvent. The halogenated organic compound is selected from aryl halides, benzyl halides or vinylic halides. The hydrolytically-stable, vinylically-unsaturated precursor compound is selected from hydrocarbon compounds or compounds containing at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom or a combination thereof.
    Type: Grant
    Filed: May 1, 1992
    Date of Patent: September 7, 1993
    Assignee: The Dow Chemical Company
    Inventors: Robert A. DeVries, Hughie R. Frick, deceased
  • Patent number: 5138081
    Abstract: A process for purifying an impure vinylically-unsaturated organosilicon product compound prepared by reaction between a vinylically-unsaturated organosilicon precursor and a halogenated organic compound in the presence of a homogeneous zerovalent palladium catalyst complex, the catalyst complex including an organophosphine or organoarsine ligand, in the presence of a hydrogen halide acceptor in an essentially anhydrous diluent, comprising treating a mixture containing the impure vinylically-unsaturated organosilicon product compound with a peroxide for a time sufficient to oxidize organophosphine or organoarsine impurities present in a mixture being treated. The peroxide can be selected from aqueous hydrogen peroxide or organic peroxides. The thus-treated mixture can be further treated by chromatography over silica gel or alumina. In optional embodiments, chromatography over silica gel or alumina can precede treatment with the peroxide.
    Type: Grant
    Filed: April 30, 1991
    Date of Patent: August 11, 1992
    Assignee: The Dow Chemical Company
    Inventors: Robert A. DeVries, Mary L. Ash, Hughie R. Frick, deceased
  • Patent number: 5136069
    Abstract: A process for preparing a vinylically-unsaturated product compound comprises reacting a halogenated organic compound with a hydrolytically-stable, vinylically-unsaturated precursor compound in the presence of (a) a homogeneous zerovalent palladium catalyst complex, (b) an inorganic hydrogen halide acceptor and (c) diluent, wherein the diluent is water or an aqueous solution containing up to 95% by volume of an organic solvent. The halogenated organic compound is selected from aryl halides, benzyl halides or vinylic halides. The hydrolytically-stable, vinylically-unsaturated precursor compound is selected from hydrocarbon compounds or compounds containing at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom, silicon atom or a combination thereof.
    Type: Grant
    Filed: March 28, 1991
    Date of Patent: August 4, 1992
    Assignee: The Dow Chemical Company
    Inventors: Robert A. DeVries, Hughie R. Frick, deceased
  • Patent number: 4830846
    Abstract: A method for the separation of anhydrous HCl and HBr from mixtures of the two acids comprising treating the mixture with a hindered pyridine to form a mixture of hindered pyridine salts of the acids, and heating the mixture of salts to a temperature at which thermal cleavage of at least the hydrochloride salt is induced. The hindered pyridines are defined as aromatic compounds having one or more nitrogen atoms in an aromatic ring, or a polymer with pendant aromatic moieties having one or more nitrogens in an aromatic ring, having an appropriate degree of steric hindrance such that the salt formed by the nitrogen atom of the aromatic compound and a strong protic base will undergo dissociation to the aromatic compound and the protic acid at a temperature below the decomposition temperature of the aromatic compound. The formation of salts and their cleavage can be done as either a one-step or two-step process.
    Type: Grant
    Filed: January 29, 1988
    Date of Patent: May 16, 1989
    Assignee: The Dow Chemical Company
    Inventors: Herbert C. Jackson, Jr., Robert A. DeVries, Hughie R. Frick
  • Patent number: 3996200
    Abstract: Two new organic compounds are disclosed, perfluorocyclohexane-1,4-dione and perfluorocyclohexene-1,4-dione, which are obtained concurrently or alternatively by reacting fluoranil with substantially pure anhydrous cobalt trifluoride. These compounds are clear, colorless liquids which are useful as monomers in the synthesis of thermally stable elastomeric polymers. Also disclosed is the dihydrate of said perfluorocyclohexane-1,4-dione, namely, octafluoro-1,1,4,4-cyclohexanetetraol.
    Type: Grant
    Filed: September 11, 1975
    Date of Patent: December 7, 1976
    Assignee: The Dow Chemical Company
    Inventors: Harold E. Doorenbos, Hughie R. Frick
  • Patent number: 3931325
    Abstract: Two new organic compounds are disclosed, perfluorocyclohexane-1,4-dione and perfluorocyclohexene-1,4-dione, which are obtained concurrently or alternatively by reacting fluoranil with substantially pure anhydrous cobalt trifluoride. These compounds are clear, colorless liquids which are useful as monomers in the synthesis of thermally stable elastomeric polymers. Also disclosed is the dihydrate of said perfluorocyclohexane-1,4-dione, namely, octafluoro-1,1,4,4-cyclohexanetetraol.
    Type: Grant
    Filed: March 4, 1974
    Date of Patent: January 6, 1976
    Assignee: The Dow Chemical Company
    Inventors: Harold E. Doorenbos, Hughie R. Frick