Patents Represented by Attorney Patricia J. Hogan

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  • Haloethylation of aromatic hydrocarbons
    Patent number: 4990704
    Abstract: A monoalkylaromatic hydrocarbon is haloethylated to a 1-halo-1-arylethane with minimal co-formation of diarylalkane and acetaldehyde by-products by reacting it with hydrogen chloride or bromide and a stoichiometric deficit of acetaldehyde in the presence of sulfuric acid in an amount such as to provide at least two mols of hydrogen sulfate per mol of acetaldehyde and less than 1.5 mols of hydrogen sulfate per mol of the monoalkylaromatic hydrocarbon.
    Type: Grant
    Filed: October 10, 1989
    Date of Patent: February 5, 1991
    Assignee: Ethyl Corporation
    Inventor: Barbara C. Stahly
  • Coupling process
    Patent number: 4982035
    Abstract: An alkene selected from ethene, propene, and mixtures thereof is coupled with an aromatic hydrocarbon having an active hydrogen on a saturated alpha-carbon in the presence of a supported potassium or potassium alloy as a catalyst and cesium oxide as a co-catalyst. In a preferred embodiment of the invention, the active hydrogen-containing aromatic hydrocarbon is an alkylbenzene, such as toluene.
    Type: Grant
    Filed: June 27, 1989
    Date of Patent: January 1, 1991
    Assignee: Ethyl Corporation
    Inventor: R. Scott Smith
  • Methylthio substituted diaminotoluenes
    Patent number: 4982002
    Abstract: 3,5-Di(methylthio)-2,6-diaminotoluene is a novel compound which, alone or in admixture with 3,5-di(methylthio)-2,4-diaminotoluene, is particularly useful as a chain extender in the preparation of polyurethanes.
    Type: Grant
    Filed: July 14, 1989
    Date of Patent: January 1, 1991
    Assignee: Ethyl Corporation
    Inventors: Bonnie G. McKinnie, Paul F. Ranken
  • Alkene coupling
    Patent number: 4982044
    Abstract: A normal 1-alkene containing 3-8 carbons is coupled with itself, another such alkene, or ethene in the presence of a supported alkali metal as a catalyst and about 10-100 mol %, based on the amount of alkali metal catalyst, of an alkali metal hydroxide as a co-catalyst; the support being a silica having a surface area not greater than 5 m.sup.2 /g. In preferred embodiments of the invention, the alkene is propene or a mixture of propene and ethene, the alkali metal is potassium or a potassium alloy, and the co-catalyst is potassium hydroxide.
    Type: Grant
    Filed: June 30, 1989
    Date of Patent: January 1, 1991
    Assignee: Ethyl Corporation
    Inventor: R. Scott Smith
  • Catalyst composition for coupling process
    Patent number: 4977124
    Abstract: A catalyst composition having enhanced effectiveness in coupling an alkene with an aromatic hydrocarbon having an active hydrogen on a saturated .alpha.-carbon is obtained by dispersing an alkali metal onto a supported oxide of sodium, potassium, rubidium, cesium, barium, strontium, calcium, or magnesium in the absence of a diluent.
    Type: Grant
    Filed: June 30, 1989
    Date of Patent: December 11, 1990
    Assignee: Ethyl Corporation
    Inventor: R. Scott Smith
  • Polyurethanes
    Patent number: 4975515
    Abstract: Novel polyurethanes having superior high temperature performance are prepared by reacting 3,5-di(methylthio)2,6-diaminotoluene with a toluenediisocyanate prepolymer having a free --NCO content of 0.1-20% by weight, preferably a toluenediisocyanate/polyether glycol prepolymer having a free --NCO content of 2-7% by weight. The elastomers have good dynamic properties, such as resilience, that make them attractive as tire-forming materials.
    Type: Grant
    Filed: February 21, 1989
    Date of Patent: December 4, 1990
    Assignee: Ethyl Corporation
    Inventors: Christopher J. Nalepa, James H. Simon
  • Aromatic diamines
    Patent number: 4973760
    Abstract: Novel aromatic diamines which are useful as chain extenders for urethane and urea polymers are compounds corresponding to the formula: ##STR1## wherein two of the R, R', and R" substituents are alkyl groups containing 1-6 carbons and the other substituent is a hydrocarbylthio group containing 1-6 carbons.
    Type: Grant
    Filed: October 7, 1988
    Date of Patent: November 27, 1990
    Assignee: Ethyl Corporation
    Inventor: Robert L. Davis
  • Organoborosiloxazane polymers
    Patent number: 4970282
    Abstract: Preceramic polymers which have particular utility in providing protective ceramic coatings on carbon/carbon composites, graphite, carbon fibers, and other normally oxidizable materials are prepared by reacting about 0.25-20 parts by weight of a trialkoxy-, triaryloxy-, or tri(arylalkoxy)boroxine with one part by weight of a polysiloxazane in an organic solvent to form an organoborosiloxazane polymer.
    Type: Grant
    Filed: February 6, 1989
    Date of Patent: November 13, 1990
    Assignee: Ethyl Corporation
    Inventor: Leonard M. Niebylski
  • Resolution of racemic mixtures
    Patent number: 4968837
    Abstract: Racemic 2-(N-propylamino)-5-methoxytetralin is resolved by treating it with a chiral diaroyltartaric acid in an organic solvent at an elevated temperature to form a salt of the amine and chiral diaroyltartaric acid which is soluble in the solvent at the elevated temperature, cooling to precipitate the salt, isolating it, and converting it to the free amine. The product is useful as an intermediate in the synthesis of optionally-active pharmaceutical, such as N-0437.
    Type: Grant
    Filed: July 28, 1989
    Date of Patent: November 6, 1990
    Assignee: Ethyl Corporation
    Inventors: Thanikavelu Manimaran, Fred J. Impastato
  • Catalyst for making amines from alcohols
    Patent number: 4957893
    Abstract: Mono- and di-lower alkylamines, e.g. methylamine or dimethylamine, are alkylated by reaction with C.sub.8-22 alcohol in the presence of hydrogen at a temperature of about 105.degree.-275.degree. C. in contact with a copper-zinc-alkaline earth metal base containing catalyst (e.g., CuO--ZnO--Ba(OH).sub.2) while removing water formed in the reaction.
    Type: Grant
    Filed: June 12, 1989
    Date of Patent: September 18, 1990
    Assignee: Ethyl Corporation
    Inventors: Pak Y. Fong, Kim R. Smith, Joe D. Sauer
  • Reduction of cyanohydrins
    Patent number: 4952718
    Abstract: Arylacetonitriles corresponding to the formula Ar-CH(R)CN are prepared by reducing a cyanohydrin corresponding to the formula Ar-C(R)(OH)CN with phosphorus pentasulfide in an inert solvent; Ar in the formulas representing aryl and R being hydrogen or alkyl. The products are primarily useful as pharmaceutical and agricultural intermediates.
    Type: Grant
    Filed: November 14, 1988
    Date of Patent: August 28, 1990
    Assignee: Ethyl Corporation
    Inventor: Barbara C. Stahly
  • Coupling process
    Patent number: 4950831
    Abstract: An alkene is coupled with an aromatic hydrocarbon having an active hydrogen on a saturated alpha-carbon in the presence of an unsupported alkali metal as a catalyst under high shear agitation conditions. In preferred embodiments of the invention, the alkene is an alkene of 2-20 carbons, such as ethene or propene; the active hydrogen-containing aromatic hydrocarbon is an alkyl-benzene, such as toluene; the alkali metal is potassium or a potassium alloy; and the high shear agitation conditions are attained by operating a turbine-type impeller at a tip speed of at least about 5 m/sec.
    Type: Grant
    Filed: September 28, 1989
    Date of Patent: August 21, 1990
    Assignee: Ethyl Corporation
    Inventors: James S. Staton, Ronald A. Turnblad, Jr., Robert B. Agee
  • Preceramic compositions and ceramic products
    Patent number: 4942145
    Abstract: Preceramic molding compositions capable of forming low density ceramics having acceptable strength and improved wear resistance are compositions having a particle size not larger than about 105 micrometers and comprising an intimate mixture of (A) about 50-90 parts by weight of powder ingredients comprising about 2-50% by weight of graphite powder and about 98-50% by weight of a second powder selected from silicon carbide, silicon nitride, and mixtures thereof and (B) correspondingly, about 50-10 parts by weight of a preceramic polysilazane binder.
    Type: Grant
    Filed: May 26, 1989
    Date of Patent: July 17, 1990
    Assignee: Ethyl Corporation
    Inventors: William E. Moehle, John J. Rogers, John Semen
  • Thiation process
    Patent number: 4935513
    Abstract: An amide is thiated to the corresponding thioamide by reacting it with phosphorus pentasulfide in the presence of a Group IIA metal fluoride as an adjuvant.
    Type: Grant
    Filed: June 7, 1989
    Date of Patent: June 19, 1990
    Assignee: Ethyl Corporation
    Inventor: Barbara C. Stahly
  • Thiation process
    Patent number: 4935514
    Abstract: An amide is thiated to the corresponding thioamide by reacting it with phosphorus pentasulfide in the presence of an adjuvant selected from diatomaceous earth, zeolites, and molecular sieves.
    Type: Grant
    Filed: June 6, 1989
    Date of Patent: June 19, 1990
    Assignee: Ethyl Corporation
    Inventor: Barbara C. Stahly
  • Thiation process
    Patent number: 4935510
    Abstract: Ammonium hydroxide is used in the recovery of a thiono compound prepared by reacting an organic carbonyl compound with phosphorus pentasulfide to improve the product yield.
    Type: Grant
    Filed: June 7, 1989
    Date of Patent: June 19, 1990
    Assignee: Ethyl Corporation
    Inventor: Barbara C. Stahly
  • Process for preparing 2-deoxynucleosides
    Patent number: 4929723
    Abstract: An O-, S-, or N-silyl- or O-, S-, or N-alkylpyrimidine is reacted with a protected 1-halo-, 1-alkoxy-, or 1-acyloxy-2-deoxy sugar in the presence of cuprous iodide and a halohydrocarbon solvent to prepare a nucleoside having an improved beta-anomer/alpha-anomer ratio. In a preferred embodiment of the invention, 2,4-bis(trimethylsilyloxy)-5-methylpyrimidine or 2,4-bis(trimethylsilyloxy)-5-ethylpyrimidine is reacted with 2-deoxy-3,5-di-O-p-toluyl-D-erythro-ribofuranosyl chloride in the presence of cuprous iodide and chloroform.
    Type: Grant
    Filed: April 21, 1989
    Date of Patent: May 29, 1990
    Assignee: Ethyl Corporation
    Inventor: John N. Freskos
  • Coupling process
    Patent number: 4929783
    Abstract: An alkene selected from ethene, propene, and mixtures thereof is coupled with an aromatic hydrocarbon having an active hydrogen on a saturated alpha-carbon in the presence of a supported potassium or potassium alloy as a catalyst and an alkaline earth metal oxide as a co-catalyst. In a preferred embodiment of the invention, the active hydrogen-containing aromatic hydrocarbon is an alkylbenzene, such as toluene.
    Type: Grant
    Filed: June 27, 1989
    Date of Patent: May 29, 1990
    Assignee: Ethyl Corporation
    Inventor: R. Scott Smith
  • Process for polymerizing monoallylamine
    Patent number: 4927896
    Abstract: A water-soluble salt of monoallylamine is polymerized in an aqueous reaction medium at a temperature of about 30.degree.-80.degree. C. in the presence of a polymerization initiator comprising about 3-15% by weight of hydrogen peroxide and about 1-700 ppm of a multi-valent metal ion, based on the weight of the monomer charge. The hydrogen peroxide is preferably introduced continuously or periodically during a substantial portion of the polymerization reaction. Preferred sources of the metal ion are water-soluble iron salts, such as ferric or ferrous chloride.
    Type: Grant
    Filed: July 3, 1989
    Date of Patent: May 22, 1990
    Assignee: Ethyl Corporation
    Inventors: Wesley C. Blocker, David N. Roark, Edwin D. Hornbaker
  • Organoborosilazane polymers
    Patent number: 4921925
    Abstract: Preceramic polymers which have particular utility in providing protective ceramic coatings on carbon/carbon composites, graphite, carbon fibers, and other normally oxidizable materials, are prepared by reacting about 0.25-20 parts by weight of a triaryloxyboroxine with one part by weight of a polysilazane to form a organoborosilazane polymer.
    Type: Grant
    Filed: November 17, 1988
    Date of Patent: May 1, 1990
    Assignee: Ethyl Corporation
    Inventor: Leonard M. Niebylski