Patents Represented by Attorney Patricia J. Hogan

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  • Aldehyde synthesis
    Patent number: 4562297
    Abstract: 3,5-Dihydrocarbyl-4-hydroxybenzaldehydes are prepared by intimately contacting a 4-(1-alkenyl)-2,5-dihydrocarbylphenol, such as 1,1-dimethyl-2-(3,5-di-t-butyl-4-hydroxyphenyl)ethene, with at least a stoichiometric amount of an oxygen-containing gas at about 50.degree.-25.degree. C. in the presence of an alcohol solvent and a catalytic amount of an alkali or alkaline earth metal hydroxide.
    Type: Grant
    Filed: November 2, 1984
    Date of Patent: December 31, 1985
    Assignee: Ethyl Corporation
    Inventor: Jerry M. Roper
  • Preparation of 1-alkyl-1,4-dihydro-4-oxo-7-(4-pyridyl)-3-quinolinecarboxylic acid
    Patent number: 4554352
    Abstract: 4-(Bromophenyl)pyridines, useful in preparing bactericides, are prepared by reacting a 4-phenylpyridine with bromine in the presence of an excess of a Lewis acid catalyst, preferably aluminum chloride.
    Type: Grant
    Filed: September 29, 1983
    Date of Patent: November 19, 1985
    Assignee: Ethyl Corporation
    Inventor: Paul F. Ranken
  • 2-Nitro-4-(4-pyridinyl) benzoic acids and derivatives
    Patent number: 4552966
    Abstract: 2-Nitro-4-(4-pyridinyl)benzoic acids, such as 2-nitro-4-(4-pyridinyl)benzoic acid, are prepared by oxidizing the appropriate 4-(4-alkyl-3-nitrophenyl)pyridine with, e.g., potassium permanganate or nitric acid. The products are particularly useful in the preparation of antibacterial 1-alkyl-1,4-dihydro-4-oxo-7-pyridinyl-3-quinolinecarboxylic acids.
    Type: Grant
    Filed: July 8, 1983
    Date of Patent: November 12, 1985
    Assignee: Ethyl Corporation
    Inventors: Paul F. Ranken, Thomas J. Walter
  • 4-(1-Chlorocyclohex-3-enyl)pyridines and preparation of 1-alkyl-1,4-dihydro-4-oxo-7-(4-pyridyl)-3-quinolinecarboxylic acid
    Patent number: 4552964
    Abstract: A 4-(1-chlorovinyl)pyridine, preferably 4-(1-chlorovinyl)pyridine itself, is reacted with a butadiene, preferably chloroprene, to prepare a 4-(1-chlorocyclohex-3-enyl)pyridine. The preferred products are useful as intermediates in the preparation of antibacterial 1-alkyl-1,4-dihydro-4-oxo-7-pyridinyl-3-quinolinecarboxylic acids.
    Type: Grant
    Filed: September 16, 1983
    Date of Patent: November 12, 1985
    Assignee: Ethyl Corporation
    Inventor: Venkataraman Ramachandran
  • Preparation of 1-alkyl-1,4-dihydro-4-oxo-7-(4-pyridyl)-3-quinolinecarboxylic acid
    Patent number: 4552963
    Abstract: The yield of Diels-Alder product obtained by reacting a haloprene with a 4-vinylpyridine is increased by conducting the reaction in the presence of a boron trifluoride catalyst, preferably a boron trifluoride etherate. The product obtained by the reaction, a mixture of 4-(chlorocyclohex-3-enyl)pyridines, is useful in the production of antibacterial 1-alkyl-1,4-dihydro-4-oxo-7-pyridinyl-3-quinolinecarboxylic acids.
    Type: Grant
    Filed: May 23, 1983
    Date of Patent: November 12, 1985
    Assignee: Ethyl Corporation
    Inventor: Venkataraman Ramachandran
  • Preparation of 1-alkyl-1,4-dihydro-4-oxo-7-(4-pyridyl)-3-quinoline carboxylic acid
    Patent number: 4550167
    Abstract: Diels-Alder products obtained by reacting a haloprene with a 4-vinylpyridine, i.e., mixtures of 4-(halocyclohex-3-enyl)pyridine isomers, are reacted with a relatively strong acid, i.e., an acid having a dissociation constant of at least 1.7.times.10.sup.-5 at 25.degree. C., to form salts which are readily separated and/or reduced.
    Type: Grant
    Filed: May 23, 1983
    Date of Patent: October 29, 1985
    Assignee: Ethyl Corporation
    Inventor: Venkataraman Ramachandran
  • Preparation of (hydrocarbylthio)phenols
    Patent number: 4547593
    Abstract: (Hydrocarbylthio)phenols, such as 2-(alkylthio)phenols, are prepared by heating one or more (hydrocarbylthio)phenols selected from 2-, 3-, 4-, and poly(hydrocarbylthio)phenols in the presence of a catalytic amount of an aluminum phenoxide to redistribute the starting materials.
    Type: Grant
    Filed: March 26, 1984
    Date of Patent: October 15, 1985
    Assignee: Ethyl Corporation
    Inventor: Paul F. Ranken
  • Aryl coupling process
    Patent number: 4544509
    Abstract: An arylamine is coupled with an aromatic compound in the presence of water, an inorganic nitrite, and an alkanoic acid containing 5-7 carbons. In a preferred embodiment of the invention, 2-(4-amino-3-fluorobenzene)propionitrile is coupled with benzene in the presence of water, sodium nitrite, and hexanoic acid to form a flurbiprofen intermediate.
    Type: Grant
    Filed: August 15, 1983
    Date of Patent: October 1, 1985
    Assignee: Ethyl Corporation
    Inventor: Robert I. Davidson
  • Preparation of 4-(3-cyano-4-nitrophenyl)phenols
    Patent number: 4541962
    Abstract: 4-(3-Cyano-4-nitrophenyl)phenols are prepared by reacting a 2-cyano-1-nitrobenzene having a replaceable hydrogen in the 4-position with a phenol having a replaceable hydrogen in the 4-position in an inert solvent and in the presence of a strong base. The 2-cyano-1-nitrobenzene and phenol may be substituted or unsubstituted, and preferred phenols include phenol and 2,6-dialkylphenols.
    Type: Grant
    Filed: May 7, 1984
    Date of Patent: September 17, 1985
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • Nitrile purification
    Patent number: 4541961
    Abstract: Nitriles, such as 2-(2-fluoro-4-biphenyl)propionitrile, contaminated with ketones having similar boiling points are purified by treating the nitrile/ketone mixture with an alkali metal borohydride, e.g., sodium borohydride, to complex the ketone. After complexing of the ketone, the nitrile can be separated therefrom by distillation.
    Type: Grant
    Filed: August 29, 1983
    Date of Patent: September 17, 1985
    Assignee: Ethyl Corporation
    Inventor: Robert I. Davidson
  • Fluoronitroaralkyloxazolines, derivatives thereof, and nucleophilic substitution processes for preparing them
    Patent number: 4540795
    Abstract: Fluoronitroaralkyloxazolines are prepared by reacting a fluoronitroaromatic compound with an alpha-substituted 2-alkyloxazoline in an inert solvent and in the presence of a base. Fluoronitroaralkyloxazolines are useful intermediates for the synthesis of pharmaceuticals, such as flurbiprofen.
    Type: Grant
    Filed: February 25, 1983
    Date of Patent: September 10, 1985
    Assignee: Ethyl Corporation
    Inventor: Kenneth C. Lilje
  • Substituted pyridines
    Patent number: 4540793
    Abstract: 4-(1-Chlorovinyl)pyridines are prepared by heating an acid salt of 4-(1,2-dichloroethyl)pyridine in an inert solvent until dehydrohalogenation is effected.
    Type: Grant
    Filed: September 16, 1983
    Date of Patent: September 10, 1985
    Assignee: Ethyl Corporation
    Inventor: Venkataraman Ramachandran
  • (Alkoxydiazo)halobenzeneacetonitriles
    Patent number: 4539397
    Abstract: The coupling of an aminohalobenzeneacetonitrile with a benzene compound in the presence of an alkyl nitrite to form a halobiphenylacetonitrile via a diazo intermediate is improved by conducting the reaction at a temperature of about 0.degree.-15.degree. C. until diazotization of the aminohalobenzeneacetonitrile is substantially complete. Use of the low diazotization temperature leads to an increased yield of halobiphenylacetonitrile.
    Type: Grant
    Filed: July 27, 1984
    Date of Patent: September 3, 1985
    Assignee: Ethyl Corporation
    Inventor: Venkataraman Ramachandran
  • Aromatic coupling process
    Patent number: 4538005
    Abstract: 4-(2-Trifluoromethyl-4-nitrophenyl)phenols are prepared by reacting a 3-trifluoromethyl-1-nitrobenzene having a replaceable hydrogen in the 4-position with a phenol having a replaceable hydrogen in the 4-position in an inert solvent and in the presence of a strong base. The 3-trifluoromethyl-1-nitrobenzene and phenol may be substituted or unsubstituted, and preferred phenols include phenol and 2,6-dialkylphenols.
    Type: Grant
    Filed: May 7, 1984
    Date of Patent: August 27, 1985
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • Aromatic coupling process
    Patent number: 4538004
    Abstract: 4-(3-Trifluoromethyl-4-nitrophenyl)phenols are prepared by reacting a 2-trifluoromethyl-1-nitrobenzene having a replaceable hydrogen in the 4-position with a phenol having a replaceable hydrogen in the 4-position in an inert solvent and in the presence of a strong base. The 2-trifluoromethyl-1-nitrobenzene and phenol may be substituted or unsubstituted, and preferred phenols include phenol and 2,6-dialkylphenols.
    Type: Grant
    Filed: May 4, 1984
    Date of Patent: August 27, 1985
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • 4H-1-benzopyrans and lubricant compositions containing same
    Patent number: 4537920
    Abstract: 4H-1-Benzopyrans are prepared by reacting an aminomethylphenol with an alkali metal hydroxide or an alkaline earth metal hydroxide and a 1,3-diketone. The products are useful as antioxidants.
    Type: Grant
    Filed: August 18, 1983
    Date of Patent: August 27, 1985
    Assignee: Ethyl Corporation
    Inventor: Jerry M. Roper
  • Aromatic coupling process
    Patent number: 4538006
    Abstract: 4-(2,4-Dinitrophenyl)phenols are prepared by reacting a 1,3-dinitrobenzene having a replaceable hydrogen in the 4-position with a phenol having a replaceable hydrogen in the 4-position in an inert solvent and in the presence of a strong base. The 1,3-dinitrobenzene and phenol may be substituted or unsubstituted, and preferred phenols include phenol and 2,6-dialkylphenols.
    Type: Grant
    Filed: May 4, 1984
    Date of Patent: August 27, 1985
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • Process for preparing alpha-arylacrylonitriles
    Patent number: 4536343
    Abstract: An alpha-arylacrylonitrile is prepared by reacting an aryl ketone having a removable hydrogen alpha to the carbonyl group with an alkali metal cyanide and aluminum chloride, preferably in the presence of a solvent and a phase transfer catalyst. In a preferred embodiment, the aryl ketone is a tetralone, and the product is a 1-cyano-3,4-dihydronaphthalene which may then be dehydrogenated to a 1-cyanonaphthalene.
    Type: Grant
    Filed: November 29, 1984
    Date of Patent: August 20, 1985
    Assignee: Ethyl Corporation
    Inventor: Venkataraman Ramachandran
  • (Hydrocarbylthio)phenols and their preparation
    Patent number: 4533753
    Abstract: (Hydrocarbylthio)phenols containing at least two hydrocarbylthio groups on a phenolic ring are prepared by reacting phenolic compounds with an excess of hydrocarbyl disulfide in the presence of catalytic amounts of an aluminum phenoxide. Novel and useful (hydrocarbylthio)phenols containing at least two hydrocarbylthio groups on a phenolic ring can be prepared by this process. (Hydrocarbylthio)phenols containing at least two hydrocarbylthio groups on a phenolic ring are effective antioxidants for organic material normally susceptible to oxidative deterioration, such as mineral oil.
    Type: Grant
    Filed: April 12, 1983
    Date of Patent: August 6, 1985
    Assignee: Ethyl Corporation
    Inventors: Bonnie G. McKinnie, Paul F. Ranken
  • Process for preparing antibacterial compounds
    Patent number: 4533735
    Abstract: 4-(4-Halo-3-nitrophenyl)pyridines, useful as intermediates in the synthesis of antibacterial 1-alkyl-1,4-dihydro-4-oxo-7-pyridinyl-3-quinolinecarboxylic acids, are obtained by nitrating 4-(4-halophenyl)pyridines. The 4-(4-halo-3-nitrohenyl)pyridines may be converted to the antibacterial agents by reducing them to 4-(3-aminophenyl)pyridines and then subjecting the amino compounds to suitable known reactions.
    Type: Grant
    Filed: May 19, 1983
    Date of Patent: August 6, 1985
    Assignee: Ethyl Corporation
    Inventor: Thomas J. Walter