Patents Represented by Attorney Donald L. Johnson

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  • Catalytic alkylation of aromatic amines with alkanols
    Patent number: 4599449
    Abstract: Aromatic amines are alkylated by reaction with an alcohol in the presence of a Group VII-B metal oxide alkylation catalyst, preferably a major proportion of a Group VII-B metal oxide such as MnO.sub.2 in combination with a minor proportion of a Group VIII metal oxide such as Fe.sub.2 O.sub.3, so that alkylation of the aromatic amine occurs. Under most reaction conditions a considerable portion of the alcohol alkylating agent such as ethanol not consumed in the alkylation reaction passes through the reaction zone undecomposed and thus can be readily recovered for recycle or other use.
    Type: Grant
    Filed: June 25, 1984
    Date of Patent: July 8, 1986
    Assignee: Ethyl Corporation
    Inventor: Duane C. Hargis
  • Preparation of 6-carboxy-3,4-dihydro-2H-pyran
    Patent number: 4599435
    Abstract: 6-Carboxy-3,4-dihydro-2H-pyran and ring-substituted derivatives thereof are prepared by reacting a 1,4-disubstituted butane having leaving groups at the one and four positions in a liquid solvent medium with carbon monoxide at elevated temperature and pressure in the presence of a catalytic amount of a metal carbonyl compound and an alkali metal inorganic base or an alkaline earth metal inorganic base.
    Type: Grant
    Filed: March 25, 1985
    Date of Patent: July 8, 1986
    Assignee: Ethyl Corporation
    Inventors: Joachim W. Wolfram, John Y. Lee
  • Di(alkylthio)diamine chain extenders for polyurethane elastomers
    Patent number: 4595742
    Abstract: Polyurethanes and a process for their preparation with aromatic diamines having an aromatic ring, one of said at least one aromatic ring having thereon at least two alkylthio substituents and at least one amino substituent. An isocyanate prepolymer may be combined with a diamine chain extender of the invention and cured at suitable processing temperatures to form elastomers with good physical properties.
    Type: Grant
    Filed: March 4, 1985
    Date of Patent: June 17, 1986
    Assignee: Ethyl Corporation
    Inventors: Christopher J. Nalepa, Paul F. Ranken, Karl E. Wiegand
  • Fuel compositions
    Patent number: 4594077
    Abstract: Coking in and around the injector nozzles of indirect injection compression ignition engines is reduced by means of distillate fuel with which has been blended suitable concentrations of (i) organic nitrate ignition accelerator, and (ii) 1,3,5-trimethyl-2,4,6-tri(3,5-dialkyl-4-hydroxybenzyl)benzene.Also described are additive mixtures of (i) and (ii) for use in distillate fuels in amounts sufficient to reduce the coking tendencies of such fuels when used in the operation of indirect injection compression ignition engines.
    Type: Grant
    Filed: September 20, 1985
    Date of Patent: June 10, 1986
    Assignee: Ethyl Corporation
    Inventors: Edward F. Zaweski, Leonard M. Niebylski
  • Process for preparing (hydrocarbylthio)aromatic amines
    Patent number: 4594453
    Abstract: (Hydrocarbylthio)aromatic amines are prepared by reacting an aromatic amine, such as an aminobenzene, with a hydrocarbyl disulfide, such as an alkyl disulfide. The reaction is preferably conducted in the presence of a Lewis acid catalyst, such as aluminum chloride.
    Type: Grant
    Filed: June 11, 1984
    Date of Patent: June 10, 1986
    Assignee: Ethyl Corporation
    Inventors: Paul F. Ranken, Bonnie G. McKinnie
  • Polyphosphazene process
    Patent number: 4593129
    Abstract: A process for making an alkali metal alkoxide (e.g. sodium alkoxide) of a halogen-substituted alcohol (e.g. fluorine-substituted alcohols) by dispersing an alkali metal (e.g. sodium) in a cycloalkane (e.g. cyclohexane) containing a phenol (e.g. o-allylphenol) and adding the resultant dispersion to an ether (e.g. THF) solution of a halogen-substituted alcohol. The resultant alkali metal haloalkoxide solution contains phenoxides and can be reacted with a phosphonitrilic chloride polymer to introduce haloalkoxide and phenoxide substituents.
    Type: Grant
    Filed: April 18, 1984
    Date of Patent: June 3, 1986
    Assignee: Ethyl Corporation
    Inventors: R. Woodrow Wilson, Jr., Dustin H. Thomas
  • Mammary implant
    Patent number: 4592755
    Abstract: A prosthesis for subcutaneous implantation such as a mammary implant used in reconstructive surgery is made from a polyphosphazene elastomer (e.g. polyfluoroalkoxy phosphazene) sac containing a silicone gel. The sac is essentially impermeable to the silicone gel fill and overcomes a gel migration problem encountered with implants made using polysiloxane sacs.
    Type: Grant
    Filed: June 11, 1985
    Date of Patent: June 3, 1986
    Assignee: Ethyl Corporation
    Inventors: Harold R. Penton, Michael E. Kucsma, F. Alexander Pettigrew
  • 2-amido-3-aminocarboxylic acid esters and process of preparation thereof
    Patent number: 4593118
    Abstract: 2,3-Diaminocarboxylic acid compounds are prepared by (A) nitrosating a .beta.-keto ester to form a 3-keto-2-oximino ester, (B) converting the resultant oxime to a protected 2-amine, (C) reductively aminating the 3-position of the protected 2-amine to form a 2,3-diaminocarboxylic acid ester wherein the 2-amino group is protected, and (D) when desired, treating the 2,3-diaminocarboxylic acid ester to deprotect one or more of the amino and carboxyl groups.
    Type: Grant
    Filed: March 6, 1985
    Date of Patent: June 3, 1986
    Assignee: Ethyl Corporation
    Inventor: Beverly A. Bauer
  • Fuel compositions
    Patent number: 4592761
    Abstract: Coking in and around the injector nozzles of indirect injection compression ignition engines is reduced by means of distillate fuel with which has been blended suitable concentrations of (i) organic nitrate ignition accelerator, and (ii) a mixture of ortho-tert-butylated phenols.Also described are additive mixtures of (i) and (ii) for use in distillate fuels in amounts sufficient to reduce the coking tendencies of such fuels when used in the operation of indirect injection compression ignition engines.
    Type: Grant
    Filed: September 20, 1985
    Date of Patent: June 3, 1986
    Assignee: Ethyl Corporation
    Inventors: Edward F. Zaweski, Leonard M. Niebylski
  • Substituted naphthoic acid process
    Patent number: 4590010
    Abstract: 6-Alkoxy-5-trifluoromethyl-1-naphthoic acids are prepared by (1) cyanating a 6-alkoxytetralone so as to form a 6-alkoxy-1-cyano-3,4-dihydronaphthalene, (2) converting the 6-alkoxy-1-cyano-3,4-dihydronaphthalene to a naphthoic acid precursor selected from a 6-alkoxy-1-cyanonaphthalene and a hydrocarbyl 6-alkoxy-1-naphthoate, (3) halogenating the naphthoic acid precursor to the corresponding 5-halo derivative, (4) trifluoromethylating the 5-halo derivative to replace the 5-halo substituent with a 5-trifluoromethyl group, and (5) hydrolyzing the resultant product to a 6-alkoxy-5-trifluoromethyl-1-naphthoic acid. In a preferred embodiment of the invention, the process is conducted so as to prepare 6-methoxy-5-trifluoromethyl-1-naphthoic acid, which, like the other products, is known to be useful as a pharmaceutical intermediate.
    Type: Grant
    Filed: April 18, 1985
    Date of Patent: May 20, 1986
    Assignee: Ethyl Corporation
    Inventors: Venkataraman Ramachandran, Robert I. Davidson, John R. Maloney
  • Process for preparing alpha-arylacrylonitriles
    Patent number: 4590012
    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 a Lewis acid other than aluminum chloride, preferably in the presence of a solvent. In a preferred embodiment, the aryl ketone is a tetralone, the cyanide is sodium cyanide, the Lewis acid is boron trifluoride, and the product is a 1-cyano-3,4-dihydronaphthalene.
    Type: Grant
    Filed: May 17, 1985
    Date of Patent: May 20, 1986
    Assignee: Ethyl Corporation
    Inventor: Venkataraman Ramachandran
  • Process for preparing alpha arylacrylonitriles
    Patent number: 4590013
    Abstract: An alpha-arylacrylonitrile is prepared by reacting an aryl ketone having a removable hydrogen alpha to the carbonyl group with a cyanide ion source which is free of radicals that would stabilize a cyanohydrin corresponding to the aryl ketone and with a Lewis acid, preferably in the presence of a solvent. In a preferred embodiment, the aryl ketone is a tetralone, the cyanide ion source is hydrogen cyanide, the Lewis acid is aluminum chloride, and the product is a 1-cyano-3,4-dihydronaphthalene.
    Type: Grant
    Filed: May 17, 1985
    Date of Patent: May 20, 1986
    Assignee: Ethyl Corporation
    Inventors: John R. Maloney, Venkataraman Ramachandran
  • Chemical composition
    Patent number: 4588534
    Abstract: An ether sulfinate/sulfonate or disulfonate having the following formula: ##STR1## wherein: R is a hydrocarbon group having from about 6 to about 24 carbon atoms,Y is SO.sub.2 M or SO.sub.3 M,Z is hydrogen or a methyl group, andM is an alkali metal, alkylammonium or ammonium cation and mixtures of each of said sulfinate/sulfonate and said disulfonate with an ether monosulfonate having the following formula:ROCH.sub.2 CH(Z)CH.sub.2 SO.sub.3 Mwherein:R is a hydrocarbon group having from about 6 to about 24 carbon atoms,Z is hydrogen or a methyl group, andM is an alkali metal, alkylammonium or ammonium cation.
    Type: Grant
    Filed: October 29, 1980
    Date of Patent: May 13, 1986
    Assignee: Ethyl Corporation
    Inventors: Lawrence H. Shepherd, Jr., William J. DeWitt, Gerhard O. Kuehnhanss
  • Synthesis of (alkoxyalkyl) amines
    Patent number: 4588843
    Abstract: It has been discovered that when reaction is effected between an alkali metal omega-amino-alkoxide and an alkyl halide, nucleophilic attack of the alkoxide on the alkyl halide occurs so that an (alkoxyalkyl)amine is formed. The conventional Hofmann displacement reaction (elimination of CH.sub.3 Br) does not occur to any significant extent. Nor does the common olefin elimination reaction occur to any significant extent when using alkali metal omega-aminoalkoxides having one or two C.sub.2 or higher alkyl substituents on the nitrogen atom.
    Type: Grant
    Filed: April 26, 1984
    Date of Patent: May 13, 1986
    Assignee: Ethyl Corporation
    Inventor: Everett M. Marlett
  • Method of preparing acyloxybenzenesulfonic acids and salts thereof
    Patent number: 4588533
    Abstract: Alkali metal salts and alkaline earth metal salts of acyloxybenzenesulfonate are prepared by sulfonating an aryl ester of an organic acid with gaseous sulfur trioxide to produce a sulfonation reaction mixture containing acyloxybenzenesulfonic acid, neutralizing the sulfonation reaction mixture with alkali metal hydroxide or alkaline earth metal hydroxide to produce an alkali metal salt or alkaline earth metal salt of an acyloxybenzenesulfonic acid and thereafter recovering from the reaction mixture the acyloxybenzenesulfonic acid salt product thus formed.
    Type: Grant
    Filed: May 18, 1984
    Date of Patent: May 13, 1986
    Assignee: Ethyl Corporation
    Inventor: C. Bernard Berry, Jr.
  • Fuel compositions
    Patent number: 4588415
    Abstract: Coking in and around the injector nozzles of indirect injection compression ignition engines is reduced by means of distillate fuel with which has been blended suitable concentrations of (i) organic nitrate ignition accelerator, and (ii) a dihydrocarbyl phosphite.Also described are additive mixtures of (i) and (ii) for use in distillate fuels in amounts sufficient to reduce the coking tendencies of such fuels when used in the operation of indirect injection compression ignition engines.
    Type: Grant
    Filed: September 20, 1985
    Date of Patent: May 13, 1986
    Assignee: Ethyl Corporation
    Inventors: Edward F. Zaweski, Leonard M. Niebylski
  • Fuel compositions
    Patent number: 4588416
    Abstract: Coking in and around the injector nozzles of indirect injection compression ignition engines is reduced by means of distillate fuel with which has been blended suitable concentrations of (i) organic nitrate ignition accelerator, and (ii) a basic sulfurized alkaline earth metal alkyl phenate.Also described are additive mixtures of (i) and (ii) for use in distillate fuels in amounts sufficient to reduce the coking tendencies of such fuels when used in the operation of indirect injection compression ignition engines.
    Type: Grant
    Filed: September 20, 1985
    Date of Patent: May 13, 1986
    Assignee: Ethyl Corporation
    Inventors: Edward F. Zaweski, Leonard M. Niebylski
  • Fuel compositions
    Patent number: 4588417
    Abstract: Coking in and around the injector nozzles of indirect injection compression ignition engines is reduced by means of distillate fuel with which has been blended suitable concentrations of (i) organic nitrate ignition accelerator, and (ii) diphenylamine or alkylated diphenylamine.Also described are additive mixtures of (i) and (ii) for use in distillate fuels in amounts sufficient to reduce the coking tendencies of such fuels when used in the operation of indirect injection compression ignition engines.
    Type: Grant
    Filed: September 20, 1985
    Date of Patent: May 13, 1986
    Assignee: Ethyl Corporation
    Inventors: Edward F. Zaweski, Leonard M. Miebylski
  • Olefin isomerization process
    Patent number: 4587374
    Abstract: Vinylidene olefins which contain the olefinic unit ##STR1## are isomerized in high yield to form di-substituted internal olefins containing the olefinic unit --CH.dbd.CH-- by heating to 150.degree.-350.degree. C. in contact with an iron carbonyl catalyst. Only minor amounts of tri-substituted internal olefins which contain the olefinic unit ##STR2## are formed.
    Type: Grant
    Filed: March 25, 1985
    Date of Patent: May 6, 1986
    Assignee: Ethyl Corporation
    Inventor: Bruce C. Peters
  • Flame retardant, self-extinguishing polyurethanes and polyurethane foams
    Patent number: 4585806
    Abstract: A reactive fire retardant mixture useful in the preparation of polyurethane foams. The mixture contains a halogenated imide-containing polyol having the formula: ##STR1## and the corresponding ether having the formula: ##STR2## wherein R is a hydrocarbon group having the valance n+2 and is selected from the group consisting of benzene groups, naphthalene groups and alicyclic hydrocarbon groups containing 5 to 10 carbon atoms, R' is an aliphatic hydrocarbon group containing 3-12 carbon atoms, X is selected from the group consisting of bromine and chlorine, n is an integer from 1-6 and p is an integer from 2-6. They are prepared by reacting an alcohol (e.g. isopropyl alcohol), a halogenated dicarboxylic anhydride (e.g. tetrabromophthalic anhydride) and an aminopolyol (e.g. 2-amino-2-ethyl-1,3-propanediol).
    Type: Grant
    Filed: December 12, 1984
    Date of Patent: April 29, 1986
    Assignee: Ethyl Corporation
    Inventor: Henry J. Barda