Patents Represented by Attorney, Agent or Law Firm John F. Hunt
  • Patent number: 4524222
    Abstract: Dinitro alkyl phenols are produced free of tar when the precursor orthoalkylphenol is contacted with a molecular sieve prior to sulfonation, nitration, and air drying. The dinitro alkylphenols produced are free of tars or similar resins and avoid processing problems that are shown in impure prior art products.
    Type: Grant
    Filed: January 26, 1984
    Date of Patent: June 18, 1985
    Assignee: Ethyl Corporation
    Inventor: Charles F. Weidig
  • Patent number: 4514577
    Abstract: Phenols having an unsubstituted ortho-position are benzylated by reaction with a benzyl alcohol in contact with an activated alumina catalyst especially gamma alumina at a temperature sufficient to maintain the reactants in the vapor phase.
    Type: Grant
    Filed: October 15, 1982
    Date of Patent: April 30, 1985
    Assignee: Ethyl Corporation
    Inventors: Allen H. Filbey, Henry G. Braxton, Jr., Bernard R. Meltsner
  • Patent number: 4512966
    Abstract: An effective two stage process for the production of sodium aluminum tetrahydride which facilitates use of equipment at moderate hydrogen pressure of 700-1500 psig. An aluminum alkyl is added to provide a catalyst species in a hydrocarbon reaction medium containing aluminum and sodium reactants. A reaction at about 130.degree.-170.degree. C. is carried out to form Na.sub.3 AlH.sub.6. The reaction temperature is then lowered to about 80.degree.-120.degree. C. and the hydrogen pressure is continued to convert the Na.sub.3 AlH.sub.6 to NaAlH.sub.4.
    Type: Grant
    Filed: December 2, 1983
    Date of Patent: April 23, 1985
    Assignee: Ethyl Corporation
    Inventor: Gunner E. Nelson
  • Patent number: 4492798
    Abstract: A process for the production of an arylalkylpyruvic acid of the general formula:(R).sub.n --A--(CH.sub.2).sub.m CH.sub.2 COCOOHwherein:A represents an aromatic hydrocarbon radical containing 1 or 2 condensed benzene rings,each R, which may be the same or different, represents hydrogen or a linear or branched alkyl radical with up to 4 carbon atoms which is unsubstituted or substituted by a nitro group or by an alkoxy group containing 1 to 4 carbon atoms, or an alkoxy group containing 1 to 4 carbon atoms, or a halogeno, nitrile, nitro or alkylcarbonyloxy group,n is 0 or an integer from 1-3 when A contains one benzene ring, and n is 0 or an integer from 1-5 when A contains two condensed benzene rings and m is 1-20, which comprises carbonylating an arylalkyl halide of the general formula:(R).sub.n --A--(CH.sub.2).sub.m CH.sub.
    Type: Grant
    Filed: January 13, 1983
    Date of Patent: January 8, 1985
    Assignee: Ethyl Corporation
    Inventors: John Y. Lee, Joachim W. Wolfram
  • Patent number: 4481368
    Abstract: A process for the production of .alpha.-keto-carboxylic acids of the general formula: ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and are hydrogen, hydrocarbyl radicals, substituted hydrocarbyl radicals or hydrocarbyloxy radicals by reacting an acyl halide of the formula: ##STR2## wherein R.sub.1 and R.sub.2 are as defined above and X represents halogen, in a liquid solvent medium, with an alkali metal tetracarbonyl cobaltate complex of the formula:MCo(CO).sub.4wherein M is an alkali metal to form the corresponding acylcobaltcarbonyl complex of the formula: ##STR3## wherein R.sub.1 and R.sub.2 are as defined above, reacting the acylcobaltcarbonyl complex thus formed with carbon monoxide and an alkali metal hydroxide or an alkaline earth metal hydroxide at elevated temperature and elevated pressure in a liquid solvent medium to form the corresponding alkali metal salt or alkaline earth metal salt of the product .alpha.-keto-carboxylic acid and thereafter acidifying the salt of the .alpha.
    Type: Grant
    Filed: July 28, 1983
    Date of Patent: November 6, 1984
    Assignee: Ethyl Corporation
    Inventor: Joachim W. Wolfram
  • Patent number: 4481369
    Abstract: A process for the production of .alpha.-keto-carboxylic acids of the general formula: ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and are hydrogen, hydrocarbyl radicals, substituted hydrocarbyl radicals or hydrocarbyloxy radicals by reacting an acyl halide of the formula: ##STR2## wherein R.sub.1 and R.sub.2 are as defined above and X represents halogen, in a liquid solvent medium, with an alkali metal tricarbonyl[triphenylphosphine]cobaltate complex of the formula:MCo(CO).sub.3 Ph.sub.3wherein M is an alkali metal to form the corresponding phenylacetyl tricarbonyl[triphenylphosphine]cobalt complex of the formula: ##STR3## wherein R.sub.1 and R.sub.2 are as defined above, reacting the acylcobaltcarbonyl complex thus formed with carbon monoxide and an alkali metal hydroxide or an alkaline earth metal hydroxide at elevated temperature and elevated pressure in a liquid solvent medium to form the corresponding alkali metal salt or alkaline earth metal salt of the product .alpha.
    Type: Grant
    Filed: July 28, 1983
    Date of Patent: November 6, 1984
    Assignee: Ethyl Corporation
    Inventor: Joachim W. Wolfram
  • Patent number: 4474917
    Abstract: Phenolic-phosphite antioxidants for use alone in polyolefins or in admixture with synergists, phenolic/phosphite antioxidants, and the like. The adduct formed by reacting a phosphorus trihalide, preferably PCl.sub.3, with 1,3,5-trimethyl-2,4,6-tris(3',5'-di-tert-butyl-4'-hydroxybenzyl)benzene, e.g., is useful for antioxidant activity in organic materials. Various other phenolic adducts also show antioxidant activity. The adducts are formed by reacting PCl.sub.3, e.g., with a large phenolic compound having three or more phenolic moieties. The adducts contain components which are noncyclic with respect to phosphite moieties.
    Type: Grant
    Filed: May 27, 1982
    Date of Patent: October 2, 1984
    Assignee: Ethyl Corporation
    Inventor: Lester P. J. Burton
  • Patent number: 4474743
    Abstract: A process for the coproduction of silane and AlF.sub.3 is described. SiF.sub.4 and amine alane (AlH.sub.3.NR.sub.3) complexes are reacted to produce gaseous silane and AlF.sub.3 coproduct. The amine tends to complex somewhat with coproduct AlF.sub.3 but is released therefrom by heating. AlF.sub.3 is a very saleable commodity thereby making the invention an improvement over other hydride reactions which produce less usable coproducts.
    Type: Grant
    Filed: July 21, 1983
    Date of Patent: October 2, 1984
    Assignee: Ethyl Corporation
    Inventor: Everett M. Marlett
  • Patent number: 4473706
    Abstract: Cyclic-keto-acids of the general formula: ##STR1## wherein R is hydrogen or a monovalent alkyl radical which can be either straight chain or branched having from 1 to about 20 carbon atoms and X=1, 3, or 4, are prepared by reacting a functionalized 1-bromoalkane of the formula: ##STR2## wherein R and X are as defined above and Y is a leaving group, preferably the halogens, 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 or an alkaline earth metal inorganic base.
    Type: Grant
    Filed: August 6, 1982
    Date of Patent: September 25, 1984
    Assignee: Ethyl Corporation
    Inventors: John Y. Lee, Thomas J. Walter
  • Patent number: 4467106
    Abstract: A process for making polyether/polyester glycols and the products formed thereby. Polyether/polyester glycols having a molecular weight of about 200 to 2,200 are formed by heating any of various glycols at about 150.degree. to 250.degree. C. under carbon monoxide pressure in the presence of a halide promoter. Preferably, iodide or bromide and a transition metal-containing catalyst are used to produce polyether/polyester glycols having a molecular weight in the range of 900 to 1,200.
    Type: Grant
    Filed: April 15, 1982
    Date of Patent: August 21, 1984
    Assignee: Ethyl Corporation
    Inventors: Sundar J. Rajan, Edmund F. Perozzi
  • Patent number: 4459399
    Abstract: A polyamine mixture formed from formaldehyde, an ortho-alkylaniline, and an ortho,ortho-dialkylaniline. The polyamine mixture is prepared by heating one of the anilines with formaldehyde, mixing the other aniline with an acid catalyst, and slowly adding the former to the latter. The mixtures are useful as chain extenders in polyurethane processes including reaction injection molding. The novel mixtures give unexpected mold gel and set times as compared to corresponding unmixed compounds formed from a single aniline or formed by previous typical condensation reactions. Also, the proportion of polyamines made by the novel mixtures may be varied to give excellent physical characteristics.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: July 10, 1984
    Assignee: Ethyl Corporation
    Inventors: Kryn G. Ihrman, Kestutis A. Keblys, Donald H. Lucast
  • Patent number: 4456745
    Abstract: A process for the production of a polycarbonate glycol wherein a cyclic carbonate is catalyzed at elevated temperature by a cationic initiator. Compounds of structure (I) ##STR1## where R is alkylene, R' and R" are independently hydrogen, alkyl, alkaryl, aralkyl, or aryl, are heated at an elevated temperature in the presence of cationic initiators such as trimethyl aluminum to form a polymer. Production of a glycol product is assured by subsequent heating at about 200.degree.-220.degree. C. to form a polymer containing carbonate units of ##STR2## and having hydroxy end units bonded to a carbon not part of a carbonate function. The molecular weight of polycarbonate glycol is preferably at least about 1,000. Valuable new prepolymer mixes and polyurethanes may be prepared using the novel polycarbonate glycols of the invention.
    Type: Grant
    Filed: July 11, 1983
    Date of Patent: June 26, 1984
    Assignee: Ethyl Corporation
    Inventor: Sundar J. Rajan
  • Patent number: 4456541
    Abstract: Organic material such as lubricating oil is stabilized against gradual oxidative degradation by the addition of aromatic diamines such as 3,5-diethyltoluene-2,4-diamine, 3,5-diethyltoluene-2,6-diamine, mixtures thereof, and the like.
    Type: Grant
    Filed: April 24, 1981
    Date of Patent: June 26, 1984
    Assignee: Ethyl Corporation
    Inventor: William E. Wright
  • Patent number: 4456584
    Abstract: To improve reactor throughput and raw material utilization, the direct synthesis process for producing sodium aluminum tetrahydride is conducted in a semi-continuous manner whereby in at least one run (and preferably in each of a plurality of successive runs) the reaction is conducted (and preferably the respective reactions are conducted) to a stage at or before which the reaction rate would begin to significantly decrease due to consumption of the sodium. At that stage at least a portion of the liquid reaction solution is separated from the unreacted aluminum and sodium to leave a highly active sodium- and aluminum- containing heel for use in initiating the ensuing run. Preferably the aluminum used in at least some of the runs contains a reaction-promoting amount of another metal such as titanium. Use of an ether reaction medium (which need not be pre-treated to remove small amounts of alcohols and/or water) is also preferred. Sodium aluminum tetrahydride is a well-known chemical reducing agent.
    Type: Grant
    Filed: May 20, 1983
    Date of Patent: June 26, 1984
    Assignee: Ethyl Corporation
    Inventor: Marcelian F. Gautreaux
  • Patent number: 4454270
    Abstract: Various antioxidant-protected polyolefins are protected against initial discoloration from processing, subsequent discoloration, loss of whiteness, and yellowing with time and upon exposure to elevated temperature by addition of various compounds such as triisopropanolamine, bipyridines, and N,N-bis-(2-hydroxymethyl)soyaamine.
    Type: Grant
    Filed: March 31, 1982
    Date of Patent: June 12, 1984
    Assignee: Ethyl Corporation
    Inventors: William Kolodchin, Kestutis A. Keblys
  • Patent number: 4440952
    Abstract: A process for monoalkylating 1-alkyl-2,4-diaminobenzene or 1-alkyl-2,6-diaminobenzene. Propylene is reacted with 2,4-diaminotoluene in the presence of aluminum anilide catalyst. Aniline is an optional ingredient.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: April 3, 1984
    Assignee: Ethyl Corporation
    Inventor: Kryn G. Ihrman
  • Patent number: 4423205
    Abstract: A process for the production of a polycarbonate glycol wherein a cyclic carbonate is catalyzed at elevated temperature by a cationic initiator. Compounds of structure (I) ##STR1## where R is alkylene, R' and R" are independently hydrogen, alkyl, alkaryl, aralkyl, or aryl, are heated at an elevated temperature in the presence of cationic initiators such as trimethyl aluminum to form a polymer. Production of a glycol product is assured by subsequent heating at about 200.degree.-220.degree. C. to form a polymer containing carbonate units of ##STR2## and having hydroxy end units bonded to a carbon not part of a carbonate function. The molecular weight of polycarbonate glycol is preferably at least about 1,000.
    Type: Grant
    Filed: May 24, 1982
    Date of Patent: December 27, 1983
    Assignee: Ethyl Corporation
    Inventor: Sundar J. Rajan
  • Patent number: 4423262
    Abstract: A process for the preparation of an ar-dibromostyrene which comprises aqueous alcoholic alkali dehydrobromination of 2-bromoethyl dibromobenzene in the presence of a phase transfer catalyst at a temperature of between about 0.degree. C. and about 150.degree. C. The ar-dibromostyrenes have the particular utility as a co-monomer for the preparation of a co-polymer exhibiting a flame retardancy.
    Type: Grant
    Filed: March 13, 1980
    Date of Patent: December 27, 1983
    Assignee: Ethyl Corporation
    Inventor: Philip F. Jackisch
  • Patent number: 4398921
    Abstract: Liquid fuels for use in internal combustion engines comprising (i) a major fraction of hydrocarbons boiling in the gasoline boiling range, (ii) a minor amount of ethanol and (iii) a detergent amount of(I) from about 20 to about 40 weight percent of the reaction product of:(A) one mole part of an alkylphenol having the formula: ##STR1## wherein n is an integer from 1 to 2, and R.sub.1 is an aliphatic hydrocarbon radical having an average molecular weight of from about 400 to 1500;(B) from 1-5 mole parts of an aldehyde having the formula: ##STR2## wherein R.sub.2 is selected from hydrogen and alkyl radicals containing 1-6 carbon atoms; and(C) from 0.5-5 mole parts of an amine having at least one active hydrogen atom bonded to an amino nitrogen atom, and(II) from about 3.0 to about 6.0 weight percent of a demulsifying agent containing:(A) at least one oil-soluble polyether characterized by the presence within its structure of a group of the formula:(--O-A--).sub.
    Type: Grant
    Filed: November 2, 1981
    Date of Patent: August 16, 1983
    Assignee: Ethyl Corporation
    Inventors: Ellis B. Rifkin, Martin E. Gluckstein, Warren L. Perilstein
  • Patent number: 4395876
    Abstract: Hydrocarbon and carbon monoxide emission of an internal combustion engine fitted with a non-catalytic thermal exhaust reactor is substantially lowered by operating the engine lean during normal modes of engine operation and switching to rich operation during idle using restricted air injection such that the idle exhaust contains about 2-5 volume percent oxygen.
    Type: Grant
    Filed: July 11, 1977
    Date of Patent: August 2, 1983
    Assignee: Ethyl Corporation
    Inventors: Frederick J. Marsee, Jeffrey C. Hamilton