Patents by Inventor John M. Larkin

John M. Larkin 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: 4810261
    Abstract: A novel gasoline-soluble reaction product, a concentrate comprising the reaction product dissolved in a hydrocarbon solvent, and a haze-free, deposit-resistant and ORI-inhibited motor fuel composition comprising the reaction product is described. The reaction product is obtained by reacting a dibasic acid anhydride, a novel diamine containing block copolymers with polyoxyalkylene backbones, and a hydrocarbyl polyamine. Motor fuel compositions containing the reaction product additive of the instant invention are haze-free and show improved deposit-resistance and ORI control in comparison with motor fuels without the reaction product. Motor fuel compositions of the instant invention may optionally comprise a polyolefin polymer/copolymer component having a molecular weight range of about 500-3500.
    Type: Grant
    Filed: February 19, 1988
    Date of Patent: March 7, 1989
    Assignee: Texaco Inc.
    Inventors: Rodney L. Sung, Milton D. Behrens, Michael A. Caggiano, John F. Knifton, John M. Larkin, Robert L. Zimmerman
  • Patent number: 4806517
    Abstract: This invention is directed to novel catalyst compositions based on a pelleted group IVb transition metal oxide to which about 0.5 to about 7 wt. % of phosphorus is thermally chemically bonded by a novel process wherein the pellets are impregnated with a liquid water-soluble phosphorus compound containing phosphorus-oxygen bonds, thermally treated after removal of unabsorbed liquid for 0.5 to 5 hours at 100.degree.-150.degree. C. to chemically bond the recited amount of phosphorus to the pellets followed by calcination at 200.degree. to 900.degree. C. to stabilize the pellets. Also disclosed is a regenerative process for preparing predominantly linear polyethylenepolyamines from ethylenediamine and monoethanolamine using the novel catalyst compositions.
    Type: Grant
    Filed: March 12, 1987
    Date of Patent: February 21, 1989
    Assignee: Texaco Inc.
    Inventors: Steven H. Vanderpool, Lewis W. Watts, Jr., John M. Larkin, Terry L. Renken
  • Patent number: 4766245
    Abstract: An improved method for the manufacture of high molecular weight polyoxyalkylene amines wherein a hydroxy-terminated polyoxyalkylene compound having a molecular weight of at least 500 is reacted with ammonia in the presence of hydrogen and Raney nickel/aluminum under anhydrous reductive amination conditions to provide the corresponding polyoxyalkylene amine in good yield and selectivity.The Raney nickel/aluminum is a nickel/aluminum alloy treated with a base, such as sodium hydroxide, so as to only partially leach the aluminum from the alloy, such that the final product contains from about 60 wt. % to about 75 wt. % of nickel and, correspondingly, from about 25 wt. % to about 40 wt. % of aluminum and is preferably used in nugget form.
    Type: Grant
    Filed: March 1, 1985
    Date of Patent: August 23, 1988
    Assignee: Texaco Inc.
    Inventors: John M. Larkin, Terry L. Renken
  • Patent number: 4747851
    Abstract: A novel gasoline-soluble polyoxyalkylene diamine compound, a concentrate comprising the compound dissolved in a hydrocarbon solvent, and a haze-free, deposit-resistant and ORI-inhibited motor fuel composition comprising the compound is described. Motor fuel compositions comprising the novel polyoxyalkylene diamine compound of the instant invention are haze-free and show improved ORI control and carbonaceous deposit inhibition in comparison with conventional motor fuels. Motor fuel compositions of the instant invention may optionally comprise a polyolefin polymer/copolymer component having a molecular weight range of about 500-3500.
    Type: Grant
    Filed: January 2, 1987
    Date of Patent: May 31, 1988
    Assignee: Texaco Inc.
    Inventors: Rodney L. Sung, Milton D. Behrens, Michael A. Caggiano, John F. Knifton, John M. Larkin, Robert L. Zimmerman
  • Patent number: 4705903
    Abstract: Motor-fuel grade tertiary butyl alcohol which is prepared, for example, by reacting propylene with tertiary butyl hydroperoxide to form propylene oxide and a tertiary butyl alcohol reaction product contaminated with residual amounts of tertiary butyl hydroperoxide and ditertiary butyl peroxide can be effectively catalytically treated under mild conversion conditions including a temperature of about 80.degree. to 280.degree. C. with a catalyst composed of iron, copper, chromia and cobalt, or the oxides thereof in order to substantially selectively convert the two peroxide contaminants to tertiary butyl alcohol and to thereby provide a treated tertiary butyl alcohol product substantially free from contaminating quantities of such peroxides.
    Type: Grant
    Filed: November 20, 1986
    Date of Patent: November 10, 1987
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, John M. Larkin
  • Patent number: 4602062
    Abstract: It has been surprisingly discovered in accordance with the present invention that polyvinyl alcohol can be substantially selectively converted to an acrylic acid polymer or copolymer by first reacting the polyvinyl alcohol with a desired predetermined amount of formic acid to form an intermediate reaction product of the formic acid with the hydroxyl groups of the polyvinyl alcohol and by bringing the intermediate into contact with a bed of activated carbon in the presence of carbon monoxide and an alkyl halide promoted group VIII soluble transition metal catalyst, optionally in the presence of a solvent. When substantially all of the hydroxyl groups are reacted with formic acid to form a polyvinyl formate intermediate, the final product will be a polyacrylic acid. When the intermediate contains both hydroxyl groups and formate groups, the final product will be a poly (vinyl alcohol, acrylic acid) copolymer.
    Type: Grant
    Filed: December 24, 1984
    Date of Patent: July 22, 1986
    Assignee: Texaco Inc.
    Inventor: John M. Larkin
  • Patent number: 4588834
    Abstract: Carboxylic acids, for example n-butyric and isobutyric are prepared from an olefin such as propylene in a process comprising passing a liquid feed consisting of an olefin, an alkyl halide or heterocyclic amine promoter, a protonic coreactant, and a low concentration of a soluble metal catalyst, optionally in the presence of a solvent, and a gas consisting essentially of carbon monoxide over a carbon bed maintained at a temperature of from about 200.degree. C. to about 400.degree. C. and a pressure of from about 500 psi to about 4000 psi or greater.
    Type: Grant
    Filed: October 4, 1984
    Date of Patent: May 13, 1986
    Assignee: Texaco Inc.
    Inventor: John M. Larkin
  • Patent number: 4552862
    Abstract: A method for forming a pelletized catalyst having improved stability during a hydrogenation process such as the hydrogenation of a nitrile to an amine, includes the steps of mixing a metal having a melting point below about 400.degree. C. or a hydrogen reducible compound of the low melting point metal with at least one material which is an effective hydrogenation catalyst, and then compressing the mixture to form a pellet. This pellet can then be heated in a stream of gas comprising hydrogen at a temperature above the melting point of the metal. The pellet is then cooled and can then preferably be exposed to air or other oxygen containing gases. Preferred low melting point metals include cadmium and tin. Preferred hydrogenation catalysts include nickel and cobalt either alone or with other metals and metal compounds.
    Type: Grant
    Filed: March 7, 1983
    Date of Patent: November 12, 1985
    Assignee: Texaco Inc.
    Inventor: John M. Larkin
  • Patent number: 4540821
    Abstract: A process for the manufacture of aminopolyols and polyaminopolyols by continuous reductive amination of sugars in aqueous solution is described. Syrups such as corn syrups may be used directly for this process. It has been found that the lower the mol ratio of NH.sub.3 to the sugar, with a ratio of 1 as the lower limit, the higher is the degree of nitrogen incorporation into the sugar. It is essential that the streams of ammonia and aqueous sugar solution be pumped to the reaction zone separately.
    Type: Grant
    Filed: January 26, 1981
    Date of Patent: September 10, 1985
    Assignee: Texaco Inc.
    Inventors: John M. Larkin, Ernest L. Yeakey, Lewis W. Watts, Jr.
  • Patent number: 4434308
    Abstract: An improved process for the manufacture of synthetic lubricant additives from internal olefins is described. The process utilizes boron trifluoride catalysis with a promoter to produce oligomer mixtures that have surprisingly low viscosities at low temperatures and surprisingly high viscosity indexes as compared with the oligomers found in other methods. It is important that internal olefins be used almost exclusively in the method of this invention.
    Type: Grant
    Filed: April 28, 1982
    Date of Patent: February 28, 1984
    Assignee: Texaco Inc.
    Inventors: John M. Larkin, Lewis W. Watts, Jr., Edward T. Marquis
  • Patent number: 4434309
    Abstract: A mixture of predominantly low molecular weight alpha olefins may be oligomerized over a boron trifluoride catalyst and a protonic promoter. When the oligomers are hydrogenated they provide a synthetic lubricant base stock having excellent properties. The alpha olefins may be derived from ethylene polymerization or wax pyrolysis. An inert organic solvent may be present. Preferably, the olefin mixture is made up of greater than 50 weight weight percent of at least one low molecular weight alpha olefin having 4 to 6 carbon atoms and less than 50 weight percent of at least one higher molecular weight alpha olefin having 8 to 18 carbon atoms.
    Type: Grant
    Filed: June 18, 1982
    Date of Patent: February 28, 1984
    Assignee: Texaco Inc.
    Inventors: John M. Larkin, Walter H. Brader, Jr.
  • Patent number: 4420647
    Abstract: A synthetic lubricating oil composition comprising a major portion of a synthetic lubricant component or a mixture of a synthetic lubricant component and a hydrocarbon mineral base oil and a minor portion of various additive components is described. The synthetic lubricant component is manufactured from internal olefins.The process for making the synthetic lubricant component utilizes boron trifluoride catalysis with a promoter to produce oligomer mixtures that have surprisingly low viscosities at low temperatures and surprisingly high viscosity indexes as compared with the oligomers found in other methods. It is important that internal olefins be used predominantly to make the oligomers. Alpha olefins make up the balance of the olefins.
    Type: Grant
    Filed: April 26, 1982
    Date of Patent: December 13, 1983
    Assignee: Texaco Inc.
    Inventors: Kenneth G. Hammond, Joseph C. Sendra, Lewis W. Watts, Jr., Edward T. Marquis, John M. Larkin
  • Patent number: 4417082
    Abstract: Alpha olefins may be oligomerized over a boron trifluoride catalyst and a protonic promoter, and then held at a temperature between 60.degree. and 150.degree. C. to increase the molecular weight of the oligomers. When the oligomers are hydrogenated they provide a synthetic lubricant base stock having excellent properties. The alpha olefins may be derived from ethylene polymerization or wax pyrolysis. An inert organic solvent may be present.
    Type: Grant
    Filed: June 18, 1982
    Date of Patent: November 22, 1983
    Assignee: Texaco Inc.
    Inventors: John M. Larkin, Lewis W. Watts, Jr.
  • Patent number: 4415755
    Abstract: Primary alcohols may be treated with ammonia and hydrogen in the vapor phase in the presence of a catalyst containing copper and chromium to produce nitriles and primary amines. The nitriles produced are readily convertible to the same corresponding primary amines. The reaction may be conducted at a temperature in the range of 240.degree. to 320.degree. C. which is substantially lower than the temperatures used in other methods used to make nitriles. Conversions of the alcohols are 95% or higher, and selectivities to the combined primary amines and nitriles are higher than other methods.
    Type: Grant
    Filed: November 10, 1981
    Date of Patent: November 15, 1983
    Assignee: Texaco Inc.
    Inventor: John M. Larkin
  • Patent number: 4395578
    Abstract: Alpha olefins may be oligomerized over a boron trifluoride catalyst and a promoter containing a transition metal cation. When the oligomers are hydrogenated they provide a synthetic lubricant base stock having excellent properties. The alpha olefins may be derived from ethylene polymerization or wax pyrolysis. A protonic promoter and an inert organic solvent may be present.
    Type: Grant
    Filed: June 18, 1982
    Date of Patent: July 26, 1983
    Assignee: Texaco, Inc.
    Inventor: John M. Larkin
  • Patent number: 4214083
    Abstract: Lubricating oil additives, including the calcium salts of sulfurized alkylphenols and dispersants consisting of the reaction products of halogenated polyalkylenes and heterocyclic amines, are substantially decolorized by treatment with small amounts of alkali metal hydrides in a polar solvent at 20.degree. to 120.degree. C. Color improvement is obtained at concentrations ranging from 1 to 75 parts of an alkali metal hydride per 1000 parts of additive.
    Type: Grant
    Filed: April 17, 1978
    Date of Patent: July 22, 1980
    Assignee: Texaco Inc.
    Inventors: John M. Larkin, William P. Cullen, Rodney L. Sung, Benjamin H. Zoleski
  • Patent number: 4159996
    Abstract: A method for preparing alkane diamines by initially reacting a vicinal nitroketone with a primary amine hydrochloride thereby forming a nitroalkyliminoalkane or a nitrooximinoalkane and thereafter catalytically hydrogenating the nitroalkylimino- or nitrooximinoalkane to a diamine.
    Type: Grant
    Filed: October 31, 1977
    Date of Patent: July 3, 1979
    Assignee: Texaco Inc.
    Inventors: Richard F. Love, Stanley R. Newman, John M. Larkin
  • Patent number: 4146560
    Abstract: Covers a process for preparing polyamines from the corresponding polynitriles via a pelleted cobalt-copper-chromium hydrogenation catalyst which comprises contacting a polynitrile with hydrogen in presence of said catalyst and a stabilizing agent comprising a polyamine or a hydroxyl-amine whereby catalyst pellet disintegration is inhibited by the presence of said stabilizing agent.
    Type: Grant
    Filed: November 28, 1977
    Date of Patent: March 27, 1979
    Assignee: Texaco Development Corp.
    Inventors: John M. Larkin, Philip H. Moss
  • Patent number: 4137254
    Abstract: Aromatic nitriles are prepared from methylated aromatic hydrocarbons, such as toluene, xylene, tri- and tetramethylbenzenes by contacting at an elevated temperature with a nitroaromatic compound and ammonia in the presence of a catalyst composed of two or more metal oxides of the metals of Groups I B, III B, V A, VI B, VII B and VIII of the Periodic Table. A valuable coproduct of the method is an aromatic amine.
    Type: Grant
    Filed: July 27, 1977
    Date of Patent: January 30, 1979
    Assignee: Texaco, Inc.
    Inventor: John M. Larkin
  • Patent number: 4124608
    Abstract: 2-oxoalkanoic acids are prepared by contacting an alpha-nitroketone with an alkanoic acid anhydride, such as acetic anhydride, and a tertiary amine, such as pyridine, thereby forming a 2-alkanoyloxy-2-alkenoic acid and thereafter hydrolyzing the alkenoic acid with an aqueous non-oxidizing acid, such as hydrochloric acid.
    Type: Grant
    Filed: August 3, 1977
    Date of Patent: November 7, 1978
    Assignee: Texaco Inc.
    Inventor: John M. Larkin