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).
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Patent number: 4810261Abstract: 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: GrantFiled: February 19, 1988Date of Patent: March 7, 1989Assignee: Texaco Inc.Inventors: Rodney L. Sung, Milton D. Behrens, Michael A. Caggiano, John F. Knifton, John M. Larkin, Robert L. Zimmerman
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Patent number: 4806517Abstract: 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: GrantFiled: March 12, 1987Date of Patent: February 21, 1989Assignee: Texaco Inc.Inventors: Steven H. Vanderpool, Lewis W. Watts, Jr., John M. Larkin, Terry L. Renken
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Patent number: 4766245Abstract: 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: GrantFiled: March 1, 1985Date of Patent: August 23, 1988Assignee: Texaco Inc.Inventors: John M. Larkin, Terry L. Renken
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Patent number: 4747851Abstract: 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: GrantFiled: January 2, 1987Date of Patent: May 31, 1988Assignee: Texaco Inc.Inventors: Rodney L. Sung, Milton D. Behrens, Michael A. Caggiano, John F. Knifton, John M. Larkin, Robert L. Zimmerman
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Patent number: 4705903Abstract: 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: GrantFiled: November 20, 1986Date of Patent: November 10, 1987Assignee: Texaco Inc.Inventors: John R. Sanderson, John M. Larkin
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Patent number: 4602062Abstract: 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: GrantFiled: December 24, 1984Date of Patent: July 22, 1986Assignee: Texaco Inc.Inventor: John M. Larkin
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Patent number: 4588834Abstract: 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: GrantFiled: October 4, 1984Date of Patent: May 13, 1986Assignee: Texaco Inc.Inventor: John M. Larkin
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Patent number: 4552862Abstract: 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: GrantFiled: March 7, 1983Date of Patent: November 12, 1985Assignee: Texaco Inc.Inventor: John M. Larkin
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Patent number: 4540821Abstract: 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: GrantFiled: January 26, 1981Date of Patent: September 10, 1985Assignee: Texaco Inc.Inventors: John M. Larkin, Ernest L. Yeakey, Lewis W. Watts, Jr.
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Manufacture of synthetic lubricant additives from internal olefins using boron trifluoride catalysis
Patent number: 4434308Abstract: 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: GrantFiled: April 28, 1982Date of Patent: February 28, 1984Assignee: Texaco Inc.Inventors: John M. Larkin, Lewis W. Watts, Jr., Edward T. Marquis -
Patent number: 4434309Abstract: 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: GrantFiled: June 18, 1982Date of Patent: February 28, 1984Assignee: Texaco Inc.Inventors: John M. Larkin, Walter H. Brader, Jr.
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Patent number: 4420647Abstract: 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: GrantFiled: April 26, 1982Date of Patent: December 13, 1983Assignee: Texaco Inc.Inventors: Kenneth G. Hammond, Joseph C. Sendra, Lewis W. Watts, Jr., Edward T. Marquis, John M. Larkin
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Patent number: 4417082Abstract: 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: GrantFiled: June 18, 1982Date of Patent: November 22, 1983Assignee: Texaco Inc.Inventors: John M. Larkin, Lewis W. Watts, Jr.
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Patent number: 4415755Abstract: 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: GrantFiled: November 10, 1981Date of Patent: November 15, 1983Assignee: Texaco Inc.Inventor: John M. Larkin
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Patent number: 4395578Abstract: 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: GrantFiled: June 18, 1982Date of Patent: July 26, 1983Assignee: Texaco, Inc.Inventor: John M. Larkin
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Patent number: 4214083Abstract: 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: GrantFiled: April 17, 1978Date of Patent: July 22, 1980Assignee: Texaco Inc.Inventors: John M. Larkin, William P. Cullen, Rodney L. Sung, Benjamin H. Zoleski
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Patent number: 4159996Abstract: 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: GrantFiled: October 31, 1977Date of Patent: July 3, 1979Assignee: Texaco Inc.Inventors: Richard F. Love, Stanley R. Newman, John M. Larkin
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Patent number: 4146560Abstract: 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: GrantFiled: November 28, 1977Date of Patent: March 27, 1979Assignee: Texaco Development Corp.Inventors: John M. Larkin, Philip H. Moss
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Patent number: 4137254Abstract: 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: GrantFiled: July 27, 1977Date of Patent: January 30, 1979Assignee: Texaco, Inc.Inventor: John M. Larkin
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Patent number: 4124608Abstract: 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: GrantFiled: August 3, 1977Date of Patent: November 7, 1978Assignee: Texaco Inc.Inventor: John M. Larkin