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: 6888030Abstract: Inclusion of a branched alcohol in the catalytic hydrogenation reaction involving an aliphatic nitro compound dramatically increases the efficiency of the conversion of nitro groups into amino groups. This discovery is of particular value in the production of polyalkyleneamines via nitration of a polyalkene, such as a polybutene, and its subsequent reduction. The polyalkyleneamines so produced are useful as dispersant additives for motor oils and fuels.Type: GrantFiled: October 22, 2002Date of Patent: May 3, 2005Assignee: Huntsman Petrochemical CorporationInventors: Wei-Yang Su, Wheeler C. Crawford, John M. Larkin
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Publication number: 20030078344Abstract: Inclusion of a branched alcohol in the catalytic hydrogenation reaction involving an aliphatic nitro compound dramatically increases the efficiency of the conversion of nitro groups into amino groups. This discovery is of particular value in the production of polyalkyleneamines via nitration of a polyalkene, such as a polybutene, and its subsequent reduction. The polyalkyleneamines so produced are useful as dispersant additives for motor oils and fuels.Type: ApplicationFiled: October 22, 2002Publication date: April 24, 2003Applicant: Huntsman Petrochemical CorporationInventors: Wei-Yang Su, Wheeler C. Crawford, John M. Larkin
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Patent number: 6063145Abstract: This invention concerns a fuel additive comprising an etheramine alkoxylate, and fuel compositions and additive concentrates made therefrom. The etheramine alkoxylate may be of formula: ##STR1## where R.sup.1 is a straight or branched alkyl, or alkylaryl; R.sup.2 is independently in each occurrence hydrogen or alkyl from 1 to 6 carbons; R.sup.3 is independently in each occurrence hydrogen or alkyl of from 1 to 6 carbons; m averages from about 2 to about 20; and x and y each independently average from about 0 to 2, where x+y averages from about 1 to about 4.Type: GrantFiled: June 26, 1998Date of Patent: May 16, 2000Assignee: Huntsman Petrochemical CorporationInventors: John M. Larkin, Wei-Yang Su, Terry L. Renken
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Patent number: 5616811Abstract: Etheramine alkoxylates are described which have the formula: ##STR1## where R.sup.1 is a straight or branched alkyl, aryl or alkylaryl group of 6 to 22 carbon atoms; R.sup.3 are independently hydrogen or C.sub.1 to C.sub.3 alkyl; m averages from about 1 to about 20; and x and y each independently average from about 0 to 30, where x+y averages from about 2 to about 60. These etheramine alkoxylates have surfactant properties. Further, they may be quaternized to make other compounds which will have useful surfactant properties.Type: GrantFiled: June 6, 1995Date of Patent: April 1, 1997Assignee: Huntsman Petrochemical CorporationInventors: Jeffrey J. Vipond, John M. Larkin, Terry L. Renken, Howard M. Stridde
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Patent number: 5269956Abstract: Solutions of potassium, aliphatic monocarboxylate, hydrocarbyl dicarboxylate and hydrocarbyl triazole, with one or more silicate, phosphate, borate, or nitrate, have superior compatibility and anticorrosion properties, useful in heat transfer fluids, antifreezes and metal corrosion inhibition.Type: GrantFiled: September 25, 1991Date of Patent: December 14, 1993Assignee: Texaco Chemical Co.Inventors: David L. Miller, John M. Larkin
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Patent number: 5191139Abstract: An improved process is disclosed for preparing synthetic lubricant base stocks. Synthetic lubricant base stocks are prepared in good yield by oligomerizing linear olefins using a sulfate-activated Group IV oxide particularly zirconium dioxide, as the catalyst.Type: GrantFiled: November 4, 1991Date of Patent: March 2, 1993Assignee: Texaco Chemical CompanyInventors: John R. Sanderson, John F. Knifton, John M. Larkin
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Patent number: 5189233Abstract: Disclosed is an improvement in a process for production of cyclohexane by liquid phase hydrogenation of benzene wherein no diluent is necessary, which comprises contacting benzene and hydrogen in the presence of a mixed catalyst bed comprising a first catalyst which is a less active hydrogenation catalyst selected from elements of Group VIII of the Periodic Table and a second, more active catalyst, comprising a Group VIII metal supported on an oxide, such as, for example, alumina, silica or titania at a temperature of about 40.degree. C. to about 300.degree. C. and pressure sufficient to keep the benzene liquid at the chosen reaction temperature.Type: GrantFiled: August 23, 1991Date of Patent: February 23, 1993Assignee: Texaco Chemical CompanyInventors: John M. Larkin, James H. Templeton, Donald H. Champion
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Patent number: 5099073Abstract: A process for the conversion of a polyoxypropylene glycol to the corresponding diketone derivative by dehydrogenation in the presence of an unsupported nickel, copper, chromia catalyst or a Raney nickel catalyst.Type: GrantFiled: February 11, 1991Date of Patent: March 24, 1992Assignee: Texaco Chemical CompanyInventors: John R. Sanderson, John M. Larkin
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Patent number: 5085793Abstract: A corrosion-inhibited antifreeze composition is disclosed. Specifically, the antifreeze composition comprises a major portion of a liquid alcohol freezing point depressant and a minor portion of at least one hydroxyl-substituted aromatic carboxylic acid having the hydroxyl radical disposed proximate to the carboxylic radical. The above described acid is employed as a corrosion inhibitor. Other conventional corrosion inhibitors may be employed in conjunction with the acids.In another embodiment, the present invention relates to a process for inhibitig the corrosion of metals present in the cooling system of an internal combustion engine which comprises intimately contacting the metal surface to be inhibited against corrosion with the antifreeze composition described above. Most preferably, the target substrate is high lead solder.Type: GrantFiled: November 19, 1990Date of Patent: February 4, 1992Assignee: Texaco Chemical CompanyInventors: Jeffrey M. Burns, John R. Sanderson, John M. Larkin, David R. McCoy
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Patent number: 5072050Abstract: Mono-, di- and tri-ketones of polyoxyalkylene compounds prepared by a method whereby the terminal hydroxyl groups of polyoxyalkylene compounds are oxidized to ketone groups with an alkali metal or an alkaline earth metal hypochlorite oxidant in the presence of acetic acid are disclosed. These compounds are useful for preparing surface active agents or they may be reacted with amines to provide fuel additives.Type: GrantFiled: October 9, 1990Date of Patent: December 10, 1991Assignee: Texaco Chemical CompanyInventors: John R. Sanderson, Edward T. Marquis, John M. Larkin
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Patent number: 5003107Abstract: Poly(oxytetramethylene) diamines useful in the preparation of polyamide and polyurea elastomers are prepared by the catalytic reductive amination of a poly(oxytetramethylene) glycol feedstock under reductive amination conditions in the presence of ammonia and hydrogen using a hydrogenation/dehydrogenation catalyst composed of, on an oxide-free basis, about 70 to 75 wt. % of nickel, about 20 to about 25 wt. % of copper, about 0.5 to 5 wt. % of chromium and about 1 to 5 wt. % of molybdenum.Type: GrantFiled: December 18, 1989Date of Patent: March 26, 1991Assignee: Texaco Chemical CompanyInventors: Robert L. Zimmerman, John M. Larkin
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Patent number: 4992590Abstract: A process in which a polyamine initiator is oxyalkylated to form the corresponding polyamine polyoxyalkylene glycol which is then catalytically aminated to provide a polyoxyalkylenepolyamine is disclosed. These compounds are useful as curing agents for epoxy resins and for reaction with isocyanates to manufacture articles, such as automotive body panels, by reaction injection molding.Type: GrantFiled: October 2, 1989Date of Patent: February 12, 1991Assignee: Texaco Chemical CompanyInventors: Michael Cuscurida, John M. Larkin, Kathy B. Sellstrom, Robert A. Grigsby, Jr.
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Patent number: 4980503Abstract: It has been surprisingly discovered in accordance with the present invention that glycol formates and their alkyl ether derivatives can be substantially selectively converted to monocarboxylic acids by bringing a glycol formate or an alkyl ether derivative thereof into contact with a bed of activated carbon in the presence of carbon monoxide and a halide promoted group VIII soluble transition metal catalyst optionally in the presence of a solvent.Type: GrantFiled: August 15, 1986Date of Patent: December 25, 1990Assignee: Texaco Inc.Inventors: John M. Larkin, George P. Speranza
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Patent number: 4978785Abstract: Carboxylic acid derivatives and methyl ketone derivatives of polyoxypropylene glycols are prepared by the selective nitric acid oxidation of a polyoxypropylene glycol in the presence of an alkali metal nitrite. If the alkali metal nitrite is added to an aqueous solution of nitric acid and the polyoxypropylene glycol is thereafter added, carboxylic acid derivatives of the polyoxypropylene glycol are provided. If a mixture of an alkali metal nitrite and a polyoxypropylene glycol is added to an aqueous solution of nitric acid, a reaction product containing a predominant amount of methyl ketone derivatives of the polyoxypropylene glycol is provided.Type: GrantFiled: December 11, 1989Date of Patent: December 18, 1990Assignee: Texaco Chemical CompanyInventors: John R. Sanderson, John M. Larkin
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Patent number: 4873380Abstract: Motor-fuel grade tertiary butyl alcohol contaminated with residual amounts of tertiary butyl hydroperoxide and ditertiary butyl peroxide (which is prepared, for example, by reacting propylene with tertiary butyl hydroperoxide to form propylene oxide and a motor fuel grade tertiary butyl alcohol reaction product) can be effectively catalytically treated under mild conversion conditions including a temperature of about 80.degree. to 200.degree. C. with a catalyst consisting essentially of nickel, copper, chromium and barium 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: January 20, 1987Date of Patent: October 10, 1989Assignee: Texaco Inc.Inventors: John R. Sanderson, John M. Larkin
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Patent number: 4847417Abstract: A method for converting a bis(polyalkoxy)-N-alkylamine to a bis(diaminopolyalkoxy)-N-alkylamine has been discovered. The method comprises alkoxylating an alkylamine to a bis(polyalkoxy)-N-alkylamine. The alkylamine is selected to sterically hinder the resulting tertiary amine. The alkoxylate is then catalytically aminated according to well known procedures with a high yield of the diamine resulting.Compounds prepared by this method are of the formula:R--N--(PO.sub.x --NH.sub.2).sub.2wherein:PO is propylene oxide,x ranges from 2 to 40, andR is a sterically hindering alkyl such as isopropyl or tertiary butyl.The compounds are useful for curing epoxy thermoset resins. They are uniquely suited to reactions with polyisocyanates to prepare plastic parts, such as automobile body panels, by reaction injection molding.Type: GrantFiled: October 26, 1988Date of Patent: July 11, 1989Assignee: Texaco Inc.Inventors: John M. Larkin, George P. Speranza
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Patent number: 4831191Abstract: Allyl formate is substantially selectively converted to isobutyric acid, n-butyric acid and/or glutaric acid by bringing the alyl formate into contact with activated carbon in the presence of carbon monoxide, water and formic acid and a halide promoted group VIII soluble metal catalyst optionally in the presence of a solvent. Isobutyric and n-butyric acids are preferentially formed in the presence of relatively low concentrations of water and formic acid whereas glutaric acid is preferentially formed in the presence of relatively higher concentrations of water and formic acid.Type: GrantFiled: May 23, 1986Date of Patent: May 16, 1989Assignee: Texaco Inc.Inventor: John M. Larkin
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Patent number: 4827039Abstract: The invention is an amine terminated polyether of the formula:N--[(CH.sub.2 CH(CH.sub.3)O).sub.x --CH.sub.2 CH(CH.sub.3)NH.sub.2 ].sub.3of 3000 to 7000 molecular weight.The polyamines are particularly suited for reaction with isocyanates to manufacture articles such as automobile body panels by reaction injection molding (RIM).Type: GrantFiled: August 3, 1987Date of Patent: May 2, 1989Assignee: Texaco Inc.Inventors: John M. Larkin, Michael Cuscurida
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Patent number: 4827038Abstract: A method for converting a bis(polyalkoxy)-N-alkylamine to a bis(diaminopolyalkoxy)-N-alkylamine has been discovered. The method comprises alkoxylating an alkylamine to a bis(polyalkoxy)-N-alkylamine. The alkylamine is selected to sterically hinder the resulting tertiary amine. The alkoxylate is then catalytically aminated according to well known procedures with a high yield of the diamine resulting.Compounds prepared by this method are of the formula:R--N--(PO.sub.x --NH.sub.2).sub.2wherein:PO is propylene oxide,x ranges from 2 to 40, andR is a sterically hindering alkyl such as isopropyl or tertiary butyl.The compounds are useful for curing epoxy thermoset resins. They are uniquely suited to reactions with polyisocyanates to prepare plastic parts, such as automobile body panels, by reaction injection molding.Type: GrantFiled: August 3, 1987Date of Patent: May 2, 1989Assignee: Texaco Inc.Inventors: John M. Larkin, George P. Speranza
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Patent number: 4825000Abstract: A series of polyoxyalkylene diamines modified with phenoxy groups is disclosed. This series of diamines is of the general formula: ##STR1## wherein R.sub.1 and R.sub.2 are independently hydrogen or an alkyl of 1 to 4 carbon atoms, R.sub.3 is a alkyl of 1 to 4 carbon atoms, Ph is phenyl, x ranges from 2 to 40, y ranges from 1 to 20 and z ranges from 1 to 40.These diamines are cured with liquid epoxy resins. The cured resins demonstrated improved tensile strength and modulus, elongation and flexural strength and modulus over a commercially used curative.The diamines are also useful in RIM elastomers, in polyamides and as chain extenders in polyurethane foams.Type: GrantFiled: July 31, 1986Date of Patent: April 25, 1989Assignee: Texaco Inc.Inventors: John M. Larkin, Robert L. Zimmerman, Michael Cuscurida, Harold G. Waddill