Texaco Inc.

Texaco Chemical Company

Huntsman Petrochemical Corporation

Texaco Development Corporation

John M Larkin

John R Sanderson

Lewis W Watts, Jr

Robert L Zimmerman

Terry L Renken

Roger G Duranleau

John F Knifton

George P Speranza

Edward T Marquis

Rodney L Sung

Michael Cuscurida

Wei-Yang Su

Michael A Caggiano

Milton D Behrens

Stanley R Newman

Harold G Waddill

Ernest L Yeakey

David R McCoy

Wheeler C Crawford

Benjamin H Zoleski

Harry Chafetz

Steven H Vanderpool

Robert A Grigsby, Jr

Kathy B Sellstrom

Donald H Champion

Richard F Love

Philip H Moss

Mahmoud S Kablaoui

William P Cullen

Kenneth G Hammond

Howard M Stridde

Walter H Brader, Jr

David L Miller

James H Templeton

Robert E Reid

Jeffrey M Burns

Joseph C Sendra

Jeffrey J Vipond

Roger D Duranleau

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.

Advances in amination

Disclosed herein is a process for producing alkanolamines from the reaction between a polyolefin epoxide and an organic amino compound under conditions of elevated temperature and pressure, in the presence of a catalytic amount of an alcohol. Higher reaction rates for alkanolamine production than provided in the prior art may be achieved by use of a process according to the invention. Alkanolamines having various levels of nitrogen may be produced by the invention.

Process for preparing alkanolamines from polyolefin epoxides

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.

Fuel compositions containing etheramine alkoxylates

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.

Etheramine alkoxylates

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.

Compatible corrosion inhibitor combinations

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.

Process for oligomerizing olefins using sulfate-activated group IV oxides

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.

Process for the production of cyclohexane by liquid phase hydrogenation

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.

Catalytic process for the production of diketone derivatives of

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.

Corrosion-inhibited antifreeze/coolant composition

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.

Ketone-terminated polyoxyalkylene compounds

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.

Catalytic method for the reductive amination of poly(oxytetramethyle)

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.

Polyamines by amination of polyamino initiated polyoxyalkylene glycols

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.

Conversion of glycol formates to monocarboxylic acids

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.

Oxidation of polyoxypropylene glycols to acids and ketones

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.

Growing community of inventors

Austin, TX, United States of America

John M Larkin