Texaco Development Corporation

Texaco Inc.

Jefferson Chemical Company, Inc.

Philip H Moss

Ernest L Yeakey

Michael E Brennan

Edward C Nieh

Harold G Waddill

Lewis W Watts, Jr

John F Knifton

John M Larkin

Walter H Brader, Jr

New hydroxy-containing alkyl-substituted bicycloalkane ether compositions useful in the preparation of valuable detergent and lubricating compositions are obtained by reacting an alkyl-substituted 2-norbornene with a polyhydric alcohol in the presence of an acidic catalyst.

Hydroxy-containing bicycloalkane ether compounds

This invention concerns the synthesis of linear alkyl primary amines from a-olefins via an oxoamination process comprising (a) hydrogen and carbon monoxide addition to olefinic substrates to obtain aldehyde-containing compounds in the presence of ligand-stabilized platinum(II) halide catalysts with Group IVB metal halide cocatalysts, and (b) reductive amination of said aldehydic intermediates in the presence of oxide-supported, nickel catalysts.

Selective oxoamination process

Covers a method of purifying ether sulfonates by contact with ethylene oxide or propylene oxide.

Process of purifying ether sulfonates

A novel epoxy resin curing accelerator comprises oligomeric poly(ethylenepiperazine). The resins comprise a vicinal polyepoxide, a curing agent, and an amount of oligomeric poly(ethylenepiperazine) effective for accelerating the cure of the polyepoxide.

Epoxy curing accelerator

A novel epoxy resin curing agent comprises oligomeric poly(ethylenepiperazine). The resins comprise a vicinal polyepoxide and a curing amount of oligomeric poly(ethylenepiperazine).

Novel epoxy curing system

Covers a new composition of matter comprising an acrylamide or methacrylamide monomer characterized by the following structural formula: ##STR1## where R.sub.1, R.sub.2 and R.sub.5 are hydrogen or methyl, R.sub.3 and R.sub.4 are lower alkyl, n is an integer ranging from 1 to 6 and A represents an anion.

Acrylamide or methacrylamide quaternary compounds

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.

Catalyst pellet stabilization in the preparation of polyamines from

Motor fuel composition comprising a mixture of hydrocarbons in a gasoline boiling range containing a compound represented by the formula: ##STR1## in which R is an aliphatic hydrocarbon radical having from about 8 to 20 carbon atoms, X and Y alternatively represent hydrogen and an aliphatic hydrocarbon radical having from 6 to 16 carbon atoms, n is an integer from 3 to 4 and m is an integer from 2 to 5.

Detergent and corrosion inhibited motor fuel composition

Covers a new composition of matter comprising an acrylamide or methacrylamide monomer characterized by the following structural formula: ##STR1## where R.sub.1 is hydrogen or methyl, R.sub.2 and R.sub.3 are hydrogen or lower alkyl, R.sub.4 is a primary or secondary alkyl group or an alkaryl group, each group containing 6-25 carbon atoms, and n is an integer ranging from 2 to 30.

N-polyalkoxyalkyl acrylamides or methacrylamides

An improved process is disclosed for selectively producing a bis-(morpholino-N-alkyl) ether directly from the corresponding N-(hydroxyalkyl)morpholine compound. The improved process includes contacting the N-(hydroxyalkyl)morpholine compound with a catalytically effective amount of a silica-alumina or certain phosphorus containing substances at a temperature of about 200.degree. C to 300.degree. C under a pressure sufficient to maintain the mixture substantially in liquid phase and recovering from the resultant reaction mixture the bis-(morpholino-N-alkyl) ether. According to the preferred embodiment, N-(2-hydroxyethyl)morpholine is heated in the presence of a catalytic amount of a silica-alumina catalyst having an alumina content of from about 5 to about 50 wt. % at temperatures of from about 240.degree. C to about 290.degree. C in liquid phase to selectively produce the corresponding N,N',2,2'-dimorpholinodiethyl ether (DMDEE).

Production of bis-(morpholino-N-alkyl) ethers

An improved process for selectively preparing an N-(aminoalkyl)piperazine compound is disclosed wherein piperazine is contacted with a primary or secondary amino alkanol compound in the presence of a catalytically effective amount of a phosphorus-containing substance at a temperature of from about 250.degree. to about 350.degree. C under a pressure sufficient to maintain the mixture essentially in liquid phase and the N-(aminoalkyl)piperazine is then recovered from the resultant reaction mixture. In a preferred embodiment piperazine is contacted with monoethanolamine to produce N-(2-aminoethyl)-piperazine.

Preparation of N-(aminoalkyl)piperazine

An improved process for selectively preparing a predominantly noncyclic polyalkylene polyamine compound is disclosed wherein an alkyleneamine compound is contacted with a diol compound in the presence of a catalytically effective amount of a phosphorus-containing substance at a temperature of from about 250.degree. to about 350.degree. C under a pressure sufficient to maintain the mixture essentially in liquid phase and the polyalkylene polyamine is then recovered from the resultant reaction mixture. In a preferred embodiment ethylenediamine is contacted with monoethylene diol to produce a predominantly linear polyethylene polyamine product with very low yields of heterocyclic amine materials. The desired polyethylene polyamines produced can be directly recovered from the reaction products by known purification procedures.

Preparation of polyalkylene polyamines

Covers a new composition of matter comprising a stable N-(.omega.-monoalkylaminoalkyl) acrylamide or methacrylamide monomer characterized by the following structural formula: ##STR1## where R.sub.1 and R.sub.2 are hydrogen or methyl, R.sub.3 is isopropyl or t-butyl and n is 2 or 3, with the proviso that when R.sub.1 is hydrogen, R.sub.3 is t-butyl. Also covers a method of preparing said monomer by condensing one mole of an acrylic or methacrylic compound with two moles of an appropriate amine to form an intermediate substituted amide, followed by heating said intermediate to split off one mole of reactant diamine leaving the desired substituted aminoalkyl acrylamide or acrylamide monomer.

Stable substituted acrylamides or methacrylamides

An improved process is disclosed for selectively producing a bis-(morpholino-N-alkyl) ether directly from the corresponding N-(hydroxyalkyl)morpholine compound. The improved process includes contacting the N-(hydroxyalkyl) morpholine compound with a catalytically effective amount of a silica-alumina or certain phosphorus containing substances at a temperature of about 200.degree. C to 300.degree. C under a pressure sufficient to maintain the mixture substantially in liquid phase and recovering from the resultant reaction mixture the bis-morpholino-N-alkyl) ether. According to the preferred embodiment, N-(2-hydroxyethyl)morpholine is heated in the presence of a catalytic amount of a silica-alumina catalyst having an alumina content of from about 5 to about 50 wt. % at temperatures of from about 240.degree. C to about 280.degree. C in liquid phase to selectively produce the corresponding N,N',2,2'-dimorpholinodiethyl ether (DMDEE).

Novel polyhalo, N-substituted aniline compounds are prepared which have the following structural formula: ##STR1## where R is selected from the group consisting of cyano, nitro, and alkyl sulfone, X is halo and Z represents a radical as follows: ##STR2## where R' and R' are hydrogen or lower alkyl, X is a number ranging from 1 to 5, and Y is 0-3. These compounds are prepared by reacting a polyhalo aromatic compound having the formula ##STR3## where X and R have a significance as just discussed with an appropriate polyamino reactant or aminohydroxy compound which additionally may contain either linkages. These new compounds have biological activity and are also useful as chemical intermediates.

Growing community of inventors

Austin, TX, United States of America

Philip H Moss