Ethyl Corporation

Ethyl Corportation

Jerry M Roper

Charles R Everly

Frank J Smith

Joel F Carpenter

A synthetic oil composition comprising the reaction product of an .alpha.-olefin oligomer derived from an .alpha.-olefin monomer containing from about 6 to 20 carbon atoms and from about 0.01 to 1 mole of a phenol per mole of oligomer. The oil composition can be further reacted to form alkoxylated products and can be mixed with polar additives to form homogeneous synthetic lubricants.

.alpha.-olefin oligomer-phenol lubricant oil adducts

(S) .alpha.-cyano-3-phenoxy-benzyl acetate having the formula: ##STR1## and a novel process for its preparation.

(S) .alpha.-cyano-3-phenoxy-benzyl acetate

(S) .alpha.-(cyano-3-phenoxy-benzyl acetate

Alpha-cyano-phenoxybenzyl esters are prepared by reacting an acid halide with an ester of an alpha-cyano-phenoxybenzyl alcohol in the presence of an inert polar aprotic solvent and a transition metal alkoxide catalyst.

Preparation of alpha-cyano-phenoxybenzyl esters

3,5-Dihydrocarbyl-4-hydroxybenzaldehydes are prepared by intimately contacting a 4-(1-alkenyl)-2,5-dihydrocarbylphenol, such as 1,1-dimethyl-2-(3,5-di-t-butyl-4-hydroxyphenyl)ethene, with at least a stoichiometric amount of an oxygen-containing gas at about 50.degree.-25.degree. C. in the presence of an alcohol solvent and a catalytic amount of an alkali or alkaline earth metal hydroxide.

Aldehyde synthesis

Spiro[5.5]undeca-1,4,8-trien-3-ones are prepared by reacting a phenol having a free p-position with formaldehyde, a nitrogen compound selected from ammonia and primary and secondary amines, and a conjugated diene in an inert solvent at a temperature of at least about 190.degree. C.

Spiroketone process

Spiro[5.5]undeca-1,4,8-trien-3-ones are prepared by heating a reaction mixture consisting essentially of a 4-aminomethylphenol, a conjugated diene, and an inert solvent at a temperature of at least about 190.degree. C.

4H-1-Benzopyrans are prepared by reacting an aminomethylphenol with an alkali metal hydroxide or an alkaline earth metal hydroxide and a 1,3-diketone. The products are useful as antioxidants.

4H-1-benzopyrans and lubricant compositions containing same

Novel bis(3',5'-mono or dihydrocarbyl-4'-hydroxybenzyl)-1,3-diketones are prepared by reacting a (3',5'-mono or dihydrocarbyl-4'-hydroxybenzyl)-1,3-diketone with an N,N-dihydrocarbyl-2,6-mono or dihydrocarbyl-4-aminomethylphenol and an alkyl halide in the presence of an alkaline earth metal halide. The products are useful as antioxidants.

Chemical process

4-(.alpha.-hydrocarbyl-.alpha.-cyanomethyl)2,6-di-hydrocarbyl-substituted phenols having the formula ##STR1## wherein R.sub.1 and R.sub.2 are the same or different monovalent substituents selected from the group consisting of alkyl, aralkyl and cyclic alkyl radicals and R.sub.3 is selected from hydrogen, hydrocarbyl radicals, substituted hydrocarbyl radicals and hydrocarbyloxy radicals are prepared by reacting an N,N-di-hydrocarbyl-4-(.alpha.-hydrocarbyl-.alpha.-aminomethyl)2,6-di-hydro carbyl-substituted phenol having the formula ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined above and R.sub.4 and R.sub.5 are the same or different and are selected from hydrogen, hydrocarbyl radicals and substituted hydrocarbyl radicals with an alkali metal cyanide or an alkaline earth metal cyanide in a suitable solvent. The 4-(.alpha.-hydrocarbyl-.alpha.-cyanomethyl)2,6-di-substituted phenol thus formed can readily be converted to the corresponding 4-(.alpha.-hydrocarbyl-.alpha.-cyanomethyl)phenol by dealkylating the substituent groups ortho to the hydroxyl group from the 4-(.alpha.-hydrocarbyl-.alpha.-cyanomethyl)2,6-di-substituted phenol which then can be converted on hydrolysis to the corresponding .alpha.-hydrocarbyl-4-hydroxyphenylacetic acid. These acids have utility as insecticidal and acaricidal intermediates and are deemed to have utility as insecticides themselves as are the 4-(.alpha.-hydrocarbyl-.alpha.-cyanomethyl)2,6-di-substituted phenols of the present invention.

Method of preparing

4-(.alpha.-hydrocarbyl-.alpha.-cyanomethyl)2,6-di-substituted phenols having the formula ##STR1## wherein R.sub.1 and R.sub.2 are the same or different monovalent substituents selected from the group consisting of alkyl, aralkyl and cyclic alkyl radicals and R.sub.3 is selected from hydrogen, hydrocarbyl radicals, substituted hydrocarbyl radicals and hydrocarbyloxy radicals are prepared by reacting a 4-(.alpha.-hydrocarbyl-.alpha.-hydrocarbyloxymethyl)2,6-di-substituted phenol having the formula ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined above and R.sub.4 is selected from hydrocarbyl radicals or substituted hydrocarbyl radicals with an alkali metal cyanide or an alkaline earth metal cyanide in a suitable solvent. The 4-(.alpha.-hydrocarbyl-.alpha.-cyanomethyl)2,6-di-substituted phenol thus formed can readily be converted to the corresponding 4-(.alpha.-hydrocarbyl-.alpha.-cyanomethyl)phenol by dealkylating the substituent groups ortho to the hydroxyl group from the 4-(.alpha.-hydrocarbyl-.alpha.-cyanomethyl)2,6-di-substituted phenol which then can be converted on hydrolysis to the corresponding .alpha.-hydrocarbyl-4-hydroxyphenylacetic acid. These acids have utility as insecticidal and acaricidal intermediates and are deemed to have utility as insecticides themselves as are the 4-(.alpha.-hydrocarbyl-.alpha.-cyanomethyl)2,6-di-substituted phenols of the present invention.

Preparation of

Novel 2,4-dihydrocarbylspiro[5.5]undeca-1,4,8-trien-3-one compounds are prepared by reacting an N,N-dihydrocarbyl,2,6-dihydrocarbyl-4-aminomethylphenol with a conjugated diene and an alkyl halide in a liquid solvent medium.

Esters of 3,5-dihydrocarbyl-4-hydroxybenzylmalonic acid are prepared by reacting a 2,6-dihydrocarbyl-4-hydroxymethylphenol with an ester of a 1,3-dicarboxylic acid in the presence of an alkali or an alkaline earth metal hydride. The products are useful as antioxidants.

Process for the preparation of 3,5-dihydrocarbyl-4-hydroxybenzylmalonic

Esters of 3,5-dihydrocarbyl-4-hydroxybenzylmalonic acid are prepared by reacting a 2,6-dihydrocarbyl-4-halomethylphenol with an ester of a 1,3-dicarboxylic acid in the presence of an alkali or an alkaline earth metal hydride. The products are useful as antioxidants.

Novel (3',5'-dihydrocarbyl-4'-hydroxybenzyl)-1,3-diketones are prepared by reacting an N,N-dihydrocarbyl-2,6-dihydrocarbyl-4-aminomethylphenol with a 1,3-diketone in the presence of a basic substance. The products are useful as antioxidants.

Growing community of inventors

Baton Rouge, LA, United States of America

Jerry M Roper