Process for the preparation of alkaline sulfate esters of N-alkyl-substituted hydroxypolyalkoxymethylcyclohexenes
AssigneeUniversal Oil Products Company
InventorHerman S. Bloch
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Abstract
Anionic biodegradable detergents as exemplified by alkaline sulfate esters of n-alkyl-substituted hydroxypolyalkoxymethylcyclohexenes may be prepared by condensing butadiene with allyl alcohol, ring alkylating the resultant hydroxymethylcyclohexene with an olefin in the presence of a free-radical generating compound to form an alkyl-substituted hydroxymethylcyclohexene, alkoxylating this compound to form an alkyl-substituted hydroxypolyalkoxymethylcyclohexene, sulfating the latter compound and neutralizing the sulfate ester with an alkaline material to form the desired product.
Claims7
A process for the preparation of a biodegradable detergent which comprises the steps of:
- a. condensing butadiene with allyl alcohol in a Diels-Alder reaction at a temperature in the range of from about 50.degree. to 190.degree. C. and a pressure in the range of from atmospheric to about 100 atmospheres to form hydroxymethylcyclohexene;
- b. ring alkylating said hydroxymethylcyclohexene with a 3 to 20 carbon atom 1-alkene in the presence of an organic peroxy free-radical generating compound and hydrogen chloride at a temperature at least as high as the decomposition temperature of said free-radical generating compound;
- c. alkoxylating the resultant n-alkyl-substituted hydroxymethylcyclohexene with an alkoxylating agent selected from the group consisting of ethylene oxide and propylene oxide at a temperature in the range of from about 20.degree. to 125.degree. C. and at a pressure of from about 50 to about 1000 pounds per square inch to form an n-alkyl-substituted hydroxypolyalkoxymethylcyclohexene;
- d. sulfating said n-alkyl-substituted hydroxypolyalkoxymethylcyclohexene with a sulfating agent at a temperature of from about 0.degree. to about 60.degree. C. to form the sulfate ester thereof;
- e. neutralizing said sulfate ester with a neutralizing agent to form the alkaline sulfate ester of said n-alkyl-substituted hydroxypolyalkoxymethylcyclohexene;
- and
- f. recovering said alkaline sulfate ester.
Dependencies are inferred from the claim text.