GB792155A - Substituted caprolactone and method for the production thereof - Google Patents

Abstract

The invention comprises a ,d -dimethyl-d -hydroxy-e -caprolactone. The novel compound may be obtained by hydrolysing methacrolein dimer in the presence of excess water and a strong acid, such as hydrochloric, sulphuric, phosphoric or formic acid, at a temperature between 0 DEG and 150 DEG C., preferably 90 DEG to 100 DEG C., partially neutralizing the reaction mixture with a base to give a mildly acidic medium having a pH of substantially 6.5 and distilling the required product from the reaction mixture. An inert water-soluble solvent for methacrolein dimer, such as dioxane, may be present during the hydrolysis. Any inorganic base may be used to effect the partial neutralization but sodium bicarbonate is preferred. In a detailed example (2), methacrolein dimer is hydrolysed by refluxing with a mixture of dioxane, water and sulphuric acid, the reaction mixture is neutralized to pH 6.5 with sodium bicarbonate, and a ,d -dimethyl-d -hydroxy-e -caprolactone is recovered by distillation. The compound is reacted with acetic anhydride to give the corresponding acetate. The lactone may be reacted with butanol to form the butyl ester and then acetylated to form a compound useful as a plasticizer for vinyl resins, and cellulose derivatives. Polymers may be formed by reacting the lactone with amino acids, polyamines and polybasic acids. In a comparative example (1), a methacrolein dimer is similarly hydrolysed and then completely neutralized, whereupon the product of distillation is a mixture of 2,5-dimethyl-2-hydroxy-adipaldehyde and 2,5-dimethyl-2-formyl-tetrahydropyran-5-ol. Specification 725,161 is referred to.