Some Reactions of the Glycidyl Esters of Sulfonic Acids

Abstract

Abstract 1-Chloro-2-hydroxypropyl sulfonates are obtained by the reaction of glycidyl sulfonates with hydrochloric acid at room temperature. They are converted into 1,3-dichloro-2-propanol by the action of hydrochloric acid at 100°C, or into epichlorohydrin by that of bases. The reaction of glycidyl sulfonates and sodium carboxylates affords glycidyl carboxylates. In the preparation of glycidyl carboxylates, glycidyl sulfonates act as a direct alkylation agent for sodium carboxylates. The addition of amines to the epoxide is carried out at first in the reaction of glycidyl sulfonates and amines. The adducts are converted into glycidyl amines by the action of sodium hydroxide, or into N-[β-hydroxypropylene(α,γ)]-ammonium sulfonates by the isomerization, by heating them or letting them stand for a long time. The latter is an intermediate used in preparing 1,4-dioxane derivatives in the presence of sodium hydroxide.