Synthesis and Properties of Soap Types of Cleavable Surfactants Bearing a 1, 3-Dioxolane Ring Derived from Long-chain Epoxides and Ethyl Levulinate

Abstract

Sodium carboxylates of surfactants bearing a 1, 3-dioxolane ring were synthesized by reactions of epoxides and ethyl levulinate in the presence of BF3·Et2O as a catalyst at room temperature, followed by alkaline hydrolysis. Two surfactants, derived from long-chain alkyl epoxide or from long-chain alkyl glycidyl ether, respectively, showed excellent surface-active properties and good acid-decomposition. The latter surfactants from alkyl glycidyl ether had higher water solubility and solubility in hard water compared to the corresponding former. Critical micelle concentration (cmc) and area per molecule at the surface of the latter somewhat exceeded those of the former. The hydrophilicity and bulkiness of the oxymethylene group in the side chain of the 1, 3-dioxolane ring may have been responsible for this.