Solvent-free synthesis of phytosterol linoleic acid esters at low temperature

Abstract

Phytosterol unsaturated fatty acid esters show much higher oil solubility than free phytosterol. Thus, development of a green and low-cost method for the preparation of phytosterol fatty acid esters is highly desirable in the food industry. Herein, we have developed a simple chemical method toward efficient preparation of phytosterol linoleic acid esters at very mild temperature (60 °C) using 4-dodecylbenzenesulfonic acid (DBSA) as the catalyst. In this work, low-temperature esterification of phytosterols (soybean sterol) with linoleic acid could produce the corresponding phytosterol esters above 95% conversion under solvent-free conditions. In addition, this simple method could be applied to produce phytosterol esters through esterification of phytosterol with an unsaturated fatty acid mixture resulting from the hydrolysis of various vegetable oils. Importantly, no extra organic solvents and no extra water-removal operations or equipment were required in this chemical esterification method. The mechanism investigation suggested that the DBSA-catalyzed low-temperature esterification would form micro-emulsions of water-in-oil (W/O), which could achieve automatic separation of water from the hydrophobic system to avoid reverse reaction hydrolysis and rapidly promote the equilibrium reaction towards phytosterol esters.