Synthesis and evaluation of a series of α-hydroxy ethers derived from isopropyl oleate

Several fatty derivatives with bulky moieties were prepared by treatment of epoxidized isopropyl oleate with a number of alcohols in the presence of sulfuric acid catalyst to provide a series of a-hydroxy ethers in good yield. The materials were analyzed for cold flow performance through cloud point and pour point determinations. The most promising a-hydroxy ether produced in this study, with respect to both low temperature behavior and economic criteria, was isopropyl 9(10)-(2-ethylhexoxy)10(9)-hydroxystearate, which has a cloud point of -23 degrees C and pour point of -24 degrees C.