Abstract
We report the synthesis of five useful branched methyl α-hydroxy stearate esters from commercially available methyl oleate and common organic acids. Of special interest is the synthesis utilizing the natural byproduct, levulinic acid. The other common organic acids, used herein, were propionic acid, hexanoic acid, octanoic acid, and 2-ethylhexanoic acid. The kinetics of the ring opening reaction were studied under pseudo-first-order conditions in the propionic acid system. An Arrhenius activation energy of 66.7 kJ mol-1 (16.0 kcal mol-1) was found. One product, the octanoic ester of methyl hydroxy stearate, was shown to have pour point, cloud point, and viscosity indices of −31 °C, −33 °C, and 101, respectively, all favorable properties in the synthesis of a bio-based lubrication fluid. These products may also prove useful in the synthesis of agriculturally based surfactants and fuel additives.
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