Synthesis of Branched Biolubricant Base Oil from Oleic Acid

The mature manufacturing of synthetic lubricants (poly-alpha-olefins, PAO) proceeds through oligomerization, polymerization, and hydrogenation reactions of petrochemical ethylene. In this work, we utilize the inexpensive bio-derived oleic acid as raw material to synthesize a crotch-type C(45)biolubricant base oil via a full-carbon chain synthesis without carbon loss. It contains several cascade chemical processes: oxidation of oleic acid to azelaic acid (further esterification to dimethyl azelate) and nonanoic acid (both C(9)chains). The latter is then selectively hydrogenated to nonanol and brominated to the bromo-Grignard reagent. In a next step, a C(45)biolubricant base oil is formed by nucleophilic addition (NPA) of excessive C(9)bromo-Grignard reagent with dimethyl azelate, followed by subsequent hydrodeoxygenation. The specific properties of the prepared biolubricant base oil are almost equivalent to those of the commercial lubricant PAO6 (ExxonMobil). This process provides a new promising route for the production of value-added biolubricant base oils.