CHAPTER 10: Lubricity Characteristics of Seed Oils Modified by Acylation

Seed oils chemically modified via acylation of their epoxidized and polyhydroxylated derivatives, were investigated for their potential as candidates for lubrication.  The native oil was preliminarily epoxidized and ring opened in a one-pot reaction using formic acid/H₂O₂ followed by aqueous HCl treatment to give the polyhydroxy intermediate.  The latter was then acylated with C2 to C5 anhydrides to avail the polyacetyl-, polybutyroyl- and polypentanoyl esters of the oil. Also using the oxirane as the starting material, the vicinal polyformates were generated. Tribological study of these seed oil derivatives revealed low coefficients of friction as well as low wear scar in four-ball tribometric tests.