Enzymatic synthesis of TMP esters based on pelargonic acid from the cleavage of oleic acid: Evaluation of synthetic process, physicochemical properties and lubrication performance

Abstract

Biolubricants produced by chemically modifying vegetable oils are promising to replace mineral-based lubricants. However, the performances of biolubricants synthesized through traditional chemical modification routes, such as transesterification/esterification, epoxidation with further ring opening, and estolide formation, cannot satisfy the demands of extreme conditions. Meanwhile, complicated multi-step reactions cause expensive costs, which hinders their large-scale application. In this study, pelargonic acid (PA) derived from the cleavage of oleic acid was esterified with trimethylolpropane (TMP) to produce branched-chain esters (tri-TMP esters) catalyzed by the lipase (Candida sp. 99–125), focusing on batch stability of the lipase, thermal-oxidation stability and lubrication performance of the product. The lipase maintained high activity for 4 continuous batches in 5 L enzyme reactor with the conversion of PA > 96% and the accumulation of tri-TMP esters > 84% in each batch. The obtained tri-TMP esters had a pour point of − 56 °C, a viscosity index of 137, and a flash point of 276 °C. Anti-oxidation stability test and thermogravimetric behaviors showed that the biolubricant had favorable thermal-oxidative stability. Friction tests verified that the product displayed excellent lubrication performance with a minimum coefficient of friction (COF) of 0.099 and an average wear spot diameter (WSD) of 221.5 µm. The green and high-selective synthetic pathway fills the defect of existing routes for the preparation of biolubricants from chemically modified vegetable oils.