Preparation and properties of lubricant basestocks from epoxidized soybean oil and 2‐ethylhexanol

Synthetic lubricant basestocks were prepared from epoxidized soybean oil (ESO) and 2‐ethylhexanol (2‐EH) to be used alone or with polyalphaolefin (PAO). Sulfuric acid‐catalyzed reaction of ESO with 2‐EH involves a ring‐opening reaction at the epoxy group followed by transesterification at the ester group. Reaction with other catalysts including p‐toluenesulfonic acid, Dowex 50W‐8X, boron trifluoride, and sodium methoxide was also examined. Pour points of the products were observed as lows as −21 and −30°C without and with 1% of pour point depressant, respectively. When the hydroxy groups in the products were esterified with an acid anhydride, lower pour points were observed. Pour point depression of the product by adding PAO has been tested. Oxidative stability of the product was examined using pressurized DSC and compared with those of synthetic lubricant basestocks, PAO, and a synthetic ester.