Synthetic lubricant basestocks from epoxidized soybean oil and Guerbet alcohols

Vegetable oils are biodegradable and therefore good candidates for environmentally friendly base stocks. They have excellent lubricity, but poor oxidation and low temperature stabilities. For this study, synthetic lubricant basestocks with oxidative stabilities and pour points comparable with commercial synthetic lubricant basestocks have been prepared by reacting epoxidized soybean oil with Guerbet alcohols. Four different Guerbet alcohols, C12-, C14-, C16-, and C18-Guerbet alcohols were used. Reaction of epoxidized soybean oil with a Guerbet alcohol in the presence of a catalytic amount of sulfuric acid provided open-ringed products. 1H NMR has shown that transesterification follows after ring-opening reaction under the given reaction conditions. Two types of ring-opened products, 0%- and 100%-transesterified products, could be obtained under controlled reaction conditions. Pour points of the ring-opened products ranged from −18 to −36 °C without pour point depressant (PPD) and from −21 to −42 °C with 1% of PPD. Acetylation of hydroxy groups in the ring-opened products further lowered pour points that ranged from −27 to −42 °C without PPD and from −30 to −48 °C with 1% of PPD. Oxidative stability was examined using a modified Penn State microoxidation test and compared with those of synthetic lubricant basestocks and mineral oil. Oxidative evaporations of two selected products in the microoxidation test were similar to mineral oil and less than synthetic lubricant-based oils, polyalphaolefin (PAO 4) and diisododecyl adipate. Deposits of these products were similar to synthetic lubricant-based oils and less than mineral oil.