Ester hydroxy derivatives of methyl oleate: tribological, oxidation and low temperature properties

Five branched oleochemicals were prepared from commercially available methyl oleate and common organic acids; and their lubricant properties were determined. These branched oleochemicals are characterized as 9(10)-hydroxy-10(9)-ester derivatives of methyl oleate. These derivatives show improved low temperature properties, over olefinic oleochemicals, as determined by pour point and cloud point measurements. The derivatization also increased thermo-oxidative stability, measured using both pressurized differential scanning calorimetry (PDSC) and thin film micro oxidation (TFMO) methods. Branched oleochemicals were used as additives both in soybean oil and in polyalphaolefin. Their lubrication enhancement was evaluated by both four-ball and ball-on-disk wear determinations. These derivatives have good anti-wear and friction-reducing properties at relatively low concentrations, under all test loads. Their surface tensions were also determined and a trend was observed. The materials with larger side chain branches had lower surface tension than those containing smaller side chain branches. An exception to this trend was found when studying the compound with the carbonyl containing levulinic acid side chain, which had the highest surface tension of the branched oleochemicals studied. Overall, the data indicate that some of these derivatives have significant potential as a lubricating oil or fuel additives.