The aim of this study was to synthesize environmentally adapted Trimethylolpropane (TMP) esters from cottonseed and soybean oils and to examine their quality parameters and tribological properties as potential lubricant basestocks. A two stage production process was followed. At first the above mentioned vegetable oils were transformed to the corresponding methyl esters via methanolysis in the presence of sodium methoxide. The desired TMP esters were finally synthesized by alkaline transesterification of the previously produced methylesters with TMP using sodium methoxide as catalyst. Following the purification phase the physicochemical characteristics of the synthesized TMP esters were examined. The tribological properties were evaluated by employing a Four-Ball apparatus. An additive-free mineral oil base oil was used as a reference lubricating fluid. Furthermore, the synthesized esters were treated with a commercially available EP/AW additive and a comparative assessment of the load-carrying properties was conducted by repeating the four ball measurements.