Preparing vegetable oils-based metalworking fluids by a hydrolysis-esterification two-step process

Abstract

Oil-soluble esters of free fatty acids were synthesized with a 2-step process including the first step of reacting vegetable oil with water in the presence of sulfuric acid and p-Toluenesulfonic acid as a catalyst, followed by removing water and glycerol, and the second step of reacting the obtained free fatty acids with various polyhydric and fatty alcohols. The best conditions were 190 °C, 6 h, 30 to 1 water to oil molar ratio, 5 wt% PTSA catalyst loading in the hydrolysis reaction (the 1st step), and 150 °C, 10 h, 4 to 1 fatty acid to trimethylolpropane molar ratio, 1 wt% PTSA catalyst loading in the esterification reaction (the 2nd step). Under the best conditions, the process achieved the final product with the 87% yield of free fatty acid trimethylolpropane ester and 82% conversion of free fatty acid. Different esters were made concurring to the aforementioned conditions with distinctive polyhydric and fatty alcohols. Hydrolysis reactions facilitated by catalysts offer an alternative approach to traditional hydrolysis in supercritical conditions, enabling efficient substrate conversion under milder operating conditions. Furthermore, the inclusion of the obtained esters mixed with base oil and additives produced bio-based metalworking fluids with exceptionally lubricant performance in wear resistance, with a wear scar diameter of 0.33 mm.