To address the detrimental effects of the residue of catalysts on the tribological performances of ester lubricants, a novel and efficient bi-functional ionic liquid 1-(3,5-di-tert-butyl-4-hydroxybenzyl)-3-methylimidazole di(2-ethylhexyl) phosphate ([(BHT-1)MIM][DEHP]) was prepared. The catalyst not only facilitates the synthesis of pentaerythritol tetra-hexanoate (PETH) through the catalytic esterification reaction—achieving up to 96% conversion with a 94% yield—but also enhances the tribological performance of ester oil PETH when used as a lubricant additive. The tribological property has been improved remarkably: the mean friction coefficient for PETH + [(BHT-1)MIM][DEHP] is notably lower, at 0.110, compared to the PETH, which has a coefficient of 0.180. Meanwhile, the wear scar diameter of the steel ball, when lubricated with PETH + [(BHT-1)MIM][DEHP], is notably smaller than that of a steel ball lubricated solely with PETH. Especially, the reduction in the wear volume at 100 °C is up to 81.46% compared with the base oil PETH. [(BHT-1)MIM][DEHP], PETH + [(BHT-1)MIM][DEHP], and the worn track of the upper running ball and lower disc were systematically characterized by using Nuclear Magnetic Resonance (NMR) spectra, a Fourier Transform Infrared Spectrometer (FT-IR), a field emission scanning electron microscope (FESEM), Thermal gravity analysis (TG), X-ray photoelectron spectroscopy (XPS), and an optical microscope (OM). The wear mechanism of the tailored lubricant oil was discussed in terms of the chemical composition of the worn surface.
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