Synthesis and tribological investigation of 4-vinyl guaiacol–based thioether derivatives as multifunctional additives and their interactions with the tribo surface using quantum chemical calculations

Abstract

Novel 4-vinyl guaiacol based thioether derivatives were synthesized in a three-step reaction procedure by thiol-ene coupling as the key step. The synthesized compounds were characterised by spectroscopic techniques and evaluated for their tribological and antioxidant properties in two different base oils namely epoxy2-ethylhexyl esters of karanja fatty acids (EKE) and dioctyl sebacate (DOS). It was found that the synthesized products were exhibited superior antioxidant performance compared to butylated hydroxytoluene (BHT). All the three synthesized additives were improved the tribological properties of the base oil EKE and DOS. Dithio derivative at 0.75 wt% reduced the wear scar diameter by 36% and at 1 wt% improved the weld point by 33% of base oil EKE. Surface and elemental analysis result suggests that in the tribochemical process the synthesized thioether derivatives decompose and form an effective tribofilms on interacting surfaces. X-ray Photoelectron Spectroscopy (XPS) of the surface lubricated with base oil containing DMFD was evidence for the formation of tribofilm with FeS, FeSO4 and Fe2O3. The antiwear behaviour of the additives was well correlated with quantum chemical calculations. Overall the dithio derivative is more effective as antiwear, extreme pressure and antioxidant bio lubricant additive than other thioether derivatives.

Keywords

• 4-Vinyl guaiacol
• Thiol-ene addition
• Quantum chemical calculations
• Antiwear
• Thioether