Investigation of anti-wear additives for low viscous synthetic esters: Hydroxyalkyl phosphonates

Various synthetic esters are widely applied as lubricating fluid to reduce friction and wear at tribological contact. Among them low viscous synthetic esters are expected to improve fuel efficiency by minimizing the fluid friction. These low viscous esters are composed of short-chain fatty acids. Therefore, low viscous synthetic esters are inherently polar molecules. Since efficiency of anti-wear additives decreases with increase of polarity of the base oil, new additive technology is requested. In this work, hydroxyalkyl phosphates [P(O)(OCHRCH 2OH) 3], and hydroxyalkyl phosphonates [P(OH) n (OCHRCH 2OH) 3− n , where n=1,2] are proposed as novel anti-wear additives for polar synthetic esters. The anti-wear additives are evaluated under the boundary conditions. The additives prevent wear in polar esters, in which conventional anti-wear additives do not work at all. Interestingly, effects of substituent in additive molecule on anti-wear properties are found. Alkyl and aryl derivatives reduce wear remarkably, whereas allyl derivatives exhibit poor results. It is speculated that the anti-wear inefiiciency of allylic compounds is due to auto-oxidation of the additives. A facile preparative method for hydroxyalkyl derivatives characterizes the present additive system. They are prepared in situ by simply mixing phosphonic acid and substituted epoxides. Flexiblity of lubricant design can be made possible by the present additive system.