Friction Reducing Properties and Stability of Epoxidized Oleochemicals

Abstract

The properties of epoxidized oleochemical methyl esters were studied. Epoxidized soybean oil, epoxidized methyl oleate, epoxidized methyl linoleate, and epoxidized methyl linolenate were compared with each other and with similar series of unmodified olefins. Several interesting trends were uncovered including: epoxidation of olefinic materials improves their oxidative stability, epoxidation of oleochemicals increases their adsorption to metal surfaces, and epoxidation has a deleterious effect on the pour point and viscosity index of the oleochemicals. In addition, a simple qualitative method where lubrication performance can be compared by examination of wear scars generated by ball-on-disk friction measurement under a simple optical microscope is reported.

Chemical transformations of renewable lubricant feedstocks

“…Such fi lm formation in ESBO is achieved through the -O-cross-linking on the metal surface, thus reducing friction between the moving parts [71]. Doll et al [235,236] have examined the properties of SBO-based olefi ns and the epoxided methyl esters of oleic, linoleic and linolenic acid (EMO, EMLO and EMLEN, respectively) relevant to lubricant application such as oxidative stability, PP, VI and CoF (see Table 6.17). Neat SBO has a very high VI (>200), and methyl oleate is nearly as good.…”

“…Unmodifi ed olefi nic oleochemicals of Table 6.17 all have PPs suitable for use in most lubrication applications. Compounds of increased unsaturation display even lower PPs, which are adversely affected by epoxidation [235]. However, these materials will still fl ow above 3 °C and, therefore, are suitable for operation at room temperature.…”

Increased functionality of methyl oleate using alkene metathesis

“…The use of epoxidized methyl oleate (Biswas et al 2009;Bunker and Wool 2002;Doll, Sharma, and Erhan 2008) as a reaction substrate as well as that of multiple epoxide systems (Doll and Erhan 2005a;Doll, Sharma, and Erhan 2008) have been reported. By limiting the epoxidation reaction to incomplete conversion, it is possible to synthesize partially epoxidized methyl linoleate.…”

Emulsification of Chemically Modified Vegetable Oils for Lubricant Use

“…Biobased oil lubricants have been the subject of recent interest [29,30], including genetically modified [31] and chemically modified oils and methyl esters [32], but emulsion-based lubricants of these systems have not been previously reported. For example, epoxidized oils [33][34][35][36] and thermally modified oils [30,37] have been shown to have favorable lubricity, oxidation properties, and viscosities for use in lubricant industries, but their emulsion stability has not been previously studied in detail.…”