Technical Abstract: Using a catalytic system, methyl oleate is transformed into long chain keto and diketo derivatives via an epoxide route. Methyl 9(10)-oxooctadecanoate and methyl 9,10-dioxooctadecanoate were made by a ring opening reaction of epoxidized methyl oleate using bismuth triflate catalyst. Lower reaction temperatures favor the mono-ketone whereas higher temperatures are required to produce the diketone. The second synthesis also requires the use of dimethylsulfoxide to serve as an oxygen atom donor and is also needed to keep the catalyst in its active form. The ketone was also evaluated as a lubricity additive in soybean oil where it was found that it reduced wear, but did not improve oxidative stability. This drawback, while not good in lubricant formulations, is desirable in many applications such as paints and linoleum productions and also makes these materials potential substrates for further derivatizations such as the Bayer Villiger reaction. Overall, this is an effective synthesis of promising materials, with high biobased content, useful for industries of the future.