Bismuth(III) Trifluoromethanesulfonate Catalyzed Ring-Opening Reaction of Mono Epoxy Oleochemicals To Form Keto and Diketo Derivatives

作者：Doll Kenneth M^*; Bantchev Grigor B; Murray Rex E

来源：ACS Sustainable Chemistry and Engineering, 2013, 1(1): 39-45.

DOI：10.1021/sc300092r

• Bismuth(III) trifluoromethanesulfonate
• Bismuth triflate
• Diketone
• Long-chain dioxo compound
• Epoxidized methyl oleate

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(III) trifluoromethanesulfonate (bismuth triflate) catalyst. Lower reaction temperatures favor the 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 that reagent also is 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 had a minimal effect in reducing wear and did not improve oxidative stability. This drawback, while not good in lubricant formulations, is desirable in many applications such as paint and linoleum production. Also, the structure of the ketone could make it a desirable dielectric fluid, where the water sequestering ability of the carbonyl group would be desirable. Overall, this is an effective synthesis of promising materials, with high biobased content, useful for industries of the future.

• 出版日期2013-1