Levulinic acid (LA) is an attractive bio-based chemical. Its synthesis from lignocellulosic sugars is relatively straightforward, and its multifunctional nature opens the door to numerous downstream options. We recently reported that the aerobic, oxidative scission of the ketone moiety in levulinic acid forms maleic anhydride (MA). The reaction occurs in the gas phase over supported vanadates, and we have observed single-pass MA yields as high as 71% of the theoretical maximum at 573K. This result is intriguing because oxidative scission of a ketone over supported vanadium oxides will, in general, break C-C bonds positioned internally to the ketone group, yet formation of maleic anhydride (C4) from levulinic acid (C5) requires cleavage of its terminal C-C bond. As such, the observation runs counter to expectations for ketone oxidation. To resolve the origin of this disparity, we consider NMR and vibrational spectra, and we examine trends in oxidative cleavage rate and selectivity with variation in ketone structure.

Mechanistic origins of maleic anhydride selectivity during the oxidation of levulinic acid

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.