Understanding Ketone Hydrodeoxygenation for the Production of Fuels and Feedstocks From Biomass

Although we can efficiently convert bioderived furans into linear alkanes, the most energy-intensive step in this approach is the hydrodeoxygenation of the intermediate polyketone. To fully understand this process, we have examined the hydrodeoxygenation of a model compound, 3-pentanone, which allows us to follow this process stepwise using Pd/C, H-2 (200 psi), and La(OTf)(3) in acetic acid to remove the oxygen atom at temperatures between 25 and 200 degrees C. We have found that ketone reduction to an alcohol is followed by acetoxylation, which provides a more facile route to C-O bond cleavage relative to the parent alcohol.