Abstract
The alcohol group of hydroxymethylfurfural (compound 1, HMF) is preferentially oxidized by dioxygen and metal/bromide catalysts [Co/Mn/Br, Co/Mn/Zr/Br; Co/Mn=Br/(Co+Mn) = 1.0 mol/mol] to form the dialdehyde, 2,5-diformylfuran (compound 2, DFF) in 57% isolated yield. HMF can be also oxidized, via a network of identified intermediates, to the highly insoluble 2,5-furandicarboxylic acid (compound 5, FDA) in 60% yield. For comparison, benzyl alcohol gives benzaldehyde in 80% using the same catalyst system. Over-oxidation (to CO2) of HMF is much higher than that of the benzyl alcohol but can be greatly reduced by increasing catalyst concentration.
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