Abstract
AbstractA novel catalytic strategy involving protective chemistry is presented for the selective production of 5‐formylfuran‐2‐carboxylic acid (FFCA) and furan‐2,5‐dicarboxylic acid (FDCA) from concentrated 5‐hydroxymethylfurfural (HMF) solutions. By protecting the reactive formyl group of HMF by acetalization with 1,3‐propanediol (PDO), degradation and premature oxidation of HMF is suppressed. A hydroxyapatite‐supported Au catalyst can selectively oxidize HMF‐acetal in a 10 wt % solution to FFCA‐acetal in 94 % yield in 2 hours at 373 K under 0.5 MPa of O2. Deprotection of FFCA‐acetal by mineral acids affords FFCA in 98 % yield and recovers nearly all PDO. FFCA in a 20 wt % solution can be oxidized to FDCA in 95 % yield under similar reaction conditions. The presented chemistry contributes to the development of novel manufacturing routes of prospective biobased monomer precursors using protecting agents.
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