Efficient mild oxidation of 5-hydroxymethylfurfural to 5-hydroxymethyl-2(5H)-furanone, a versatile chemical intermediate

Abstract

The 5-hydroxymethyl-2(5H)-furanone is a versatile chemical intermediate used to produce a variety of products such as unsaturated (+) muscarine, microbial metabolites, (+) trans-burseran, (−) isostegane, (+) steganacin, (−) verrucarinolactone and certain analogues of prostacyclin and chrysanthemic acid. In this study, we have successfully tested a sodium perborate (NaBO3·4H2O) known by its acronym, SPB, in the oxidation of 5-hydroxymethylfurfural (5-HMF) using acetic acid (AcOH) as solvent. SPB has been proven to be an efficient reagent for the oxidation of 5-HMF into 5-hydroxymethyl-2(5H)-furanone in one step. A reaction mechanism has been proposed for this purpose. In this work, a variety of important reaction parameters, such as SPB amount, reaction temperature, and time were explored. The maximum yield to 5-hydroxymethyl-2(5H)-furanone was achieved in 94 % at room temperature in 24 h, with 5-HMF conversion of 100 % being obtained in SPB/5-HMF mol ratio = 1.5 under optimal reaction conditions. Then, it could be obtained in a high yield of 87 % at 50 °C after a short reaction time of 4 h. At high temperature (100 °C), 5-hydroxymethyl-2(5H)-furanone yield decreased dramatically.