Chloroperoxidase-catalyzed oxidation of 5-hydroxymethylfurfural

Article abstract of DOI:10.1080/07328309708006531

Chloroperoxidase (CPO) catalyzes the oxidation of 5-hydroxymethylfurfural (HMF) with hydrogen peroxide as the oxidant. The reaction proceeds with 60-74% selectivity to furan-2,5-dicarboxaldehyde (FDC). The main byproduct is 5-hydroxymethyl-2-furancarboxylic acid (HFCA); a minor amount of 5-formylfuran-2-carboxylic acid (FFCA) was also detected. When H₂¹⁸O₂ was used a virtually quantitative incorporation of ¹⁸O was observed in the HFCA product, whereas no ¹⁸O was incorporated from H₂¹⁸O. Hence, the CPO-catalyzed oxidation of aldehydes to acids proceeds with direct oxygen transfer from the iron-oxo complex of CPO. Controlling the H₂O₂-addition with a H₂O₂-stat facilitated the reaction procedure and a conversion of 87% of HMF was reached within 21 min.

Full text of DOI:10.1080/07328309708006531

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Journal of Carbohydrate Chemistry
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Chloroperoxidase-Catalyzed Oxidation of
5-Hydroxymethylfurfural
M. P.J. van Deurzen a , F. van Rantwijk a & R. A. Sheldon a
a Laboratory of Organic Chemistry and Catalysis, Julianalaan 136,
2628 BL, Delft, The Netherlands
Published online: 19 Aug 2006.
To cite this article: M. P.J. van Deurzen , F. van Rantwijk & R. A. Sheldon (1997) Chloroperoxidase-
Catalyzed Oxidation of 5-Hydroxymethylfurfural, Journal of Carbohydrate Chemistry, 16:3, 299-309
To link to this article: http://dx.doi.org/10.1080/07328309708006531
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