Singlet-oxygen oxidation of 5-hydroxymethylfurfural (5-HMF) was performed in continuous flow mode using rose Bengal as photosensitizer. The resulting butenolide (H(2) MF) was formed selectively in high yield. The procedure proved to be scalable and applicable to related bio-based furfurals. Furthermore, preliminary data show that H(2) MF can be readily isomerized thermally to 5-hydroxy-4-keto-pentenoic acid oligomers.
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Heugebaert et al. (2014) studied this question.
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