5-(Chloromethyl)furfural (CMF), a stable, hydrophobic analogue of 5-(hydroxymethyl)furfural (HMF), is prepared under mild conditions and in excellent yield from sugars, cellulose, or cellulosic biomass by treatment with hydrochloric acid in a biphasic reactor. In recent years, it has been shown how CMF can be utilized as a platform chemical for the synthesis of products ranging from biofuels to polymers to pharmaceuticals and agrochemicals. Renewable fuel-additives such as 5-(ethoxymethyl)furfural and 5-methylfurfural have been synthesized from CMF. Syntheses of agrochemicals and pharmaceuticals including the natural herbicide/photodynamic therapy drug 5-aminolevulinic acid and the anti-ulcer preparation ranitidine (ZantacTM) have also been reported recently. Currently, CMF is being used to access 2,5-dimethylfuran, which can be used both as a fuel and chemical precursor for the synthesis of terephthalate-based polymers. Synthesis of furan-2,5-dicarboxylic acid, a renewable alternative of terephthalic acid, can also be sourced from CMF. The syntheses of important chemical intermediates such as succinic acid, and 3-hydroxypropionic acid have also been demonstrated. Finally, CMF has also been exploited for the synthesis of gasoline-range, branched hydrocarbons in three steps starting from levulinic acid (a derivative of CMF) .

Renewable synthesis of fuels and chemicals from biomass-derived 5-(chloromethyl)furfural

247th National Meeting (2014)

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