Glycerol is a viable renewable feedstock that has emerged as a consequence of triglyceride conversion to biodiesel. In addition to glycerol conversion to commodity chemicals such as propylene glycol and epichlorohydrin, formation of higher-value specialty chemical products such as 1,3-dihydroxyacetone (DHA) will provide income for the biorefinery.
DHA is the active ingredient in sunless tanning products. Currently, DHA is industrially produced by fermentation of glycerol, but this microbial approach is challenged because of low production rates and high recovery costs. As a result, the high selling price of DHA limits access of sunless tanning products in the general population.
We present here a novel chemical process to convert glycerol to DHA that greatly improves the efficiency and reduces cost. The essential feature of this process is the selective formation of a 6-membered acetal of glycerol via reactive distillation, followed by selective oxidation of the secondary alcohol to its corresponding ketone product using ruthenium metal and a chemical oxidant. The ketone product is then hydrolyzed to obtain the final DHA product.
A continuous process of making DHA from glycerol has been designed and will be presented. Reactions involved in the process are rapid and can be carried out under mild conditions. Yields of individual process steps are all in excess of 90%, suggesting that this process has good potential to reduce DHA production costs.
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