9561604 Kendall This Small Business Innovation Research Phase I project is involved with the direct electrosynthesis of two types of commercially important, high value-added carbohydrate intermediates. The first transformation to be studied is the oxidative decarboxylation of a sugar acid, as exemplified by conversion of D-gluconic acid (or salts thereof) to D-arabinose. The second transformation is the cleavage of a 1,2-diol to a dicarbonyl compound, as exemplified by the conversion of mannitol diacetonide to 2,3-isopropylidene-D-glyceraldehyde; this reaction is customarily accomplished using sodium periodate, but a direct synthesis would be preferable from both cost and environmental standpoints. Both D-arabinose and isopropylidene glyceraldehyde are important and useful intermediates in their own right, but in order to demonstrate the generality of the processes studied, each process will be extended to another substrate. For each of the specified processes, a number of anode materials will be evaluated in Phase I; in addition, the effects of solvent and pH will be examined. Some small-scale optimization studies will also be carried out on a selected process. Upon successful completion of the Phase I work, Phase II studies would include further optimization and evaluation of the processes in flow cells, as well as extension to other substrates. The availability of clean, efficient methods for the synthesis of aldopentoses and for the cleavage of 1,2-diols will allow for the cost-effective manufacture of a wide range of valuable chemical intermediates. This will provide benefits to the US chemical and pharmaceutical industries.
