A highly efficient approach to Solketal from acetone and glycerol with the supramolecular catalysis of cucurbit[6]uril

Abstract

The conversion of glycerol with acetone to (2,2-dimethyl-1,3-dioxolan-4yl)methanol (Solketal) via a ketalization reaction provides an effective route for preparing high-value-added glycerol derivatives. In the presence of cucurbit[6]uril (Q[6]), a supramolecular catalytic strategy for the ketalization of acetone with glycerol to Solketal has been successfully established without any acid or base. With 100% conversion and 98% yield, the catalysis exhibits high selectivity and reactivity, and the reaction time of only 20 min outperforms that reported previously. The analysis of supramolecular interactions and catalytic mechanism suggests that the selective binding of acetone by Q[6] activates the carbonyl group to realize the efficient catalysis. The Q[6]-catalytic ketalization reaction was scaled up to a 10-gram scale, and the high Solketal yield implies its potential for practical application.