Prilezhaev dihydroxylation of olefins in a continuous flow process

Epoxidation of both terminal and non-terminal olefins with peroxy acids is a well-established and powerful tool in a wide variety of chemical processes. In an additional step, the epoxide can be readily converted into the corresponding trans-diol. Batch-wise scale-up, however, is often troublesome because of the thermal instability and explosive character of the peroxy acids involved. This article describes the design and semi-automated optimization of a continuous flow process and subsequent scale-up to preparative production volumes in an intrinsically safe manner.