Olefin Autoxidation in Flow

Abstract

Handling hazardous multiphase reactions in flow brings not only safety advantages but also significantly improved performance, due to better mass transfer characteristics. In this paper, we present a continuous microreactor setup, capable of performing olefin autoxidations with O[subscript 2], under solvent-free and catalyst-free conditions. Owing to the transparent reactor design, consumption of O[subscript 2] can be visually followed and exhaustion of the gas bubbles marks a clear end point along the channel length coordinate. Tracking the position of this end point enables measuring effective rate constants. The developed system was calibrated using the well-studied β-pinene substrate, and was subsequently applied to the synthetically interesting transformation of (+)-valencene to (+)-nootkatone. For the latter, a space-time yield was obtained that is at least 3 orders of magnitude larger than that realized with established biotechnology approaches.