Optimization of lipase-mediated synthesis of 1-nonene oxide using phenylacetic acid and hydrogen peroxide

Abstract

Herein, an efficient epoxidation of 1-nonene is described. In a simple epoxidation system, commercially available Novozym 435, an immobilized Candida antarctica lipase B, and hydrogen peroxide (H 2 O 2) were utilized to facilitate the in situ oxidation of phenylacetic acid to the corresponding peroxy acid which then reacted with 1-nonene to give 1-nonene oxide with high yield and selectivity. The aliphatic terminal alkene was epoxidised efficiently in chloroform to give an excellent yield (97%-99%)under the optimum reaction conditions, including temperature (35 °C), initial H 2 O 2 concentration (30%), H 2 O 2 amount (4.4 mmol), H 2 O 2 addition rate (one step), acid amount (8.8 mmol), and stirring speed (250 rpm). Interestingly, the enzyme was stable under the single-step addition of H 2 O 2 with a catalytic activity of 190.0 Ug -1. The entire epoxidation process was carried out within 12 h using a conventional water bath shaker. © 2012 by the authors; licensee MDPI, Basel, Switzerland.