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Optimization of Lipase-Mediated Synthesis of 1-Nonene Oxide Using Phenylacetic Acid and Hydrogen Peroxide
Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia
Structural and Synthetic Biology Research Centre, Malaysia Genome Institute, 43000 Bangi, Selangor, Malaysia
* Author to whom correspondence should be addressed.
Received: 27 July 2012; in revised form: 1 September 2012 / Accepted: 21 September 2012 / Published: 12 October 2012
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 (H2O2) 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 H2O2 concentration (30%), H2O2 amount (4.4 mmol), H2O2 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 H2O2 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.
Keywords: enzymatic epoxidation; 1-nonene oxide; phenylacetic acid; lipase
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Abdulmalek, E.; Arumugam, M.; Basri, M.; Rahman, M.B.A. Optimization of Lipase-Mediated Synthesis of 1-Nonene Oxide Using Phenylacetic Acid and Hydrogen Peroxide. Int. J. Mol. Sci. 2012, 13, 13140-13149.
Abdulmalek E, Arumugam M, Basri M, Rahman MBA. Optimization of Lipase-Mediated Synthesis of 1-Nonene Oxide Using Phenylacetic Acid and Hydrogen Peroxide. International Journal of Molecular Sciences. 2012; 13(10):13140-13149.
Abdulmalek, Emilia; Arumugam, Mahashanon; Basri, Mahiran; Rahman, Mohd B.A. 2012. "Optimization of Lipase-Mediated Synthesis of 1-Nonene Oxide Using Phenylacetic Acid and Hydrogen Peroxide." Int. J. Mol. Sci. 13, no. 10: 13140-13149.