Optimization of Lipase-Mediated Synthesis of 1-Nonene Oxide Using Phenylacetic Acid and Hydrogen Peroxide

International Journal of Molecular Sciences

Emilia Abdulmalek¹  Mahashanon Arumugam¹  Mahiran Basri¹ 

[1] Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia; E-Mails:

关键词: enzymatic epoxidation;    1-nonene oxide;    phenylacetic acid;    lipase;   

DOI  :  10.3390/ijms131013140

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2012 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland.