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

Abdul Malek, Emilia and Arumugam, Mahashanon and Basri, Mahiran and Abdul Rahman, Mohd Basyaruddin (2012) Optimization of lipase-mediated synthesis of 1-nonene oxide using phenylacetic acid and hydrogen peroxide. International Journal of Molecular Sciences, 13 (10). pp. 13140-13149. ISSN 1422-0067

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Official URL: http://www.mdpi.com/1422-0067/13/10/13140

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.

Item Type:Article
Keyword:1-nonene oxide; Enzymatic epoxidation; Lipase; Phenylacetic acid
Faculty or Institute:Faculty of Science
Publisher:MDPI AG
DOI Number:10.3390/ijms131013140
Altmetrics:http://www.altmetric.com/details.php?domain=psasir.upm.edu.my&doi=10.3390/ijms131013140
ID Code:16615
Deposited By: Nabilah Mustapa
Deposited On:08 Apr 2016 09:18
Last Modified:08 Apr 2016 09:18

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