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

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 a...

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Main Authors: Abdul Malek, Emilia, Arumugam, Mahashanon, Basri, Mahiran, Abdul Rahman, Mohd Basyaruddin
Format: Article
Language:English
Published: MDPI AG 2012
Online Access:http://psasir.upm.edu.my/id/eprint/16615/1/16615.pdf
http://psasir.upm.edu.my/id/eprint/16615/
http://www.mdpi.com/1422-0067/13/10/13140
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spelling my.upm.eprints.166152016-04-08T01:18:23Z http://psasir.upm.edu.my/id/eprint/16615/ Optimization of lipase-mediated synthesis of 1-nonene oxide using phenylacetic acid and hydrogen peroxide Abdul Malek, Emilia Arumugam, Mahashanon Basri, Mahiran Abdul Rahman, Mohd Basyaruddin 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. MDPI AG 2012-10-12 Article PeerReviewed application/pdf en http://psasir.upm.edu.my/id/eprint/16615/1/16615.pdf 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 http://www.mdpi.com/1422-0067/13/10/13140 10.3390/ijms131013140
institution Universiti Putra Malaysia
building UPM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Putra Malaysia
content_source UPM Institutional Repository
url_provider http://psasir.upm.edu.my/
language English
description 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.
format Article
author Abdul Malek, Emilia
Arumugam, Mahashanon
Basri, Mahiran
Abdul Rahman, Mohd Basyaruddin
spellingShingle Abdul Malek, Emilia
Arumugam, Mahashanon
Basri, Mahiran
Abdul Rahman, Mohd Basyaruddin
Optimization of lipase-mediated synthesis of 1-nonene oxide using phenylacetic acid and hydrogen peroxide
author_facet Abdul Malek, Emilia
Arumugam, Mahashanon
Basri, Mahiran
Abdul Rahman, Mohd Basyaruddin
author_sort Abdul Malek, Emilia
title Optimization of lipase-mediated synthesis of 1-nonene oxide using phenylacetic acid and hydrogen peroxide
title_short Optimization of lipase-mediated synthesis of 1-nonene oxide using phenylacetic acid and hydrogen peroxide
title_full Optimization of lipase-mediated synthesis of 1-nonene oxide using phenylacetic acid and hydrogen peroxide
title_fullStr Optimization of lipase-mediated synthesis of 1-nonene oxide using phenylacetic acid and hydrogen peroxide
title_full_unstemmed Optimization of lipase-mediated synthesis of 1-nonene oxide using phenylacetic acid and hydrogen peroxide
title_sort optimization of lipase-mediated synthesis of 1-nonene oxide using phenylacetic acid and hydrogen peroxide
publisher MDPI AG
publishDate 2012
url http://psasir.upm.edu.my/id/eprint/16615/1/16615.pdf
http://psasir.upm.edu.my/id/eprint/16615/
http://www.mdpi.com/1422-0067/13/10/13140
_version_ 1643826266044891136
score 13.211869

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