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...
Published in: | International Journal of Molecular Sciences |
---|---|
Main Authors: | , , , |
Format: | Text |
Language: | English |
Published: |
Multidisciplinary Digital Publishing Institute
2012
|
Subjects: | |
Online Access: | https://doi.org/10.3390/ijms131013140 |
id |
ftmdpi:oai:mdpi.com:/1422-0067/13/10/13140/ |
---|---|
record_format |
openpolar |
spelling |
ftmdpi:oai:mdpi.com:/1422-0067/13/10/13140/ 2023-08-20T04:01:49+02:00 Optimization of Lipase-Mediated Synthesis of 1-Nonene Oxide Using Phenylacetic Acid and Hydrogen Peroxide Emilia Abdulmalek Mahashanon Arumugam Mahiran Basri Mohd Basyaruddin Abdul Rahman agris 2012-10-12 application/pdf https://doi.org/10.3390/ijms131013140 EN eng Multidisciplinary Digital Publishing Institute Green Chemistry https://dx.doi.org/10.3390/ijms131013140 https://creativecommons.org/licenses/by-nc-sa/3.0/ International Journal of Molecular Sciences; Volume 13; Issue 10; Pages: 13140-13149 enzymatic epoxidation 1-nonene oxide phenylacetic acid lipase Text 2012 ftmdpi https://doi.org/10.3390/ijms131013140 2023-07-31T20:30:15Z 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. Text Antarc* Antarctica MDPI Open Access Publishing International Journal of Molecular Sciences 13 12 13140 13149 |
institution |
Open Polar |
collection |
MDPI Open Access Publishing |
op_collection_id |
ftmdpi |
language |
English |
topic |
enzymatic epoxidation 1-nonene oxide phenylacetic acid lipase |
spellingShingle |
enzymatic epoxidation 1-nonene oxide phenylacetic acid lipase Emilia Abdulmalek Mahashanon Arumugam Mahiran Basri Mohd Basyaruddin Abdul Rahman Optimization of Lipase-Mediated Synthesis of 1-Nonene Oxide Using Phenylacetic Acid and Hydrogen Peroxide |
topic_facet |
enzymatic epoxidation 1-nonene oxide phenylacetic acid lipase |
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 |
Text |
author |
Emilia Abdulmalek Mahashanon Arumugam Mahiran Basri Mohd Basyaruddin Abdul Rahman |
author_facet |
Emilia Abdulmalek Mahashanon Arumugam Mahiran Basri Mohd Basyaruddin Abdul Rahman |
author_sort |
Emilia Abdulmalek |
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 |
Multidisciplinary Digital Publishing Institute |
publishDate |
2012 |
url |
https://doi.org/10.3390/ijms131013140 |
op_coverage |
agris |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
International Journal of Molecular Sciences; Volume 13; Issue 10; Pages: 13140-13149 |
op_relation |
Green Chemistry https://dx.doi.org/10.3390/ijms131013140 |
op_rights |
https://creativecommons.org/licenses/by-nc-sa/3.0/ |
op_doi |
https://doi.org/10.3390/ijms131013140 |
container_title |
International Journal of Molecular Sciences |
container_volume |
13 |
container_issue |
12 |
container_start_page |
13140 |
op_container_end_page |
13149 |
_version_ |
1774725026926297088 |