title: Optimization of lipase-mediated synthesis of 1-nonene oxide using phenylacetic acid and hydrogen peroxide.
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 (H(2)O(2)) 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 H(2)O(2) concentration (30%), H(2)O(2) amount (4.4 mmol), H(2)O(2) 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 H(2)O(2) 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.
authors.affiliation: Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia. emilia@science.upm.edu.my.
authors.forename: Emilia
authors.initials: E
authors.lastname: Abdulmalek
authors.forename: Mahashanon
authors.initials: M
authors.lastname: Arumugam
authors.forename: Mahiran
authors.initials: M
authors.lastname: Basri
authors.forename: Mohd Basyaruddin Abdul
authors.initials: MB
authors.lastname: Rahman
mesh_terms: D000475:Alkenes / Q000737:chemistry / Q000378:metabolism*; D055162:Biocatalysis; D004800:Enzymes, Immobilized / Q000737:chemistry / Q000378:metabolism; D004852:Epoxy Compounds / Q000737:chemistry / Q000378:metabolism*; D005656:Fungal Proteins; D006861:Hydrogen Peroxide / Q000737:chemistry / Q000378:metabolism*; D008049:Lipase / Q000737:chemistry / Q000378:metabolism*; D010087:Oxides / Q000737:chemistry; D010648:Phenylacetates / Q000737:chemistry / Q000378:metabolism*; D013696:Temperature
chemical_list: D000475:Alkenes; D004800:Enzymes, Immobilized; D004852:Epoxy Compounds; D005656:Fungal Proteins; D010087:Oxides; D010648:Phenylacetates; D006861:Hydrogen Peroxide; C093667:Novozyme 435; D008049:Lipase; C025136:phenylacetic acid