Enzyme-facilitated synthesis of 1-nonene oxide and simple GC-MS SIM method for rapid screening of epoxidation processes

Abstract

Here, we describe an improved enzyme-facilitated epoxidation of 1-nonene using a conventional water bath shaker at ambient temperature. Enzymes were used to produce peroxy acids instantly from hydrogen peroxide (H₂O₂) and various perhydrolysis substrates. The peroxy acid generated was then utilised directly for in-situ oxidation of 1-nonene to 1-nonene oxide. Various parameters affecting the reaction were studied such as the nature of the peroxy acids, organic solvents, enzyme sources and enzyme concentrations. The highest conversion rate was achieved using phenylacetic acid as an oxygen carrier. 1-Nonene was converted most efficiently with 95% of the maximum yield by Novozym 435, an immobilised Candida antarctica lipase B, using dichloromethane as the reaction media. A minimum amount (16 mg, 1.4% w/w) of Novozym 435 was needed to maintain catalytic activity (160.0 Ug⁻¹). In addition, a simple and rapid Gas chromatography mass spectroscopy selective ion monitoring (GC-MS SIM) method was developed using a HP-5ms column for determining 1-nonene oxide. The method was found to be linear in the range of 29.9 to 298.8 mg/L with R² = 0.9981.

Keywords::

• epoxidation
• enzymatic
• 1-nonene oxide
• GC-MS
• SIM method

Acknowledgements

The authors are thankful to the Ministry of Higher Education of Malaysia (MOHE) and the Ministry of Science Technology and Innovation Malaysia (MOSTI) via the Genomics and Molecular Biology Initiative (GMBI) for financial support. We would also like to thank Universiti Puta Malaysia for the Graduate Research Fellowship (GRF) for M. Arumugam.

Declaration of interest: The authors report no conflict of interest. The authors alone are responsible for the content and writing of the paper.