Chemo-Enzymatic Baeyer–Villiger Oxidation Facilitated with Lipases Immobilized in the Supported Ionic Liquid Phase

oleh: Anna Szelwicka, Anna Wolny, Miroslawa Grymel, Sebastian Jurczyk, Slawomir Boncel, Anna Chrobok

Format: Article
Diterbitkan: MDPI AG 2021-06-01

Deskripsi

A novel method for chemo-enzymatic Baeyer–Villiger oxidation of cyclic ketones in the presence of supported ionic liquid-like phase biocatalyst was designed. In this work, multi-walled carbon nanotubes were applied as a support for ionic liquids which were anchored to nanotubes covalently by amide or imine bonds. Next, lipases B from <i>Candida antarctica</i>, <i>Candida rugosa,</i> or <i>Aspergillus oryzae</i> were immobilized on the prepared materials. The biocatalysts were characterized using various techniques, like thermogravimetry, IR spectroscopy, XPS, elemental analysis, and SEM-EDS microscopy. In the proposed approach, a biocatalyst consisting of a lipase as an active phase allowed the generation of peracid in situ from the corresponding precursor and a green oxidant–hydrogen peroxide. The activity and stability of the obtained biocatalysts in the model oxidation of 2-adamantanone were demonstrated. High conversion of substrate (92%) was achieved under favorable conditions (toluene: <i>n</i>-octanoic acid ratio 1:1 = v:v, 35% aq. H<sub>2</sub>O<sub>2</sub> 2 eq., 0.080 g of biocatalyst per 1 mmol of ketone at 20 °C, reaction time 4 h) with four reaction cycles without a drop in its activity. Our ‘properties-by-design’ approach is distinguished by its short reaction time at low temperature and higher thermal stability in comparison with other biocatalysts presented in the literature reports.