Optimization and kinetic modeling of lipase mediated enantioselective kinetic resolution of (±)-2-octanol

Jyoti B. Sontakke, Ganapati D. Yadav

Department of Chemical Engineering, Institute of Chemical Technology, Mumbai, India.

DOI: 10.4236/ns.2013.59127                

Abstract

Chiral 2-octanol is one of the key intermediates for preparation of liquid crystal materials, as well as many optically active pharmaceuticals. Lipase catalyzed kinetic resolution has proved to be an efficient technique for synthesis of enantiomerically enriched compounds. In the present study, optimization and kinetic modeling of kinetic resolution of (±)-2-octanol was done by using vinyl acetate as an acyl donor in n-heptane as a solvent. Response surface methodology (RSM) and four-factor-five-level Centre Composite Rotatable Design (CCRD) were employed to evaluate the effect of various parameters such as speed of agitation, enzyme loading, temperature and acyl donor/alcohol molar ratio on conversion, enantiomeric excess (ee), enantioselectivity and initial rate of reaction. Acylation of 2-octanol with vinyl acetate catalyzed by Novozyme 435 follows the ternary complex mechanism (ordered bi-bi mechanism) with inhibition by 2-octanol.

Keywords

Immobilized Lipase; Novozyme 435; 2-Octanol; Response Surface Methodology; Kinetic Modeling; Enantioselectivity

Conflicts of Interest

The authors declare no conflicts of interest.

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