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Issue 11, 2012
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A clean enzymatic process for producing flavour esters by direct esterification in switchable ionic liquid/solid phases

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Abstract

A clean biocatalytic approach for producing flavour esters using switchable ionic liquid/solid phases as reaction/separation media has been developed. The phase behaviour of different IL/flavour acetyl ester (geranyl acetate, citronellyl acetate, neryl acetate and isoamyl acetate) mixtures was studied at several concentrations, resulting for all cases in fully homogeneous liquid media at 50 °C, and solid systems at room temperature. By using an iterative centrifugation protocol on the solid IL/flavour ester mixtures at controlled temperatures, the solid IL phase and the liquid flavour ester phase can be easily separated. The excellent suitability of an immobilized Candida antarctica lipase B (Novozym 435) catalyst in the esterification reaction between an aliphatic carboxylic acid (acetic, propionic, butyric or valeric) and a flavour alcohol (isoamyl alcohol, nerol, citronellol or geraniol) in N,N′,N′′,N′′′-hexadecyltrimethyl-ammonium bis(trifluoromethylsulfonyl)imide ([C16tma][NTf2])IL has been demonstrated, the product yield being improved up to 100% under appropriate reaction conditions (enzyme amount, dehydrating molecular sieves, etc.) at 50 °C. The enzymatic synthesis of sixteen different flavour esters was carried out in [C16tma][NTf2] by means of this approach, providing products of up to 0.757 g mL−1 concentration after IL separation. The residual activity of the enzyme/IL system during seven consecutive operation cycles was shown to be practically unchanged after reuse.

Graphical abstract: A clean enzymatic process for producing flavour esters by direct esterification in switchable ionic liquid/solid phases

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Supplementary files

Article information


Submitted
12 Jul 2012
Accepted
20 Aug 2012
First published
20 Aug 2012

Green Chem., 2012,14, 3026-3033
Article type
Paper

A clean enzymatic process for producing flavour esters by direct esterification in switchable ionic liquid/solid phases

P. Lozano, J. M. Bernal and A. Navarro, Green Chem., 2012, 14, 3026 DOI: 10.1039/C2GC36081K

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