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

Pedro Lozano; Juana M. Bernal; Alicia Navarro

doi:10.1039/C2GC36081K

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

Pedro Lozano,*^a Juana M. Bernal^a and Alicia Navarro^a

* Corresponding authors

^a Departamento de Bioquímica y Biología Molecular B e Inmunología. Facultad de Química, Regional Campus of International Excellence “Campus Mare Nostrum”, Universidad de Murcia, P.O. Box 4021, E-30100 Murcia, Spain
E-mail: plozanor@um.es
Fax: +34 868 884148
Tel: +34 868 887392

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.

This article is part of the themed collection: Green Solvents

Supplementary files

Publication details

The article was received on 12 Jul 2012, accepted on 20 Aug 2012 and first published on 20 Aug 2012

Article type: Paper

DOI: 10.1039/C2GC36081K

Citation: Green Chem., 2012,14, 3026-3033

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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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Green Chemistry

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

Abstract

Supplementary files

Publication details

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

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