DES-Based Biocatalysis as a Green Alternative for the l-menthyl Ester Production Based on l-menthol Acylation

• Published in: Molecules (Basel, Switzerland) Vol. 27; no. 16; p. 5273
• Main Authors: Ion, Sabina, Olănescu, Florentina, Teodorescu, Florina, Tincu, Robert, Gheorghe, Daniela, Pârvulescu, Vasile I, Tudorache, Mădălina
• Format: Journal Article
• Language: English
• Published: Basel MDPI AG 01.08.2022; MDPI
• Subjects: Acrylic resins; Acylation; Binary mixtures; biocatalysis; Biocatalysts; Calorimetry; Catalysis; Conversion; DES; Differential scanning calorimetry; Enzymes; fatty acid; Fatty acids; Homogeneity; immobilized lipase; l -menthol; l -menthyl ester (FME); Linoleic acid; Linolenic acid; Linolenic acids; Lipase; Menthol; Microemulsions; Monounsaturated fatty acids; Octanoic acid; Oleic acid; Recyclability; Refractivity; Saturated fatty acids; Solvents; Romania
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules27165273

The deep eutectic solvent (DES)-based biocatalysis of l-menthol acylation was designed for the production of fatty acid l-menthyl ester (FME) using fatty acid methyl ester (FAME). The biocatalytic reaction was assisted by a lipase enzyme in the DES reaction medium. ւՒ-menthol and fatty acids (e.g., CA—caprylic acid; OA—oleic acid; LiA—linoleic acid; and LnA—linolenic acid) were combined in the binary mixture of DES. In this way, the DES provided a nonpolar environment for requested homogeneity of a biocatalytic system with reduced impact on the environment. The screening of lipase enzyme demonstrated better performance of immobilized lipase compared with powdered lipase. The performance of the biocatalytic system was evaluated for different DES compositions (type and concentration of the acid component). l-menthol:CA = 73:27 molar ratio allowed it to reach a maximum conversion of 95% methyl lauric ester (MLE) using a NV (Candida antarctica lipase B immobilized on acrylic resin) lipase biocatalyst. The recyclability of biocatalysts under optimum conditions of the system was also evaluated (more than 80% recovered biocatalytic activity was achieved for the tested biocatalysts after five reaction cycles). DES mixtures were characterized based on differential scanning calorimetry (DSC) and refractive index analysis.