Performance of Different Immobilized Lipases in the Syntheses of Short- and Long-Chain Carboxylic Acid Esters by Esterification Reactions in Organic Media

Abstract

Short-chain alkyl esters and sugar esters are widely used in the food, pharmaceutical and cosmetic industries due to their flavor and emulsifying characteristics, respectively. Both compounds can be synthesized via biocatalysis using lipases. This work aims to compare the performance of commercial lipases covalently attached to dry acrylic beads functionalized with oxirane groups (lipases from Candida antarctica type B—IMMCALB-T2-350, Pseudomonas fluorescens—IMMAPF-T2-150, and Thermomyces lanuginosus—IMMTLL-T2-150) and a home-made biocatalyst (lipase from Pseudomonas fluorescens adsorbed onto silica coated with octyl groups, named PFL-octyl-silica) in the syntheses of short- and long-chain carboxylic acid esters. Esters with flavor properties were synthetized by esterification of acetic and butyl acids with several alcohols (e.g., ethanol, 1-butanol, 1-hexanol, and isoamyl alcohol), and sugar esters were synthetized by esterification of oleic and lauric acids with fructose and lactose. All biocatalysts showed similar performance in the syntheses of short-chain alkyl esters, with conversions ranging from 88.9 to 98.4%. However, in the syntheses of sugar esters the performance of PFL-octyl-silica was almost always lower than the commercial IMMCALB-T2-350, whose conversion was up to 96% in the synthesis of fructose oleate. Both biocatalysts showed high operational stability in organic media, thus having great potential for biotransformations.

Lipozyme 435-Mediated Synthesis of Xylose Oleate in Methyl Ethyl Ketone

“…The esterification activity of Lipozyme 435 was determined through the esterification of butyric acid (0.1 mol/L) with butanol (0.1 mol/L) in heptane (10 mL) at 37 °C. The reaction was conducted in agitated closed flasks (250–300 rpm) and monitored by the consumption of butyric acid by titration with 0.02 mol/L KOH solution, using phenolphthalein as an indicator [ 13 , 29 , 91 ].…”

“…The synthesis of xylose fatty esters may occur through either an esterification or a transesterification reaction in the presence of chemical catalysts or enzymes. Xylose acts as the acceptor for the acyl group, while fatty acids/fatty acid esters perform as donors (or activated acyl donors) of this acyl group [ 13 , 14 ]. In the chemical route, the reaction is carried out at high temperatures with an alkaline or metallic catalyst.…”

Evaluation of Designed Immobilized Catalytic Systems: Activity Enhancement of Lipase B from Candida antarctica

“…Soriano-Maldonado et al [56] performed bio-enzymatic production of enantiopure L-α-amino acids using IB-A161 with good results: the enantiomeric excess of the amino acid was >99.5%. De Lima et al [57] performed the synthesis of short-chain carboxylic acid esters by esterification catalyzed, among others, by lipase Thermomyces lanuginosus immobilized on IB-150, achieving significant results of conversion (>80%) after 24 h of reaction. Becker et al [58] immobilized the laccase on Immobead IB-EC-1 to apply in the investigation of the degradation of endocrine-disrupting compounds.…”

PTFE-Carbon Nanotubes and Lipase B from Candida antarctica—Long-Lasting Marriage for Ultra-Fast and Fully Selective Synthesis of Levulinate Esters

“…The fundamental way to obtain LAEs can be the direct esterification of LA with alcohols in the presence of acidic catalysts [ 10 ]. Esterification is a thermodynamically controlled process; thus, yields are related to thermodynamics of the reaction [ 11 , 12 , 13 ]. The formation of water as a by-product in a thermodynamically controlled process is the reason for non-quantitative atom economy [ 14 ].…”