Attempt to Develop an Effective Method for the Separation of Gamma-Decalactone from Biotransformation Medium

Abstract

Gamma-decalactone (GDL) is a fragrance compound obtained in the process of β-oxidation of ricinoleic acid, which is derived from the hydrolysis of castor oil. The biotechnological method of the synthesis of this lactone has been improved for over two decades, but the vast majority of research results have been based only on determining the concentration of the lactone by chromatographic methods without separating it from the biotransformation medium. In this study, we attempted to separate GDL from the medium in which the lactone was synthesized by Yarrowia lipolytica from castor oil. The effectiveness of liquid–liquid extraction, hydrodistillation, and adsorption on the porous materials (zeolite, vermiculite and resin Amberlite XAD-4) was compared. The influence of the solvent on the efficiency of GDL extraction, the influence of the acidity of the medium on the amount of GDL in the distillate, and the level of lactone adsorption on the above-mentioned adsorbents were compared by calculating the initial adsorption rate. The adsorption isotherm was determined for the most effective adsorbent. Among the five solvents tested, the most effective was diethyl ether, used at the ratio of 1:1. The extraction was characterized by higher efficiency than hydrodistillation; the difference in GDL determinations by these two methods ranged from 12.8 to 22%. The purity of the distillates was much higher than that of the extracts at 88.0 ± 3.4% compared to 53.0 ± 1.8%. The acidification of the biotransformation medium increased the concentration of the lactone in both the reaction mixture and the distillate. GDL was most efficiently adsorbed on Amberlite XAD-4 resin, for which the lactone isotherm adsorption was linear. The amount of lactone adsorbed on Amberlite XAD-4 within 1 h was approx. 80% (2.45 g), of which 1.96 g was then desorbed with ethanol. In the context of industrial applications, adsorption of GDL on Amberlite XAD-4 seems to be the most appropriate method due to material costs, the ease of the process, and low environmental burden.