Separation of (2E,4E)-deca-2,4-dienal from a Biocatalytic Reaction Mixture Using Hydrophobic Adsorbents

Abstract

Biocatalytic oxidation of a fatty acid preparation by enzymes released from a plant extract provided (2E,4E)-deca-2,4-dienal (2,4-DDAL), a valuable natural aroma. The post-reaction mixture contained several other compounds, from which 2,4-DDAL must be recovered. These included the main by-product trans-2-hexenal (2-HAL) and the unreacted substrate composed mainly of linoleic, palmitic, and oleic acids. The adsorption capacity and selectivity of 17 hydrophobic adsorbents were examined in batch equilibrium experiments. The highest binding capacity for 2,4-DDAL was around 30 mg/g. Due to a large excess of fatty acids in the mixture, the total adsorbed amounts of other components analyzed reached the values up to 150 mg/g. In addition, 2-HAL was always adsorbed more strongly than 2,4-DDAL, whereas fatty acids were mostly not adsorbed as effectively. The best-performing adsorbent, AmberLite FPX66, had a selectivity ratio of 6 for 2,4-DDAL with respect to the key impurity and linoleic acid. Ethanol, isopropanol, and acetone were examined as potential desorbents using batch adsorption experiments on AmberLite FPX66 from 2,4-DDAL solutions in organic solvents. Ethanol was found to be the best choice. Based on the batch equilibrium data, a column elution experiment was performed to purify 2,4-DDAL from the biocatalytic reaction mixture using elution with 96% ethanol.

Keywords

• (2E,4E)-deca-2,4-dienal
• purification
• lipoxygenase
• hydroperoxide lyase
• fatty acids
• adsorption