Functional amino acid ionic liquids as solvent and selector in chiral extraction

Amino acid ionic liquids (AAILs) have received great attention due to their potentials in catalysis and separations. In this work, functional AAILs were used as solvent and selector in chiral liquid-liquid extraction for the first time. The AAILs have shown distinct enantioselectivity in amino acid extraction. Using these functional AAILs as acceptor phase and ethylacetate as donor phase, more L-enantiomer of amino acid was extracted into the ionic liquid phase than that of D-enantiomer. The influencing factors, including AAILs structure, copper ion concentration, organic phase and amino acid concentration, were investigated. We found that the enantioselective enrichment of racemic amino acids was achieved through a chiral ligand-exchange mechanism. The enantioselectivity of single-step extraction was up to enantiomeric excess value of 50.6%. Moreover, the functional AAILs were found to be efficient extraction solvents for amino acids. The logarithm of distribution coefficient for L-Phe was in the range of 3.4-3.6 in the ionic liquid-ethylacetate two-phase system. This liquid-liquid extraction approach may extend the application of ionic liquids in chiral separations. (C) 2010 Elsevier B.V. All rights reserved.