Chiral ionic liquid-multi walled carbon nanotubes composite membrane applied to the separation of amino acid enantiomers

Various membranes are playing more and more important roles in the field of analytical and preparative applications of general interest, and some of them have been used in enantioresolution for amino acids (AAs) or similar bioactive molecules. In this study, a new composite membrane was prepared with chiral ionic liquid (CIL) of [BuPyro] [L-Pro] as chiral selector together with multi walled carbon nanotubes (MWCNTs) and additives through a simple way for the first time. Based on such a separation medium, the enantioresolution of amino acid enantiomers were achieved by forming ternary ligand complexes with Cu(II). It was comprehensively characterized by various ways, and key preparation conditions were discovered. After comparing the performance of three operation modes on the resolution of racemic phenylalanine, the effects of main influential factors were investigated and enantiomeric excess value (e.e.%) was 90.2% for the (D,L)-Phe aqueous solution (membrane thickness: 0.15 +/- 0.02 mm, total weight: 80 mg, CIL: 41.7%). Through effective desorption, up to 98.1% of the target was recovered. Finally, the mechanism of resolution was revealed by molecular simulation, kinetics and isotherm models, and the difference of interactive energy between ternary complexes of L-Phe-Cu(II)-CIL and D-Phe-Cu(II)-CIL was calculated as 1.56 kcal/mol. The membrane also remained stable after the post-treatment and showed good potential in chiral separation.

Automated summary

In this study, a new composite membrane was prepared using chiral ionic liquid and multi-walled carbon nanotubes as additives, enabling the separation of amino acids enantiomers. By optimizing the conditions and operation modes, a high enantiomeric excess value was achieved, and the mechanism of separation was revealed through molecular simulation.