[en] Nafion117® membranes modified by three cationic cyclodextrin (CD) derivatives have been prepared by strong ionic bonding. All CD derivatives contained bis(methylimidazolium) (MIM2) cationic anchor covalently bound to the CD unit, either using no spacer or using diethylene glycol (DEG) or tetraethylene glycol (TEEG) spacers. The modified membranes were tested in chiral separation of a model racemic mixture (D/L-tryptophan) from water. Different experimental set-ups for characterising membranes in enantioselective separation – pertraction, two kinds of sorption, and pressure-driven membrane separation – have been described and rigorously compared. The membranes CD-MIM2, CD-DEG-MIM2 have reached the highest enantiomeric excess, 14 and 44% respectively, in 280 days. The lowest performance of the CD-TEEG-MIM2 membrane, with the long spacer, has been visibly ameliorated by applying pertraction; enantiomeric excess rose from 2 to 27% in 80 days. Even though sorption played the main role in pertraction, this process substantially enhanced the separation of racemic mixtures. The pressure-driven approach has allowed the operation to be continuous and faster, which has the potential for continuous large-scale production of enantiopure compounds and could pave the way for many more commercial applications, satisfying the considerable demand for large-scale chiral separation techniques.
Disciplines :
Chemical engineering
Author, co-author :
Gaálová, Jana; Institute of Chemical Process Fundamentals of the CAS, Prague, Czech Republic
Michel, Marine; Institute of Chemical Process Fundamentals of the CAS, Prague, Czech Republic ; Barrer Centre, Department of Chemical Engineering, Imperial College London, London, United Kingdom
Bourassi, Mahdi; Institute of Chemical Process Fundamentals of the CAS, Prague, Czech Republic ; Institute for Environmental Studies, Faculty of Science, Charles University, Prague 2, Czech Republic
LADEWIG, Bradley Paul ; University of Luxembourg > Faculty of Science, Technology and Medicine (FSTM) > Department of Engineering (DoE) ; Barrer Centre, Department of Chemical Engineering, Imperial College London, London, United Kingdom ; Karlsruhe Institute of Technology, Institute for Micro Process Engineering, Eggenstein-Leopoldshafen, Germany
Kasal, Petr; Department of Organic Chemistry, Faculty of Science, Charles University, Prague 2, Czech Republic
Jindřich, Jindřich; Department of Organic Chemistry, Faculty of Science, Charles University, Prague 2, Czech Republic
Izák, Pavel; Institute of Chemical Process Fundamentals of the CAS, Prague, Czech Republic ; MemBrain s.r.o., Stráž pod Ralskem, Czech Republic
External co-authors :
yes
Language :
English
Title :
Nafion membranes modified by cationic cyclodextrin derivatives for enantioselective separation
Czech Science Foundation Ministry of Industry and Trade of the Czech Republic
Funding text :
This work was supported by grants of Czech Science Foundation No. 20-09980S and partially No. 19-08153Y, Czech Ministry of Industry and Trade No. FV1008. M. Michel acknowledges scholarship support from Imperial College London and CSIRO Australia.
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