Enantiomer separation using membrane systems

E. van der Ent

Research output: Thesisinternal PhD, WU

Abstract

<FONT FACE="Swis721 Lt BT,Arial" SIZE=2><p>Many compounds applied in the agrochemical, food and pharmaceutical industry contain one or more chiral centers. The enantiomers of these compounds often have different effects on their targets. To prevent unwanted side effects or environmental burden, these compounds should rather be applied in their optically pure form. In this thesis two processes for large-scale enantiomer separations have been studied based on membrane technology: direct separation using an "intrinsic" enantioselective membrane and indirect separation in which a non-selective membrane assists an enantioselective process.</p><p>For intrinsic enantioselective membranes the design criteria have been evaluated, using literature data, model calculations and experimental data. This has resulted in a categorization of these membranes into two different classes: diffusion selective membranes and sorption selective membranes.</p><p>Besides intrinsic enantioselective membranes, a new stacked membrane system is developed using chiral selectors that are retained by size-selective membranes. Applying an electrical potential, selective transport of the free enantiomer will occur, thus providing separation. This separation concept is evaluated for different process conditions, showing a distinct influence of the pH. Isothermal titration calorimetry is used to compare this pH dependency of the operational selectivity and the intrinsic selector selectivity, showing no influence of the process.</p><p>In the last part of this thesis a model is developed for the continuous multi-stage electrodialysis system. This model is evaluated using a 20-compartment counter-current electrodialysis stack. Model calculations have shown that using an electrodialysis stack of 250 membrane compartments allows for complete separation (99%+) for our low selective (</font><FONT FACE="Arial" SIZE=2>α</font><FONT FACE="Swis721 Lt BT,Arial" SIZE=2>=1.12) model system. In conclusion, the proposed multi-stage electrodialysis separation principle, which has the advantage of making use of chiral selectors developed for existing analytical separation methods, is suitable for low selectivity (1.1-2) separations. Therefore, it provides a viable addition for the current range of large-scale enantiomer separation processes
Original languageEnglish
QualificationDoctor of Philosophy
Awarding Institution
  • Wageningen University
Supervisors/Advisors
  • van 't Riet, K., Promotor
  • Keurentjes, J.T.F., Promotor, External person
  • Cohen Stuart, Martien, Promotor
Award date8 Mar 2002
Place of PublicationS.l.
Print ISBNs9789058086006
Publication statusPublished - 2002

Keywords

  • enantiomers
  • separators
  • membrane permeability
  • electrodialysis
  • membranes

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