Synthesis and characterization of (S)-amino alcohol modified M41S as effective material for the enantioseparation of racemic compounds

A new chiral stationary phase (CSP) was synthesized based on (S)-1-anilino-3-propyl-2-propanol covalently bonded to the mesoporous semi-crystalline material M41S. Direct semipreparative enantioseparation of mandelic acid could be achieved using medium pressure chromatography. Partly separated could also be the enantiomers of 2,2′-dihydroxy-1,1′-binaphthalene, cyanochromene oxide, diethyl tartrate and 2-phenyl propionic acid. The characterization of CSP was accomplished by microanalysis, cross polarized magic angle spinning (CP-MAS) 13C NMR, powder X-ray diffraction (XRD), FTIR, thermo-gravimetric analysis (TGA), N2 adsorption-desorption isotherm, scanning electron microscopy (SEM) and solid reflectance UV-vis spectroscopy. Furthermore the stability of CSP was satisfactory as it could withstand three washing and reuse experiments of enantioseparation of mandelic acid without loss in its performance.