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

Abstract

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), N 2 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.