Chiral benzyl alcohols are a series of important organic molecules with broad application in the fields of biocides, agricultural, material, and pharmaceutical industries. Herein, we report the first direct and acetonitrile-free high-performance liquid chromatographic enantioseparation of chiral benzyl alcohols under reversed-phase mode. Enantioseparation of all of the seven selected chiral benzyl alcohols on the six polysaccharide-based chiral columns are presented, and base-line separation (Rs > 2.0) can be achieved in six out of seven analytes under optimized conditions. Green chemistry concept is introduced by using economical and environmentally friendly solvents such as methanol, ethanol and water instead of acetonitrile or THF. The optimized methods are validated and applicable for chemical and pharmaceutical industries. The effect of temperature and eluting strength on the enantioseparation is investigated and discussed. Thermodynamic studies indicate transitions of conformation and/or higher order structure of the chiral stationary phases (CSPs) under specific changes in mobile phases. Entropy-enthalpy compensation under reversed-phase mode results in relatively constant in enantioselectivity while changing the solvent strength. Linear entropy-enthalpy compensation curve is obtained in two chiral columns across all of the chiral benzyl alcohols.Fig.1 Example of enantioseparation of PCF3OH on polysaccharide-based chiral column (k1 = 1.19, a = 1.35, Rs = 4.81)

Fast, direct, and acetonitrile-free enantioseparation of chiral benzyl alcohols under reversed-phase mode

244th National Meeting (2012)

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