Synthesis and characterization of cellulose 3,5-dimethylphenylcarbamate silica hybrid spheres for enantioseparation of chiral β-blockers

A cellulose derivative-based chiral stationary phase (CSP) is considered one of the most widely applied CSPs due to its powerful enantioseparation ability. The high loading capacity and mechanical strength of CSPs are crucial for their application in preparative chromatography, such as a simulated moving bed. Compared to traditional cellulose-based CSPs that have been adsorbed onto chromatographic supports, organic-inorganic hybrid CSPs exhibit a potentially higher loading capacity and mechanical strength by increasing the density of chiral recognition groups. A hybrid cellulose 3,5-dimethylphenylcarbamate chiral stationary phase (organic/inorganic: 70/30, w/w) was prepared via a sol-gel method and characterized with several analytical techniques, including Fourier transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), scanning electron microscopy (SEM), and 29Si cross polarization/magic angle spinning nuclear magnetic resonance (29Si CP/MAS NMR). In addition, the as-synthesized hybrid chiral silica spheres were treated with an end-capping process to mask the residual silica hydroxyl groups. Compared to a commercial Chiralpak IB column, better separation of β-blocker drugs, including pindolol (selectivity of 5.55), metoprolol (2.30), propranolol (1.96), bisoprolol (1.74) and atenolol (1.46), on the end-capped CSP was achieved using liquid chromatography, which suggests that the packing material synthesized in this work has sufficient chiral discriminating ability for the effective separation of β-blocker drugs.