Qing Yi,Wei-Peng Chen,Xiang-yang Zhang,Yan-Yang Wu,Bin Wu,Kui Chen,Li-Jun Ji
The isobaric vapor–liquid equilibrium (VLE) data of 2-phenylethanol (2-PE) + 2-ethylphenol (2-EP), 1-phenyl-2-propanol (1,2-PP) + 2-ethylphenol (2-EP), 2-phenylethanol (2-PE) + 1-phenyl-2-propanol (1,2-PP) and 2-phenyl-1-propanol (2,1-PP) + 2-ethylphenol (2-EP) were measured by a modified Rose type still under 101.3 kPa. Both the Fredenslund test and Redlich–Kister area test were employed to verify the consistency of the experimental data. Besides, the experimental isobaric VLE data were correlated by Wilson, nonrandom two-liquid, and universal quasi-chemical models, and the corresponding parameters were obtained accordingly. All three models showed good agreement with the experimental data, and among which the Wilson model performed slightly better than the others.
Porous organic cages (POCs) are a new subclass of porous materials, which are constructed from discrete cage molecules with permanent cavities via weak intermolecular forces. In this study, a novel chiral stationary phase (CSP) has been prepared by chemically binding a [4 + 6]-type chiral POC (C120H96N12O4) with thiol-functionalized silica gel using a thiol-ene click reaction and applied to HPLC separations. The column packed with this CSP presented good separation capability for chiral compounds and positional isomers. Thirteen racemates have been enantioseparated on this column, including alcohols, diols, ketones, amines, epoxides, and organic acids. Upon comparison with a previously reported chiral POC NC1-R-based column, commercial Chiralpak AD-H, and Chiralcel OD-H columns, this column is complementary to these three columns in terms of its enantiomeric separation; and can also separate some racemic compounds that cannot be separated by the three columns. In addition, eight positional isomers (iodoaniline, bromoaniline, chloroaniline, dibromobenzene, dichlorobenzene, toluidine, nitrobromobenzene, and nitroaniline) have also been separated. The influences of the injection weight and column temperature on separation have been explored. After the column has undergone multiple injections, the relative standard deviations (RSDs) for the retention time and selectivity were below 1.0 and 1.5%, respectively, indicating the good reproducibility and stability of the column for separation. This work demonstrates that POCs are promising materials for HPLC separation.Keywords:chiral porous organic cage;high performance liquid chromatography;chiral stationary phase;enantioseparation;thiol-ene click reaction
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