Zhang Panliang, Xie Xiaojuan, Tang Kewen, Xu Weifeng
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, P.R. China.
J Sep Sci. 2016 Jun;39(12):2300-6. doi: 10.1002/jssc.201501240. Epub 2016 Jun 2.
A recycling high-speed countercurrent chromatography protocol was proposed for the enantioseparation of brompheniramine by employing β-cyclodextrin derivatives as a chiral selector. The two-phase solvent system of n-hexane/isobutyl acetate/0.10 mol/L phosphate buffer solution with a volume ratio of 2:4:6 was selected by a series of extraction experiments. Factors that affected the distribution of the enantiomers over the two-phase system (e.g., the type and concentration of β-cyclodextrin derivatives = pH value of the aqueous solution, and the separation temperature) were also investigated. In addition, the theory of thermodynamics is applied to verify the feasibility of the enantioseparation process and the corresponding results demonstrate that this separation process is feasible. The optimized conditions include carboxymethyl-β-cyclodextrin concentration of 0.010 mol/L, pH of 7.5, and temperature of 5°C. Under the optimal conditions, the purities of both monomer molecules were over 99%, and the recovery yields were 88% for (+)-brompheniramine and 85% for (-)-brompheniramine, respectively.
提出了一种循环高速逆流色谱方法，以β-环糊精衍生物作为手性选择剂对溴苯那敏进行对映体分离。通过一系列萃取实验，选择了体积比为2:4:6的正己烷/乙酸异丁酯/0.10 mol/L磷酸盐缓冲溶液两相溶剂体系。还研究了影响对映体在两相体系中分配的因素（例如，β-环糊精衍生物的类型和浓度、水溶液的pH值以及分离温度）。此外，应用热力学理论验证了对映体分离过程的可行性，相应结果表明该分离过程是可行的。优化条件包括羧甲基-β-环糊精浓度为0.010 mol/L、pH值为7.5以及温度为5°C。在最佳条件下，两种单体分子的纯度均超过99%，(+)-溴苯那敏的回收率为88%，(-)-溴苯那敏的回收率为85%。
