高稳定性硅基杂化纤维素衍生物手性固定相的制备及其色谱拆分性能

Preparation and characterization of highly stable hybrid organosilica cellulose derivative-based chiral stationary phase

合成了含少量3-(三乙氧基硅)丙基氨基甲酸酯的纤维素3,5-二甲基苯基氨基甲酸酯衍生物(CDMPC),并采用1,2-二(三乙氧基硅基)乙烷(BTSE)为偶联剂,通过溶胶-凝胶法成功制备得到新型硅基杂化手性固定相。该固定相的CDMPC含量达60%,在含有10%氯仿的流动相中保持良好的手性识别性能和机械强度。使用其拆分了多种手性化合物,拆分效果优于商品柱Chiralpak IB,其中对2,2,2-三氟-1-(9-蒽基)乙醇和反式二苯乙烯氧化物对映体的分离选择性分别达到2.99和2.48,表明该类硅基杂化类手性固定相在制备色谱领域中有潜在应用前景。

Chiral chromatography plays an important role in obtaining optically pure enantiomers. The key to preparative chiral chromatography is the availability of chiral stationary phases （CSPs） with broad chiral recognition, high sample loading as well as solvent tolerance. In order to overcome the shortcoming of traditional coating-type or bonding-type cellulose-based CSPs, a novel hybrid CSP based on cellulose derivative bearing a small amount of 3-（triethoxysilyl）propyl groups was proposed, which was used to crosslink with bis（triethoxysilyl）ethane （BTSE）via a sol-gel reaction. The prepared stationary phase was then evaluated by HPLC. The experimental results indicated that the CSP showed excellent chiral recognition ability and could run steadily at back column pressure more than 2000 psi （1 psi=6894.76 Pa） with flow-rate up to 3 ml·min-1 in the mobile phase containing 10% chloroform. It was worth mentioning that the selectivity of 2,2,2-trifluoro-1-（9-anthryl）ethanol and trans-stilbene oxide up to 2.99 and 2.48 was achieved, respectively, confirming its excellent chiral recognition performance. In addition, the reported CSP showed a promising packing for application in preparative chromatography such as simulated moving bed chromatography.