Citation: Wei Chen, Rong Duan, Qing-chun Fan, Zheng-wu Bai, Shao-hua Huang. Preparation and Enantioseparation Property of Chiral Stationary Phases Based on Cellulose Tris(3,5-dimethylbenzoate)─A New Way to Prepare Polysaccharide-coating Type Chiral Stationary Phases[J]. Chinese Journal of Polymer Science, ;2014, 32(4): 458-466. doi: 10.1007/s10118-014-1409-x shu

Preparation and Enantioseparation Property of Chiral Stationary Phases Based on Cellulose Tris(3,5-dimethylbenzoate)─A New Way to Prepare Polysaccharide-coating Type Chiral Stationary Phases

1.
Key Laboratory of Green Chemical Process of Ministry of Education, Hubei Key Laboratory of Novel Chemical Reactor and Green Chemical Technology, Wuhan Institute of Technology, Wuhan 430073, China
2.
Key Laboratory of Biofuels of the Chinese Academy of Sciences, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101, China

Received Date: 8 July 2013
Revised Date: 29 July 2013

Fund Project: This work was financially supported by the National Natural Science Foundation of China (No. 50973086) and Hubei Provincial Department of Education of China (Z 20081501).

A new method to prepare polysaccharide-coating type chiral stationary phases (CSPs) was developed in this work. As a typical example, naked silica gel was coated by cellulose, which was then derivatized with 3,5-dimethylbenzoyl chloride to afford cellulose tris(3,5-dimethylbenzoate)-silica gel (CTDBS) complex. The silanols on CTDBS were end-capped with 3-aminopropyltriethoxysilane to obtain CSP 1. The amino groups on CSP 1 were further end-capped with 3,5-dimethylbenzoyl chloride to give CSP 2. The silanols on CTDBS were end-capped with methyltrimethoxysilane to yield CSP 3. CSPs 1-3 were characterized by FTIR, solid-state 13C-NMR and elemental analysis. The enantioseparation abilities of CSPs 1-3 were evaluated with structurally various chiral analytes. The enantioseparation results demonstrated that the end-capping moieties on CSPs 1 and 2 significantly affected enantioseparation. In addition, the effect of the structures of chiral analytes and end-capping moieties on the retention factors and the resolutions was discussed.
- Cellulose tris(3,5-dimethylbenzoate),
- Chiral recognition,
- Chiral stationary phase,
- High-performance liquid chromatography
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