Chinese Journal of Chromatography

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Study on Enantioselectivity of Celluloses Derived by Phenylcarbamate at 2,3- or 2,3,6-Positions

CHANG Yinxia1,2, ZHOU Lingling1, YUAN Liming1   

  1. 1.Faculty of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650092, China; 2.College of Chemistry and Material Science, Shanxi Normal University, Linfen 041000, China
  • Received:2006-05-30 Revised:2006-09-30 Online:2007-03-30 Published:1985-12-25
  • Contact: CHANG Yinxia

Abstract: Cellulose-2,3,6-trisphenylcarbamate, cellulose-2,3-bisphenylcarbamate, cellulose-2,3,6-tris(3,5-dimethylphenylcarbamate) and cellulose-2,3-bis(3,5-dimethylphenylcarbamate) were synthesized and respectively coated on silica gel as chiral stationary phases for high performance liquid chromatography (HPLC). Nine pairs of enantiomers, which are (±)-phenyl-1,2-ethanediol, (±)-2-phenyl-1-propanol,  DL-alpha-methylbenzylamine, DL-mandelic acid, (±)-1-(1-naphthyl) ethanol,  (±)-propranolol, (±)-3-benzyloxy-1,2-propanediol,  DL-tyrosine and (±)-di-O,O-p-toluyl-D-tartaric acid, were separated using hexane-isopropanol as mobile phase on the columns packed with the chiral stationary phases. For comparative reasons, the ratio of hexane/isopropanol in the eluent was kept at 9∶1 (v/v) in all experiments, and the chromatographic separations were performed at 30 ℃ with a flow rate of 0.5 mL/min. All the test solutes were detected at 254 nm. The results showed that enantioseparation of cellulose-2,3-bisphenylcarbamate was better than cellulose-2,3,6-trisphenylcarbamate for the test enantiomers, and cellulose-2,3-bis(3,5-dimethylphenylcarbamate) had low retention factors and short analysis times for most enantiomers and good separation factors for some racemates compared to cellulose-2,3,6-tris(3,5-dimethylphenylcarbamate).

Key words: chiral stationary phases, high performance liquid chromatography (HPLC) , cellulose derivatives