[Preparation of covalently bonded cellulose tris (4-methylbenzoate) derivative chiral stationary phases through a polymerization reaction].
Cellulose tris (4-methylbenzoate) derivatives (CTMB) having methacryloyl groups were synthesized with regio-selective or nonselective procedures, and were immobilized on gamma-methacrylatepropylated silica (gamma-MAPS) through a polymerization reaction. The obtained chiral stationary phases ( CSPs) were evaluated by high performance liquid chromatographic (HPLC) resolution of 9 racemates (3-butyl-phthalide, ketoprofen, trans-stilbene oxide, benzoin, benzoin analogue, Tröger' s base, warfarin, 4,4'-dimethoxy-5,6,5',6'-dimethylenedioxy-biphenyl-2,2'-dicarboxylate and 4,4'-dimethoxy-5,6,5',6'-dimethylenedioxy-biphenyl-2-methylcarboxylate-2'-ethylcarboxylate). For regio-nonselective procedure, increasing the content of vinyl group on CTMB would lead to higher immobilization efficiency and enantio-selectivity. CSPs prepared by regio-selective procedure possessed slightly higher enantioselectivities than those prepared by regio-nonselective procedure, while the latter showed some advantages for rapid and facile preparation. CSPs prepared with silica gel II (Fuji, 5 microm, 30 nm, ca. 150 m2/g) showed higher enantioselectivities than those prepared with silica gel I (Kromasil, 5 microm, 20 nm, ca. 240 m2/g). The prepared CSPs could keep stable under different eluents, even with 40% of tetrahydrofuran (THF) in mobile phases.
Qin
Feng
F
National Chromatographic R. & A. Center, Dalian Institute of Chemical Physics, The Chinese Academy of Sciences, Dalian 116011, China.
Chen
Xiaoming
X
Liu
Yueqi
Y
Kong
Liang
L
Zou
Hanfa
H
D001565:Benzoates / Q000737:chemistry*; D001573:Benzoin / Q000737:chemistry; D002482:Cellulose / Q000031:analogs & derivatives; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D007660:Ketoprofen / Q000737:chemistry; D011108:Polymers / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D001565:Benzoates; D011108:Polymers; D002482:Cellulose; D007660:Ketoprofen; C009504:4-toluic acid; D001573:Benzoin