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[Preparation of Covalently Bonded Cellulose Tris (4-methylbenzoate) Derivative Chiral Stationary Phases Through a Polymerization Reaction]

[Preparation of Covalently Bonded Cellulose Tris (4-methylbenzoate) Derivative Chiral Stationary Phases Through a Polymerization Reaction]

Feng Qin, Xiaoming Chen, Yueqi Liu, Liang Kong, Hanfa Zou

Se Pu. 2004 Nov;22(6):569-74.

PMID: 15807104

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP50649597	4-Pentylphenyl 4-methylbenzoate		50649-59-7	Price

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