Abstract
A process to immobilize para-methylbenzoyl cellulose (PMBC) on silica gel has been developed and applied to prepare chiral stationary phases (CSPs) for enantioselective chromatography. The immobilization was achieved by simple irradiation of the polysaccharide derivative with ultraviolet light after coating on a silica gel support. The influence of parameters such as irradiation time and solvent on immobilization effectiveness were investigated. The performance of the prepared immobilized phases were evaluated by injection of a series of racemic compounds onto the packed columns and determination of their chiral recognition ability. By contrast to the classical coated phase, the immobilized CSP can be used under various chromatographic conditions without limitation of organic solvent types as the mobile phase. This extended applicability permits to improve selectivity and to resolve chiral compounds which are not or only poorly soluble in the mobile phases which are compatible with the non-immobilized PMBC stationary phase.
Highlights
Polysaccharide-based chiral stationary phases (CSPs), especially those derived from cellulose and amylose derivatives, have proved to be versatile and effective means for enantioseparations by high performance liquid chromatography (HPLC) and supercritical fluid chromatography (SFC) [1,2]
Immobilization of para-methylbenzoyl cellulose (PMBC) after coating on silica gel was achieved by irradiation of a suspension of PMBC after coating on silica gel was achieved by irradiation of a suspension of the coatedImmobilization material in anofinert solvent for a few hours, using an immerged mercury lamp surrounded the coated material in an inert solvent for a few hours, using an immerged mercury lamp surrounded by a Pyrex cooling jacket (Figure 1)
The immobilized phase combines the advantages of the high chiral recognition ability of the cellulose derivative and the option to apply a wide range of mobile phase types, especially those which are not tolerated by the corresponding non-immobilized phase because of its high solubility in most organic solvents
Summary
Polysaccharide-based chiral stationary phases (CSPs), especially those derived from cellulose and amylose derivatives, have proved to be versatile and effective means for enantioseparations by high performance liquid chromatography (HPLC) and supercritical fluid chromatography (SFC) [1,2] They cover a large scope of applications on either analytic or preparative scale. A second generation of polysaccharide-based CSPs has appeared, consisting of the immobilized versions of the previously coated phases This second generation of phase shows the unique advantage of being more stable and tolerating almost all kind of mobile phases by contrast to the ‘classical’ non-immobilized polysaccharide-based CSPs which readily dissolve in organic solvents, such as methylene chloride, chloroform, tetrahydrofuran, etc. This feature of the non-immobilized polysaccharide CSPs was a considerable limitation for analytes which exhibit low solubility, in particular for preparative applications
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