Preparation and chiral recognition in HPLC of cellulose 3,5-dichlorophenylcarbamates immobilized onto silica gel

• Published in: Journal of separation science 2011-03, Vol.34 (5), p.536-541
• Main Authors: Qu, Hai-tao, Li, Jun-qing, Wu, Guang-shun, Shen, Jun, Shen, Xian-de, Okamoto, Yoshio
• Format: Article
• Language: English
• Subjects: Adsorption; Analytical chemistry; Cellulose; Cellulose - analogs & derivatives; Cellulose - chemistry; Character recognition; Chemistry; Chiral packing materials; Chiral stationary phase; Chromatographic methods and physical methods associated with chromatography; Chromatography; Chromatography, High Pressure Liquid - instrumentation; Chromatography, High Pressure Liquid - methods; Derivatives; Eluents; Exact sciences and technology; HPLC; Immobilization; Other chromatographic methods; Phenylcarbamates - chemistry; Recognition; Residues; Silica gel; Silica Gel - chemistry; Tetrahydrofuran
• ISSN: 1615-9306; 1615-9314; 1615-9314
• DOI: 10.1002/jssc.201000800

The 3,5-dichlorophenylcarbamates (2) of cellulose bearing a small amount of 3-(triethoxysilyl)propyl residues were synthesized by a one-pot process and immobilized onto a silica gel through intermolecular polycondensation of the triethoxysilyl groups. The obtained cellulose derivatives were characterized by ¹H NMR and elemental analysis (EA), and their recognition abilities were evaluated by high-performance liquid chromatography (HPLC). The cellulose derivatives containing about 1-5% of the 3-(triethoxysilyl)propyl residue were efficiently immobilized with a high chiral recognition ability. The immobilized chiral packing materials (CPMs) could be used with the eluents containing chloroform and tetrahydrofuran (THF), which cannot be used with the conventional coated-type chiral packing materials. By using these eluents, the chiral recognition for many racemates was improved.