Application and comparison of high performance liquid chromatography and high speed counter-current chromatography in enantioseparation of (±)-2-phenylpropionic acid

• Published in: Journal of Chromatography A 2013-03, Vol.1281, p.79-86
• Main Authors: Tong, Shengqiang, Zheng, Ye, Yan, Jizhong
• Format: Article
• Language: English
• Subjects: 2-Phenylpropionic acid; acetic acid; Analytical chemistry; Chemistry; Chromatographic methods and physical methods associated with chromatography; countercurrent chromatography; enantiomers; Exact sciences and technology; High performance liquid chromatography; High speed counter-current chromatography; Hydroxypropyl-β-cyclodextrin; methanol; Other chromatographic methods; Preparative enantioseparation; solvents; temperature; triethylamine
• ISSN: 0021-9673
• DOI: 10.1016/j.chroma.2013.01.056

► HPLC and HSCCC were successfully applied in enantioseparation of 2-phenylpropionic acid. ► The mechanism of cyclodextrin inclusion complex was investigated by analytical HPLC. ► The two-phase solvent system was selected for enantioseparation by HSCCC. ► HSCCC separation conditions were optimized by liquid–liquid extraction experiments. ► The preparative HPLC and HSCCC were compared in chiral separation. High performance liquid chromatography (HPLC) and high speed counter-current chromatography (HSCCC) were applied and compared in enantioseparation of 2-phenylpropionic acid (2-PPA) when hydroxypropyl-β-cyclodextrin (HP-β-CD) was used as chiral mobile phase additive. For HPLC, the enantioseparation was achieved on ODS C18 reverse phase column and the mobile phase was 25mmolL−1 HP-β-CD aqueous buffer solution (pH4.0, adjusted with triethylamine): methanol: glacial acetic acid (85:15:0.5 (v/v/v)). For HSCCC, the two-phase solvent system was composed of n-hexane-ethyl acetate-0.1molL−1 phosphate buffer solution pH2.67 (5:5:10 for isocratic elution and 8:2:10 for recycling elution (v/v/v)) added with 0.1molL−1 HP-β-CD. The key parameters, such as a substitution degree of HP-β-CD, the concentration of HP-β-CD, pH value of the aqueous phase and the temperature were optimized for both separation methods. Using the optimum conditions a complete HSCCC enantioseparation of 40mg of 2-propylpropionic acid in a recycling elution mode gave 15–18mg of (+)-2-PPA and (-)-2-PPA enantiomers with 95–98% purity and 85–93% recovery.