ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Biphasic recognition chiral extraction — novel way of separating pantoprazole enantiomers

Jia-Jia Liu, Chang Liu, Ke-Wen Tang, and Pan-Liang Zhang

College of Chemistry and Chemical Engineering, Central South University, Changsha, 410083, Hunan, China

E-mail: tangkewen@sina.com

Abstract: This paper presents a biphasic recognition chiral extraction system developed as a new chiral separation technology for the separation of pantoprazole enantiomers, combining a hydrophilic β-CD derivative in the aqueous phase and a hydrophobic tartaric acid in the organic phase which preferentially recognise the (R)-enantiomer and (S)-enantiomer, respectively. In this study, a number of factors which influence the efficiency of the extraction were investigated including types of organic solvents, β-CD and tartaric acid esters and their concentrations, pH and temperature. As a result, enantioselectivity for pantoprazole enantiomers can be improved up to 1.42 under optimised conditions; in addition, it is clear that the combined action of β-CD and tartaric acid esters leads to formation of the biphasic chiral extraction system with a stronger separation capacity than a monophasic chiral extraction system.

Keywords: pantoprazole – biphasic chiral extraction system – β-cyclodextrin – tartaric acid

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-013-0501-y

Chemical Papers 68 (5) 599–607 (2014)