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Enantioseparation of mandelic acid and α-cyclohexylmandelic acid using an alcohol/salt-based aqueous two-phase system

Fen-Fang Li, Zhi-Jian Tan, and Zhi-Feng Guo

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

 

E-mail: lfflqq@mail.csu.edu.cn

Abstract: An alcohol/salt-based aqueous two-phase system (ATPS) was employed for enantioseparation of (R,S)-mandelic acid (MA) and (R,S)-α-cyclohexylmandelic acid (α-CHMA). Sulfonated β-cyclodextrin (Sf-β-CD) with different degrees of substitution (DS) was considered as the chiral selector. The ethanol/(NH4)2SO4 system showed the optimal chiral recognition ability for MA. To optimize the experimental conditions, Sf-β-CD concentration, ethanol and salt concentration, temperature, and pH were studied. The recognition ability of enantiomers was mainly dependent on the type of the chiral selector but the ethanol and (NH4)2SO4 concentrations also had significant influence on the enantiomeric recognition. The maximum values of α and ee up of 1.69 and 16.3 % were obtained, respectively, for MA under the optimal conditions. A potential application of this alcohol/salt ATPS is the scale-up of chiral separation of MA.

Keywords: alcohol/salt aqueous two-phase system – chiral separation – enantiomers – sulfonated β-cyclodextrin

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-014-0594-y

 

Chemical Papers 68 (11) 1539–1545 (2014)

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