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Molecules 2016, 21(11), 1528; doi:10.3390/molecules21111528

Eluent Tolerance and Enantioseparation Recovery of Chiral Packing Materials Based on Chitosan Bis(Phenylcarbamate)-(n-Octyl Urea)s for High Performance Liquid Chromatography

1
School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430073, China
2
Key Laboratory of Biobased Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101, China
Dedicated to Professor Stig Allenmark on the Occasion of His 80th Birthday.
*
Author to whom correspondence should be addressed.
Received: 15 October 2016 / Accepted: 4 November 2016 / Published: 13 November 2016
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Abstract

The goal of the present work was to study the influence of the swelling of chitosan derivatives on the enantioseparation and the separation performance recovery of chiral stationary phases (CSPs) based on these derivatives. Therefore, six chitosan bis(phenylcarbamate)-(n-octyl urea)s were synthesized, which were coated on macroporous 3-aminopropyl silica gel affording new CSPs. Most of the CSPs demonstrated strong enantioseparation capability for the tested chiral compounds. The swelling capacity of the chitosan bis(phenylcarbamate)-(n-octyl urea)s in ethyl acetate, acetone and tetrahydrofuran (THF) was evaluated. Among the chitosan derivatives, the chitosan bis(3,5-dichlorophenylcarbamate)-(n-octyl urea) polymer showed the highest swelling capacity in ethyl acetate and THF. The polymer-based CSPs could be utilized with pure ethyl acetate and a normal phase containing 70% THF, but was damaged by pure THF. On the other hand, the separation performance of the damaged CSP could be recovered after it was allowed to stand for a period of time. The observations are important for the development and application of polysaccharide derivative-based CSPs. View Full-Text
Keywords: chitosan; chiral packing material; durability; chiral recognition; high performance liquid chromatography chitosan; chiral packing material; durability; chiral recognition; high performance liquid chromatography
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Wang, J.; Huang, S.-H.; Chen, W.; Bai, Z.-W. Eluent Tolerance and Enantioseparation Recovery of Chiral Packing Materials Based on Chitosan Bis(Phenylcarbamate)-(n-Octyl Urea)s for High Performance Liquid Chromatography. Molecules 2016, 21, 1528.

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