Synthesis of Cellulose-2,3-bis(3,5-dimethylphenylcarbamate) in an Ionic Liquid and Its Chiral Separation Efficiency as Stationary Phase

• Main Authors: Runqiang Liu, Yijun Zhang, Lianyang Bai, Mingxian Huang, Jun Chen, Yuping Zhang
• Format: Article
• Language: English
• Published: MDPI AG 2014-04-01
• Series: International Journal of Molecular Sciences
• Subjects: 1-allyl-3-methyl-imidazolium chloride; synthesis; Cellulose-2,3-bis(3,5-dimethylphenylcarbamate); high performance liquid chromatography; chiral stationary phase; enantioseparation
• Online Access: http://www.mdpi.com/1422-0067/15/4/6161

A chiral selector of cellulose-2,3-bis(3,5-dimethylphenylcarbamate) (CBDMPC) was synthesized by reacting 3,5-dimethylphenyl isocyanate with microcrystalline cellulose dissolved in an ionic liquid of 1-allyl-3-methyl-imidazolium chloride (AMIMCl). The obtained chiral selector was effectively characterized by infrared spectroscopy, elemental analysis and 1H NMR. The selector was reacted with 3-aminopropylsilanized silica gel and the CBDMPC bonded chiral stationary phase (CSP) was obtained. Chromatographic evaluation of the prepared CSPs was conducted by high performance liquid chromatographic (HPLC) and baseline separation of three typical fungicides including hexaconazole, metalaxyl and myclobutanil was achieved using n-hexane/isopropanol as the mobile phase with a flow rate 1.0 mL/min. Experimental results also showed that AMIMCl could be recycled easily and reused in the preparation of CSPs as an effective reaction media.