Preparation and evaluation of chromatographic properties of sulfobetaine zwitterionic hydrophilic interaction chromatography stationary phase

doi:10.3724/SP.J.1123.2016.09035

Abstract

Abstract:

A zwitterionic sulfobetaine functional monomer N,N-dimethyl-N-acryloyloxyethyl-N-ammonium propane sulfonate (DMAEAPS) was synthesized. Dimethyl amino ethyl acrylate (DMAEA) and 1,3-propyl sulfonic acid ester as raw materials were used to synthesize the functional monomer. The DMAEAPS functional monomer was characterized by ¹H-NMR and FT-IR. 2-Bromoisobutyryl bromide allyl silicone (Sil-Br) was used as the initiator, CuBr and 2,2-bipyridyl (Bpy) as the catalytic system, and the functional monomer DMAEAPS was grafted on the surface of Sil-Br by atom transfer radical polymerization (ATRP). Then the sulfobetaine zwitterionic stationary phase (Sil-DMAEAPS) was obtained. The Sil-DMAEAPS stationary phase was characterized by element analysis. Chromatographic evaluation in hydrophilic interaction chromatography (HILIC) mode showed that the materials were suitable for use as stationary phase, and the column showed a dual retention mechanism, HILIC mode in acetonitrile-rich mobile phases and RP mode in highly aqueous mobile phases. The separation selectivity and retention of the five polar solutes (benzoin, pyridoxine, rutin hydrate, p-coumaric acid and caffeic acid) on the Sil-DMAEAPS stationary phase were different from the commercially available ZIC^®-HILIC. A method for the determination of rutin hydrate in rutin tablets was established. It is simple and accurate for the determination of polar compounds.

Key words: atom transfer radical polymerization (ATRP), chromatographic properties, hydrophilic interaction chromatography (HILIC), sulfobetaine, zwitterionic stationary phase

CLC Number:

O658

LI Wenjing, ZHAO Lijuan, WEI Chanling, DAI Xiaojun, GONG Bolin. Preparation and evaluation of chromatographic properties of sulfobetaine zwitterionic hydrophilic interaction chromatography stationary phase[J]. Chinese Journal of Chromatography, 2017, 35(4): 382-387.

References

[1] Alpert A J. J Chromatogr, 1990, 499:177
[2] Shen A J, Guo Z M, Liang X M. Progress in Chemistry, 2014, 26(1):10沈爱金, 郭志谋, 梁鑫淼. 化学进展, 2014, 26(1):10
[3] Liu S J, Qiao X Q, Yang Y J, et al. Chinese Journal of Chromatography, 2014, 32(10):1079刘士佳, 乔晓强, 杨艳军, 等. 色谱, 2014, 32(10):1079
[4] Jiang W, Irgum K. Anal Chem, 2001, 73(9):1993
[5] Wade K L, Garrard I J, Fahey J W. J Chromatogr A, 2007, 1154(1/2):469
[6] Kuang Y Y, Wang Y, Gu X, et al. Chinese Journal of Chromatography, 2014, 32(4):388况媛媛, 王彦, 谷雪, 等. 色谱, 2014, 32(4):388
[7] Yang J, Dong J B, Ye Z D, et al. Acta Chimica Sinica, 2012, 70(16):1725杨静, 董佳斌, 冶正得, 等. 化学学报, 2012, 70(16):1725
[8] Ni G, Yang W, He X Y, et al. Progress in Chemistry, 2005, 17(6):1074倪刚, 杨武, 何晓燕, 等. 化学进展, 2005, 17(6):1074
[9] Hemstrom P, Szumski M, Irgum K. Anal Chem, 2006, 78(20):7098
[10] Wang E N, Duan S J, He X W, et al. Acta Chimica Sinica, 2010, 68(23):2421王婀娜, 段淑静, 何锡文, 等. 化学学报, 2010, 68(23):2421
[11] Gai Q Q, Qu F. Chinese Journal of Chromatography, 2015, 33(5):475盖青青, 屈锋. 色谱, 2015, 33(5):475
[12] Bai H H, Fan C, Shen B Q, et al. Chinese Journal of Chromatography, 2015, 33(3):221白海红, 范超, 沈丙权, 等. 色谱, 2015, 33(3):221
[13] Sun Y, Xu F, Gong B L. Chinese Journal of Chromatography, 2011, 29(9):918孙杨, 徐飞, 龚波林. 色谱, 2011, 29(9):918
[14] Wang F Q, Chang S P, Dai X J, et al. Chinese Journal of Analytical Chemistry, 2012, 40(3):415王富强, 常素萍, 戴小军, 等. 分析化学, 2012, 40(3):415
[15] Ma M H, Niu Y L, Gong Y R, et al. Chinese Journal of Pesticide Science, 2014, 16(2):165马梅花, 牛玉玲, 龚艳茹, 等. 农药学学报, 2014, 16(2):165
[16] Ding W, Mao C, Yu T, et al. Science and Technology in Chemical Industry, 2011, 18(5):15丁伟, 毛程, 于涛, 等. 化工科技, 2011, 18(5):15
[17] Xiao H, Hu J, Jin S L, et al. Bull Korean Chem Soc, 2013, 34(9):2616
[18] Karatapanis A E, Fiamegos Y C, Stalikas C D. J Chromatogr A, 2011, 1218(20):2871
[19] Sun Y H. Anhui Medical and Pharmaceutical Journal, 2012, 16(1):30孙银华. 安徽医药, 2012, 16(1):30