Citation: XU Lili, ZHONG Minghua, CHEN Xiaojing. Preparation and chromatographic performance of a eugenol-bonded silica gel stationary phase for high performance liquid chromatography[J]. Chinese Journal of Chromatography, ;2015, 33(5): 461-467. doi: 10.3724/SP.J.1123.2015.01039 shu

Preparation and chromatographic performance of a eugenol-bonded silica gel stationary phase for high performance liquid chromatography

1.
Department of Chemistry, Hanshan Normal University, Chaozhou 521041, China

Corresponding author: XU Lili,
Received Date: 28 January 2015

Fund Project: 潮州市科技局引导计划项目(2013H04). (2013H04)

A eugenol-bonded silica gel stationary phase (EGSP) for high performance liquid chromatography (HPLC) has been synthesized by the solid-liquid successive reaction method. The preparation process included two steps: firstly, γ-glycidoxypropyltrimethoxy-silane (KH-560) was covalently attached to the surface of spherical silica gel. Then the bonded silica gel continued to react with eugenol ligand, which was a plant active component, and obtained EGSP. The structure of EGSP was characterized by elemental analysis, thermogravimetric analysis and Fourier transform infrared spectroscopy. Using naphthalene as a probe, the column efficiency was tested under the mobile phase of acetonitrile-water (35:65, v/v) at a flow rate of 0.8 mL/min. The chromatographic properties and the retention mechanism of EGSP were evaluated by using neutral, basic and acidic analytes as solute probes. Meanwhile, the comparative study with C₁₈ column and phenyl column was also carried out under the same chromatographic conditions. The result showed that the eugenol ligand was successfully bonded to the surface of silica gel with a 0.28 mmol/g of bonded amount, and the theoretical plate number of EGSP column was about 24707 N/m. The EGSP appeared to be a kind of excellent reversed-phase stationary phase with suitable hydrophobicity and various synergistic sites. The eugenol ligand bonded on silica gel could first provideπ-πinteraction sites for different analytes because of its benzene ring and alkenyl. In addition, the methoxy groups of eugenol were responsible for dipole-dipole and hydrogen-bonding interactions between the ligand and solutes in the effective separation process. Comparing with traditional C₁₈ column and phenyl column, EGSP has an advantage in the fast separation of polar compounds under simple experimental conditions.
- high performance liquid chromatography (HPLC),
- eugenol,
- bonded silica gel stationary phase,
- chromatographic property,
- retention mechanism
1. [1]
  [1] Yu S L. Methods and Applications of High Performance Liquid Chromatography. Beijing: Chemical Industry Press (于世林. 高效液相色谱方法及应用. 北京: 化学工业出版社), 2000: 8
2. [2]
  [2] Mullangi R, Sharma K, Srinivas N R. Biomed Chromatogr, 2012, 26(8): 906
3. [3]
  [3] Jardim I C S F, Maldaner L, Lourenco J, et al. J Sep Sci, 2010, 33(19): 2917
4. [4]
  [4] Qiu H D, Liang X J, Sun M, et al. Anal Bioanal Chem, 2011, 399(10): 3307
5. [5]
  [5] Beesley T E. LC GC Eur, 2011, 24(5): 270
6. [6]
  [6] Ward T J, Ward K D. Anal Chem, 2012, 84(2): 626
7. [7]
  [7] Xiao Y, Ng S C, Tan T T Y, et al. J Chromatogr A, 2012, 1269: 52
8. [8]
  [8] Zhu Y Q, Xu X D, Feng S W, et al. Chinese Journal of Polymer Bulletin (朱元棋, 徐晓冬, 冯四伟, 等. 高分子通报), 2012(6): 92
9. [9]
  [9] Lei W, Zhang L Y, Zhu Y X, et al. Chinese Journal of Analytical Chemistry (雷雯, 张凌怡, 朱亚仙, 等. 分析化学), 2010, 38(11): 1544
10. [10]
  [10] Shen A J, Guo Z M, Liang X M. Progress in Chemistry (沈爱金, 郭志谋, 梁鑫淼. 化学进展), 2014, 26(1): 10
11. [11]
  [11] Kotoni D, D' Acquarica I, Ciogli A, et al. J Chromatogr A, 2012, 1232: 196
12. [12]
  [12] Liu S J, Qiao X Q, Yang Y J, et al. Chinese Journal of Chromatography (刘士佳, 乔晓强, 杨艳军, 等. 色谱), 2014, 32(10): 1079
13. [13]
  [13] Shen A J, Guo Z M, Yu L, et al. Chem Commun, 2011, 47(15): 4550
14. [14]
  [14] Shen A J, Li X L, Dong X F, et al. J Chromatogr A, 2013, 1314: 63
15. [15]
  [15] Fang Y S, Li L S, Chen H, et al. Chinese Journal of Applied Chemistry (方奕珊, 李来生, 陈红, 等. 应用化学), 2013, 30(1): 79
16. [16]
  [16] Zhang Y, Liu M F, Fang Y S, et al. Journal of Nanchang University: Natural Science (张杨, 刘妙芬, 方奕姗, 等. 南昌大学学报: 理科版), 2012, 36(3): 228
17. [17]
  [17] Song X M, Tang Z S. Extraction, Separation and Preparation of Chemical Components from Traditional Chinese Medicine. 2nd ed. Beijing: People's Medical Publishing House (宋小妹, 唐志书. 中药化学成分提取分离与制备. 2版. 北京: 人民卫生出版社), 2009: 62
18. [18]
  [18] Peng Z B, Zhang Q G, Dai H J, et al. Lishizhen Medicine and Materia Medica Research (彭宅彪, 张琼光, 代虹健, 等. 时珍国医国药), 2006, 17(10): 2079
19. [19]
  [19] Marszall M P, Baczek T, Kaliszan R. Anal Chim Acta, 2005, 547(2): 172
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