Citation: Zhang Xin-Xin, Liu Yong-Qiang, Yu Hong, Zhang Ren-Qing. Rapid and simultaneous determination of piperidinium and pyrrolidinium ionic liquid cations by ion pair chromatography coupled with direct conductivity detection[J]. Chinese Chemical Letters, ;2017, 28(1): 126-130. doi: 10.1016/j.cclet.2016.05.034 shu

Rapid and simultaneous determination of piperidinium and pyrrolidinium ionic liquid cations by ion pair chromatography coupled with direct conductivity detection

College of Chemistry and Chemical Engineering, Harbin Normal University, Harbin 150025, China

Corresponding author: Yu Hong, yuhonghsd@126.com
Received Date: 27 April 2016
Revised Date: 21 May 2016
Accepted Date: 30 May 2016
Available Online: 18 January 2016

Figures(2)

A method of ion-pair chromatography with direct conductivity detection was developed on a silicabased monolithic column for the fast and simultaneous determination of piperidinium and pyrrolidinium ionic liquid cations. The effects of the mobile phase, column temperature and flow rate on the retention of the cations were investigated. The retention rules were discussed. As an ion-pair reagent, sodium heptanesulfonate is more suitable than sodium pentanesulfonate for the separation and determination of piperidinium and pyrrolidinium cations. The increase of ion-pair reagent concentration led to the increased retention time of the cations. When acetonitrile content and mobile phase flow were increased, the retention time of the cations became shorter. The retention of piperidinium and pyrrolidinium cations is an exothermic process, and the retention of the cations conforms to the carbon number rule. The chromatographic analysis was performed using the Chromolith Speed ROD RP-18e column, 0.5 ǌmol/L sodium heptanesulfonate-5% acetonitrile as the mobile phase at a flow rate of 3.0 mL/min and column temperature of 30¦. Separation of N-methyl-N-ethyl piperidinium, N-methyl-N-propyl piperidinium, N-methyl-N-butyl piperidinium and N-methyl-N-ethyl pyrrolidinium, N-methyl-N-propyl pyrrolidinium, N-methyl-N-butyl pyrrolidinium cations were achieved within 10 min. The detection limits (S/N=3) were between 0.19 and 3.08 mg/L. Relative standard deviations (n=5) for peak areas were less than 1.2%. The method has been applied to the determination of piperidinium and pyrrolidinium cations in ionic liquid samples. The spiked recoveries of ionic liquid cations were between 96% and 111%. The method is accurate, reliable, rapid, and has a better practicability.
- Ion-pair chromatography,
- Conductivity detection,
- Piperidinium,
- Pyrrolidinium,
- Ionic liquids
1. [1]
  Zhang M.L., Mallik A.K., Takafuji M., Ihara H., Qiu H.D.. Versatile ligands for highperformance liquid chromatography:an overview of ionic liquid-functionalized stationary phases[J]. Anal. Chim. Acta, 2015,887:1-16. doi: 10.1016/j.aca.2015.04.022
2. [2]
  Cai Y.Q., Song G.H., Liang D.N.. Desulfurization using the 1, 2-dimethylimidazolium ionic liquid as an adsorbent[J]. Chin. Chem. Lett., 2015,26:317-319. doi: 10.1016/j.cclet.2014.11.027
3. [3]
  Qin X.X., Cheng Z.L.. Application of ionic liquids as a catalyst in the synthesis of polyvinyl butyral (PVB) polymer[J]. Chin. Chem. Lett., 2016,27:145-148. doi: 10.1016/j.cclet.2015.07.012
4. [4]
  Ma Y.J., Guan C., Dong Y.J., Yu H.. High-performance liquid chromatography utilization of ionic liquids as mobile phase additives for separation and determination of the isomers of amino benzoic acids[J]. Chin. Chem. Lett., 2016,27:749-752. doi: 10.1016/j.cclet.2016.01.023
5. [5]
  M. Paszkiewicz, P. Stepnowski, How should ionic liquids be analyzed? Curr. Org. Chem. 15(2011) 1873-1887.
6. [6]
  Ruiz M.J., Angel -, Berthod A.. Reversed phase liquid chromatography of alkylimidazolium ionic liquids[J]. J. Chromatogr. A, 2006,1113:101-108. doi: 10.1016/j.chroma.2006.01.124
7. [7]
  Studzi S., ska ń, Buszewski B.. Study of retention mechanism of imidazolium-based ionic liquids in HPLC[J]. J. Sep. Sci., 2010,33:1264-1273.
8. [8]
  Huang X., Yu H., Dong Y.J.. Rapid and simultaneous determination of imidazolium and pyridinium ionic liquid cations by ion-pair chromatography using a monolithic column[J]. Chin. Chem. Lett., 2012,23:843-846. doi: 10.1016/j.cclet.2012.04.029
9. [9]
  Lu C.X., Tang Z.G., Liu C.B.. Determination of ionic liquid cations in soil samples by ultrasound-assisted solid-phase extraction coupled with liquid chromatography-tandem mass spectrometry[J]. Anal. Methods, 2015,7:5924-5933. doi: 10.1039/C5AY00750J
10. [10]
  Hawkins C.A., Rud A., Guthrie M.L., Dietz M.L.. Rapid quantification of imidazolium-based ionic liquids by hydrophilic interaction liquid chromatography:methodology and an investigation of the retention mechanisms[J]. J. Chromatogr. A, 2015,1400:54-64. doi: 10.1016/j.chroma.2015.04.047
11. [11]
  Chen Q., Yu H., Wang J.F.. Determination of pyridinium ionic liquid cations by ion chromatography with direct conductivity detection[J]. J. Liq. Chromatogr. Relat. Technol., 2012,35:1184-1193. doi: 10.1080/10826076.2011.619028
12. [12]
  Onink F., Meindersma W., Burghoff B.. Ion chromatography as a novel method to quantify the solubility of pyridinium ionic liquids in organic solvents[J]. J. Chromatogr. Sci., 2015,53:8-15. doi: 10.1093/chromsci/bmu001
13. [13]
  Yu H., Sun Y.M., Zou C.M.. Imidazolium ionic liquid as the background ultraviolet absorption reagent for determination of morpholinium cations by high performance liquid chromatography-indirect ultraviolet detection[J]. Chin. Chem. Lett., 2014,25:1371-1374. doi: 10.1016/j.cclet.2014.05.041
14. [14]
  Guan C., Yu H.. Hydrophilic interaction liquid chromatography with indirect ultraviolet detection for the separation and quantification of pyrrolidinium ionic liquid cations[J]. Chin. Chem. Lett., 2015,26:1371-1375. doi: 10.1016/j.cclet.2015.08.004
15. [15]
  Zhang Y., Yu H., Wang M.Y.. Determination of pyrrolidinium ionic liquid cations by ion chromatography-indirect ultraviolet detection with imidazolium ionic liquids as both an ultraviolet absorption reagent and an eluting agent[J]. Anal. Methods, 2015,7:5654-5660. doi: 10.1039/C5AY01211B
16. [16]
  Yu H., Mou S.F.. Effect of temperature on the retention of amino acids and carbohydrates in high-performance anion-exchange chromatography[J]. J. Chromatogr. A, 2006,1118:118-124. doi: 10.1016/j.chroma.2005.12.051
17. [17]
  Yu H., Li R.S.. Effect of column temperature on the retention of inorganic anions and organic acids in non-suppressed anion-exchange IC[J]. Chromatographia, 2008,68:611-616. doi: 10.1365/s10337-008-0774-4
1. [1]
  Hao-Cong Li , Ming Zhang , Qiyan Lv , Kai Sun , Xiao-Lan Chen , Lingbo Qu , Bing Yu . Homogeneous catalysis and heterogeneous separation: Ionic liquids as recyclable photocatalysts for hydroacylation of olefins. Chinese Chemical Letters, 2025, 36(2): 110579-. doi: 10.1016/j.cclet.2024.110579
2. [2]
  Jiajia Wang , XinXin Ge , Yajing Xiang , Xiaoliang Qi , Ying Li , Hangbin Xu , Erya Cai , Chaofan Zhang , Yulong Lan , Xiaojing Chen , Yizuo Shi , Zhangping Li , Jianliang Shen . An ionic liquid functionalized sericin hydrogel for drug-resistant bacteria-infected diabetic wound healing. Chinese Chemical Letters, 2025, 36(2): 109819-. doi: 10.1016/j.cclet.2024.109819
3. [3]
  Luyu Zhang , Zirong Dong , Shuai Yu , Guangyue Li , Weiwen Kong , Wenjuan Liu , Haisheng He , Yi Lu , Wei Wu , Jianping Qi . Ionic liquid-based in situ dynamically self-assembled cationic lipid nanocomplexes (CLNs) for enhanced intranasal siRNA delivery. Chinese Chemical Letters, 2024, 35(7): 109101-. doi: 10.1016/j.cclet.2023.109101
4. [4]
  Qiangwei Wang , Huijiao Liu , Mengjie Wang , Haojie Zhang , Jianda Xie , Xuanwei Hu , Shiming Zhou , Weitai Wu . Observation of high ionic conductivity of polyelectrolyte microgels in salt-free solutions. Chinese Chemical Letters, 2024, 35(4): 108743-. doi: 10.1016/j.cclet.2023.108743
5. [5]
  Tong Zhang , Xiaojing Liang , Licheng Wang , Shuai Wang , Xiaoxiao Liu , Yong Guo . An ionic liquid assisted hydrogel functionalized silica stationary phase for mixed-mode liquid chromatography. Chinese Chemical Letters, 2025, 36(1): 109889-. doi: 10.1016/j.cclet.2024.109889
6. [6]
  Ying Li , Yanjun Xu , Xingqi Han , Di Han , Xuesong Wu , Xinlong Wang , Zhongmin Su . A new metal–organic rotaxane framework for enhanced ion conductivity of solid-state electrolyte in lithium-metal batteries. Chinese Chemical Letters, 2024, 35(9): 109189-. doi: 10.1016/j.cclet.2023.109189
7. [7]
  Ya Song , Mingxia Zhou , Zhu Chen , Huali Nie , Jiao-Jing Shao , Guangmin Zhou . Integrated interconnected porous and lamellar structures realized fast ion/electron conductivity in high-performance lithium-sulfur batteries. Chinese Chemical Letters, 2024, 35(6): 109200-. doi: 10.1016/j.cclet.2023.109200
8. [8]
  Xiaoning Li , Quanyu Shi , Meng Li , Ningxin Song , Yumeng Xiao , Huining Xiao , Tony D. James , Lei Feng . Functionalization of cellulose carbon dots with different elements (N, B and S) for mercury ion detection and anti-counterfeit applications. Chinese Chemical Letters, 2024, 35(7): 109021-. doi: 10.1016/j.cclet.2023.109021
9. [9]
  Jing Chen , Peisi Xie , Pengfei Wu , Yu He , Zian Lin , Zongwei Cai . MALDI coupled with laser-postionization and trapped ion mobility spectrometry contribute to the enhanced detection of lipids in cancer cell spheroids. Chinese Chemical Letters, 2024, 35(4): 108895-. doi: 10.1016/j.cclet.2023.108895
10. [10]
  Yixia Zhang , Caili Xue , Yunpeng Zhang , Qi Zhang , Kai Zhang , Yulin Liu , Zhaohui Shan , Wu Qiu , Gang Chen , Na Li , Hulin Zhang , Jiang Zhao , Da-Peng Yang . Cocktail effect of ionic patch driven by triboelectric nanogenerator for diabetic wound healing. Chinese Chemical Letters, 2024, 35(8): 109196-. doi: 10.1016/j.cclet.2023.109196
11. [11]
  Pei Cao , Yilan Wang , Lejian Yu , Miao Wang , Liming Zhao , Xu Hou . Dynamic asymmetric mechanical responsive carbon nanotube fiber for ionic logic gate. Chinese Chemical Letters, 2024, 35(6): 109421-. doi: 10.1016/j.cclet.2023.109421
12. [12]
  Ruizhi Yang , Xia Li , Weiping Guo , Zixuan Chen , Hongwei Ming , Zhong-Zhen Luo , Zhigang Zou . New thermoelectric semiconductors Pb5Sb12+xBi6-xSe32 with ultralow thermal conductivity. Chinese Journal of Structural Chemistry, 2024, 43(3): 100268-100268. doi: 10.1016/j.cjsc.2024.100268
13. [13]
  Chaozheng He , Pei Shi , Donglin Pang , Zhanying Zhang , Long Lin , Yingchun Ding . First-principles study of the relationship between the formation of single atom catalysts and lattice thermal conductivity. Chinese Chemical Letters, 2024, 35(6): 109116-. doi: 10.1016/j.cclet.2023.109116
14. [14]
  Congyan Liu , Xueyao Zhou , Fei Ye , Bin Jiang , Bo Liu . Confined electric field in nano-sized channels of ionic porous framework towards unique adsorption selectivity. Chinese Chemical Letters, 2025, 36(2): 109969-. doi: 10.1016/j.cclet.2024.109969
15. [15]
  Liang Ming , Dan Liu , Qiyue Luo , Chaochao Wei , Chen Liu , Ziling Jiang , Zhongkai Wu , Lin Li , Long Zhang , Shijie Cheng , Chuang Yu . Si-doped Li₆PS₅I with enhanced conductivity enables superior performance for all-solid-state lithium batteries. Chinese Chemical Letters, 2024, 35(10): 109387-. doi: 10.1016/j.cclet.2023.109387
16. [16]
  Zhenyu Hu , Zhenchun Yang , Shiqi Zeng , Kun Wang , Lina Li , Chun Hu , Yubao Zhao . Cationic surface polarization centers on ionic carbon nitride for efficient solar-driven H₂O₂ production and pollutant abatement. Chinese Chemical Letters, 2024, 35(10): 109526-. doi: 10.1016/j.cclet.2024.109526
17. [17]
  Rui Wang , Yang Liang , Julius Rebek Jr. , Yang Yu . Stabilization and detection of labile reaction intermediates in supramolecular containers. Chinese Chemical Letters, 2024, 35(6): 109228-. doi: 10.1016/j.cclet.2023.109228
18. [18]
  Zihong Li , Jie Cheng , Ping Huang , Guoliang Wu , Weiying Lin . Activatable photoacoustic bioprobe for visual detection of aging in vivo. Chinese Chemical Letters, 2024, 35(4): 109153-. doi: 10.1016/j.cclet.2023.109153
19. [19]
  Jiahao Xie , Jin Liu , Bin Liu , Xin Meng , Zhuang Cai , Xiaoqin Xu , Cheng Wang , Shijie You , Jinlong Zou . Yolk shell-structured pyrite-type cobalt sulfide grafted by nitrogen-doped carbon-needles with enhanced electrical conductivity for oxygen electrocatalysis. Chinese Chemical Letters, 2024, 35(7): 109236-. doi: 10.1016/j.cclet.2023.109236
20. [20]
  Hong Chen , Mao-Yin Ran , Long-Hua Li , Xin-Tao Wu , Hua Lin . [Cs14Cl][Tm71Se110]: An unusual salt-inclusion chalcogenide containing different valent Tm centers and ultralow thermal conductivity. Chinese Journal of Structural Chemistry, 2024, 43(10): 100397-100397. doi: 10.1016/j.cjsc.2024.100397

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(697)
HTML views(23)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142