Advertisement

Analytical and Bioanalytical Chemistry

, Volume 411, Issue 10, pp 2209–2221 | Cite as

A double-functionalized polymeric ionic liquid used as solid-phase microextraction coating for efficient aromatic amine extraction and detection with gas chromatography–mass spectrometry

  • Yinchenxi Zhang
  • Yixiang DuanEmail author
Research Paper

Abstract

A solid-phase microextraction (SPME) fiber based on a new polymeric ionic liquid was prepared for the extraction of trace aromatic amines in water and their detection by gas chromatography–mass spectrometry (GC–MS). The newly designed polymeric ionic liquid with two functional groups (benzene ring and ether group) was synthesized and fixed on stainless steel wire to effectively extract aromatic amines. Parameters that affect the extraction efficiency of the SPME fiber (extraction temperature, extraction time, alkali concentration, and salt concentration) were optimized to establish a headspace SPME–GC–MS method. The correlation coefficients were 0.996 or greater for concentration of the aromatic amines ranging from 0.01 to 10 μg mL-1. In addition, the limits of detection for the new fiber are as low as 0.67 ng mL-1, which is lower than that obtained with polyacrylate. The relative standard deviations of five consecutive extractions for the solution spiked at 1 μg mL-1 by the same fiber were all below 8.3%, and the interfiber relative standard deviations for the solution spiked at the same concentration ranged from 8.9% to 15.2%. Furthermore, long lifetime and good solvent resistance are exhibited by the fiber. Finally, satisfactory relative recovery in the range from 85.3% to 101.9 % was achieved for two environmental water samples.

Keywords

Solid-phase microextraction Gas chromatography–mass spectrometry Coating Polymeric ionic liquid Aromatic amines 

Notes

Acknowledgement

The authors appreciate the financial support of Sichuan Science and Technology Program (grant number 2017SZ0013).

Compliance with ethical standards

Conflict of interest

The authors declare that they have no competing interests.

Supplementary material

216_2019_1664_MOESM1_ESM.pdf (270 kb)
ESM 1 (PDF 269 kb)

References

  1. 1.
    Sun Y, Liang L, Zhao X, Yu L, Zhang J, Shi G, et al. Determination of aromatic amines in water samples by capillary electrophoresis with amperometric detection. Water Res. 2009;43(1):41–6.  https://doi.org/10.1016/j.watres.2008.10.004.Google Scholar
  2. 2.
    Shelke M, Sanghi S, Asthana A, Lamba S, Sharma M. Fast separation and sensitive detection of carcinogenic aromatic amines by reversed-phase μ-liquid chromatography coupled with electrochemical detection. J Chromatogr A. 2005;1089(1–2):52–8.  https://doi.org/10.1016/j.chroma.2005.06.029.Google Scholar
  3. 3.
    Abbasi V, Yazdi S, Amiri A, Vatani H. Determination of aromatic amines using solid-phase microextraction based on an ionic liquid-mediated sol-gel technique. J Chromatogr Sci. 2016;54(4):677–81.  https://doi.org/10.1093/chromsci/bmv195.Google Scholar
  4. 4.
    Lamani X, Horst S, Zimmermann T, Schmidt T. Determination of aromatic amines in human urine using comprehensive multi-dimensional gas chromatography mass spectrometry (GCxGC-qMS). Anal Bioanal Chem. 2015;407(1):241–52.  https://doi.org/10.1007/s00216-014-8080-5.Google Scholar
  5. 5.
    Akyuz M, Ata S. Simultaneous determination of aliphatic and aromatic amines in water and sediment samples by ion-pair extraction and gas chromatography-mass spectrometry. J Chromatogr A. 2006;1129(1):88–94.  https://doi.org/10.1016/j.chroma.2006.06.075.Google Scholar
  6. 6.
    Ge X, Wexler A, Clegg S. Atmospheric amines – part I. A review. Atmos Environ. 2011;45(3):524–46.  https://doi.org/10.1016/j.atmosenv.2010.10.012-.Google Scholar
  7. 7.
    Borosky GL. Carcinogenic carbocyclic and heterocyclic aromatic amines: a DFT study concerning their mutagenic potency. J Mol Graph Model. 2008;27(4):459–65.  https://doi.org/10.1016/j.jmgm.2008.08.002.Google Scholar
  8. 8.
    European Commission. Commission Directive 2007/19CE of 30 March 2007 amending Directive 2002/72/EC relating to plastic materials and articles intended to come into contact with food and Council Directive 85/572/EEC laying down the list of simulants to beused for testing migration of constituents of plastic materials and articles intended to come intocontact with foodstuffs. Off J Eur Union L. 2007;91:17–36.Google Scholar
  9. 9.
    Arthur CL, Pawliszyn J. Solid phase microextraction with thermal desorption using fused silica optical fibers. Anal Chem. 1990;62(19):2145–8.Google Scholar
  10. 10.
    Arthur CL, Killam LM, Motlagh S, Lim M, Potter DW, Pawliszyn J. Analysis of substituted benzene compounds in groundwater using solid-phase microextraction. Environ Sci Technol. 1992;26(5):979–83.Google Scholar
  11. 11.
    Li J, Wang Y-B, Li K-Y, Cao Y-Q, Wu S, Wu L. Advances in different configurations of solid-phase microextraction and their applications in food and environmental analysis. Trends Anal Chem. 2015;72:141–52.  https://doi.org/10.1016/j.trac.2015.04.023.Google Scholar
  12. 12.
    Portillo-Castillo OJ, Castro-Rios R, Chávez-Montes A, González-Horta A, Cavazos-Rocha N, Waksman de Torres HH, et al. Developments of solid-phase microextraction fiber coatings for environmental pharmaceutical and personal care products analysis. Rev Anal Chem. 2018;37(2):1–22.  https://doi.org/10.1515/revac-2017-0018.Google Scholar
  13. 13.
    Xu J, Chen G, Huang S, Qiu J, Jiang R, Zhu F, et al. Application of in vivo solid-phase microextraction in environmental analysis. Trends Anal Chem. 2016;85:26–35.  https://doi.org/10.1016/j.trac.2016.03.003.Google Scholar
  14. 14.
    Musteata FM, Pawliszyn J. Bioanalytical applications of solid-phase microextraction. Trends Anal Chem. 2007;26(1):36–45.  https://doi.org/10.1016/j.trac.2006.11.003.Google Scholar
  15. 15.
    Kataoka H. Recent developments and applications of microextraction techniques in drug analysis. Anal Bioanal Chem. 2010;396(1):339–64.  https://doi.org/10.1007/s00216-009-3076-2.Google Scholar
  16. 16.
    Reyes-Garcés N, Gionfriddo E, Gómez-Ríos GA, Alam MN, Boyacı E, Bojko B, et al. Advances in solid phase microextraction and perspective on future directions. Anal Chem. 2018;90(1):302–60.  https://doi.org/10.1021/acs.analchem.7b04502. Google Scholar
  17. 17.
    Piri-Moghadam H, Alam MN, Pawliszyn J. Review of geometries and coating materials in solid phase microextraction: opportunities, limitations, and future perspectives. Anal Chim Acta. 2017;984:42–65.  https://doi.org/10.1016/j.aca.2017.05.035.Google Scholar
  18. 18.
    Hashemi B, Zohrabi P, Shamsipur M. Recent developments and applications of different sorbents for SPE and SPME from biological samples. Talanta. 2018;187:337–47.  https://doi.org/10.1016/j.talanta.2018.05.053.Google Scholar
  19. 19.
    Zheng J, Huang JL, Yang Q, Ni C, Xie XT, Shi YR, et al. Fabrications of novel solid phase microextraction fiber coatings based on new materials for high enrichment capability. Trends Anal Chem. 2018;108:135–53.  https://doi.org/10.1016/j.trac.2018.08.021.Google Scholar
  20. 20.
    Lashgari M, Yamini Y. An overview of the most common lab-made coating materials in solid phase microextraction. Talanta. 2019;191:283–306.  https://doi.org/10.1016/j.talanta.2018.08.077.Google Scholar
  21. 21.
    Seddon K, Stark A, Torres M. Influence of chloride, water, and organic solvents on the physical properties of ionic liquids. Pure Appl Chem. 2000;72(12):2275–87.Google Scholar
  22. 22.
    Marsh KN, Boxall JA, Lichtenthaler R. Room temperature ionic liquids and their mixtures—a review. Fluid Phase Equilib. 2004;219(1):93–8.  https://doi.org/10.1016/j.fluid.2004.02.003.Google Scholar
  23. 23.
    Trujillo-Rodríguez MJ, Nan H, Varona M, Emaus MN, Souza ID, Anderson JL. Advances of ionic liquids in analytical chemistry. Anal Chem. 2019;91(1):505–31.  https://doi.org/10.1021/acs.analchem.8b04710.Google Scholar
  24. 24.
    Martinis EM, Castro Grijalba A, Perez MB, Llaver M, Wuilloud RG. Synergistic analytical preconcentration with ionic liquid-nanomaterial hybrids. Trends Anal Chem. 2017;97:333–44.  https://doi.org/10.1016/j.trac.2017.10.004.Google Scholar
  25. 25.
    Muginova SM, Myasnikova DA, Kazarian SG, Shekhovtsova TN. Applications of ionic liquids for the development of optical chemical sensors and biosensors. Anal Sci. 2017;33:261–74.Google Scholar
  26. 26.
    Clark KD, Emaus MN, Varona M, Bowers AN, Anderson JL. Ionic liquids: solvents and sorbents in sample preparation. J Sep Sci. 2018;41(1):209–35.  https://doi.org/10.1002/jssc.201700864.Google Scholar
  27. 27.
    Liu J-f, Li N, Jiang G-b, Liu J-m, Jönsson JÅ, Wen M-j. Disposable ionic liquid coating for headspace solid-phase microextraction of benzene, toluene, ethylbenzene, and xylenes in paints followed by gas chromatography–flame ionization detection. J Chromatogr A. 2005;1066(1–2):27–32.  https://doi.org/10.1016/j.chroma.2005.01.024.Google Scholar
  28. 28.
    Zhao F, Meng Y, Anderson JL. Polymeric ionic liquids as selective coatings for the extraction of esters using solid-phase microextraction. J Chromatogr A. 2008;1208(1–2):1–9.  https://doi.org/10.1016/j.chroma.2008.08.071.Google Scholar
  29. 29.
    Ho TD, Canestraro AJ, Anderson JL. Ionic liquids in solid-phase microextraction: a review. Anal Chim Acta. 2011;695(1–2):18–43.  https://doi.org/10.1016/j.aca.2011.03.034.Google Scholar
  30. 30.
    Nawała J, Dawidziuk B, Dziedzic D, Gordon D, Popiel S. Applications of ionic liquids in analytical chemistry with a particular emphasis on their use in solid-phase microextraction. Trends Anal Chem. 2018;105:18–36.  https://doi.org/10.1016/j.trac.2018.04.010.Google Scholar
  31. 31.
    Kissoudi M, Samanidou V. Recent advances in applications of ionic liquids in miniaturized microextraction techniques. Molecules. 2018;23(6):1437.  https://doi.org/10.3390/molecules23061437.Google Scholar
  32. 32.
    Tang Z, Duan Y. Fabrication of porous ionic liquid polymer as solid-phase microextraction coating for analysis of organic acids by gas chromatography – mass spectrometry. Talanta. 2017;172:45–52.  https://doi.org/10.1016/j.talanta.2017.05.032.Google Scholar
  33. 33.
    Yu H, Merib J, Anderson JL. Crosslinked polymeric ionic liquids as solid-phase microextraction sorbent coatings for high performance liquid chromatography. J Chromatogr A. 2016;1438:10–21.  https://doi.org/10.1016/j.chroma.2016.02.027.Google Scholar
  34. 34.
    Bini R, Bortolini O, Chiappe C, Pieraccini D, Siciliano T. Development of cation/anion "interaction" scales for ionic liquids through ESI-MS measurements. J Phys Chem B. 2007;111(3):598–604.Google Scholar
  35. 35.
    He Y, Pohl J, Engel R, Rothman L, Thomas M. Preparation of ionic liquid based solid-phase microextraction fiber and its application to forensic determination of methamphetamine and amphetamine in human urine. J Chromatogr A. 2009;1216(24):4824–30.  https://doi.org/10.1016/j.chroma.2009.04.028.Google Scholar
  36. 36.
    Zheng J, Liang Y, Liu S, Jiang R, Zhu F, Wu D, et al. Simple fabrication of solid phase microextraction fiber employing nitrogen-doped ordered mesoporous polymer by in situ polymerization. J Chromatogr A. 2016;1427:22–8.  https://doi.org/10.1016/j.chroma.2015.11.074.Google Scholar
  37. 37.
    Sarafraz-Yazdi A, Vatani H. A solid phase microextraction coating based on ionic liquid sol-gel technique for determination of benzene, toluene, ethylbenzene and o-xylene in water samples using gas chromatography flame ionization detector. J Chromatogr A. 2013;1300:104–11.  https://doi.org/10.1016/j.chroma.2013.03.039.Google Scholar
  38. 38.
    Buchholz KD, Pawliszyn J. Optimization of solid-phase microextraction conditions for determination of phenols. Anal Chem. 1994;66(1):160–7.Google Scholar
  39. 39.
    Ai Y, Zhao F, Zeng B. Novel proton-type ionic liquid doped polyaniline for the headspace solid-phase microextraction of amines. Anal Chim Acta. 2015;880:60–6.  https://doi.org/10.1016/j.aca.2015.04.028.Google Scholar
  40. 40.
    Sharma N, Jain A, Verma K. Headspace solid-phase microextraction and on-fibre derivatization of primary aromatic amines for their determination by pyrolysis to aryl isothiocyanates and gas chromatography-mass spectrometry. Anal Methods. 2011;3(4):970–6.  https://doi.org/10.1039/c0ay00745e.Google Scholar
  41. 41.
    Puente NW, Josephy PD. Analysis of the tidocaine metabolite 2,6-dimethylaniline in bovine and human milk. J Anal Toxicol. 2001;25:711–5.Google Scholar
  42. 42.
    Chen M, Yin Y, Tai C, Zhang Q, Liu J, Hu J, et al. Analyses of nitrobenzene, benzene and aniline in environmental water samples by headspace solid phase microextraction coupled with gas chromatography-mass spectrometry. Chin Sci Bull. 2006;51:1648–51.Google Scholar
  43. 43.
    DeBruin LS, Josephy PD, Pawliszyn JB. Solid-phase microextraction of monocyclic aromatic amines from biological fluids. Anal Chem. 1998;70:1986–92.Google Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.College of Life Sciences, Research Center of Analytical Instrumentation, Key Laboratory of Bio-resource and Eco-environment, Ministry of EducationSichuan UniversityChengduChina

Personalised recommendations