Advertisement

Microchimica Acta

, 186:665 | Cite as

An amino-functionalized ordered mesoporous polymer as a fiber coating for solid phase microextraction of phenols prior to GC-MS analysis

  • Lin Li
  • Lijin HuangEmail author
  • Shutang Sun
  • Qian Yan
  • Qin ShuaiEmail author
  • Shenghong Hu
Original Paper
  • 170 Downloads

Abstract

An amino-functionalized ordered mesoporous polymer (OMP-NH2) was synthesized and applied as a fiber coating for solid phase microextraction of polar phenols from environmental samples. The fiber coating was prepared by loading the OMP-NH2 powder onto a stainless steel wire through silicone gel. Combined with GC-MS, the fibers were employed to quantify trace of phenols in water through headspace-SPME. The characterization showed the OMP-NH2 to have a large specific surface area (420 m2 g−1) and good thermal stability (>400 °C). Due to its mesoporous structure and favorable interactions via hydrogen bonding and π stacking interactions with phenols, the sorbent represents a promising candidate for the separation and enrichment of polar phenols. Extraction conditions, such as temperature, extraction time, salt concentration, pH value and desorption time, were fully optimized. Under the optimized conditions, the coating exhibits an enrichment effect that is ~2–10 times better than that of a commercial polyacrylate coating. Figures of merit include (a) low limits of detection (0.05–0.16 ng L−1), (b) wide linear ranges (0.2–10,000 ng L−1), and (c) high enrichment factors (510–2272). The relative standard deviations for one fiber and fiber-to-fiber were in the range of 4.0–6.1% and 4.6–7.4%, respectively. The method was applied to the determination of phenols in water samples and gave satisfactory recoveries between 85.4 and 112.2%.

Graphical abstract

An amino-functionalized ordered mesoporous polymer (OMP-NH2) was synthesized by a solventless method and applied as headspace solid phase microextraction (HS-SPME) fiber coating for the extraction of polar phenols from the environmental samples.

Keywords

Environmental analysis Amino modification Sample preparation Fiber coating Headspace extraction mode 

Notes

Acknowledgements

This study was supported by the National Natural Science Foundation of China (21806148), Special Project of Land and Resources Public Welfare Industry (201211003), the Central University’s Basic Research Business Expenses Special Fund (China University of Geosciences (Wuhan) No. CUG170102; No. CUG180610) and the Open Funds of Key Laboratory of Analytical Chemistry for Biology and Medicine (Ministry of Education) under contract number ACBM2018001.

Compliance with ethical standards

Conflict of interest

The authors declare no conflict of interest.

Supplementary material

604_2019_3777_MOESM1_ESM.docx (728 kb)
ESM 1 (DOCX 728 kb)

References

  1. 1.
    Zhong C, He M, Liao H, Chen B, Wang C, Hu B (2016) Polydimethylsiloxane/covalent triazine frameworks coated stir bar sorptive extraction coupled with high performance liquid chromatography-ultraviolet detection for the determination of phenols in environmental water samples. J Chromatogr A 1441:8–15.  https://doi.org/10.1016/j.chroma.2016.02.073 CrossRefPubMedGoogle Scholar
  2. 2.
    Lu W, Wang X, Wu X, Liu D, Li J, Chen L, Zhang X (2017) Multi-template imprinted polymers for simultaneous selective solid-phase extraction of six phenolic compounds in water samples followed by determination using capillary electrophoresis. J Chromatogr A 1483:30–39.  https://doi.org/10.1016/j.chroma.2016.12.069 CrossRefPubMedGoogle Scholar
  3. 3.
    Li Q-L, Huang F, Wang X-L, Wang X, Zhao R-S (2017) Multiple-helix cobalt(II)-based metal-organic nanotubes on stainless steel fibers for solid-phase microextraction of chlorophenol and nitrophenols from water samples. Microchim Acta 184(6):1817–1825.  https://doi.org/10.1007/s00604-017-2167-6 CrossRefGoogle Scholar
  4. 4.
    Wang Y, Ma R, Xiao R, Hao L, Wu Q, Wang C, Wang Z (2018) A hyper-cross linked polymer as an adsorbent for the extraction of chlorophenols. Microchim Acta 185(2):108.  https://doi.org/10.1007/s00604-017-2649-6 CrossRefGoogle Scholar
  5. 5.
    Meng WK, Liu L, Wang X, Zhao RS, Wang ML, Lin JM (2018) Polyphenylene core-conjugated microporous polymer coating for highly sensitive solid-phase microextraction of polar phenol compounds in water samples. Anal Chim Acta 1015:27–34.  https://doi.org/10.1016/j.aca.2018.02.035 CrossRefPubMedGoogle Scholar
  6. 6.
    Abolghasemi MM, Yousefi V, Piryaei M (2014) Fabrication of a hierarchical dodecyl sulfate-layered double hydroxide nanocomposite on porous aluminum wire as an efficient coating for solid-phase microextraction of phenols. Microchim Acta 182(5–6):1177–1186.  https://doi.org/10.1007/s00604-014-1441-0 CrossRefGoogle Scholar
  7. 7.
    Li QL, Wang X, Chen XF, Wang ML, Zhao RS (2015) In situ hydrothermal growth of ytterbium-based metal-organic framework on stainless steel wire for solid-phase microextraction of polycyclic aromatic hydrocarbons from environmental samples. J Chromatogr A 1415:11–19.  https://doi.org/10.1016/j.chroma.2015.08.036 CrossRefPubMedGoogle Scholar
  8. 8.
    Zheng J, Liang Y, Liu S, Jiang R, Zhu F, Wu D, Ouyang G (2016) Simple fabrication of solid phase microextraction fiber employing nitrogen-doped ordered mesoporous polymer by in situ polymerization. J Chromatogr A 1427:22–28.  https://doi.org/10.1016/j.chroma.2015.11.074 CrossRefPubMedGoogle Scholar
  9. 9.
    Zheng J, Huang J, Yang Q, Ni C, Xie X, Shi Y, Sun J, Zhu F, Ouyang G (2018) Fabrications of novel solid phase microextraction fiber coatings based on new materials for high enrichment capability. TrAC Trends Anal Chem 108:135–153.  https://doi.org/10.1016/j.trac.2018.08.021 CrossRefGoogle Scholar
  10. 10.
    Cheng H, Song Y, Bian Y, Wang F, Ji R, He W, Gu C, Ouyang G, Jiang X (2017) A nanoporous carbon material coated onto steel wires for solid-phase microextraction of chlorobenzenes prior to their quantitation by gas chromatography. Microchim Acta 185(1):56.  https://doi.org/10.1007/s00604-017-2539-y CrossRefGoogle Scholar
  11. 11.
    Gong SX, Wang X, Chen Y, Cheng CG, Wang ML, Zhao RS (2015) Carboxylated solid carbon spheres as a novel solid-phase microextraction coating for sensitive determination of phenols in environmental water samples. J Chromatogr A 1401:17–23.  https://doi.org/10.1016/j.chroma.2015.04.056 CrossRefPubMedGoogle Scholar
  12. 12.
    Liu L, Meng W-K, Zhou Y-S, Wang X, Xu G-J, Wang M-L, Lin J-M, Zhao R-S (2019) β-Ketoenamine-linked covalent organic framework coating for ultra-high-performance solid-phase microextraction of polybrominated diphenyl ethers from environmental samples. Chem Eng J 356:926–933.  https://doi.org/10.1016/j.cej.2018.09.081 CrossRefGoogle Scholar
  13. 13.
    Liu L, Meng W-K, Li L, Xu G-J, Wang X, Chen L-Z, Wang M-L, Lin J-M, Zhao R-S (2019) Facile room-temperature synthesis of a spherical mesoporous covalent organic framework for ultrasensitive solid-phase microextraction of phenols prior to gas chromatography-tandem mass spectrometry. Chem Eng J 369:920–927.  https://doi.org/10.1016/j.cej.2019.03.148 CrossRefGoogle Scholar
  14. 14.
    Zhang B, Xu G, Li L, Wang X, Li N, Zhao R-S, Lin J (2018) Facile fabrication of MIL-96 as coating fiber for solid-phase microextraction of trihalomethanes and halonitromethanes in water samples. Chem Eng J 350:240–247.  https://doi.org/10.1016/j.cej.2018.05.180 CrossRefGoogle Scholar
  15. 15.
    Liu Y, Liu Y, Liu Z, Du F, Qin G, Li G, Hu X, Xu Z, Cai Z (2019) Supramolecularly imprinted polymeric solid phase microextraction coatings for synergetic recognition nitrophenols and bisphenol a. J Hazard Mater 368:358–364.  https://doi.org/10.1016/j.jhazmat.2019.01.039 CrossRefPubMedGoogle Scholar
  16. 16.
    Liu Y, Huang Y, Chen G, Huang J, Zheng J, Xu J, Liu S, Qiu J, Yin L, Ruan W, Zhu F, Ouyang G (2018) A graphene oxide-based polymer composite coating for highly-efficient solid phase microextraction of phenols. Anal Chim Acta 1015:20–26.  https://doi.org/10.1016/j.aca.2018.02.034 CrossRefPubMedGoogle Scholar
  17. 17.
    Jiang L, Li S, Yu H, Zou Z, Hou X, Shen F, Li C, Yao X (2016) Amino and thiol modified magnetic multi-walled carbon nanotubes for the simultaneous removal of lead, zinc, and phenol from aqueous solutions. Appl Surf Sci 369:398–413.  https://doi.org/10.1016/j.apsusc.2016.02.067 CrossRefGoogle Scholar
  18. 18.
    Jia Z, Jiang M, Wu G (2017) Amino-MIL-53(Al) sandwich-structure membranes for adsorption of p-nitrophenol from aqueous solutions. Chem Eng J 307:283–290.  https://doi.org/10.1016/j.cej.2016.08.090 CrossRefGoogle Scholar
  19. 19.
    Bhadra BN, Ahmed I, Jhung SH (2016) Remarkable adsorbent for phenol removal from fuel: functionalized metal–organic framework. Fuel 174:43–48.  https://doi.org/10.1016/j.fuel.2016.01.071 CrossRefGoogle Scholar
  20. 20.
    Bagheri H, Manouchehri M, Allahdadlalouni M (2017) A magnetic multifunctional dendrimeric coating on a steel fiber for solid phase microextraction of chlorophenols. Microchim Acta 184(7):2201–2209.  https://doi.org/10.1007/s00604-017-2220-5 CrossRefGoogle Scholar
  21. 21.
    Lv G, Liu J, Xiong Z, Zhang Z, Guan Z (2016) Selectivity adsorptive mechanism of different nitrophenols on UiO-66 and UiO-66-NH2 in aqueous solution. J Chem Eng Data 61(11):3868–3876.  https://doi.org/10.1021/acs.jced.6b00581 CrossRefGoogle Scholar
  22. 22.
    Zhang W, Wang Q, Wu H, Wu P, He M (2014) A highly ordered mesoporous polymer supported imidazolium-based ionic liquid: an efficient catalyst for cycloaddition of CO2 with epoxides to produce cyclic carbonates. Green Chem 16(11):4767–4774.  https://doi.org/10.1039/c4gc01245c CrossRefGoogle Scholar
  23. 23.
    Schlienger S, Graff A-L, Celzard A, Parmentier J (2012) Direct synthesis of ordered mesoporous polymer and carbon materials by a biosourced precursor. Green Chem 14(2):313–316.  https://doi.org/10.1039/c2gc16160e CrossRefGoogle Scholar
  24. 24.
    Liu F, Wu Q, Liu C, Qi C, Huang K, Zheng A, Dai S (2016) Ordered mesoporous polymers for biomass conversions and cross-coupling reactions. ChemSusChem 9(17):2496–2504.  https://doi.org/10.1002/cssc.201600822 CrossRefPubMedGoogle Scholar
  25. 25.
    Zheng J, Liang Y, Liu S, Ding Y, Shen Y, Luan T, Zhu F, Jiang R, Wu D, Ouyang G (2015) Ordered mesoporous polymers in situ coated on a stainless steel wire for a highly sensitive solid phase microextraction fibre. Nanoscale 7(27):11720–11726.  https://doi.org/10.1039/c5nr02674a CrossRefPubMedGoogle Scholar
  26. 26.
    Yang Z, Wang J, Huang K, Ma J, Yang Z, Lu Y (2008) Functional mesoporous polymers from phenolic building oligomers. Macromol Rapid Commun 29(5):442–446.  https://doi.org/10.1002/marc.200700708 CrossRefGoogle Scholar
  27. 27.
    Li G, Wang B, Sun Q, Xu WQ, Han Y (2017) Adsorption of lead ion on amino-functionalized fly-ash-based SBA-15 mesoporous molecular sieves prepared via two-step hydrothermal method. Microporous Mesoporous Mater 252:105–115.  https://doi.org/10.1016/j.micromeso.2017.06.004 CrossRefGoogle Scholar
  28. 28.
    Zhao J, Song P, Cui Y, Liu X, Sun S, Hou S, Ma F (2014) Effects of hydrogen bond on 2-aminopyridine and its derivatives complexes in methanol solvent. Spectrochim Acta Part A 131:282–287.  https://doi.org/10.1016/j.saa.2014.04.116 CrossRefGoogle Scholar
  29. 29.
    Bartak P, Cap L (1997) Determination of phenols by solid-phase microextraction. J Chromatogr A 767(1997):171–175.  https://doi.org/10.1016/S0021-9673(96)01090-4 CrossRefGoogle Scholar
  30. 30.
    Guo J, Xu Y, Jin S, Chen L, Kaji T, Honsho Y, Addicoat MA, Kim J, Saeki A, Ihee H, Seki S, Irle S, Hiramoto M, Gao J, Jiang D (2013) Conjugated organic framework with three-dimensionally ordered stable structure and delocalized pi clouds. Nat Commun 4:2736.  https://doi.org/10.1038/ncomms3736 CrossRefPubMedPubMedCentralGoogle Scholar
  31. 31.
    Shih HK, Shu TY, Ponnusamy VK, Jen JF (2015) A novel fatty-acid-based in-tube dispersive liquid-liquid microextraction technique for the rapid determination of nonylphenol and 4-tert-octylphenol in aqueous samples using high-performance liquid chromatography-ultraviolet detection. Anal Chim Acta 854:70–77.  https://doi.org/10.1016/j.aca.2014.11.021 CrossRefPubMedGoogle Scholar
  32. 32.
    Wang W, Wang J, Zhang S, Cui P, Wang C, Wang Z (2016) A novel Schiff base network-1 nanocomposite coated fiber for solid-phase microextraction of phenols from honey samples. Talanta 161:22–30.  https://doi.org/10.1016/j.talanta.2016.08.009 CrossRefPubMedGoogle Scholar
  33. 33.
    Zhu F, Liang Y, Xia L, Rong M, Su C, Lai R, Li R, Ouyang G (2012) Preparation and characterization of vinyl-functionalized mesoporous organosilica-coated solid-phase microextraction fiber. J Chromatogr A 1247:42–48.  https://doi.org/10.1016/j.chroma.2012.05.055 CrossRefPubMedGoogle Scholar

Copyright information

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

Authors and Affiliations

  1. 1.Engineering Research Center of Nano-Geomaterials of Ministry of Education, Faculty of Materials Science and ChemistryChina University of Geosciences (Wuhan)WuhanPeople’s Republic of China
  2. 2.State Key Laboratory of Biogeology and Environmental GeologyChina University of Geosciences (Wuhan)WuhanPeople’s Republic of China

Personalised recommendations