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Microchimica Acta

, 185:125 | Cite as

An amino-functionalized magnetic framework composite of type Fe3O4-NH2@MIL-101(Cr) for extraction of pyrethroids coupled with GC-ECD

  • Xi He
  • Wei Yang
  • Sijia Li
  • Yu Liu
  • Baichun Hu
  • Ting WangEmail author
  • Xiaohong HouEmail author
Original Paper

Abstract

An amino-functionalized magnetic framework composite of type Fe3O4-NH2@MIL-101(Cr) was synthesized using a solvothermal method. The material was characterized by scanning electron microscopy, X-ray diffraction, Fourier transform infrared spectroscopy, nitrogen adsorption, and magnetometry. The composite combines the advantages of amino-modified Fe3O4 and MIL-101(Cr). The presence of amino groups facilitates the fairly specific adsorption of pyrethroids. The composite was employed as a sorbent for magnetic solid phase extraction of five pyrethroids from environmental water samples. Following desorption with acidified acetone, the pyrethroids were quantified by gas chromatography with electron capture detection. The detection limits for bifenthrin, fenpropathrin, λ-cyhalothrin, permethrin, and deltamethrin range from 5 to 9 pg·mL−1. The method is rapid, accurate, and highly sensitive. The molecular interactions and free binding energies between MIL-101(Cr) and the five pyrethroids were calculated by means of molecular docking.

Graphical abstract

A novel functionalized magnetic framework composite of type Fe3O4-NH2@MIL-101(Cr) was synthesized. It was applied as a sorbent for magnetic solid phase extraction of pyrethroids prior to their quantitation by gas chromatography with electron capture detection. The molecular interactions of analytes and MIL-101(Cr) were studied.

Keywords

Sorbent Insecticides Magnetic solid phase extraction Environmental water samples Molecular docking 

Notes

Acknowledgements

This work was financially supported by the Natural Science Foundation of Liaoning Province, China (201602693), Natural Science Foundation of Liaoning Provincial Department of Education, China (2017LQN12).

Compliance with ethical standards

The author(s) declare that they have no competing interests.

Supplementary material

604_2018_2672_MOESM1_ESM.docx (4.3 mb)
ESM 1 (DOCX 4376 kb)

References

  1. 1.
    Esteve-Turrillas FA, Pastor A, MDL G (2005) Determination of pyrethroid insecticide residues in vegetable oils by using combined solid-phases extraction and tandem mass spectrometry detection. Anal Chim Acta 553:50–57CrossRefGoogle Scholar
  2. 2.
    Philip GH, Reddy PM, Sridevi G (1995) Cypermethrin-induced in vivo alterations in the carbohydrate metabolism of freshwater fish, labeo rohita. Ecotoxicol Environ Saf 31:173–178CrossRefGoogle Scholar
  3. 3.
    Le GR, Dulaurent S, Gaulier JM, Saint-Marcoux F, Moesch C, Lachâtre G (2012) Simultaneous determination of five synthetic pyrethroid metabolites in urine by liquid chromatography-tandem mass spectrometry: application to 39 persons without known exposure to pyrethroids. Toxicol Lett 210:248–253CrossRefGoogle Scholar
  4. 4.
    Giroud B, Vauchez A, Vulliet E, Wiest L, Buleté A (2013) Trace level determination of pyrethroid and neonicotinoid insecticides in beebread using acetonitrile-based extraction followed by analysis with ultra-high-performance liquid chromatography-tandem mass spectrometry. J Chromatogr A 1316:53–61CrossRefGoogle Scholar
  5. 5.
    De PC, Whiting SA, Lydy MJ (2015) A simultaneous extraction method for organophosphate, pyrethroid, and neonicotinoid insecticides in aqueous samples. Arch Environ Contam Toxicol 68:745–756CrossRefGoogle Scholar
  6. 6.
    Yıldız Z, Uzun H (2015) Prediction of gas storage capacities in metal organic frameworks using artificial neural network. Microporous Mesoporous Mater 208:50–54CrossRefGoogle Scholar
  7. 7.
    Khan NA, Jhung SH (2016) Adsorptive removal and separation of chemicals with metal-organic frameworks: Contribution of π-complexation. J Hazard Mater 325:198–213CrossRefGoogle Scholar
  8. 8.
    Kholdeeva OA (2016) Liquid-phase selective oxidation catalysis with metal-organic frameworks. ChemInform 278:22–29Google Scholar
  9. 9.
    Ma A, Luo Z, Gu C, Li B, Liu J (2017) Cytotoxicity of a metal–organic framework: Drug delivery. Inorg Chem Commun 77:68–71CrossRefGoogle Scholar
  10. 10.
    Kumar P, Deep A, Kim KH (2015) Metal organic frameworks for sensing applications. TrAC, Trends Anal Chem 73:39–53CrossRefGoogle Scholar
  11. 11.
    Chen L, Ye JW, Wang HP, Pan M, Yin SY, Wei ZW, Zhang LY, Wu K, Fan YN, Su CY (2017) Ultrafast water sensing and thermal imaging by a metal-organic framework with switchable luminescence. Nat Commun 8:15985–15995CrossRefGoogle Scholar
  12. 12.
    Férey G, Mellot-Draznieks C, Serre C, Millange F, Dutour J, Surblé S, Margiolaki I (2005) A chromium terephthalate-based solid with unusually large pore volumes and surface area. Science 309:2040–2042CrossRefGoogle Scholar
  13. 13.
    Xie L, Liu S, Han Z, Jiang R, Liu H, Zhu F, Zeng F, Su C, Ouyang G (2015) Preparation and characterization of metal-organic framework MIL-101(Cr)-coated solid-phase microextraction fiber. Anal Chim Acta 853:303–310CrossRefGoogle Scholar
  14. 14.
    Xiao Z, He M, Chen B, Hu B (2016) Polydimethylsiloxane/metal-organic frameworks coated stir bar sorptive extraction coupled to gas chromatography-flame photometric detection for the determination of organophosphorus pesticides in environmental water samples. Talanta 156–157:126–133CrossRefGoogle Scholar
  15. 15.
    Bayazit ŞS, Danalıoğlu ST, Abdel MS, Kuyumcu Kerkez Ö (2017) Preparation of magnetic MIL-101 (Cr) for efficient removal of ciprofloxacin. Environ Sci Pollut Res Int 24:25452–25461CrossRefGoogle Scholar
  16. 16.
    Wang T, Zhao P, Lu N, Chen H, Zhang C, Hou X (2016) Facile fabrication of Fe3O4 /MIL-101(Cr) for effective removal of acid red 1 and orange G from aqueous solution. Chem Eng J 295:403–413CrossRefGoogle Scholar
  17. 17.
    Asgharinezhad AA, Mollazadeh N, Ebrahimzadeh H, Mirbabaei F, Shekar N (2014) Magnetic nanoparticles based dispersive micro-solid-phase extraction as a novel technique for coextraction of acidic and basic drugs from biological fluids and waste water. J Chromatogr A 1338:1–8CrossRefGoogle Scholar
  18. 18.
    Babazadeh M, Hosseinzadehkhanmiri R, Abolhasani J, Ghorbanikalhor E, Hassanpour A (2015) Solid phase extraction of heavy metal ions from agricultural samples with the aid of a novel functionalized magnetic metal-organic framework. RSC Adv 5:19884–19892CrossRefGoogle Scholar
  19. 19.
    Babazadeh M, Khanmiri RH, Abolhasani J (2015) Synthesis and application of a novel functionalized magnetic metal-organic framework sorbent for determination of heavy metal ions in fish samples. Bull Chem Soc Jpn 88:871–879CrossRefGoogle Scholar
  20. 20.
    Ghorbani-Kalhor E (2016) A metal-organic framework nanocomposite made from functionalized magnetite nanoparticles and HKUST-1 (MOF-199) for preconcentration of Cd(II), Pb(II), and Ni(II). Microchim Acta 183:1–9CrossRefGoogle Scholar
  21. 21.
    Wei JP, Qiao B, Song WJ, Chen T, li F, Li BZ, Wang J, Han Y, Huang YF, Zhou ZJ (2015) Synthesis of magnetic framework composites for the discrimination of Escherichia coli at the strain level. Anal Chim Acta 868:36–44CrossRefGoogle Scholar
  22. 22.
    Yao W, Ying J, Zhang S, Zhang C, Wang H, Cai G (2015) Preparation of multi-walled carbon nanotubes decorated with Fe3O4 nanoparticles for determination of trace pyrethroid pesticides in water and honey samples. Chin J Chromatogr 33:342–347CrossRefGoogle Scholar
  23. 23.
    Bagheri H, Yamini Y, Safari M, Asiabi H, Karimi M, Heydari A (2016) Simultaneous determination of pyrethroids residues in fruit and vegetable samples via supercritical fluid extraction coupled with magnetic solid phase extraction followed by HPLC-UV. J Supercrit Fluids 107:571–580CrossRefGoogle Scholar
  24. 24.
    Gao L, Chen L (2013) Preparation of magnetic carbon nanotubes for separation of pyrethroids from tea samples. Microchim Acta 180(5–6):423–430CrossRefGoogle Scholar
  25. 25.
    Liu L, Zuo M, Cheng J, Matsadiq G, Zhou H, Li J (2011) Coupling polymer monolith microextraction to gas chromatography: determination of pyrethroids in water samples. Microchim Acta 173(1–2):127–133CrossRefGoogle Scholar
  26. 26.
    Dai X, Jia X, Zhao P, Wang T, Wang J, Huang P, He L, Hou X (2016) A combined experimental/computational study on metal-organic framework MIL-101(Cr) as a SPE sorbent for the determination of sulphonamides in environmental water samples coupling with UPLC-MS/MS. Talanta 154:581–588CrossRefGoogle Scholar
  27. 27.
    Wang LY, Bao J, Wang L, Zhang F, Li YD (2006) One-pot synthesis and bioapplication of amine-functionalized magnetite nanoparticles and hollow nanospheres. Chem Eur J 12:6341–6347CrossRefGoogle Scholar
  28. 28.
    Wang T, Wang J, Zhang C, Yang Z, Dai X, Cheng M, Hou X (2015) Metal-organic framework MIL-101(Cr) as a sorbent of porous membrane-protected micro-solid-phase extraction for the analysis of six phthalate esters from drinking water: a combination of experimental and computational study. Analyst 140:5308–5316CrossRefGoogle Scholar
  29. 29.
    Chang Q, Feng T, Song S, Zhou X, Wang C, Wang Z (2010) Analysis of eight pyrethroids in water samples by liquid–liquid microextraction based on solidification of floating organic droplet combined with gas chromatography. Microchim Acta 171(3–4):241–247CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2018

Authors and Affiliations

  1. 1.School of PharmacyShenyang Pharmaceutical UniversityShenyangPeople’s Republic of China
  2. 2.School of Pharmaceutical EngineeringShenyang Pharmaceutical UniversityShenyangPeople’s Republic of China

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