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Nanoporous carbon derived from a metal organic framework as a new kind of adsorbent for dispersive solid phase extraction of benzoylurea insecticides

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Abstract

We describe the preparation of nanoporous carbon using a metal-organic framework (MOF) as a template and furfuryl alcohol as the source for carbon. The MOF consists of a zeolitic framework (ZIF-8) that was obtained from 2-methylimidazole and Zn(II) ions. ZIF-8 was soaked with furfuryl alcohol which then was carbonized at 900 °C. The resulting nanoporous carbon (MOF-C) exhibits a high specific surface area and a large pore volume. It was used as a dispersive solid-phase adsorbent for the preconcentration of the benzoylurea insecticides diflubenzuron, triflumuron, hexaflumuron and teflubenzuron from water and tangerine samples. Under optimized conditions, the methods exhibits excellent extraction performance. The insecticides can be quantified via HPLC with UV detection in the 0.5 to 100 ng mL−1 concentration range in case of spiked tap water, and in the 2.0 to 200 ng g−1 concentration range in case of tangerines. The limits of detection range from 0.10 to 0.23 ng mL−1 in case of water samples, and from 0.34 to 0.71 ng g−1 for tangerine sample (at an S/N ratio of 3). Mean recoveries range from 91.7 to 107.9 %, with relative standard deviations of <7.1 %. The results indicate that the method was efficient for the preconcentration of trace levels of benzoylurea insecticides from water and tangerine samples. Conceivably, this new adsorbent has a large potential with respect to the enrichment of other organic pollutants from various kinds of samples.

Nanoporous carbon was prepared using metal-organic framework (zeolitic imidazolate framework, ZIF-8) as template with furfuryl alcohol as carbon precursor, and was used as dispersive solid phase extraction adsorbent for the enrichment of some benzoylurea insecticides from water and tangerine samples.

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References

  1. Dadfarnia S, Haji Shabani AM (2010) Recent development in liquid phase microextraction for determination of trace level concentration of metals—a review. Anal Chim Acta 658:107–119

    Article  CAS  Google Scholar 

  2. Jamali MR, Firouzjah A, Rahnama R (2013) Solvent-assisted dispersive solid phase extraction. Talanta 116:454–459

    Article  CAS  Google Scholar 

  3. Anastassiades M, Lehotay SJ, Štajnbaher D, Schenck FJ (2003) Fast and easy multiresidue method employing acetonitrile extraction/partitioning and “dispersive solid-phase extraction” for the determination of pesticide residues in produce. J AOAC Int 86:412–431

    CAS  Google Scholar 

  4. Fontana AR, Camargo A, Martinez LD, Altamirano JC (2011) Dispersive solid-phase extraction as a simplified clean-up technique for biological sample extracts. Determination of polybrominated diphenyl ethers by gas chromatography–tandem mass spectrometry. J Chromatogr A 1218:2490–2496

    Article  CAS  Google Scholar 

  5. Cerqueira MB, Caldas SS, Primel EG (2014) New sorbent in the dispersive solid phase extraction step of quick, easy, cheap, effective, rugged, and safe for the extraction of organic contaminants in drinking water treatment sludge. J Chromatogr A 1336:10–22

    Article  CAS  Google Scholar 

  6. Peng Y, Xie Y, Luo J, Nie L, Chen Y, Chen L, Du S, Zhang Z (2010) Molecularly imprinted polymer layer-coated silica nanoparticles toward dispersive solid-phase extraction of trace sulfonylurea herbicides from soil and crop samples. Anal Chim Acta 674:190–200

    Article  CAS  Google Scholar 

  7. Cai M, Chen X, Wei X, Pan S, Zhao Y, Jin M (2014) Dispersive solid-phase extraction followed by high-performance liquid chromatography/tandem mass spectrometry for the determination of ricinine in cooking oil. Food Chem 158:459–465

    Article  CAS  Google Scholar 

  8. Guo B, Huang Z, Wang M, Wang X, Zhang Y, Chen B, Li Y, Yan H, Yao S (2010) Simultaneous direct analysis of benzimidazole fungicides and relevant metabolites in agricultural products based on multifunction dispersive solid-phase extraction and liquid chromatography–mass spectrometry. J Chromatogr A 1217:4796–4807

    Article  CAS  Google Scholar 

  9. Hou XL, Wu YL, Yang T, Du XD (2013) Multi-walled carbon nanotubes–dispersive solid-phase extraction combined with liquid chromatography–tandem mass spectrometry for the analysis of 18 sulfonamides in pork. J Chromatogr B 929:107–115

    Article  CAS  Google Scholar 

  10. Jiménez-Soto JM, Cárdenas S, Valcárcel M (2012) Dispersive micro solid-phase extraction of triazines from waters using oxidized single-walled carbon nanohorns as sorbent. J Chromatogr A 1245:17–23

    Article  Google Scholar 

  11. Malone E, Elliott C, Kennedy D, Regan L (2010) Rapid confirmatory method for the determination of sixteen synthetic growth promoters and bisphenol A in bovine milk using dispersive solid-phase extraction and liquid chromatography–tandem mass spectrometry. J Chromatogr B 878:1077–1084

    Article  CAS  Google Scholar 

  12. Aiyappa HB, Pachfule P, Banerjee R, Kurungot S (2013) Porous carbons from nonporous MOFs: influence of ligand characteristics on intrinsic properties of end carbon. Cryst Growth Des 13:4195–4199

    Article  CAS  Google Scholar 

  13. Liu B, Shioyama H, Jiang H, Zhang X, Xu Q (2010) Metal–organic framework (MOF) as a template for syntheses of nanoporous carbons as electrode materials for supercapacitor. Carbon 48:456–463

    Article  CAS  Google Scholar 

  14. Ryoo R, Joo SH, Jun S (1999) Synthesis of highly ordered carbon molecular sieves via template-mediated structural transformation. J Phys Chem B 103:7743–7746

    Article  CAS  Google Scholar 

  15. Jun S, Joo SH, Ryoo R, Kruk M, Jaroniec M, Liu Z, Ohsuna T, Terasaki O (2000) Synthesis of new, nanoporous carbon with hexagonally ordered mesostructure. J Am Chem Soc 122:10712–10713

    Article  CAS  Google Scholar 

  16. Su F, Zhao X, Lv L, Zhou Z (2004) Synthesis and characterization of microporous carbons templated by ammonium-form zeolite Y. Carbon 42:2821–2831

    Article  CAS  Google Scholar 

  17. Hu M, Reboul J, Furukawa S, Torad NL, Ji Q, Srinivasu P, Ariga K, Kitagawa S, Yamauchi Y (2012) Direct carbonization of Al-based porous coordination polymer for synthesis of nanoporous carbon. J Am Chem Soc 134:2864–2867

    Article  CAS  Google Scholar 

  18. Liu J, Wang H, Wu C, Zhao Q, Wang X, Yi L (2014) Preparation and characterization of nanoporous carbon-supported platinum as anode electrocatalyst for direct borohydride fuel cell. Int J Hydrog Energy 39:6729–6736

    Article  CAS  Google Scholar 

  19. Liu B, Shioyama H, Akita T, Xu Q (2008) Metal-organic framework as a template for porous carbon synthesis. J Am Chem Soc 130:5390–5391

    Article  CAS  Google Scholar 

  20. Jiang HL, Liu B, Lan YQ, Kuratani K, Akita T, Shioyama H, Zong F, Xu Q (2011) From metal–organic framework to nanoporous carbon: toward a very high surface area and hydrogen uptake. J Am Chem Soc 133:11854–11857

    Article  CAS  Google Scholar 

  21. Hao L, Wang C, Wu Q, Li Z, Zang X, Wang Z (2014) Metal-organic framework derived magnetic nanoporous carbon: a novel adsorbent for magnetic solid-phase extraction. Anal Chem 86:12199–12205

    Article  CAS  Google Scholar 

  22. Radhakrishnan L, Reboul J, Furukawa S, Srinivasu P, Kitagawa S, Yamauchi Y (2011) Preparation of microporous carbon fibers through carbonization of Al-based porous coordination polymer (Al-PCP) with furfuryl alcohol. Chem Mater 23:1225–1231

    Article  CAS  Google Scholar 

  23. Liu RL, Ji WJ, He T, Zhang ZQ, Zhang J, Dang FQ (2014) Fabrication of nitrogen-doped hierarchically porous carbons through a hybrid dual-template route for CO2 capture and haemoperfusion. Carbon 76:84–95

    Article  CAS  Google Scholar 

  24. Pachfule P, Biswal BP, Banerjee R (2012) Control of porosity by using isoreticular zeolitic imidazolate frameworks (IRZIFs) as a template for porous carbon synthesis. Chem Eur J 18:11399–11408

    Article  CAS  Google Scholar 

  25. Yang SJ, Kim T, Im JH, Kim YS, Lee K, Jung H, Park CR (2012) MOF-derived hierarchically porous carbon with exceptional porosity and hydrogen storage capacity. Chem Mater 24:464–470

    Article  CAS  Google Scholar 

  26. Chaikittisilp W, Ariga K, Yamauchi Y (2013) A new family of carbon materials: synthesis of MOF-derived nanoporous carbons and their promising applications. J Mater Chem A 1:14–19

    Article  CAS  Google Scholar 

  27. Wang CH, Ma XX, Wang C, Wu QH, Wang Z (2014) Poly (vinylidene fluoride) membrane based thin film microextraction for enrichment of benzoylurea insecticides from water samples followed by their determination with HPLC. Chin Chem Lett 25:1625–1629

    Article  CAS  Google Scholar 

  28. Zhang J, Li M, Yang M, Peng B, Li Y, Zhou W, Gao H, Lu R (2012) Magnetic retrieval of ionic liquids: Fast dispersive liquid–liquid microextraction for the determination of benzoylurea insecticides in environmental water samples. J Chromatogr A 1254:23–29

    Article  CAS  Google Scholar 

  29. Vázquez MP, Vázquez PP, Galera MM, Moreno AU (2014) Comparison of two ionic liquid dispersive liquid–liquid microextraction approaches for the determination of benzoylurea insecticides in wastewater using liquid chromatography–quadrupole-linear ion trap–mass spectrometry: Evaluation of green parameters. J Chromatogr A 1356:1–9

    Article  Google Scholar 

  30. Tomsej T, Hajslova J (1995) Determination of benzoylurea insecticides in apples by high-performance liquid chromatography. J Chromatogr A 704:513–517

    Article  CAS  Google Scholar 

  31. Brutti M, Blasco C, Picó Y (2010) Determination of benzoylurea insecticides in food by pressurized liquid extraction and LC-MS. J Sep Sci 33:1–10

    Article  CAS  Google Scholar 

  32. Zhou Q, Zhang X (2010) Combination of ultrasound-assisted ionic liquid dispersive liquid-phase microextraction and high performance liquid chromatography for the sensitive determination of benzoylureas pesticides in environmental water samples. J Sep Sci 33:3734–3740

    Article  CAS  Google Scholar 

  33. Chaikittisilp W, Hu M, Wang H, Huang HS, Fujita T, Wu KCW, Chen LC, Yamauchi Y, Ariga K (2012) Nanoporous carbons through direct carbonization of a zeolitic imidazolate framework for supercapacitor electrodes. Chem Commun 48:7259–7261

    Article  CAS  Google Scholar 

  34. Huang Y, Zhou Q, Xie G, Liu H, Lin H (2010) Titanium dioxide nanotubes for solid phase extraction of benzoylurea insecticides in environmental water samples, and determination by high performance liquid chromatography with UV detection. Microchim Acta 172:109–115

    Article  Google Scholar 

  35. Berrada H, Font G, Molto JC (2000) Indirect analysis of urea herbicides from environmental water using solid-phase microextraction. J Chromatogr A 890:303–312

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Financial supports from the National Natural Science Foundation of China (No. 31171698, 31471643), the Innovation Research Program of the Department of Education of Hebei for Hebei Provincial Universities (LJRC009), the Scientific and Technological Research Foundation of Department of Education of Hebei Province (No. ZD20131033), and the Natural Science Foundations of Hebei (No. B2012204028) are gratefully acknowledged.

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Correspondence to Qiuhua Wu or Zhi Wang.

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Liu, X., Wang, C., Wang, Z. et al. Nanoporous carbon derived from a metal organic framework as a new kind of adsorbent for dispersive solid phase extraction of benzoylurea insecticides. Microchim Acta 182, 1903–1910 (2015). https://doi.org/10.1007/s00604-015-1530-8

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  • DOI: https://doi.org/10.1007/s00604-015-1530-8

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