Skip to main content
SpringerLink
Log in

Net-like mesoporous carbon nanocomposites for magnetic solid-phase extraction of sulfonamides prior to their quantitation by UPLC-HRMS

  • Original Paper
  • Published:
Microchimica Acta Aims and scope Submit manuscript

Abstract

A net-like mesoporous carbon nanocomposite (MCN) was hydrothermally prepared by using filter paper as the raw material. The MCN contains magnetic nanoparticles of type Fe3O4 which result from the addition of Fe(NO3)3·9H2O during synthesis. The MCN was characterized by X-ray diffraction, Fourier transform infrared spectroscopy, scanning electron microscopy, transmission electron microscopy, Raman spectra, Brunauer-Emmett-Teller methods and vibrating sample magnetometry. The MCN is shown to be a viable material for magnetic solid-phase extraction of trace sulfonamides (SAs) including sulfadiazine, sulfapyridine, sulfamerazine, sulfamethazine, sulfamethizole, sulfamethoxypridazine, sulfachloropyridazine and sulfadimethoxine. Following desorption with acetone containing 0.5% ammonia, the SAs were quantified by UPLC with high-resolution mass spectrometric detection. With sulfamethazine as an example, the adsorption equilibrium configurations and the major interaction mechanism between SAs and the MCN were calculated by using density functional theory. Under the optimal conditions, the calibration plots are linear in the 0.05–10 ng·mL−1 SA concentration ranges. The limits of detection are between 7.2 and 13.6 ng·L−1. The recoveries from spiked samples ranged from 79 to 107%, with relative standard deviations of <9.9%.

Schematic representation of nanocomposite preparation, adsorption mechanism of sulfonamide and magnetic solid-phase extraction (MSPE) for sulfadiazine (SDZ), sulfapyridine (SPD), sulfamerazine (SMR), sulfamethazine (SMZ), sulfamethizole (SMT), sulfamethoxypridazine (SMP), sulfachloropyridazine (SCP) and sulfadimethoxine (SDMX). Quantification was accomplished by UPLC with high-resolution mass spectrometric detection

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Chen Z, Yu C, Xi J, Tang S, Bao T, Zhang J (2019) A hybrid material prepared by controlled growth of a covalent organic framework on amino-modified MIL-68 for pipette tip solid-phase extraction of sulfonamides prior to their determination by HPLC. Microchim Acta 186:393. https://doi.org/10.1007/s00604-019-3513-7

    Article  CAS  Google Scholar 

  2. Doerge DR, Bajic S, Lowes S (1993) Multiresidue analysis of sulfonamides using liquid chromatography with atmospheric pressure chemical ionization mass spectrometry. Rapid Commun Mass Spectrom 7:1126–1130. https://doi.org/10.1002/rcm.1290071214

    Article  CAS  Google Scholar 

  3. Ancuceanu R (2010) Maximum residue limits of veterinary medicinal products and their regulation in European Community law. Eur Law J 9:215–240. https://doi.org/10.1111/1468-0386.00176

    Article  Google Scholar 

  4. Gao Q, Luo D, Ding J, Feng Y (2010) Rapid magnetic solid-phase extraction based on magnetite/silica/poly (methacrylic acid-co-ethylene glycol dimethacrylate) composite microspheres for the determination of sulfonamide in milk samples. J Chromatogr A 1217:5602–5609. https://doi.org/10.1016/j.chroma.2010.06.067

    Article  CAS  Google Scholar 

  5. Wu M, Fu L, Hu Y, Su J, Jing S, Zhou H, Zhan J (2018) Multiplex on-bead isotope dimethyl labeling coupled with liquid chromatography-high-resolution mass spectrometry for quantitative analysis of sulfonamides in estuarine ice. Anal Chem 90:12172–12179. https://doi.org/10.1021/acs.analchem.8b03220

    Article  CAS  Google Scholar 

  6. Dmitrienko SG, Kochuk EV, Tolmacheva VV, Apyari VV, Zolotov YA (2015) Determination of the total content of some sulfonamides in milk using solid-phase extraction coupled with off-line derivatization and spectrophotometric detection. Food Chem 188:51–56. https://doi.org/10.1016/j.foodchem.2015.04.123

    Article  CAS  Google Scholar 

  7. Jia X, Zhao P, Ye X, Zhang L, Wang T, Chen Q, Hou X (2017) A novel metal-organic framework composite MIL-101(Cr)@GO as an efficient sorbent in dispersive micro-solid phase extraction coupling with UHPLC-MS/MS for the determination of sulfonamides in milk samples. Talanta 169:227–238. https://doi.org/10.1016/j.talanta.2016.08.086

    Article  CAS  Google Scholar 

  8. Xia L, Liu L, Lv X, Qu F, Li G, You J (2017) Towards the determination of sulfonamides in meat samples: a magnetic and mesoporous metal-organic framework as an efficient sorbent for magnetic solid phase extraction combined with high-performance liquid chromatography. J Chromatogr A 1500:24–31. https://doi.org/10.1016/j.chroma.2017.04.004

    Article  CAS  Google Scholar 

  9. Fu L, Zhou H, Miao E, Lu S, Jing S, Hu Y, Wei L, Zhan J, Wu M (2019) Functionalization of amino terminated carbon nanotubes with isocyanates for magnetic solid phase extraction of sulfonamides from milk and their subsequent determination by liquid chromatography-high resolution mass spectrometry. Food Chem 289:701–707. https://doi.org/10.1016/j.foodchem.2019.03.097

    Article  CAS  Google Scholar 

  10. Xu Y, Ding J, Chen H, Zhao Q, Hou J, Yan J, Wang H, Ding L, Ren N (2013) Fast determination of sulfonamides from egg samples using magnetic multiwalled carbon nanotubes as adsorbents followed by liquid chromatography-tandem mass spectrometry. Food Chem 140:83–90. https://doi.org/10.1016/j.foodchem.2013.02.078

    Article  CAS  Google Scholar 

  11. Tolmacheva VV, Apyari VV, Furletov AA, Dmitrienko SG, Zolotov YA (2016) Facile synthesis of magnetic hypercrosslinked polystyrene and its application in the magnetic solid-phase extraction of sulfonamides from water and milk samples before their HPLC determination. Talanta 152:203–210. https://doi.org/10.1016/j.talanta.2016.02.010

    Article  CAS  Google Scholar 

  12. Deng Z, Xu G, Wang X, Wang X, Wang ML, Lin JM, Zhao RS (2018) A Zr(IV)-based porphyrinic metal-organic framework as a solid-phase sorbent for extraction of sulfonamides prior to their quantitation by LC-MS. Microchim Acta 185:450. https://doi.org/10.1007/s00604-018-2985-1

    Article  CAS  Google Scholar 

  13. Pang L, Zhang W, Zhang W et al (2017) Magnetic graphene solid-phase extraction in the determination of polycyclic aromatic hydrocarbons in water. RSC Adv 7:53720–53727. https://doi.org/10.1039/C7RA10551G

    Article  CAS  Google Scholar 

  14. Yu J, Zhu S, Pang L, Chen P, Zhu GT (2018) Porphyrin-based magnetic nanocomposites for efficient extraction of polycyclic aromatic hydrocarbons from water samples. J Chromatogr A 1540:1–10. https://doi.org/10.1016/j.chroma.2018.02.006

    Article  CAS  Google Scholar 

  15. Yu J, Zhang D, Zhu S et al (2019) Eco-friendly and facile one-step synthesis of a three dimensional net-like magnetic mesoporous carbon derived from wastepaper as a renewable adsorbent. RSC Adv 9:12419–12427. https://doi.org/10.1039/C9RA01332F

    Article  CAS  Google Scholar 

  16. Liu Z, Lin X, Liu X, Li J, Zhou W, Gao H, Zhang S, Lu R (2019) Magnetic nanoparticles modified with hyperbranched polyamidoamine for the extraction of benzoylurea insecticides prior to their quantitation by HPLC. Microchim Acta 186:351. https://doi.org/10.1007/s00604-019-3450-5

    Article  CAS  Google Scholar 

  17. Wang Y, Wu X, Zhang L (2018) Three-dimensional hollow porous raspberry-like hierarchical Co/Ni@carbon microspheres for magnetic solid-phase extraction of pyrethroids. Microchim Acta 185:1–9. https://doi.org/10.1007/s00604-018-2973-5

    Article  CAS  Google Scholar 

  18. Zuo Y, Wang G, Peng J et al (2016) Hybridization of graphene nanosheets and carbon-coated hollow Fe3O4 nanoparticles as a high-performance anode material for lithium-ion batteries. J Mater Chem A 4:2453–2460. https://doi.org/10.1039/c5ta09742h

    Article  CAS  Google Scholar 

  19. Li M, Du H, Kuai L et al (2017) Scalable dry production process of a superior 3D net-like carbon-based iron oxide anode material for lithium-ion batteries. Angew Chemie Int Ed 56:12649–12653. https://doi.org/10.1002/anie.201707647

    Article  CAS  Google Scholar 

  20. Xu Y, Deng F, Pang Q et al (2018) Development of waste-derived sorbents from biomass and brominated flame retarded plastic for elemental mercury removal from coal-fired flue gas. Chem Eng J 350:911–919. https://doi.org/10.1016/j.cej.2018.06.055

    Article  CAS  Google Scholar 

  21. Fan B, Jia L, Li B et al (2018) Study on the effects of the pyrolysis atmosphere on the elemental mercury adsorption characteristics and mechanism of biomass char. Energy Fuel 32:6869–6878. https://doi.org/10.1021/acs.energyfuels.8b00783

    Article  CAS  Google Scholar 

  22. Ma L, Fan X, Jia L, Wang J, Wang S, Zhao L (2017) Multiresidue analysis of glucocorticoids in milk by LC-MS/MS with low-temperature purification and dispersive solid-phase extraction. J Sep Sci 40:2759–2768. https://doi.org/10.1002/jssc.201700064

    Article  CAS  Google Scholar 

  23. Huang Y, Peng J, Huang X (2018) One-pot preparation of magnetic carbon adsorbent derived from pomelo peel for magnetic solid-phase extraction of pollutants in environmental waters. J Chromatogr A 1546:28–35. https://doi.org/10.1016/j.chroma.2018.03.001

    Article  CAS  Google Scholar 

  24. Chen Q, Zheng J, Xu J et al (2019) Insights into sulfamethazine adsorption interfacial interaction mechanism on mesoporous cellulose biochar: coupling DFT/FOT simulations with experiments. Chem Eng J 356:341–349. https://doi.org/10.1016/j.cej.2018.09.055

    Article  CAS  Google Scholar 

  25. Zhang Q, Li G, Xiao X, Zhan S, Cao Y (2016) Efficient and selective enrichment of ultratrace cytokinins in plant samples by magnetic perhydroxy-cucurbit[8]uril microspheres. Anal Chem 88:4055–4062. https://doi.org/10.1021/acs.analchem.6b00408

    Article  CAS  Google Scholar 

  26. Yan Y, Sun S, Song Y, Yan X, Guan W, Liu X, Shi W (2013) Microwave-assisted in situ synthesis of reduced graphene oxide-BiVO4 composite photocatalysts and their enhanced photocatalytic performance for the degradation of ciprofloxacin. J Hazard Mater 250:106–114. https://doi.org/10.1016/j.jhazmat.2013.01.051

    Article  CAS  Google Scholar 

  27. Wang H, Hu X, Guo Y et al (2018) Removal of copper ions by few-layered graphene oxide nanosheets from aqueous solutions: external influences and adsorption mechanisms. J Chem Technol Biotechnol 93:2447–2455. https://doi.org/10.1002/jctb.5601

    Article  CAS  Google Scholar 

  28. Jiang L, Liu Y, Liu S et al (2017) Fabrication of beta-cyclodextrin/poly (L-glutamic acid) supported magnetic graphene oxide and its adsorption behavior for 17 beta-estradiol. Chem Eng J 308:597–605. https://doi.org/10.1016/j.cej.2016.09.067

    Article  CAS  Google Scholar 

  29. Becke AD (1996) Density-functional thermochemistry. IV A new dynamical correlation functional and implications for exact-exchange mixing. J Chem Phys 104:1040–1046. https://doi.org/10.1063/1.470829

    Article  CAS  Google Scholar 

  30. Grimme S, Antony J, Ehrlich S, Krieg H (2010) A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu. J Chem Phys 132:154104. https://doi.org/10.1063/1.3382344

    Article  CAS  Google Scholar 

  31. Espinosa E, Molins E, Lecomte C (1998) Hydrogen bond strengths revealed by topological analyses of experimentally observed electron densities. Chem Phys Lett 285:170–173. https://doi.org/10.1016/S0009-2614(98)00036-0

    Article  CAS  Google Scholar 

  32. Casado J, Santillo D, Johnston P (2018) Multi-residue analysis of pesticides in surface water by liquid chromatography quadrupole-Orbitrap high resolution tandem mass spectrometry. Anal Chim Acta 1024:1–17. https://doi.org/10.1016/j.aca.2018.04.026

    Article  CAS  Google Scholar 

  33. Xu Y, Li J, Jiang L, Li Z, Li Y, Ding L (2018) Simultaneous determination of sulfonamides and fluoroquinolones from environmental water based on magnetic double-template molecularly imprinting technique. Environ Sci Pollut Res 25:16121–16134. https://doi.org/10.1007/s11356-018-1581-6

    Article  CAS  Google Scholar 

  34. Du X, Wu Y, Yang H, Yang T (2012) Simultaneous determination of 10 beta(2)-agonists in swine urine using liquid chromatography-tandem mass spectrometry and multi-walled carbon nanotubes as a reversed dispersive solid phase extraction sorbent. J Chromatogr A 1260:25–32. https://doi.org/10.1016/j.chroma.2012.08.066

    Article  CAS  Google Scholar 

  35. Frenich AG, Romero-González R, Gómez-Pérez ML, Vidal JLM (2011) Multi-mycotoxin analysis in eggs using a QuEChERS-based extraction procedure and ultra-high-pressure liquid chromatography coupled to triple quadrupole mass spectrometry. J Chromatogr A 1218:4349–4356. https://doi.org/10.1016/j.chroma.2011.05.005

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The study was supported by grants from Environmental Protection Department of Hubei Province (No. 2017HB04) and the Fundamental Research Funds for the Central Universities, China University of Geosciences (Wuhan) (No. CUG170102). We kindly thank Peng Yue’ e, Faculty of Materials Science and Chemistry, China University of Geosciences, for the UPLC-HRMS technology support.

Author information

Author notes

  1. Siyuan Di and Jing Yu contributed equally to this work.

Authors and Affiliations

  1. State Key Laboratory of Biogeology and Environmental Geology, China University of Geosciences, Wuhan, 430074, China

    Siyuan Di, Jing Yu, Pin Chen, Gangtian Zhu & Shukui Zhu

Authors
  1. Siyuan Di
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jing Yu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Pin Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Gangtian Zhu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Shukui Zhu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Shukui Zhu.

Ethics declarations

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

Additional information

Publisher’s note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

ESM 1

(DOCX 22161 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Di, S., Yu, J., Chen, P. et al. Net-like mesoporous carbon nanocomposites for magnetic solid-phase extraction of sulfonamides prior to their quantitation by UPLC-HRMS. Microchim Acta 187, 112 (2020). https://doi.org/10.1007/s00604-019-4072-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s00604-019-4072-7

Keywords

Search

Navigation