Abstract
A simple and fast method is described for the extraction of polycyclic aromatic hydrocarbons (PAHs) from complex samples. It is based on the use of a nanoferrofluid modified with a ternary hydrophobic deep eutectic solvent. A predictive model was used for the selection of the optimal eutectic mixture. The entire microextraction only takes a few minutes for completion. Under the optimal extraction conditions (by using menthol, borneol and camphor in a molar ratio of 5:1:4; 80 mg of nanoferrofluid), it offers marked improvements in terms of selectivity and sensitivity. The limits of detection range between 0.31 and 5.9 ng·L−1, and recoveries from spiked samples between 91.3 and 121%. In addition, the strong interactions between PAHs and the extractant were supported by quantum mechanical calculations. This results in a better insight into the microextraction mechanism, providing a fast, environmentally friendly and effective route for the optimization of pretreatment parameters. The method was successfully applied to the determination of the PAHs naphthalene, acenaphthylene, acenaphthene, fluorene, phenanthrene, anthracene, fluoranthene, pyrene, chrysene, benzo[b]fluoranthene, benzo[a]pyrene, dibenzo[a,h]anthracene, benzo[g,h,i]perylene and indeno[1,2,3-c,d]pyrene in 12 kinds of coffee samples after different roasting conditions.
Similar content being viewed by others
References
Gao P, da Silva E, Hou L, Denslow ND, Xiang P, Ma LQ (2018) Human exposure to polycyclic aromatic hydrocarbons: metabolomics perspective. Environ Int 119:466–477
da Silva SA, da Silva Torres EA, de Almeida AP, Sampaio GR (2018) Polycyclic aromatic hydrocarbons content and fatty acids profile in coconut, safflower, evening primrose and linseed oils. Food Chem 245:798–805
Payne MJ, Hurst WJ, Miller KB, Rank C, Stuart DA (2010) Impact of fermentation, drying, roasting, and Dutch processing on epicatechin and catechin content of cacao beans and cocoa ingredients. J Agric Food Chem 58(19):10518–10527
Ncube S, Madikizela L, Cukrowska E, Chimuka L (2018) Recent advances in the adsorbents for isolation of polycyclic aromatic hydrocarbons (PAHs) from environmental sample solutions. TrAC-Trend Anal Chem 99:101–116
Yang C, Wang J, Li D (2013) Microextraction techniques for the determination of volatile and semivolatile organic compounds from plants: a review. Anal Chim Acta 799:8–22
Afifah A, Syahrullail S, Sidik N (2016) Magnetoviscous effect and thermomagnetic convection of magnetic fluid: a review. Renew Sust Energ Rev 55:1030–1040
Nkurikiyimfura I, Wang Y, Pan Z (2013) Heat transfer enhancement by magnetic nanofluids-a review. Renew Sust Energ Rev 21:548–561
Hashemi B, Zohrabi P, Kim K-H, Shamsipur M, Deep A, Hong J (2017) Recent advances in liquid-phase microextraction techniques for the analysis of environmental pollutants. TrAC-Trend Anal Chem 97:83–95
Amde M, Liu J-F, Pang L (2015) Environmental application, fate, effects, and concerns of ionic liquids: a review. Environ Sci Technol 49(21):12611–12627
de los Angeles Fernandez M, Boiteux J, Espino M, Gomez FV, Silva MF (2018) Natural Deep eutectic solvents-mediated extractions: the way forward for sustainable analytical developments. Anal Chim Acta 1038:1–10. https://doi.org/10.1016/j.aca.2018.07.059
Zarei AR, Nedaei M, Ghorbanian SA (2018) Ferrofluid of magnetic clay and menthol based deep eutectic solvent: application in directly suspended droplet microextraction for enrichment of some emerging contaminant explosives in water and soil samples. J Chromatogr A 1553:32–42
Yousefi SM, Shemirani F, Ghorbanian SA (2017) Deep eutectic solvent magnetic bucky gels in developing dispersive solid phase extraction: application for ultra trace analysis of organochlorine pesticides by GC-micro ECD using a large-volume injection technique. Talanta 168:73–81
Lamei N, Ezoddin M, Ardestani MS, Abdi K (2017) Dispersion of magnetic graphene oxide nanoparticles coated with a deep eutectic solvent using ultrasound assistance for preconcentration of methadone in biological and water samples followed by GC-FID and GC-MS. Anal Bioanal Chem 409(26):6113–6121
Karimi M, Shabani AMH, Dadfarnia S (2016) Deep eutectic solvent-mediated extraction for ligand-less preconcentration of lead and cadmium from environmental samples using magnetic nanoparticles. Microchim Acta 183(2):563–571
Huang Y, Wang Y, Pan Q, Wang Y, Ding X, Xu K, Li N, Wen Q (2015) Magnetic graphene oxide modified with choline chloride-based deep eutectic solvent for the solid-phase extraction of protein. Anal Chim Acta 877:90–99
Florindo C, Branco L, Marrucho I (2017) Development of hydrophobic deep eutectic solvents for extraction of pesticides from aqueous environments. Fluid Phase Equilib 448:135–142
Wazeer I, Hayyan M, Hadj-Kali MK (2018) Deep eutectic solvents: designer fluids for chemical processes: designer fluids for chemical processes. J Appl Chem Biotechnol 93(4):945–958
Fan C, Liang Y, Dong HQ, Ding GL, Zhang WB, Tang G, Yang JL, Kong DD, Wang D, Cao YS (2017) In-situ ionic liquid dispersive liquid-liquid microextraction using a new anion-exchange reagent combined Fe3O4 magnetic nanoparticles for determination of pyrethroid pesticides in water samples. Anal Chim Acta 975:20–29
Wagle DV, Deakyne CA, Baker GA (2016) Quantum chemical insight into the interactions and thermodynamics present in choline chloride based Deep eutectic solvents. J Phys Chem B 120(27):6739–6746
Verma R, Banerjee T (2018) Liquid-liquid extraction of lower alcohols using menthol-based hydrophobic Deep eutectic solvent: experiments and COSMO-SAC predictions. Ind Eng Chem Res 57(9):3371–3381
Mullins E, Liu YA, Ghaderi A, Fast SD (2008) Sigma profile database for predicting solid solubility in pure and mixed solvent mixtures for organic pharmacological compounds with COSMO-based thermodynamic methods. Ind Eng Chem Res 47(5):1707–1725
Orecchio S, Ciotti VP, Culotta L (2009) Polycyclic aromatic hydrocarbons (PAHs) in coffee brew samples: analytical method by GC-MS, profile, levels and sources. Food Chem Toxicol 47(4):819–826
Ribeiro BD, Florindo C, Iff LC, Coelho MAZ, Marrucho IM (2015) Menthol-based eutectic mixtures: hydrophobic low viscosity solvents. ACS Sustain Chem Eng 3(10):2469–2477
Luo Q, Liu ZH, Yin H, Dang Z, Wu PX, Zhu NW, Lin Z, Liu Y (2018) Migration and potential risk of trace phthalates in bottled water: a global situation. Water Res 147:362–372
Cao J, Chen LY, Li MH, Cao FL, Zhao LG, Su EZ (2018) Two-phase systems developed with hydrophilic and hydrophobic deep eutectic solvents for simultaneously extracting various bioactive compounds with different polarities. Green Chem 20(8):1879–1886
Cao J, Yang M, Cao FL, Wang JH, Su EZ (2017) Tailor-made hydrophobic deep eutectic solvents for cleaner extraction of polyprenyl acetates from Ginkgo biloba leaves. J Clean Prod 152:399–405
Naik PK, Paul S, Banerjee T (2017) Liquid liquid equilibria measurements for the extraction of poly aromatic nitrogen hydrocarbons with a low cost deep eutectic solvent: experimental and theoretical insights. J Mol Liq 243:542–552
Ghatee MH, Moosavi F (2011) Physisorption of hydrophobic and hydrophilic 1-Alkyl-3-methylimidazolium ionic liquids on the Graphenes. J Phys Chem C 115(13):5626–5636
Gutiérrez-Serpa A, Napolitano-Tabares PI, Pino V, Jiménez-Moreno F, Jiménez-Abizanda AI (2018) Silver nanoparticles supported onto a stainless steel wire for direct-immersion solid-phase microextraction of polycyclic aromatic hydrocarbons prior to their determination by GC-FID. Microchim Acta 185(7):341
Yousefi SM, Shemirani F, Ghorbanian SA (2018) Hydrophobic deep eutectic solvents in developing microextraction methods based on solidification of floating drop: application to the trace HPLC/FLD determination of PAHs. Chromatographia 81(8):1201–1211
Farajzadeh MA, Mogaddam MRA, Feriduni B (2016) Simultaneous synthesis of a deep eutectic solvent and its application in liquid–liquid microextraction of polycyclic aromatic hydrocarbons from aqueous samples. RSC Adv 6(53):47990–47996
Du J, Wang H, Zhang R, Wang X, Du X, Lu X (2018) Oriented ZnO nanoflakes on nickel-titanium alloy fibers for solid-phase microextraction of polychlorinated biphenyls and polycyclic aromatic hydrocarbons. Microchim Acta 185(9):441
Wang W, Li Z, Wang W, Zhang L, Zhang S, Wang C, Wang Z (2018) Microextraction of polycyclic aromatic hydrocarbons by using a stainless steel fiber coated with nanoparticles made from a porous aromatic framework. Microchim Acta 185(1):20
Ko JH, Das G, Kim JE, Shin HS (2018) Study on formation of nitrated polycyclic aromatic hydrocarbons from different roasting condition in coffee. J Food Sci Tech Mys 55(10):3991–4000
Acknowledgements
The authors acknowledge financial support of this work by the National Key Research and Development Program of China (2018YFC1604306) and Natural Science Foundation of Beijing (2184100).
Author information
Authors and Affiliations
Corresponding author
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 43 kb)
Rights and permissions
About this article
Cite this article
Fan, C., Cao, X., Han, T. et al. Selective microextraction of polycyclic aromatic hydrocarbons using a hydrophobic deep eutectic solvent composed with an iron oxide-based nanoferrofluid. Microchim Acta 186, 560 (2019). https://doi.org/10.1007/s00604-019-3651-y
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s00604-019-3651-y