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Acute Toxicity of Imidazole Nitrate Ionic Liquids with Varying Chain Lengths to Earthworms (Eisenia foetida)

Abstract

When ionic liquids (ILs) first came into use, we thought that they were safe. However, upon further investigation, researchers found that ILs are not harmless. In this study, the model soil organism, earthworms (Eisenia foetida), were used to study the acute toxicity of imidazole nitrate ionic liquids with varying chain lengths from 2 to 12. The experiment used two different methods, a filter paper contact test (48 h) and an artificial soil test (14 days), to determine the toxicity. These results demonstrated that the toxicity increased with the length of carbon chains until C8 and that the cut-off effect occurred at 1-octyl-3-methyl imidazole nitrates.Then, the toxicity began to increase again. At the same time, the concentrations of [C10mim]NO3 and [C12mim]NO3 were determined by high performance liquid chromatography and demonstrated that ILs were stable throughout the experiment. The present study revealed the acute toxicity of ILs with varying chain lengths.

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References

  1. Bubalo MC, Radošević K, Redovniković IR, Halambek J, Srček VG (2014) A brief overview of the potential environmental hazards of ionic liquids. Ecotoxicol Environ Saf 99:1–12

    Article  Google Scholar 

  2. Cho CW, Pham TPT, Jeon YC et al (2007) Toxicity of imidazolium salt with anion bromide to a phytoplankton Selenastrum capricornutum: effect of alkyl-chain length. Chemosphere 69:1003–1007

    CAS  Article  Google Scholar 

  3. Cho CW, Jeon YC, Pham TPT, Vijayaraghavan K, Yun YS (2008) The ecotoxicity of ionic liquids and traditional organic solvents on microalga Selenastrum capricornutum. Ecotoxicol Environ Saf 71:166–171

    CAS  Article  Google Scholar 

  4. Couling DJ, Bernot RJ, Docherty KM, Dixon JK, Maginn EJ (2006) Assessing the factors responsible for ionic liquid toxicity to aquatic organisms via quantitative structure-property relationship modeling. Green Chem 8:82–90

    CAS  Article  Google Scholar 

  5. Das RN, Roy K (2013) Advances in QSPR/QSTR models of ionic liquids for the design of greener solvents of the future. Mol Divers 17:151–196

    CAS  Article  Google Scholar 

  6. Farwell JK, Mitchell RE, Everett DJ, Hill RE (1999) The toxicity of cyanobacterial toxins in the mouse: I. Microcystin-LR. Hum Exp Toxicol 18:162–167

    Article  Google Scholar 

  7. Huddleston JG, Visser AE, Reichert WM et al (2001) Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation. Green Chem 3:156–164

    CAS  Article  Google Scholar 

  8. Julianne M, Thomas PT, Ryan AL, Brendan FG (2015) Galleria mellonella as a novel in vivo model for assessment of the toxicity of 1-alkyl-3-methylimidazolium chloride ionic liquids. Chemosphere 139:197–201

    Article  Google Scholar 

  9. Kelsey JW, Peters R, Slizovskiy IB (2008) Effects of incubation time and organism density on the bioaccumulation of soil-borne p,p′-DDE by the earthworm, Eisenia foetida. Bull Environ Contam Toxicol 81:266–269

    CAS  Article  Google Scholar 

  10. Li XY, Luo YR, Yun MX et al (2010) Effects of 1-methyl-3-octylimidazolium bromide on the anti-oxidant system of earthworm. Chemosphere 78:853–858

    CAS  Article  Google Scholar 

  11. Liu T, Zhu LS, Xie H et al (2014) Effects of the ionic liquid 1-octyl-3-methylimidazolium hexafluorophosphate on the growth of wheat seedlings. Environ Sci Pollut Res 21:3936–3945

    CAS  Article  Google Scholar 

  12. Liu HJ, Zhang XQ, Chen CD, Du ST, Dong Y (2015) Effects of imidazolium chloride ionic liquids and their toxicity to Scenedesmus obliquus. Ecotoxicol Environ Saf 122:83–90

    CAS  Article  Google Scholar 

  13. Liu T, Wang J, Wang J et al (2016a) Growth, physiological and biochemical responses of wheat seedlings to imidazolium-based ionic liquids 1-octyl-3-methylimidazolium chloride and 1-octyl-3-methylimidazolium bromide. Bull Environ Contam Toxicol 94:544–549

    Article  Google Scholar 

  14. Liu XY, Zhang SM, Wang JH et al (2016b) Biochemical responses and DNA damage in earthworms (Eisenia fetida) induced by ionic liquid [Omim]PF6. Environ Sci Pollut Res 23:6836–6844

    CAS  Article  Google Scholar 

  15. Luo YR, Wang SH, Yun MX et al (2009) The toxic effects of ionic liquids on the activities of acetyl cholinesterase and cellulase in earthworms. Chemosphere 77:313–318

    CAS  Article  Google Scholar 

  16. Ma JM, Cai LL, Zhang BJ et al (2010) Acute toxicity and effects of 1-alkyl-3-methylimidazolium bromide ionic liquids on green algae. Ecotox Environ Safe 73:1465–1469

    CAS  Article  Google Scholar 

  17. McFarlane J, Ridenour WB, Luo H et al (2005) Room temperature ionic liquids for separating organics from produced water. Sep Sci Technol 40:1245–1265

    CAS  Article  Google Scholar 

  18. Nichthauser J, Mrozik W, Markowska A, Stepnowski P (2009) Analysis of residual ionic liquids in environmental samples: development of extraction methods. Chemosphere 74:515–521

    CAS  Article  Google Scholar 

  19. Organisation for Economic Co-operation and Development (2004) Test No. 222: Earthworm Reproduction Test (Eisenia foetida/andrei)

  20. Panz K, Miksch K, Sójka T (2013) Synergetic toxic effect of an explosive material mixture in soil. Bull Environ Contam Toxicol 91:555–559

    CAS  Article  Google Scholar 

  21. Peter W, Annegret S (2010) Handbook of green chemistry. Wiley, New York

    Google Scholar 

  22. Pham TPT, Cho CW, Yun YS (2010) Environmental fate and toxicity of ionic liquids: a review. Water Res 44:352–372

    CAS  Article  Google Scholar 

  23. Ranke J, Mlter K, Stock F et al (2004) Biological effects of imidazolium ionic liquids with varying chain lengths in acute Vibrio fischeri and WST-1 cell viability assays. Ecotoxicol Environ Saf 58:396–404

    CAS  Article  Google Scholar 

  24. Sheldon R (2001) Catalytic reactions in ionic liquids. Chem Commun 23:2399–2407

    Article  Google Scholar 

  25. Stepnowski P (2005) Preliminary assessment of the sorption of some alkyl imidazolium cations as used in ionic liquids to soils and sediments. Aust J Chem 58:170–173

    CAS  Article  Google Scholar 

  26. Sun X, Zhu LS, Wang JH et al (2017) Toxic effects of ionic liquid 1-octyl-3-methylimidazolium tetrafluoroborate on soil enzyme activity and soil microbial community diversity. Ecotoxicol Environ Saf 135:201–208

    CAS  Article  Google Scholar 

  27. Tsarpali V, Dailianis S (2015) Toxicity of two imidazolium ionic liquids, [Bmim][BF4] and [Omim][BF4], to standard aquatic test organisms: role of acetone in the induced toxicity. Ecotoxicol Environ Saf 117:62–71

    CAS  Article  Google Scholar 

  28. Zhou HM, Shen YY, Lv P, Wang JJ, Li P (2015) Degradation pathway and kinetics of 1-alkyl-3-methylimidazoliumbromides oxidation in an ultrasonic nanoscale zero-valentiron/hydrogen peroxide system. J Hazard Mater 284:241–252

    CAS  Article  Google Scholar 

Download references

Acknowledgements

The present study was supported by grants from the National Key Research and Devel opment Plan (No. 2016YFD0800202) and the National Natural Science Foundation of China (Nos. 21377075, 41671320). All applicable international, national, and/or institutional guidelines for the care and use of animals were followed.

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Correspondence to Lusheng Zhu.

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Shao, Y., Du, Z., Zhang, C. et al. Acute Toxicity of Imidazole Nitrate Ionic Liquids with Varying Chain Lengths to Earthworms (Eisenia foetida). Bull Environ Contam Toxicol 99, 213–217 (2017). https://doi.org/10.1007/s00128-017-2082-x

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Keywords

  • LC50
  • Filter paper contact
  • Artificial soil
  • Cut-off effect
  • Concentration measure