Skip to main content

Ionic Liquids and Deep Eutectic Solvents in the Field of Environmental Monitoring

  • Chapter
  • First Online:
Green Analytical Chemistry

Abstract

A growing number of compounds resulting from human activities are continuously released into the environment. Many of these compounds may pose serious environmental threats, reinforcing the need of environmental monitoring to understand their impact on the environment and on human health and to create strategies to revert these risks. Although with serious impact, these pollutants are usually present in trace levels in environmental samples, turning their identification and accurate quantification a major challenge. To overcome this drawback, pretreatment techniques are usually employed, both to eliminate interferences and enrich the sample in the target pollutants. Within the significant developments achieved in this field, ionic liquids (ILs) and deep eutectic solvents (DESs) have shown to lead to relevant improvements in the enrichment factor and target pollutants recovery and in the limit of detection of the analytical technique when used as alternative solvents in pretreatment techniques of environmental matrices. These have been applied in the pretreatment of wastewaters, industrial effluents, human fluids, wine, milk, honey, fish, macroalgae, vegetables and soil. A wide number of pollutants, such as polyaromatic hydrocarbons (PAHs), active pharmaceutical ingredients (APIs), endocrine disruptors, pesticides, UV filters and heavy metals, are some of the most analyzed pollutants. In this work, we review and discuss the use of ILs and DESs as alternative solvents in pretreatment strategies in the field of environmental monitoring. We also highlight the most recent works on this area and provide new insights and directions to follow in this field.

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

Access this chapter

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Similar content being viewed by others

References

  1. Bolong N, Ismail AF, Salim MR, Matsuura T (2009) A review of the effects of emerging contaminants in wastewater and options for their removal. Desalination 239:229–246

    Article  CAS  Google Scholar 

  2. Gavrilescu M, Demnerová K, Aamand J et al (2015) Emerging pollutants in the environment: present and future challenges in biomonitoring, ecological risks and bioremediation. N Biotechnol 32:147–156

    Article  CAS  Google Scholar 

  3. Namiesnik J (2001) Modern trends in monitoring and analysis of environmental pollutants. Polish J Environ Stud 10:127–140

    CAS  Google Scholar 

  4. Jiang JQ, Zhou Z, Sharma VK (2013) Occurrence, transportation, monitoring and treatment of emerging micro-pollutants in waste water—a review from global views. Microchem J 110:292–300

    Article  CAS  Google Scholar 

  5. Schwarzenbach RP, Egli T, Hofstetter T et al (2010) Global water pollution and human health. Annu Rev Environ Resour 35:109–136

    Article  Google Scholar 

  6. Mateo-Sagasta J, Marjani S, Turral H, Burke J (2017) Water pollution from agriculture: a global review. Int Water Manag Inst 35

    Google Scholar 

  7. Tchounwou PB, Yedjou CG, Patlolla AK, Sutton DJ (2012) Heavy metal toxicity and the environment. Mol Clin Environ Toxicol 101:133–164

    Article  Google Scholar 

  8. Zenker A, Cicero MR, Prestinaci F et al (2014) Bioaccumulation and biomagnification potential of pharmaceuticals with a focus to the aquatic environment. J Environ Manag 133:378–387

    Article  CAS  Google Scholar 

  9. Sousa JCG, Ribeiro AR, Barbosa MO et al (2018) A review on environmental monitoring of water organic pollutants identified by EU guidelines. J Hazard Mater 344:146–162

    Article  CAS  Google Scholar 

  10. do Nascimento RF (ed) (2017) Advances in chromatographic analysis. Avid Science

    Google Scholar 

  11. Fang G, Chen J, Wang J et al (2010) N-Methylimidazolium ionic liquid-functionalized silica as a sorbent for selective solid-phase extraction of 12 sulfonylurea herbicides in environmental water and soil samples. J Chromatogr A 1217:1567–1574

    Article  CAS  Google Scholar 

  12. Gure A, Lara FJ, García-Campaña AM et al (2015) Vortex-assisted ionic liquid dispersive liquid-liquid microextraction for the determination of sulfonylurea herbicides in wine samples by capillary high-performance liquid chromatography. Food Chem 170:348–353

    Article  CAS  Google Scholar 

  13. Zanella R, Primel EG, Machado SLO et al (2002) Monitoring of the herbicide clomazone in environmental water samples by solid-phase extraction and high-performance liquid chromatography with ultraviolet detection. Chromatographia 55:573–577

    Article  CAS  Google Scholar 

  14. Shah J, Rasul Jan M, Ara B, Shehzad F-N (2011) Quantification of triazine herbicides in soil by microwave-assisted extraction and high-performance liquid chromatography. Environ Monit Assess 178:111–119

    Article  CAS  Google Scholar 

  15. Radović T, Grujić S, Petković A et al (2015) Determination of pharmaceuticals and pesticides in river sediments and corresponding surface and ground water in the Danube River and tributaries in Serbia. Environ Monit Assess 187:4092

    Article  Google Scholar 

  16. Papadakis EN, Vryzas Z, Kotopoulou A et al (2015) A pesticide monitoring survey in rivers and lakes of northern Greece and its human and ecotoxicological risk assessment. Ecotoxicol Environ Saf 116:1–9

    Article  CAS  Google Scholar 

  17. Farajzadeh MA, Shahedi Hojghan A, Afshar Mogaddam MR (2018) Development of a new temperature-controlled liquid phase microextraction using deep eutectic solvent for extraction and preconcentration of diazinon, metalaxyl, bromopropylate, oxadiazon, and fenazaquin pesticides from fruit juice and vegetable samples. J Food Compos Anal 66:90–97

    Article  CAS  Google Scholar 

  18. Cacho JI, Campillo N, Viñas P, Hernández-Córdoba M (2017) In situ ionic liquid dispersive liquid-liquid microextraction coupled to gas chromatography-mass spectrometry for the determination of organophosphorus pesticides. J Chromatogr A 1559:95–101

    Article  Google Scholar 

  19. Fan C, Liang Y, Dong H et al (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

    Article  CAS  Google Scholar 

  20. Florindo C, Branco LC, Marrucho IM (2017) Development of hydrophobic deep eutectic solvents for extraction of pesticides from aqueous environments. Fluid Phase Equilib 448:135–142

    Article  CAS  Google Scholar 

  21. Wang H, Hu L, Li W et al (2016) A rapid and simple pretreatment method for benzoylurea insecticides in honey samples using in-syringe dispersive liquid–liquid microextraction based on the direct solidification of ionic liquids. J Chromatogr A 1471:60–67

    Article  CAS  Google Scholar 

  22. Makoś P, Przyjazny A, Boczkaj G (2018) Hydrophobic deep eutectic solvents as “green” extraction media for polycyclic aromatic hydrocarbons in aqueous samples. J Chromatogr A 1570:28–37

    Article  Google Scholar 

  23. Helalat-Nezhad Z, Ghanemi K, Fallah-Mehrjardi M (2015) Dissolution of biological samples in deep eutectic solvents: an approach for extraction of polycyclic aromatic hydrocarbons followed by liquid chromatography-fluorescence detection. J Chromatogr A 1394:46–53

    Article  CAS  Google Scholar 

  24. Pena MT, Casais MC, Mejuto MC, Cela R (2009) Development of an ionic liquid based dispersive liquid-liquid microextraction method for the analysis of polycyclic aromatic hydrocarbons in water samples. J Chromatogr A 1216:6356–6364

    Article  CAS  Google Scholar 

  25. Lau EV, Gan S, Ng HK (2010) Extraction techniques for polycyclic aromatic hydrocarbons in soils. Int J Anal Chem 2010:1–9

    Article  Google Scholar 

  26. Abdolmohammad-Zadeh H, Sadeghi GH (2009) A novel microextraction technique based on 1-hexylpyridinium hexafluorophosphate ionic liquid for the preconcentration of zinc in water and milk samples. Anal Chim Acta 649:211–217

    Article  CAS  Google Scholar 

  27. Habibi E, Ghanemi K, Fallah-Mehrjardi M, Dadolahi-Sohrab A (2013) A novel digestion method based on a choline chloride-oxalic acid deep eutectic solvent for determining Cu, Fe, and Zn in fish samples. Anal Chim Acta 762:61–67

    Article  CAS  Google Scholar 

  28. Herce-Sesa B, López-López JA, Moreno C (2019) Selective ionic liquid solvent bar micro-extraction for estimation of ultra-trace silver fractions in marine waters. Sci Total Environ 650:27–33

    Article  CAS  Google Scholar 

  29. Habibollahi MH, Karimyan K, Arfaeinia H et al (2018) Extraction and determination of heavy metals in soil and vegetables irrigated with treated municipal wastewater using new mode of dispersive liquid-liquid microextraction based on the solidified deep eutectic solvent followed by GFAAS. J Sci Food Agric 99:656–665

    Article  Google Scholar 

  30. Passos H, Sousa ACA, Pastorinho MR et al (2012) Ionic-liquid-based aqueous biphasic systems for improved detection of bisphenol A in human fluids. Anal Methods 4:2664–2667

    Article  CAS  Google Scholar 

  31. Dinis TBV, Passos H, Lima DLD et al (2015) One-step extraction and concentration of estrogens for an adequate monitoring of wastewater using ionic-liquid-based aqueous biphasic systems. Green Chem 17:2570–2579

    Article  CAS  Google Scholar 

  32. Paíga P, Lolić A, Hellebuyck F et al (2015) Development of a SPE-UHPLC-MS/MS methodology for the determination of non-steroidal anti-inflammatory and analgesic pharmaceuticals in seawater. J Pharm Biomed Anal 106:61–70

    Article  Google Scholar 

  33. Kasprzyk-Hordern B, Dinsdale RM, Guwy AJ (2007) Multi-residue method for the determination of basic/neutral pharmaceuticals and illicit drugs in surface water by solid-phase extraction and ultra performance liquid chromatography-positive electrospray ionisation tandem mass spectrometry. J Chromatogr A 1161:132–145

    Article  CAS  Google Scholar 

  34. Yao C, Li T, Twu P et al (2011) Selective extraction of emerging contaminants from water samples by dispersive liquid-liquid microextraction using functionalized ionic liquids. J Chromatogr A 1218:1556–1566

    Article  CAS  Google Scholar 

  35. Wang R, Li W, Chen Z (2018) Solid phase microextraction with poly(deep eutectic solvent) monolithic column online coupled to HPLC for determination of non-steroidal anti-inflammatory drugs. Anal Chim Acta 1018:111–118

    Article  CAS  Google Scholar 

  36. Abujaber F, Zougagh M, Jodeh S et al (2017) Magnetic cellulose nanoparticles coated with ionic liquid as a new material for the simple and fast monitoring of emerging pollutants in waters by magnetic solid phase extraction. Microchem J 137:490–495

    Article  Google Scholar 

  37. Almeida HFD, Freire MG, Marrucho IM (2017) Improved monitoring of aqueous samples by the preconcentration of active pharmaceutical ingredients using ionic-liquid-based systems. Green Chem 19:4651–4659

    Article  CAS  Google Scholar 

  38. Net S, Delmont A, Sempéré R et al (2015) Reliable quantification of phthalates in environmental matrices (air, water, sludge, sediment and soil): a review. Sci Total Environ 515–516:162–180

    Article  Google Scholar 

  39. Zhou Q, Zhang X, Xiao J (2009) Ultrasound-assisted ionic liquid dispersive liquid-phase micro-extraction: a novel approach for the sensitive determination of aromatic amines in water samples. J Chromatogr A 1216:4361–4365

    Article  CAS  Google Scholar 

  40. Shi F, Liu J, Liang K, Liu R (2016) Tris(pentafluoroethyl)trifluorophosphate-basd ionic liquids as advantageous solid-phase micro-extraction coatings for the extraction of organophosphate esters in environmental waters. J Chromatogr A 1447:9–16

    Article  CAS  Google Scholar 

  41. Chisvert A, Benedé JL, Salvador A (2018) Current trends on the determination of organic UV filters in environmental water samples based on microextraction techniques—a review. Anal Chim Acta 1034:22–38

    Article  CAS  Google Scholar 

  42. Holbrey JD, Rogers RD (2002) Green chemistry and ionic liquids: synergies and ironies green chemistry approach—process management. Am Chem Soc 2–14

    Google Scholar 

  43. Espino M, de los Ángeles Fernández M, Gomez FJV, Silva MF (2016) Natural designer solvents for greening analytical chemistry. TrAC—Trends Anal Chem 76:126–136

    Article  CAS  Google Scholar 

  44. Zhao H, Xia S, Ma P (2005) Use of ionic liquids as “green” solvents for extractions. J Chem Technol Biotechnol 80:1089–1096

    Article  CAS  Google Scholar 

  45. Liu Y, Friesen JB, McAlpine JB et al (2018) Natural deep eutectic solvents: properties, applications, and perspectives. J Nat Prod 81:679–690

    Article  CAS  Google Scholar 

  46. Passos H, Freire MG, Coutinho JAP (2014) Ionic liquids solutions as extractive solvents of value-added compounds from biomass. Green Chem 16:4786–4815

    Article  CAS  Google Scholar 

  47. Dupont J, De Souza RF, Suarez PAZ (2002) Ionic liquid (molten salt) phase organometallic catalysis. Chem Rev 102:3667–3692

    Article  CAS  Google Scholar 

  48. Freire MG, Cláudio AFM, Araújo JMM et al (2012) Aqueous biphasic systems: a boost brought about by using ionic liquids. Chem Soc Rev 41:4966–4995

    Article  CAS  Google Scholar 

  49. Ranke J, Stolte S, Störmann R et al (2007) Design of sustainable chemical products-the example of ionic liquids. Chem Rev 107:2183–2206

    Article  CAS  Google Scholar 

  50. Hallett JP, Welton T (2011) Room-temperature ionic liquids: Solvents for synthesis and catalysis. Chem Rev 111:3508–3576

    Article  CAS  Google Scholar 

  51. Plechkova NV, Seddon KR (2008) Applications of ionic liquids in the chemical industry. Chem Soc Rev 37:123–150

    Article  CAS  Google Scholar 

  52. Zhao H (2006) Innovative applications of ionic liquids as “green” engineering liquids. Chem Eng Commun 193:1660–1677

    Article  CAS  Google Scholar 

  53. Freire MG, Neves CMSS, Marrucho IM et al (2010) Hydrolysis of tetrafluoroborate and hexafluorophosphate counter ions in imidazolium-based ionic liquids. J Phys Chem A 114:3744–3749

    Article  CAS  Google Scholar 

  54. Mondal D, Sharma M, Quental MV et al (2016) Suitability of bio-based ionic liquids for the extraction and purification of IgG antibodies. Green Chem 18:6071–6081

    Article  CAS  Google Scholar 

  55. Hulsbosch J, De Vos DE, Binnemans K, Ameloot R (2016) Biobased ionic liquids: solvents for a green processing industry? ACS Sustain Chem Eng 4:2917–2931

    Article  CAS  Google Scholar 

  56. Paiva A, Craveiro R, Aroso I et al (2014) Natural deep eutectic solvents—solvents for the 21st century. ACS Sustain Chem Eng 2:1063–1071

    Article  CAS  Google Scholar 

  57. Abbott AP, Capper G, Davies DL et al (2001) Preparation of novel, moisture-stable, Lewis-acidic ionic liquids containing quaternary ammonium salts with functional side chains. Chem Commun 2010–2011

    Google Scholar 

  58. Vanda H, Dai Y, Wilson EG et al (2018) Green solvents from ionic liquids and deep eutectic solvents to natural deep eutectic solvents. Comptes Rendus Chim 21:628–638

    Article  CAS  Google Scholar 

  59. Smith EL, Abbott AP, Ryder KS (2014) Deep eutectic solvents (DESs) and their applications. Chem Rev 114:11060–11082

    Article  CAS  Google Scholar 

  60. Primel EG, Caldas SS, Marube LC, Escarrone ALV (2017) An overview of advances in dispersive liquid–liquid microextraction for the extraction of pesticides and emerging contaminants from environmental samples. Trends Environ Anal Chem 14:1–18

    Article  CAS  Google Scholar 

  61. Shamsipur M, Yazdanfar N, Ghambarian M (2016) Combination of solid-phase extraction with dispersive liquid-liquid microextraction followed by GC-MS for determination of pesticide residues from water, milk, honey and fruit juice. Food Chem 204:289–297

    Article  CAS  Google Scholar 

  62. Płotka-Wasylka J, Szczepańska N, de la Guardia M, Namieśnik J (2015) Miniaturized solid-phase extraction techniques. TrAC—Trends Anal Chem 73:19–38

    Article  Google Scholar 

  63. Sun J, Liang Q, Han Q et al (2015) One-step synthesis of magnetic graphene oxide nanocomposite and its application in magnetic solid phase extraction of heavy metal ions from biological samples. Talanta 132:557–563

    Article  CAS  Google Scholar 

  64. Yrieix C, Gonzalez C, Deroux JM et al (1996) Countercurrent liquid/liquid extraction for analysis of organic water pollutants by GC/MS. Water Res 30:1791–1800

    Article  CAS  Google Scholar 

  65. López-Montilla JC, Pandey S, Shah DO, Crisalle OD (2005) Removal of non-ionic organic pollutants from water via liquid-liquid extraction. Water Res 39:1907–1913

    Article  Google Scholar 

  66. Andrade-Eiroa A, Canle M, Leroy-Cancellieri V, Cerdà V (2016) Solid-phase extraction of organic compounds: a critical review (Part I). TrAC—Trends Anal Chem 80:641–654

    Article  CAS  Google Scholar 

  67. Dinis TBV, Passos H, Lima DLD et al (2018) Simultaneous extraction and concentration of water pollution tracers using ionic-liquid-based systems. J Chromatogr A 1559:69–77

    Article  CAS  Google Scholar 

  68. Hamed Mosavian MT, Es’Haghi Z, Razavi N, Banihashemi S (2012) Pre-concentration and determination of amitriptyline residues in waste water by ionic liquid based immersed droplet microextraction and HPLC. J Pharm Anal 2:361–365

    Article  CAS  Google Scholar 

  69. Zhou QX, Gao YY (2014) Combination of ionic liquid dispersive liquid-phase microextraction and high performance liquid chromatography for the determination of triazine herbicides in water samples. Chinese Chem Lett 25:745–748

    Article  CAS  Google Scholar 

  70. Vichapong J, Burakham R, Santaladchaiyakit Y, Srijaranai S (2016) A preconcentration method for analysis of neonicotinoids in honey samples by ionic liquid-based cold-induced aggregation microextraction. Talanta 155:216–221

    Article  CAS  Google Scholar 

  71. Wang YL, You LQ, Mei YW et al (2016) Benzyl functionalized ionic liquid as new extraction solvent of dispersive liquid-liquid microextraction for enrichment of organophosphorus pesticides and aromatic compounds. Chin J Anal Chem 44:942–949

    Article  CAS  Google Scholar 

  72. Benedé JL, Anderson JL, Chisvert A (2018) Trace determination of volatile polycyclic aromatic hydrocarbons in natural waters by magnetic ionic liquid-based stir bar dispersive liquid microextraction. Talanta 176:253–261

    Article  Google Scholar 

  73. Zhang Y, Lee HK (2012) Ionic liquid-based ultrasound-assisted dispersive liquid-liquid microextraction followed high-performance liquid chromatography for the determination of ultraviolet filters in environmental water samples. Anal Chim Acta 750:120–126

    Article  CAS  Google Scholar 

  74. Ge D, Lee HK (2012) Ionic liquid based hollow fiber supported liquid phase microextraction of ultraviolet filters. J Chromatogr A 1229:1–5

    Article  CAS  Google Scholar 

  75. Hashemi B, Zohrabi P, Kim KH et al (2017) Recent advances in liquid-phase microextraction techniques for the analysis of environmental pollutants. TrAC—Trends Anal Chem 97:83–95

    Article  CAS  Google Scholar 

  76. Al-Saidi HM, Emara AAA (2011) The recent developments in dispersive liquid–liquid microextraction for preconcentration and determination of inorganic analytes. J Saudi Chem Soc 18:745–761

    Article  Google Scholar 

  77. Freire MG, Neves CMSS, Carvalho PJ et al (2007) Mutual solubilities of water and hydrophobic ionic liquids. J Phys Chem B 111:13082–13089

    Article  CAS  Google Scholar 

  78. Sharifan H, Klein D, Morse AN (2016) UV filters are an environmental threat in the Gulf of Mexico: a case study of Texas coastal zones. Oceanologia 58:327–335

    Article  Google Scholar 

  79. Torbati M, Mohebbi A, Farajzadeh MA, Afshar Mogaddam MR (2018) Simultaneous derivatization and air–assisted liquid–liquid microextraction based on solidification of lighter than water deep eutectic solvent followed by gas chromatography–mass spectrometry: an efficient and rapid method for trace analysis of aromatic amines in aqueous samples. Anal Chim Acta 1032:48–55

    Article  CAS  Google Scholar 

  80. Abbott AP, Boothby D, Capper G et al (2004) Deep eutectic solvents formed between choline chloride and carboxylic acids: versatile alternatives to ionic liquids. J Am Chem Soc 126:9142–9147

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was developed within the scope of the project CICECO-Aveiro Institute of Materials, FCT Ref. UID/CTM/50011/2019, financed by national funds through the FCT/MCTES. This work was financially supported by the project POCI-01-0145-FEDER-031106 (IonCytDevice) and DeepBiorefinery (PTDC/AGR-TEC/1191/2014) funded by FEDER, through COMPETE2020—Programa Operacional Competitividade e Internacionalização (POCI), and by national funds (OE), through FCT/MCTES. Inês S. Cardoso acknowledges FCT for her Ph.D. grant (SFRH/BD/139801/2018). M.G. Freire acknowledges the European Research Council under the European Union’s Seventh Framework Program (FP7/2007-2013)/ERC grant agreement n° 337753.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Mara G. Freire .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2019 Springer Nature Singapore Pte Ltd.

About this chapter

Check for updates. Verify currency and authenticity via CrossMark

Cite this chapter

Cardoso, I.S., Pedro, A.Q., Silvestre, A.J.D., Freire, M.G. (2019). Ionic Liquids and Deep Eutectic Solvents in the Field of Environmental Monitoring. In: Płotka-Wasylka, J., Namieśnik, J. (eds) Green Analytical Chemistry. Green Chemistry and Sustainable Technology. Springer, Singapore. https://doi.org/10.1007/978-981-13-9105-7_8

Download citation

Publish with us

Policies and ethics