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Selected issues related to the toxicity of ionic liquids and deep eutectic solvents—a review

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Abstract

Green Chemistry plays a more and more important role in implementing rules of sustainable development to prevent environmental pollution caused by technological processes, while simultaneously increasing the production yield. Ionic liquids (ILs) and deep eutectic solvents (DESs) constitute a very broad group of substances. Apart from many imperfections, ILs and DESs have been the most promising discoveries in the world of Green Chemistry in recent years. The main advantage of ILs is their unique physicochemical properties—they are very desirable from the technological point of view, but apart from these benefits, ILs appear to be highly toxic towards organisms from different trophic levels. DES areas of usage are very spread, because they cover organic synthesis, extraction processes, electrochemistry, enzymatic reactions and many others. Moreover, DESs seem to be a less toxic alternative to ionic liquids. New possibilities of applications and future development trends are sought and presented, including such important solutions of life branches as pharmaceuticals’ production and medicine.

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References

  • Abbott AP, Capper G, Gray S (2006) Design of improved deep eutectic solvents using hole theory. ChemPhysChem 7:803–806

    Article  CAS  Google Scholar 

  • Abbott AP, Capper G, McKenzie KJ, Ryder KS (2007) Electrodeposition of zinc–tin alloys from deep eutectic solvents based on choline chloride. J Electroanal Chem 599:288–294

    Article  CAS  Google Scholar 

  • Ali E, Hadj-Kali MK, Mulyono S, Alnashef I, Fakeeha A, Mjalli F, Hayyan A (2014) Solubility of CO2 in deep eutectic solvents: experiments and modelling using the Peng–Robinson equation of state. Chem Eng Res Des 92:1898–1906

    Article  CAS  Google Scholar 

  • Anugwom I, Maki-Arvela P, Salmi T, Mikkola JP (2011) Ionic liquid assisted extraction of nitrogen and sulfur-containing air pollutants from model oil and regeneration of the spent ionic liquid. J Environ Prot 2:769–802

    Article  Google Scholar 

  • Arednarczyk A, Zgórska A, Grabińska-Sota E (2011) Toksyczność chlorku 1-heksylo-3-metyloimidazoliowego względem wybranych organizmów wodnych. Inżynieria i Ochrona Środowiska 14:137–143 (in Polish)

    Google Scholar 

  • Biczak R, Pawłowska B, Bałczewski P, Rychter P (2014) The role of the anion in the toxicity of imidazolium ionic liquids. J Hazard Mater 274:181–190

    Article  CAS  Google Scholar 

  • Caparanga A, Leron RB, Li M-H (2013) Carbon dioxide solubility in a deep eutectic solvent based on choline chloride and urea at T = 303.15–343.15 K and moderate pressures. J Taiwan Inst Chem E 44:879–885

    Article  Google Scholar 

  • Cheng Y, Wrigh SH, Hooth MJ, Sipes IG (2009) Characterization of the disposition and toxicokinetics of N-butylpyridinium chloride in male F-344 rats and female B6C3F1 mice and its transport by organic cation transporter. Drug Metab Dispos 37:909–916

    Article  CAS  Google Scholar 

  • Cho CW, Pham TPT, Jeon YC, Vijayaraghavan K, Choe WS, Yun YS (2007) Toxicity of imidazolium salt with anion bromide to a phytoplankton Selenastrum capricornutum: effect of alkyl chainlength. Chemosphere 69:1003–1007

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  • Dai Y, van Spronsen J, Witkamp G-J, Verpoorte R, Hae Choi Y (2013) Natural deep eutectic solvents as new potential media for green technology. Anal Chim Acta 766:61–68

    Article  CAS  Google Scholar 

  • De Santi V, Cardellini F, Brinchi L, Germani R (2012) Novel Bronsted acidic deep eutectic solvent as reaction media for esterification of carboxylic acid with alcohols. Tetrahedron Lett 53:5151–5155

    Article  Google Scholar 

  • Dominguez de Maria P (2012) Ionic liquids in biotransformation and organocatalysis. Solvents and beyond, Wiley

  • Dominguez de Maria P, Maugeri Z (2011) Ionic liquids in biotransformations: from proof-of-concept to emerging deep-eutectic-solvent. Curr Opin Chem Biol 15:220–225

    Article  CAS  Google Scholar 

  • Duarte dos Santos A, Morais ARC, Melo C, Bogel-Łukasik R, Bogel-Łukasik E (2013) Solubility of pharmaceutical compounds in ionic liquids. Fluid Phase Equilib 356:18–29

    Article  CAS  Google Scholar 

  • Durand E, Lecomte J, Baréa B, Piombo G, Dubreucq E, Villeneuve P (2012) Evaluation of deep eutectic solvents as new media for Candida antarctica B lipase catalyzed reactions. Proc Biochem 47:2081–2089

    Article  CAS  Google Scholar 

  • Durand E, Lecomte J, Baréa B, Piombo G, Villeneuve P (2014) Towards a better understanding of how to improve lipase-catalyzed reactions using deep eutectic solvents based on choline chloride. Eur J Lipid Sci Technol 116:16–23

    Article  CAS  Google Scholar 

  • Ferraz R, Branco LC, Prudencio C, Noronha JP, Petrovski Z (2011) Ionic liquids as active pharmaceutical ingredient. ChemMedChem 6:975–985

    Article  CAS  Google Scholar 

  • Gałuszka A, Migaszewski Z, Namieśnik J (2013) The 12 principles of green analytical chemistry and the significance mnemonic of green analytical practice. Trends Anal Chem 50:78–84

    Article  Google Scholar 

  • Ge H-L, Liu S-S, Su B-X, Qin L-T (2014) Predicting synergistic toxicity of heavy metals and ionic liquids on photobacterium Q67. J Hazard Mater 268:77–83

    Article  CAS  Google Scholar 

  • Gorke JT, Srienc F, Kazlauskas RJ (2008) Hydrolase-catalyzed biotransformations in deep eutectic solvents. Chem Commun (Camb) 1235–1237

  • Gouveia W, Jorge TF, Martins S, Meireles M, Carolino M, Cruz C, Almeida TV, Araújo MEM (2014) Toxicity of ionic liquids prepared from biomaterial. Chemosphere 104:51–56

    Article  CAS  Google Scholar 

  • Gräsvik J, Eliasson B, Mikkola JP (2012) Halogen-free ionic liquids and their utilization as cellulose solvent. J Mol Struct 1028:156–163

    Article  Google Scholar 

  • Gulhane PA, Gomashe AV, Deo NV (2014) Influence of ionic liquid 1-butyl-3-methylmidazolium chloride on the soil micro-ecological system. Int J Curr Microbiol App Sci 3:805–813

    Google Scholar 

  • 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 

  • Hafiidz A, Fauzi M, Aishah N, Amin S (2012) An overview of ionic liquids as solvents in biodiesel synthesis. Renew Sust Energ Rev 16:5770–5786

    Article  Google Scholar 

  • Hayyan A, Hashim MA, Hayyan M, Mjalli FS, AlNashef IM (2013a) A novel ammonium based eutectic solvent for the treatment of free fatty acid and synthesis of biodiesel fuel. Ind Crop Prod 46:392–398

    Article  CAS  Google Scholar 

  • Hayyan M, Hashim MA, Hayyan A, Al-Saadi MA, AlNashef IM, Mirghani MES, Saheed OK (2013b) Are deep eutectic solvents benign or toxic? Chemosphere 90:2193–2195

    Article  CAS  Google Scholar 

  • Hayyan M, Hashim MA, Hayyan A, Al-Saadi MA, AlNashef IM, Mirghani MES, Saheed OK (2013c) Assessment of cytotoxicity and toxicity for phosphonium-based deep eutectic solvents. Chemosphere 93:455–459

    Article  CAS  Google Scholar 

  • Hayyan M, Looi CY, Hayyan A, Wong WF, Hashim MA, Papaccio G (2015) In vitro and In vivo toxicity profiling of ammonium-based deep eutectic solvents. PLoS ONE. doi:10.1371/journal.pone.0117934

    Google Scholar 

  • Hough W, Smiglak M, Rodríguez H, Swatloski R, Spear S, Daly D, Pernak J, Grisel J, Carliss R, Soutullo M, Davis J, Rogers R (2007) The third evolution of ionic liquids: active pharmaceutical ingredients. New J Chem 31:1429–1436

    Article  CAS  Google Scholar 

  • Huang Z-L, Wu B-P, Wen Q, Yang T-X, Yanga Z (2014) Deep eutectic solvents can be viable enzyme activators and stabilizers. J Chem Technol Biotechnol 89:1975–1981

    Article  CAS  Google Scholar 

  • Jodynis-Liebert J, Nowicki M, Murias M, Adamska T, Ewertowska M, Kujawska M, Piotrowska H, Konwerska A, Ostalska-Nowicka D, Pernak J (2010) Cytotoxicity, acute and subchronic toxicity of ionic liquid, didecyldimethylammonium saccharinate, in rats. Regul Toxicol Pharmacol 57:266–273

    Article  CAS  Google Scholar 

  • Karande P, Mitragotri S (2009) Enhancement of transdermal drug delivery via synergistic action of chemicals. Biochimic Biophys Acta 1788:2362–2373

    Article  CAS  Google Scholar 

  • Kareem MA, Mjalli FS, Hashim MA, Hadj-Kali MKO, Saadat F, Bagh G, Alnashef IM (2012) Phase equilibria of toluene/heptane with tetrabutylphosphonium bromide based deep eutectic solvents for the potential use in the separation of aromatics from naphtha. Fluid Phase Equilib 333:47–54

    Article  CAS  Google Scholar 

  • Kumar V, Malhotra SV (2009) Study on the potential anti-cancer activity of phosphonium and ammonium-based ionic liquids. Bioorg Med Chem Lett 19:4643–4646

    Article  CAS  Google Scholar 

  • Leron RB, Li M-H (2013) Solubility of carbon dioxide in a choline chloride–ethylene glycol based deep eutectic solvent. Thermochim Acta 551:14–19

    Article  CAS  Google Scholar 

  • Li X-Y, Miao X-Q, Zhang L-F, Wang J-J (2012) Immunotoxicity of1-methyl-3-octyl imidazolium bromide on brocarded carp (Cyprinuscarpio L.). Ecotoxicol Environ Saf 75:180–186

    Article  CAS  Google Scholar 

  • Lim GS, Zidar J, Cheong D, Jaenicke S, Klahn M (2014) Impact of ionic liquids in aqueous solution on bacterial plasma membranes studied with molecular dynamics simulations. J Phys Chem B 118:10444–10459

    Article  CAS  Google Scholar 

  • Lindberg D, de la Fuente RM, Widersten M (2010) Deep eutectic solvents (DESs) are viable cosolvents for enzyme-catalyzed epoxide hydrolysis. J Biotechnol 147:169–171

    Article  CAS  Google Scholar 

  • Luo Y-L, Wang S-H, Li X-Y, Yun M-X, Wang J-J, Sun Z-J (2010) Toxicity of ionic liquids on the growth, reproductive ability, and ATPase activity of earthworm. Ecotoxicol Environ Saf 73:1046–1050

    Article  CAS  Google Scholar 

  • Mikkola S-K, Robciuc A, Lokajova J, Holding A, Lammerhofer M, Kilpelainen I, Holopainen JM, King AWT, Wiedmer S (2015) Impact of amphiphilic biomass-dissolving ionic liquids on biological cells and liposomes. Environ Sci Technol 49:1870–1878

    Article  CAS  Google Scholar 

  • Morrison HG, Sun CC, Neervannan S (2009) Characterization of thermal behavior of deep eutectic solvents and their potential as drug solubilization vehicles. Int J Pharm 378:136–139

    Article  CAS  Google Scholar 

  • Paiva A, Craveiro R, Arosso I, Martins M, Reis RL, Duarte ARC (2014) Natural deep eutectic solvents—solvents for the 21st century. Sustainable Chem Eng 2:1063–1071

    Article  CAS  Google Scholar 

  • Paryjczak T (2008) Promowanie zrównoważonego rozwoju przez zieloną chemię. Probl ekorozwoju 3:45–51 (in Polish)

    Google Scholar 

  • Pena-Pereira F, Namieśnik J (2014) Ionic liquids and deep eutectic mixtures: sustainable solvents for extraction processes. ChemSusChem 7:1784–800

    Article  CAS  Google Scholar 

  • Phadtare SB, Jarag KJ, Shankarling GS (2013) Greener protocol for one pot synthesis of coumarin styryl dyes. Dyes Pigments 97:105–112

    Article  CAS  Google Scholar 

  • Pham T, Cho C-W, Yun Y-S (2010) Environmental fate and toxicity of ionic liquids: a review. Water Res 44:352–372

    Article  CAS  Google Scholar 

  • Radošević K, Cvjetko M, Kopjar N, Novak R, Dumić J, Srček VG (2013) In vitro cytotoxicity assessment of imidazolium ionic liquids: biological effects in fish Channel Catfish Ovary (CCO) cell line. Ecotoxicol Environ Saf 92:112–118

    Article  Google Scholar 

  • Radošević K, Cvjetko M, Srček VG, Grgas D, Dragičević DL, Redovniković I (2015) Evaluation of toxicity and biodegradability of choline chloride based deep eutectic solvents. Ecotoxicol Environ Saf 112:46–53

    Article  Google Scholar 

  • Rodrigues F, do Nascimento GM, Santos PS (2007) Studies of ionic liquid solutions by soft X-ray absorption spectroscopy. J Electron Spectrosc Relat Phenom 155:148–154

    Article  CAS  Google Scholar 

  • Siedlecka EM, Fabiańska A, Stolte S, Nienstedt A, Ossowski SP, Thöming J (2013) Electrocatalytic oxidation of 1-butyl-3-methylimidazolium chloride: effect of the electrode material. Int J Electrochem Sci 8:5560–5574

    CAS  Google Scholar 

  • Simka W, Puszczyk D, Nawrat G (2009) Electrodeposition of metals from non-aqueous solutions. Electrochim Acta 54:5307–5319

    Article  CAS  Google Scholar 

  • Singh BS, Lobo HR (2011) Selective N-alkylation of aromatic primary amines catalyzed by bio-catalyst or deep eutectic solvent. Catal Lett 141:178–182

    Article  CAS  Google Scholar 

  • Singh BS, Lobo HR, Pinjari DV, Jarag KJ, Pandit AB, Shankarling GS (2013) Ultrasound and deep eutectic solvent (DES): a novel blend of techniques for rapid and energy efficient synthesis of oxazoles. Ultrason Sonochem 20:287–293

    Article  CAS  Google Scholar 

  • Smiglak M, Metlen A, Rogers R (2007) The second evolution of ionic liquids: from solvents and separations to advanced materials—energetic examples from the ionic liquid cookbook. Acc Chem Res 40:1182–1192

    Article  CAS  Google Scholar 

  • Smith E L, Abbott A P, Ryder K S (2014), Deep Eutectis Solvents (DESs) and Their Applications, Chem Rev 114: 11060–11082

  • Stasiewicz M, Mulkiewicz E, Tomczak-Wandzel R, Kumirska J, Siedlecka EM, Gołębiowski M, Gajdus J, Czerwicka M, Stepnowski P (2008) Assessing toxicity and biodegradation of novel, environmentally benign ionic liquids (1-alkoxymethyl-3-hydroxypyridinium chlorides, saccharinates and acesulfamates) on cellular and molecular level. Ecotoxicol Environ Saf 71(Gajdus, J):157–165, CrossRef

    Article  CAS  Google Scholar 

  • Tang B, Row KH (2013) Recent developments in deep eutectic solvents in chemical sciences. Monatsh Chem 144:1427–1454

    Article  CAS  Google Scholar 

  • Taubert J, Keswani M, Raghavan S (2013) Post-etch residue removal using choline chloride–malonic acid deep eutectic solvent (DES). Microelectron Eng 102:81–86

    Article  CAS  Google Scholar 

  • Vidal C, Suárez FJ, García-Álvarez J (2014) Deep eutectic solvents (DES) as green reaction media for the redox isomerization of allylic alcohols into carbonyl compounds catalyzed by the ruthenium complex [Ru(η3:η3-C10H16)Cl2(benzimidazole)]. Catal Commun 44:76–79

    Article  CAS  Google Scholar 

  • Wang C, Wei Z, Wang L, Sun P, Wang Z (2015) Assessment of bromide-based ionic liquid toxicity toward aquatic organisms and QSAR analysis. Ecotoxicol Environ Saf 115:112–118

    Article  CAS  Google Scholar 

  • Wen Q, Chen J-X, Tang Y-L, Wang J, Yang Z (2015) Assessing the toxicity and biodegradability of deep eutectic solvents. Chemosphere 132:63–69

    Article  CAS  Google Scholar 

  • Wilkes JS (2002) A short history of ionic liquids—from molten salts to neoteric solvent. Green Chem 4:73–80

    Article  CAS  Google Scholar 

  • Wójciuk K (2014) Ciecze jonowe, czyli zielone związki [in Polish], Ionic liquids thus green chemicals. http://www.laboratoria.net. Accessed 13 May 2015

  • Wu B-P, Wen Q, Xu H, Yang Z (2014) Insights into the impact of deep eutectic solvents on horseradish peroxidase: activity, stability and structure. J Mol Catal B Enzym 101:101–107

    Article  CAS  Google Scholar 

  • You YH, Gu CD, Wang XL, Tu JP (2012) Electrodeposition of Ni–Co alloys from a deep eutectic solvent. Surf Coat Technol 206:3632–3638

    Article  CAS  Google Scholar 

  • Zabielska–Matejuk J (2009) Ionic liquids in wood preservation (in Polish) http://www.itd.poznan.pl/pl/Foresight%20-%20Jadwiga%20Zabielska-matejuk%2025.06.2009.pdf (accessed on 29.11.2014)

  • Zhao H, Baker GA, Holmes S (2011) Protease activation in glycerol-based deep eutectic solvents. J Mol Catal B Enzym 72:163–167

    Article  CAS  Google Scholar 

  • Zhao H, Zhang C, Crittle TD (2013) Choline-based deep eutectic solvents for enzymatic preparation of biodiesel from soybean oil. J Mol Catal B Enzym 85–86:243–247

    Article  Google Scholar 

  • Zhou H, Shen Y, Li P, Wang J, Fan J (2013) Degradation of 1-butyl-3-methylimidazolium chloride ionic liquid by ultrasound and zero-valent iron/activated carbon. Sep Purif Technol 104:208–213

    Article  CAS  Google Scholar 

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Acknowledgments

The work has been co-financed by the Polish Ministry of Science and Higher Education grant no. IP2011 028071.

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Correspondence to Katarzyna Owczarek.

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Kudłak, B., Owczarek, K. & Namieśnik, J. Selected issues related to the toxicity of ionic liquids and deep eutectic solvents—a review. Environ Sci Pollut Res 22, 11975–11992 (2015). https://doi.org/10.1007/s11356-015-4794-y

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