journal article·2020-05-01Open access

Heavy Metal Extraction under Environmentally Relevant Conditions Using 3-Hydroxy-2-Naphthoate- Based Ionic Liquids: Extraction Capabilities vs. Acute Algal Toxicity

Philip Pirkwieser, José A. López-López, Michael Schagerl, Wolfgang Kandioller, Bernhard K. Keppler, Carlos Moreno, Franz Jirsa

Applied Sciences· Volume 10· Issue 9

Abstract

We investigated the applicability of three task-specific ionic liquids (ILs) as heavy metal extracting agents by contrasting extraction capabilities with algal toxicity. The compounds tested were trihexyltetradecylphosphonium-, methyltrioctylphosphonium- and methyltrioctylammonium 3-hydroxy-2-naphthoates. Experiments were performed to assess if these ILs can provide environmentally safe residual concentrations of the target metals after extraction. Both pure water and natural mineral water samples were spiked with 20 µg L−1 of Cu, Ag, Cd, Hg and Pb, respectively. Quantitative extraction (> 99%) of Hg and Ag was achieved. Cu and Hg were below the respective no-observed-effect-concentrations (NOECs) after extraction and Ag below 0.03 µg L−1. Acute toxicity assays were conducted using two freshwater green algae Raphidocelis subcapitata and Tetradesmus obliquus. Growth inhibition and maximum photochemical quantum yield of photosystem II after 72 h were assessed. ILs were less toxic than similar compounds, but still must be classified as acute toxicants for algae. An inhibiting effect on both growth and chlorophyll fluorescence was observed. The leaching of the ILs into the samples remains a limitation regarding their environmental-friendly applicability. Nonetheless, the extremely efficient removal of Cu, Ag and Hg under environmentally relevant conditions calls for further research, which should focus on the immobilization of the ILs.
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Research context

OpenAlex topics: Ionic liquids properties and applications · Electrochemical Analysis and Applications · Analytical chemistry methods development

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Institute of Inorganic Chemistry, Faculty of Chemistry, University of Vienna, Waehringer Strasse 42, 1090 Vienna, Austria

Department of Analytical Chemistry, Faculty of Marine and Environmental Sciences, Instituto de Investigación Marina (INMAR), University of Cádiz, 11510 Puerto Real, Spain

Department of Limnology and Bio-Oceanography, Faculty of Life Sciences, Althanstraße 14, 1090 Vienna, Austria

Department of Zoology, University of Johannesburg, PO Box 524, Auckland Park, 2006 Johannesburg, South Africa

References (61)

Show source-provided references
1. Ionic liquids: A brief history10.1007/s12551-018-0419-2 ↗
2. Introduction: Ionic Liquids10.1021/acs.chemrev.7b00246 ↗
3. Use of ionic liquids as ‘green’ solvents for extractions10.1002/jctb.1333 ↗
4. Recent advances on ionic liquid uses in separation techniques10.1016/j.chroma.2017.09.044 ↗
5. Ionic Liquids—Designer Solvents for the Synthesis of New Compounds and Functional Materials10.1002/zaac.201700001 ↗
6. Ionic liquids and derived materials for lithium and sodium batteries10.1039/C7CS00464H ↗
7. Ionic-Liquid-Based CO2 Capture Systems: Structure, Interaction and Process10.1021/acs.chemrev.7b00072 ↗
8. Zhang, W., and Cue, B.W. (2018). Ionic Liquids in Pharmaceutical Industry. Green Techniques for Organic Synthesis and Medicinal Chemistry, John Wiley & Sons.10.1002/9781119288152 ↗
9. Ionic Liquids as Extracting Agents for Heavy Metals10.1080/01496395.2011.620587 ↗
10. Task-Specific Ionic Liquids for the Extraction of Metal Ions from Aqueous Solutions10.1039/b008041l ↗
11. Ionic liquids for extraction of metals and metal containing compounds from communal and industrial waste water10.1016/j.watres.2011.06.011 ↗
12. Novel thiosalicylate-based ionic liquids for heavy metal extractions10.1016/j.jhazmat.2016.04.038 ↗
13. Thioglycolate-based task-specific ionic liquids: Metal extraction abilities vs. acute algal toxicity10.1016/j.jhazmat.2017.06.053 ↗
14. Greener synthesis of new ammonium ionic liquids and their potential as extracting agents10.1016/j.tetlet.2008.02.138 ↗
15. Task-specific thioglycolate ionic liquids for heavy metal extraction: Synthesis, extraction efficacies and recycling properties10.1016/j.jhazmat.2016.10.054 ↗
16. Ion-exchange as a mode of cation transfer into room-temperature ionic liquids containing crown ethers: Implications for the ’greenness’ of ionic liquids as diluents in liquid-liquid extraction10.1039/b104349h ↗
17. Task-specific ionic liquid with coordinating anion for heavy metal ion extraction: Cation exchange versus ion-pair extraction10.1016/j.seppur.2013.01.015 ↗
18. A ternary mechanism for the facilitated transfer of metal ions into room-temperature ionic liquids (RTILs): implications for the “greenness” of RTILs as extraction solvents10.1039/b508604c ↗
19. Long alkyl-chain imidazolium ionic liquids: Antibiofilm activity against phototrophic biofilms10.1016/j.colsurfb.2017.04.040 ↗
20. Ionic Liquids: The Neglected Issues10.1071/CH04272 ↗
21. Environmental fate and toxicity of ionic liquids: A review10.1016/j.watres.2009.09.030 ↗
22. Toxicity of Ionic Liquids: Eco(Cyto)Activity as Complicated, but Unavoidable Parameter for Task-Specific Optimization10.1002/cssc.201300459 ↗
23. Are Ionic Liquids Chemically Stable?10.1021/acs.chemrev.6b00594 ↗
24. A brief overview of the potential environmental hazards of ionic liquids10.1016/j.ecoenv.2013.10.019 ↗
25. In vitrocytotoxicities of ionic liquids: Effect of cation rings, functional groups, and anions10.1002/tox.20443 ↗
26. The ecotoxicity of ionic liquids and traditional organic solvents on microalga Selenastrum capricornutum10.1016/j.ecoenv.2007.07.001 ↗
27. The influence of anion species on the toxicity of 1-alkyl-3-methylimidazolium ionic liquids observed in an (eco)toxicological test battery10.1039/b705795d ↗
28. Novel 3-Hydroxy-2-Naphthoate-Based Task-Specific Ionic Liquids for an Efficient Extraction of Heavy Metals10.3389/fchem.2018.00172 ↗
29. Stein, J.R. (1980). Handbook of Phycological Methods: Culture Methods and Growth Measurements, Cambridge University Press.
30. Chlorophyll Fluorescence-a Practical Guide10.1093/jexbot/51.345.659 ↗
31. Quenching of chlorophyll fluorescence and primary photochemistry in chloroplasts by dibromothymoquinone10.1016/0005-2728(75)90209-1 ↗
32. How to correctly determine the different chlorophyll fluorescence parameters and the chlorophyll fluorescence decrease ratio RFd of leaves with the PAM fluorometer10.1007/s11099-005-0062-6 ↗
33. Evaluation of different algal species sensitivity to mercury and metolachlor by PAM-fluorometry10.1016/S0045-6535(01)00034-0 ↗
34. Pirkwieser, P., López-López, J.A., Kandioller, W., Keppler, B.K., Moreno, C., and Jirsa, F. (2018). Solvent Bar Micro-Extraction of Heavy Metals from Natural Water Samples Using 3-Hydroxy-2-Naphthoate-Based Ionic Liquids. Molecules, 23.10.3390/molecules23113011 ↗
35. Mercury extraction by ionic liquids: temperature and alkyl chain length effect10.1016/j.tetlet.2007.01.038 ↗
36. EU (2000). Directive 2000/60/Ec of the European Parliament and the Council Establishing a Framework for the Community in the Field of Water Policy, European Union.
37. Republic of Austria (2001). Verordnung des Bundesministers Für Soziale Sicherheit Und Generationen Über Die Qualität Von Wasser Für Den Menschlichen Gebrauch (Trinkwasserverordnung—TWV). BGBl. II Nr. 304/2001, Bundeskanzleramt Österreich.
38. EU (2008). Directive 2008/105/Ec of the European Parliament and of the Council of 16 December 2008 on Environmental Quality Standards in the Field of Water Policy, Amending and Subsequently Repealing Council Directives 82/176/Eec, 83/513/Eec, 84/156/Eec, 84/491/Eec, 86/280/Eec and Amending Directive 2000/60/Ec of the European Parliament and of the Council, European Parliament: European Union.
39. Mercury Toxicity to Freshwater Organisms: Extrapolation Using Species Sensitivity Distribution10.1007/s00128-013-1029-0 ↗
40. Wood, C.M. (2012). Silver. Homeostasis and Toxicology of Non-Essential Metals, Elsevier.10.1016/S1546-5098(11)31023-0 ↗
41. Bioaccumulation and Toxicity of Silver Compounds: A Review10.1002/etc.5620180112 ↗
42. Schmittschmitt, J.P., Shaw, J.R., and Birge, W.J. (1996, January 25–28). Effects of Silver on Green Algae and Prospects for Trophic Transfer. Proceedings of the 4th International Conference Proceedings: Transport, Fate and Effects of Silver in the Environment, Madison, WI, USA.
43. Effect of Varying Physicochemistry of European Surface Waters on the Copper Toxicity to the Green Alga Pseudokirchneriella subcapitata10.1007/s10646-005-0014-8 ↗
44. Metal extraction to ionic liquids: the relationship between structure, mechanism and application10.1080/0144235X.2015.1088217 ↗
45. Anion effects on the cytotoxicity of ionic liquids10.1039/b602161a ↗
46. Anti-diabetic effect of 3-hydroxy-2-naphthoic acid, an endoplasmic reticulum stress-reducing chemical chaperone10.1016/j.ejphar.2016.03.023 ↗
47. Acute toxicity and effects of 1-alkyl-3-methylimidazolium bromide ionic liquids on green algae10.1016/j.ecoenv.2009.10.004 ↗
48. Effects of imidazolium chloride ionic liquids and their toxicity to Scenedesmus obliquus10.1016/j.ecoenv.2015.07.010 ↗
49. The toxicity of ionic liquid 1-decylpyridinium bromide to the algae Scenedesmus obliquus: Growth inhibition, phototoxicity, and oxidative stress10.1016/j.scitotenv.2017.10.021 ↗
50. UN (2011). Globally Harmonized System of Classification and Labelling of Chemicals (Ghs), United Nations.
51. Algal photosynthetic responses to toxic metals and herbicides assessed by chlorophyll a fluorescence10.1016/j.ecoenv.2014.01.042 ↗
52. Chlorophyll a fluorescence as a biomarker for rapid toxicity assessment10.1897/06-394R1.1 ↗
53. Biodegradable Naphthenic Acid Ionic Liquids: Synthesis, Characterization, and Quantitative Structure-Biodegradation Relationship10.1002/chem.200800620 ↗
54. Current and future emissions of selected heavy metals to the atmosphere from anthropogenic sources in Europe10.1016/j.atmosenv.2007.07.040 ↗
55. Influence of Some Experimental Factors on Metal Toxicity to Selenastrum capricornutum10.1002/tox.2540030308 ↗
56. Optimization and Performance Evaluation of the Continuous Algal Toxicity Test10.1002/etc.5620160701 ↗
57. A novel algal toxicity testing technique for assessing the toxicity of both metallic and organic toxicants10.1016/j.watres.2005.02.015 ↗
58. Toxicity of Metals on the Growth of Raphidocelis Subcapitata and Chlorella Kessleri Using Microplate Assays
59. Toxicity of cadmium and zinc on two microalgae, Scenedesmus obliquus and Desmodesmus pleiomorphus, from Northern Portugal
60. PAM Fluorometry in the Determination of the Sensitivity of Chlorella vulgaris, Selenastrum capricornutum, and Chlamydomonas reinhardtii to Copper10.1007/s00244-001-0027-0 ↗
61. Solvent bar micro-extraction for greener application of task specific ionic liquids in multi-elemental extraction10.1016/j.jclepro.2018.08.008 ↗