Sorption to dissolved humic acid and its impacts on the toxicity of imidazolium based ionic liquids

Environmental Science and Technology

Volumn 45, Issue 4, 2011, Pages 1688-1694

  Zhang, Zhen ^a,b   Liu, Jing Fu ^a   Cai, Xiao Qiang ^a   Jiang, Wei Wei ^a   Luo, Wen Ru ^a   Jiang, Gui Bin ^a  

^a RESEARCH CENTER FOR ECO ENVIRONMENTAL SCIENCES   (China)

^b JIANGSU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1-BUTYL-3-METHYLIMIDAZOLIUM CHLORIDE; ACUTE TOXICITY; CELL VIABILITY; DEATH RATES; DISSOLVED ORGANIC CARBON; DISSOLVED ORGANIC MATTERS; DISTRIBUTION COEFFICIENT; ENVIRONMENTAL FATE; ENVIRONMENTAL RISKS; FREE FRACTION; FREELY DISSOLVED CONCENTRATION; GENOTOXICITIES; HEPG2 CELL LINE; HUMIC ACID; IMIDAZOLIUM; IMIDAZOLIUM-BASED IONIC LIQUID; MEDIAN LETHAL CONCENTRATION; METHYLIMIDAZOLIUM CHLORIDE; MINIMUM VALUE; MTT ASSAYS; MUTAGENICITY; SOS/UMU TEST; TRACE AMOUNTS;

BIOCHEMISTRY; BIOLOGICAL MATERIALS; CELL CULTURE; CHLORINE COMPOUNDS; CONCENTRATION (PROCESS); DISSOLUTION; ORGANIC ACIDS; ORGANIC CARBON; POPULATION STATISTICS; SORPTION; TOXICITY;

IONIC LIQUIDS;

1 BUTYL 3 METHYLIMIDAZOLIUM CHLORIDE; 1 OCTYL 3 METHYLIMIDAZOLIUM CHLORIDE; DISSOLVED ORGANIC MATTER; HUMIC ACID; IMIDAZOLE DERIVATIVE; IONIC LIQUID; ORGANIC CARBON; UNCLASSIFIED DRUG; 1-BUTYL-3-METHYLIMIDAZOLIUM CHLORIDE; 1-OCTYL-3-METHYLIMIDAZOLIUM; BORIC ACID; HUMIC SUBSTANCE; WATER POLLUTANT;

BIOAVAILABILITY; DISSOLVED ORGANIC MATTER; ENVIRONMENTAL FATE; ENVIRONMENTAL RISK; GENOTOXICITY; HUMIC ACID; MUTAGENICITY; SORPTION; TELEOST;

ADSORPTION; ARTICLE; BIOAVAILABILITY; BIOMASS DISTRIBUTION; CELL DEATH; CELL VIABILITY; CONCENTRATION (PARAMETERS); CYTOTOXICITY; GENOTOXICITY; HUMAN; HUMAN CELL; LC 50; MUTAGENICITY; NONHUMAN; ORYZIAS; ANIMAL; CHEMISTRY; HEPG2 CELL LINE; HUMIC SUBSTANCE; SALMONELLA ENTERICA SUBSP. ENTERICA SEROVAR TYPHIMURIUM; TOXICITY; TOXICITY TESTING; WATER POLLUTANT;

ORYZIINAE;

ANIMALS; BORATES; HEP G2 CELLS; HUMANS; HUMIC SUBSTANCES; IMIDAZOLES; IONIC LIQUIDS; ORYZIAS; SALMONELLA TYPHIMURIUM; TOXICITY TESTS; WATER POLLUTANTS, CHEMICAL;

EID: 79951657376     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es103514s     Document Type: Article

References (53)

1. Welton, T. Room-Temperature Ionic Liquids. Solvents for synthesis and catalysis Chem. Rev. 1999, 99, 2071-2083 (Pubitemid 129585179)
2. Ropel, L.; Belveze, L. S.; Aki, S. N. V. K.; Stadtherr, M. A.; Brennecke, J. F. Octanol-water partition coefficients of imidazolium-based ionic liquids Green Chem. 2005, 7, 83-90 (Pubitemid 40311509)
3. Ranke, J.; Stolte, S.; Störmann, R.; Arning, J.; Jastorff, B. Design of sustainable chemical products-the example of ionic liquids Chem. Rev. 2007, 107, 2183-2206 (Pubitemid 47029092)
4. Boethling, R. S.; Sommer, E.; DiFiore, D. Designing small molecules for biodegradability Chem. Rev. 2007, 107, 2207-2227 (Pubitemid 47033768)
5. Pham, T. P. T.; Cho, C. W.; Yun, Y. S. Environmental fate and toxicity of ionic liquids: A review Water Res. 2010, 44, 352-372
6. Yu, M.; Li, S.-M.; Li, X.-Y.; Zhang, B.-J.; Wang, J. J. Acute effects of 1-octyl-3-methylimidazolium bromide ionic liquid on the antioxidant enzyme system of mouse liver Ecotox. Environ. Saf. 2009, 71, 903-906
7. Pernak, J.; Sobaszkiewicz, K.; Mirska, I. Anti-microbial activities of ionic liquids Green Chem. 2003, 5, 52-56 (Pubitemid 37465266)
8. Docherty, K. M.; Kulpa, C. F. Toxicity and antimicrobial activity of imidazolium and pyridinium ionic liquids Green Chem. 2005, 7, 185-189 (Pubitemid 40592193)
9. Latala, A.; Stepnowski, P.; Nedzi, M.; Mrozik, W. Marine toxicity assessment of imidazolium ionic liquids: acute effects on the Baltic algae Oocystis submarina and Cyclotella meneghiniana Aquat. Toxicol. 2005, 73, 91-98 (Pubitemid 40693929)
10. Stolte, S.; Matzke, M.; Arning, J.; Boschen, A.; Pitner, W. R.; Welz-Biermann, U.; Jastorff, B.; Ranke, J. Effects of different head groups and functionalized side chains on the aquatic toxicity of ionic liquids Green Chem. 2007, 9, 1170-1179
11. Pretti, C.; Chiappe, C.; Baldetti, I.; Brunini, S.; Monni, G.; Intorre, L. Acute toxicity of ionic liquids for three freshwater organisms: Pseudokirchneriella subcapitata, Daphnia magna and Danio rerio Ecotoxicol. Environ. Saf. 2009, 72, 1170-1176
12. Jastorff, B.; Molter, K.; Behrend, P.; Bottin-Weber, U.; Filser, J.; Heimers, A.; Ondruschka, B.; Ranke, J.; Schaefer, M.; Schroder, H.; Stark, A.; Stepnowski, P.; Stock, F.; Stormann, R.; Stolte, S.; Welz-Biermann, U.; Ziegert, S.; Thoming, J. Progress in evaluation of risk potential of ionic liquids-basis for an eco-design of sustainable products Green Chem. 2005, 7, 362-372 (Pubitemid 40745568)
13. Matzke, M.; Stolte, S.; Arning, J.; Uebersa, U.; Filser, J. Imidazolium based ionic liquids in soils: effects of the side chain length on wheat (Triticum aestivum) and cress (Lepidium sativum) as affected by different clays and organic matter Green Chem. 2008, 10, 584-591 (Pubitemid 351624332)
14. Larson, J. H.; Frost, P. C.; Lamberti, G. A. Variable toxicity of ionic liquid-forming chemicals to Lemna minor and the influence of dissolved organic matter Environ. Toxicol. Chem. 2008, 27, 676-681 (Pubitemid 351413536)
15. Stepnowski, P.; Sk1adanowski, A. C.; Ludwiczak, A.; Laczynska, E. Evaluating the cytotoxicity of ionic liquids using human cell line HeLa Hum. Exp. Toxicol. 2004, 23, 513-517 (Pubitemid 39627220)
16. Wang, X.; Ohlin, C. A.; Lu, Q.; Fei, Z.; Hu, J.; Dyson, P. J. Cytotoxicity of ionic liquids and precursor compounds towards human cell line HeLa Green Chem. 2007, 9, 1191-1197
17. Kumar, R. A.; Papaiconomou, N.; Lee, J. M.; Salminen, J.; Clark, D. S.; Prausnitz, J. M. In vitro cytotoxicities of ionic liquids: effect of cation rings, functional groups, and anions Environ. Toxicol. 2009, 24, 388-395
18. Ranke, J.; Molter, K.; Stock, F.; Bottin-Weber, U.; Poczobutt, J.; Hoffmann, J.; Ondruschka, B.; Filser, J.; Jastorff, B. Biological effects of imidazolium ionic liquids with varying chain lengths in acute Vibrio fischeri and WST-1 cell viability assays Ecotoxicol. Environ. Saf. 2004, 28, 396-404 (Pubitemid 38833689)
19. Stolte, S.; Arning, J.; Bottin-Weber, U.; Matzke, M.; Stock, F.; Thiele, K.; Uerdingen, M.; Welz-Biermann, U.; Jastorff, B.; Ranke, J. Anion effects on the cytotoxicity of ionic liquids Green Chem. 2006, 8, 621-629 (Pubitemid 43993087)
20. Bernot, R. J.; Brueseke, M. A.; Evans-White, M. A.; Lamberti, G. A. Acute and chronic toxicity of imidazolium-based ionic liquids on Daphnia magna Environ. Toxicol. Chem. 2005, 24, 87-92 (Pubitemid 39658146)
21. Bernot, R. J.; Kennedy, E. E.; Lamberti, G. A. Effects of ionic liquids on the survival, movement, and feeding behavior of the freshwater snail, Physa acuta Environ. Toxicol. Chem. 2005, 24, 1759-1765 (Pubitemid 40917199)
22. Costello, D. M.; Brown, L. M.; Lamberti, G. A. Acute toxic effects of ionic liquids on zebra mussel (Dreissena polymorpha) surviving and feeding Green Chem. 2009, 11, 548-553
23. Pretti, C.; Chiappe, C.; Pieraccini, D.; Gregori, M.; Abramo, F.; Monni, G.; Intorre, L. Acute toxicity of ionic liquids to the zebrafish (Danio rerio) Green Chem. 2006, 8, 238-240 (Pubitemid 43344124)
24. Bailey, M. M.; Townsend, M. B.; Jernigan, P. L.; Sturdivant, J.; Hough-Troutman, W. L.; Rasco, J. F.; Swatloski, R. P.; Rogers, R. D.; Hood, R. D. Developmental toxicity assessment of the ionic liquid 1-butyl-3- methylimidazolium chloride in CD-1 mice Green Chem. 2008, 10, 1213-1217
25. Studzinska, S.; Buszewski, B. Study of toxicity of imidazolium ionic liquids to watercress (Lepidium sativum L.) Anal. Bioanal. Chem. 2009, 393, 983-990
26. Gorman-Lewis, D. J.; Fein, J. B. Experimental study of the adsorption of an ionic liquid onto bacterial and mineral surfaces Environ. Sci. Technol. 2004, 38, 2491-2495 (Pubitemid 38481057)
27. Stepnowski, P. Preliminary assessment of the sorption of some alkyl imidazolium cations as used in ionic liquids to soils and sediments Aust. J. Chem. 2005, 58, 170-173 (Pubitemid 40541991)
28. Stepnowski, P.; Mrozik, W.; Nichthauser, J. Adsorption of alkylimidazolium and alkylpyridinium ionic liquids onto natural soils Environ. Sci. Technol. 2007, 41, 511-516 (Pubitemid 46106284)
29. Beaulieu, J. J.; Tank, J. L.; Kopacz, M. Sorption of imidazolium-based ionic liquids to aquatic sediments Chemosphere 2008, 70, 1320-1328
30. Studzinska, S.; Sprynskyy, M.; Buszewski, B. Study of sorption kinetics of some ionic liquids on different soil types Chemosphere 2008, 71, 2121-2128
31. Matzke, M.; Thiele, K.; Muller, A.; Filser, J. Sorption and desorption of imidazolium based ILs in different soil types Chemosphere 2009, 74, 568-574
32. Studzinska, S.; Kowalkowski, T.; Buszewski, B. Study of ionic liquid cations transport in soil J. Hazard. Mater. 2009, 168, 1542-1547
33. Koopal, L. K.; Goloub, T. P.; Davis, T. A. Binding of ionic surfactants to purified humic acid J. Colloid Interface Sci. 2004, 275, 360-367 (Pubitemid 38737200)
34. Ishiguro, M.; Tan, W.; Koopal, L. K. Binding of cationic surfactants to humic substances Colloid Surf. A. 2007, 306, 29-39 (Pubitemid 47198461)
35. Escher, B. I.; Hermens, J. L. M. Internal exposure: linking bioavailability to effects Environ. Sci. Technol. 2004, 38, 455A-462A (Pubitemid 39578627)
36. Hu, X. L.; Liu, J. F.; Jönsson, J. Å.; Jiang, G.-B. Development of negligible depletion hollow fiber-protected liquid-phase microextraction for sensing the freely dissolved triazines Environ. Toxicol. Chem. 2009, 28, 231-238
37. Mosmann, T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays J. Immunol. Methods 1983, 65, 55-63 (Pubitemid 14203433)
38. Oda, Y.; Nakamura, S.; Oki, I.; Kato, T.; Shinagawa, H. Evaluation of a new system (umu-test) for the detection of environmental mutagens and carcinogens Mutat. Res. 1985, 147, 219-229 (Pubitemid 15235246)
39. Yasunaga, K.; Kiyonari, A.; Oikawa, T.; Abe, N.; Yoshikawa, K. Evaluation of the Salmonella umu test with 83 NTP chemicals Environ. Mol. Mutagen. 2004, 44, 329-345 (Pubitemid 39447237)
40. Xiao, R. Y.; Wang, Z.; Wang, C. X.; Yu, G.; Zhu, Y. G. Genotoxic risk identification of soil contamination at a major industrialized city in Northeast China by a combination of in vitro and in vivo bioassays Environ. Sci. Technol. 2006, 40, 6170-6175 (Pubitemid 44507277)
41. Li, J.; Ma, M.; Cui, Q.; Wang, Z. Assessing the potential risk of oil-field produced waters using a battery of bioassays/biomarkers Bull. Environ. Contam. Toxicol. 2008, 80, 492-496
42. Kukkonen, J.; Oikari, A.; Johnsen, S.; Gjessing, E. Effects of humus concentrations on benzo[A] pyrene accumulation from water to daphnia-magna-comparison of natural-waters and standard preparations Sci. Total Environ. 1989, 79, 197-207
43. ISO. International Organization for Standardization: Geneva, Switzerland, 1996; ISO/DIS 7346-1.
44. Arnold, C. G.; Ciani, A.; Muller, S. R.; Amirbahman, A.; Schwarzenbach, R. P. Association of triorganotin compounds with dissolved humic acids Environ. Sci. Technol. 1998, 32, 2976-2983 (Pubitemid 28475662)
45. Kahle, M.; Stamm, C. Sorption of the veterinary antimicrobial sulfathiazole to organic materials of different origin Environ. Sci. Technol. 2007, 41, 132-138 (Pubitemid 46047834)
46. Sibley, S. D.; Pedersen, J. A. Interaction of the macrolide antimicrobial clarithromycin with dissolved humic acid Environ. Sci. Technol. 2008, 42, 422-428 (Pubitemid 351461888)
47. Lee, S.; Gan, J.; Liu, W. P.; Anderson, M. A. Evaluation of Kd underestimation using solid phase microextraction Environ. Sci. Technol. 2003, 37, 5597-5602 (Pubitemid 37541730)
48. Docherty, K. M.; Hebbeler, S. Z.; Kulpa, C. F. An assessment of ionic liquid mutagenicity using the Ames Test Green Chem. 2006, 8, 560-567 (Pubitemid 43856612)
49. Versteeg, D. J.; Shorter, S. J. Effect of organic carbon on the uptake and toxicity of quaternary ammonium compounds to the fathead minnow, Pimephales promelas Environ. Toxicol. Chem. 1992, 11, 571-580
50. Mott, H. V. Association of hydrophobic organic contaminants with soluble organic mater: Evaluation of the database of Kdoc values Adv. Environ. Res. 2002, 6, 577-593 (Pubitemid 34855356)
51. Chiou, C. T.; Malcolm, R. L.; Brinton, T. I.; Kile, D. E. Water solubility enhancement of some organic pollutants and pesticides by dissolved humic and fulvic acids Environ. Sci. Technol. 1986, 20, 502-508 (Pubitemid 16042608)
52. Niederer, C.; Schwarzenbach, R. P.; Goss, K. U. Elucidating differences in the sorption properties of 10 humic and fulvic acids for polar and nonpolar organic chemicals Environ. Sci. Technol. 2007, 41, 6711-6717 (Pubitemid 47548085)
53. Chin, Y. P.; Aiken, G. R.; Danielsen, K. M. Binding of pyrene to aquatic and commercial humic substances: the role of molecular weight and aromaticity Environ. Sci. Technol. 1997, 31, 1630-1635 (Pubitemid 27241971)