Correlating the structure and composition of ionic liquids with their toxicity on Vibrio fischeri: A systematic study

Journal of Hazardous Materials

Volumn 215-216, Issue , 2012, Pages 40-48

  Viboud, Sylvie ^a   Papaiconomou, Nicolas ^a   Cortesi, Aurélien ^a   Chatel, Grégory ^a   Draye, Micheline ^a   Fontvieille, Dominique ^a  

^a UNIVERSITÉ DE SAVOIE   (France)

Author keywords

EC 50; Ionic liquids; Toxicity; Vibrio fischeri

Indexed keywords

ALIPHATIC CARBON; BIS(TRIFLUOROMETHANE SULFONYL)IMIDE; CATION RING; DICYANAMIDE; EC 50; ECOTOXICOLOGICAL; IMIDAZOLIUM; LINEAR CORRELATION; LOW TOXICITY; MARINE BACTERIUM; MULTIFACTORIAL ANALYSIS; PLANARITY; PYRIDINIUM; PYRIDINIUM CATIONS; PYRROLIDINIUM; STRUCTURE PARAMETER; SYSTEMATIC STUDY; TETRAFLUOROBORATES; TETRAPHENYLBORATES; TOXICITY VALUES; VIBRIO FISCHERI;

DIAGNOSIS; HYDROPHILICITY; HYDROPHOBICITY; IONIC LIQUIDS; POSITIVE IONS;

TOXICITY;

(TRIFLUOROMETHANESULFONYL)IMIDE; BORIC ACID; IMIDAZOLIUM; IMIDE; IONIC LIQUID; PIPERIDINIUM; PYRIDINIUM DERIVATIVE; PYRROLIDINIUM; TETRACYANOBORATE; TETRAFLUOROBORATE TETRAPHENYLBORATE; UNCLASSIFIED DRUG;

BACTERIUM; BIOASSAY; BIOLUMINESCENCE; CATION; CORRELATION; ECOTOXICOLOGY; HYDROPHOBICITY; IONIC COMPOSITION; MARINE ECOSYSTEM; TOXICITY;

ARTICLE; HYDROPHILICITY; HYDROPHOBICITY; NONHUMAN; VIBRIO FISCHERI;

ALIIVIBRIO FISCHERI; IONIC LIQUIDS; LUMINESCENCE; STRUCTURE-ACTIVITY RELATIONSHIP; WATER POLLUTANTS, CHEMICAL;

VIBRIO FISCHERI;

EID: 84859268980     PISSN: 03043894     EISSN: 18733336     Source Type: Journal    
DOI: 10.1016/j.jhazmat.2012.02.019     Document Type: Article

References (49)

1. Huddleston J.G., Visser A.E., Reichert W.M., Willauer H.D., Broker G.A., Rogers R.D. Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation. Green Chem. 2001, 3:156-164.
2. Gerhard D., Alpaslan S.C., Gores H.J., Uerdingen M., Wasserscheid P. Trialkylsulfonium dicyanamides - A new family of ionic liquids with very low viscosities. Chem. Commun. 2005, 5080-5082.
3. MacFarlane D.R., Meakin P., Sun J., Amini N., Forsyth M. Pyrrolidinium imides: a new family of molten salts and conductive plastic crystal phases. J. Phys. Chem. B 1999, 103:4164-4170.
4. Crosthwaite J.M., Muldoon M.J., Dixon J.K., Anderson J.L., Brennecke J.F. Phase transition and decomposition temperatures, heat capacities and viscosities of pyridinium ionic liquids. J. Chem. Thermodyn. 2005, 37:559-568.
5. Kilaru P., Baker G.A., Scovazzo P. Density and surface tension measurements of imidazolium-, quaternary phosphonium-, and ammonium-based room-temperature ionic liquids: data and correlations. J. Chem. Eng. Data 2007, 52:2306-2314.
6. Hiroyuki O., Masahiro Y., Tomonobu M. Ionic conductivity. Electrochemical Aspects of Ionic Liquids 2005, 75-81. John Wiley & Sons, Inc. O. Hiroyuki (Ed.).
7. Parvulescu V.I., Hardacre C. Catalysis in ionic liquids. Chem. Rev. 2007, 107:2615-2665.
8. Van Rantwijk F., Sheldon R.A. Biocatalysis in ionic liquids. Chem. Rev. 2007, 107:2757-2785.
9. Plechkova N.V., Seddon K.R. Applications of ionic liquids in the chemical industry. Chem. Soc. Rev. 2008, 37:123-150.
10. Albinet A., Papaiconomou N., Estager J., Suptil J., Besombes J.L. A new ozone denuder for aerosol sampling based on an ionic liquid coating. Anal. Bioanal. Chem. 2010, 396:857-864.
11. Albinet A., Papaiconomou N., Estager J., Suptil J., Draye M., Besombes J.L. Erratum to: a new ozone denuder for aerosol sampling based on an ionic liquid coating. Anal. Bioanal. Chem. 2010, 397:887.
12. Docherty K.M., Kulpa C.F. Toxicity and antimicrobial activity of imidazolium and pyridinium ionic liquids. Green Chem. 2005, 7:185-189.
13. Zhao D., Liao Y., Zhang Z. Toxicity of ionic liquids. Clean - Soil, Air, Water 2007, 35:42-48.
14. Petkovic M., Ferguson J., Bohn A., Trindade J., Martins I., Carvalho M.B., Leitao M.C., Rodrigues C., Garcia H., Ferreira R., Seddon K.R., Rebelo L.P.N., Silva Pereira C. Exploring fungal activity in the presence of ionic liquids. Green Chem. 2009, 11:889-894.
15. Wood N., Stephens G. Accelerating the discovery of biocompatible ionic liquids. Phys. Chem. Chem. Phys. 2010, 12:1670-1674.
16. Petkovic M., Seddon K.R., Rebelo L.P.N., Silva Pereira C. Ionic liquids: a pathway to environmental acceptability. Chem. Soc. Rev. 2011, 40:1383-1403.
17. Romero A., Santos A., Tojo J., Rodríguez A. Toxicity and biodegradability of imidazolium ionic liquids. J. Hazard. Mater. 2008, 151:268-273.
18. Kumar R.A., Papaïconomou 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.
19. Matzke M., Stolte S., Thiele K., Juffernholz T., Arning J., Ranke J., Welz-Biermann U., Jastorff B. The influence of anion species on the toxicity of 1-alkyl-3-methylimidazolium ionic liquids observed in an (eco)toxicological test battery. Green Chem. 2007, 9:1198-1207.
20. Wells A.S., Coombe V.T. On the freshwater ecotoxicity and biodegradation properties of some common ionic liquids. Org. Process Res. Dev. 2006, 10:794-798.
21. Stolte S., Matzke M., Arning J., Böhen A., Pitner W.R., Welz-Biermann U., Ranke J. Effects of different head groups and functionalised side chains on the aquatic toxicity of ionic liquids. Green Chem. 2007, 9:1170-1179.
22. Billard I., Ouadi A., Gaillard C. Liquid-liquid extraction of actinides, lanthanides, and fission products by use of ionic liquids: from discovery to understanding. Anal. Bioanal. Chem. 2011, 400:1555-1566.
23. Chapeaux A., Stadherr M.A., Brennecke J.F. Liquid phase behavior of ionic liquids with water and 1-octanol and modeling of 1-octanol/water partition coefficients. J. Chem. Eng. Data 2007, 52:2462-2467.
24. Freire M.G., Neves C.M.S.S., Carvalho P.J., Gardas R.L., Fernandes A.M., Marrucho I.M., Santos L.M.N.B.F., Coutinho J.A.P. Mutual solubilities of water and hydrophobic ionic liquids. J. Phys. Chem. B 2007, 111:13082-13089.
25. Papaiconomou N., Salminen J., Lee J.-M., Prausnitz J.M. Physicochemical properties of hydrophobic ionic liquids containing 1-octylpyridinium, 1-octyl-2-methylpyridinium, or 1-octyl-4-methylpyridinium cations. J. Chem. Eng. Data 2007, 52:833-840.
26. Germani R., Mancini M.V., Savelli G., Spreti N. Mercury extraction by ionic liquids: temperature and alkyl chain length effect. Tetrahedron Lett. 2007, 48:1767-1769.
27. Yan-Ying Y., Wei Z., Shu-Wen C. Extraction of ferulic acid and caffeic acid with ionic liquids. Chin. J. Anal. Chem. 2007, 35:1726-1730.
28. Giridhar P., Venkatesan K.A., Subramaniam S., Srinivasan T.G., Vasudeva Rao P.R. Extraction of uranium (VI) by 1.1M tri-n-butylphosphate/ionic liquid and the feasibility of recovery by direct electrodeposition from organic phase. J. Alloys Compd. 2008, 448:104-108.
29. Papaiconomou N., Lee J.-M., Salminen J., von Stosch M., Prausnitz J.M. Selective extraction of copper, mercury, silver, and palladium ions from water using hydrophobic ionic liquids. Ind. Eng. Chem. Res. 2008, 47:5080-5086.
30. Salminen J., Papaiconomou N., Kumar R.A., Lee J.-M., Kerr J., Newman J., Prausnitz J.M. Physicochemical properties and toxicities of hydrophobic piperidinium and pyrrolidinium ionic liquids. Fluid Phase Equilib. 2007, 261:421-426.
31. Papaiconomou N., Estager J., Traore Y., Bauduin P., Bas C., Legeai S., Viboud S., Draye M. Synthesis, physicochemical properties, and toxicity data of new hydrophobic ionic liquids containing dimethylpyridinium and trimethylpyridinium cations. J. Chem. Eng. Data 2010, 55:1971-1979.
32. ISO 11348-3 Water Quality - Determination of the Inhibitory Effect of Water Samples on the Light Emission of Vibrio fischeri (Luminescent Bacteria Test) - Part 3: Method Using Freeze-Dried Bacteria 1998, ISO, Geneva.
33. ASTM Test Method for Assessing the Microbial Detoxification of Chemically Contaminated Water and Soil Using a Toxicity Test with a Luminescent Marine Bacterium 2009, ASTM international Designation: D5660-96, West Conshohocken, PA.
34. Benzécri J.P. L'analyse des données: l'analyse des correspondances 1973, Dunod, Paris.
35. Greenacre M. Theory and Applications of Correspondence Analysis 1984, Academic Press Inc., London, Orlando, FL.
36. Aruoja V., Sihtmäe M., Dubourguier H.C., Kahru A. Toxicity of 58 substituted anilines and phenols to algae Pseudokirchneriella subcapitata and bacteria Vibrio fischeri: Comparison with published data and QSARs. Chemosphere 2011, 84:1310-1320.
37. Kaiser K.L.E., Palabrica V.S. Photobacterium phosphoreum toxicity data index. Water Pollut. Res. J. Can. 1991, 26:361-431.
38. Couling D.J., Bernot R.J., Docherty K.M., Dixon J.K., Maginn E.J. Assessing the factors responsible for ionic liquid toxicity to aquatic organisms via quantitative structure-property relationship modeling. Green Chem. 2006, 8:82-90.
39. 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.
40. Petkovic M., Ferguson J.L., Gunaratne H.Q.N., Ferreira R., Leitao M.C., Seddon K.R., Rebelo L.P., Pereira C.S. Novel biocompatible cholinium-based ionic liquids-toxicity and biodegradability. Green Chem. 2010, 12:643-649.
41. Lacrãmã A.-M., Putz M., Ostafe V. A spectral-SAR model for the anionic-cationic interaction in ionic liquids: application to Vibrio fischeri ecotoxicity. Int. J. Mol. Sci. 2007, 8:842-863.
42. Jastorff B., Störmann R., Ranke J. Thinking in structure-activity relationships - a way forward towards sustainable chemistry. Clean - Soil, Air, Water 2007, 35:399-405.
43. Alvarez-Guerra M., Irabien A. Design of ionic liquids: an ecotoxicity (Vibrio fischeri) discrimination approach. Green Chem. 2011, 13:1507-1516.
44. MacFarlane D.R., Golding J., Forsyth S., Forsyth M., Deacon G.B. Low viscosity ionic liquids based on organic salts of the dicyanamide anion. Chem. Commun. 2001, 1430-1431.
45. Deng M.J., Chen P.Y., Leong T.I., Sun I.W., Chang J.K., Tsai W.T. Dicyanamide anion based ionic liquids for electrodeposition of metals. Electrochem. Commun. 2008, 10:213-216.
46. Evans K. Supported phospholipid bilayer interaction with components found in typical room-temperature ionic liquids - a QCM-D and AFM study. Int. J. Mol. Sci. 2008, 9:498-511.
47. Cromie S.R.T., Del Poópolo M.G., Ballone P. Interaction of room temperature ionic liquid solutions with a cholesterol bilayer. J. Phys. Chem. B 2009, 113:11642-11648.
48. Mrozik W., Jungnickel C., Ciborowski T., Pitner W., Kumirska J., Kaczynski Z., Stepnowski P. Predicting mobility of alkylimidazolium ionic liquids in soils. J. Soils Sed. 2009, 9:237-245.
49. Stepnowski P., Mrozik W., Nichthauser J. Adsorption of alkylimidazolium and alkylpyridinium ionic liquids onto natural soils. Environ. Sci. Technol. 2006, 41:511-516.