Theoretical descriptor for the correlation of aquatic toxicity of ionic liquids by quantitative structure-toxicity relationships

Chemical Engineering Journal

Volumn 175, Issue 1, 2011, Pages 17-23

  Bruzzone, S ^a   Chiappe, C ^a   Focardi, S E ^b   Pretti, C ^a   Renzi, M ^c  

^a UNIVERSITY OF PISA   (Italy)

^b UNIVERSITY OF SIENA   (Italy)

^c Centro Ricerche di Ecologia Lagunare Pesca ed Acquacoltura   (Italy)

Author keywords

Ionic liquid; Polarizable continuum model; QSAR; Toxicity; Vibrio fischeri

Indexed keywords

AQUATIC TOXICITY; DESCRIPTORS; GASPHASE; POLARIZABLE CONTINUUM MODEL; QSAR; VIBRIO FISCHERI;

COMPUTATIONAL CHEMISTRY; CONTINUUM MECHANICS; IONS; TOXICITY; WATER TREATMENT;

IONIC LIQUIDS;

VIBRIO FISCHERI;

EID: 80755128223     PISSN: 13858947     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cej.2011.08.073     Document Type: Article

References (46)

1. Arning J., Stolte S., Baschen A., Stock F., Pitner W.R., Welz-Biermann U., Jastorff B., Ranke J. Qualitative and quantitative structure activity relationships for the inhibitory effects of cationic head groups, functionalised side chains and anions of ionic liquids on acetylcholinesterase. Green Chem. 2008, 10:47-58.
2. Austin R.P., Barton P., Davis A.M., Manners C.N., Stansfield M.C. The effect of ionic strength on liposome-buffer and 1-octanol-buffer distribution coefficients. J. Pharm. Sci. 1998, 87:599-607.
3. Bini R., Bortolini O., Chiappe C., Pieraccini D., Siciliano T. Development of cation/anion "interaction" scales for ionic liquids through esi-ms measurements. J. Phys. Chem. B 2007, 111:598-604.
4. Bini R., Malvaldi M., Pitner W.R., Chiappe C. Qspr correlation for conductivities and viscosities of low-temperature melting ionic liquids. J. Phys. Org. Chem. 2008, 21:622-629.
5. Chiappe C., Melai B., Sanzone A., Valentini G. Basic ionic liquids based on monoquaternized 1,4-diazobicyclo[2.2.2]octane (dabco) and dicyanamide anion: physicochemical and solvent properties. Pure Appl. Chem. 2009, 81:2035-2043.
6. Chiappe C., Pieraccini D. Ionic liquids: solvent properties and organic reactivity. J. Phys. Org. Chem. 2005, 18:275-287.
7. European Community, European Community Regulation on Registration, Evaluation, Authorisation and Restriction of Chemicals.
8. Couling D.J., Bernot R.J., Docherty K.M., Dixon J.K., Maginn E.J. Effects of different head groups and functionalised side chains on the aquatic toxicity of ionic liquids. Green Chem. 2006, 8:82-90.
9. Devillers J., Chambon P. Acute toxicity and qsar of chlorophenols on daphnia magna. Bull. Environ. Contam. Toxicol. 1986, 37:599-605.
10. Docherty K.M., Kulpa C.F. Toxicity and antimicrobial activity of imidazolium and pyridinium ionic liquids. Green Chem. 2005, 7:185-189.
11. Domanska U., Rekawek A., Marciniak A. Solubility of 1-alkyl-3-ethylimidazolium-based ionic liquids in water and 1-octanol. J. Chem. Eng. Data 2008, 53:1126-1132.
12. Freire M.G., Carvalho P.J., Silva A.M.S., Santos L.M.N.B.F., Rebelo L.P.N., Marrucho I.M., Coutinho J.A.P. Ion specific effects on the mutual solubilities of water and hydrophobic ionic liquids. J. Phys. Chem. B 2009, 113:202-211.
13. Garcia M.T., Gathergood N., Scammells P.J. Biodegradable ionic liquids part ii. effect of the anion and toxicology. Green Chem. 2005, 7:9-14.
14. Gardas R.L., Coutinho J.A.P. Applying a qspr correlation to the prediction of surface tensions of ionic liquids. Fluid Phase Equilib. 2008, 265:57-65.
15. Heintz A. Recent developments in thermodynamics and thermophysics of non-aqueous mixtures containing ionic liquids. A review. J. Chem. Thermodyn. 2005, 37:525-536.
16. 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.
17. Hussey C.L. Room temperature haloaluminate ionic liquids. Novel solvents for transition metal solution chemistry. Pure Appl. Chem. 1988, 60:1763-1772.
18. ISO11348-3, 2007. 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.
19. Frisch M.J., et al. Gaussian 03 (Revision A.1) 2003, Gaussian, Inc., Pittsburgh, PA.
20. 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., Ziegerta S., Thominga J. Progress in evaluation of risk potential of ionic liquids basis for an eco-design of sustainable products. Green Chem. 2005, 7:362-372.
21. Jastorff B., Stormann R., Ranke J., Molter K., Stock F., Oberheitmann B., Hoffmann W., Hoffmann J., Nuchter M., Ondruschka B., Filser J. How hazardous are ionic liquids? Structure-activity relationships and biological testing as important elements for sustainability evaluation. Green Chem. 2003, 5:136-142.
22. Jennings V.L.K., Rayner-Brandes M.H., Bird D.J. Assensing chemical toxicity with the bioluminescent photobacterium (Vibrio fischeri): a comparison of three commercial systems. Water Res. 2001, 35:3448-3456.
23. Katritzky A.R., Jain R., Lomaka A., Petrukhin R., Karelson M., Visser A.E., Rogers R.D. Correlation of the melting points of potential ionic liquids (imidazolium bromides and benzimidazolium bromides) using the codessa program. J. Chem. Inf. Comput. Sci. 2002, 42:225-231.
24. Katritzky A.R., Tatham D.B. Theoretical descriptors for the correlation of aquatic toxicity of environmental pollutants by quantitative structure-toxicity relationships. J. Chem. Inf. Comput. Sci. 2001, 41:1162-1176.
25. 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.
26. Liu H., Liu Y., Li J. Ionic liquids in surface electrochemistry. Phys. Chem. Chem. Phys. 2010, 12:1685-1697.
27. Lopez-Martin I., Burello E., Davey P.N., Seddon K.R., Rothenberg G. Anion and cation effects on imidazolium salt melting points: a descriptor modelling study. ChemPhysChem 2007, 8:690-695.
28. Luis P., Garea A., Irabien A. Quantitative structure-activity relationships (qsars) to estimate ionic liquids ecotoxicity ec50 (Vibrio fischeri). J. Mol. Liq. 2010, 152:28-33.
29. Luis P., Ortiz I., Aldaco R., Irabien A. A novel group contribution method in the development of a qsar for predicting the toxicity (Vibrio fischeri ec50) of ionic liquids. Ecotoxicol. Environ. Saf. 2007, 67:423-429.
30. McFarlane J., Ridenour W.B., Lou H., Hunt R.D., Depaoli D.W., Ren R.X. Room temperature ionic liquids for separating organics from produced water. Sep. Sci. Technol. 2005, 40:1245-1265.
31. Moniruzzaman M., Nakashima K., Kamiya N., Goto M. Recent advances of enzymatic reactions in ionic liquids. Biochem. Eng. J. 2010, 48:295-314.
32. Muginova S.V., Galimova A.Z., Polyakov A.E., Shekhovtsova T.N. Ionic liquids in enzymatic catalysis and biochemical methods of analysis: capabilities and prospects. J. Anal. Chem. 2010, 65:331-351.
33. Pernak J., Sobaszkiewicz K., Mirska I. Anti-microbial activities of ionic liquids. Green Chem. 2003, 5:52-56.
34. 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, 58:396-404.
35. Ranke J., Othman A., Fan P., Muller A. Explaining ionic liquid water solubility in terms of cation and anion hydrophobicity. Int. J. Mol. Sci. 2009, 10:1271-1289.
36. Revelli A.L., Mutelet F., Jaubert J.N. Prediction of partition coefficients of organic compounds in ionic liquids: use of a linear solvation energy relationship with parameters calculated through a group contribution method. Ind. Eng. Chem. Res. 2010, 49:3883-3892.
37. Ropel L., Belvèze 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.
38. Schultz T.W., Cronin M.T.D., Netzeva T.I. The present status of qsar in toxicology. J. Mol. Struct. Theochem. 2003, 622:23-38.
39. Sheldon R.A. Green solvents for sustainable organic synthesis: state of the art. Green Chem. 2005, 7:267-278.
40. Stolte S., Matzke M., Arning J., Boschen A., Pitner W.R., Welz-Biermann U., Jastorff B., Ranke J. Effects of different head groups and functionalised side chains on the aquatic toxicity of ionic liquids. Green Chem. 2007, 9:1170-1179.
41. Swatloski R.P., Holbrey J.D., Memon S.B., Caldwell G.A., Caldwell K.A., Rogers R.D. Using Caenorhabditis elegans to probe toxicity of 1-alkyl-3-methylimidazolium chloride based ionic liquids. Chem. Commun. 2004, 6:668-669.
42. Torimoto T., Tsuda T., Okazaki K., Kuwabata S. New frontiers in materials science opened by ionic liquids. Adv. Mater. 2010, 22:1196-1221.
43. Torrecilla J.S., Garcia J., Rojo E., Rodriguez F. Estimation of toxicity of ionic liquids in leukemia rat cell line and acetylcholinesterase enzyme by principal component analysis, neural networks and multiple lineal regressions. J. Hazard. Mater. 2009, 164:182-194.
44. Welton T. Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem. Rev. 1999, 99:2071-2084.
45. Wood N., Stephens G. Accelerating the discovery of biocompatible ionic liquids. Phys. Chem. Chem. Phys. 2010, 12:1670-1674.
46. Yan C.Q., Han M.J., Wan H., Guan G.F. Qsar correlation of the melting points for imidazolium bromides and imidazolium chlorides ionic liquids. Fluid Phase Equilib. 2010, 292:104-109.