Designing ionic liquids: the chemical structure role in the toxicity

Ecotoxicology - Tập 22 Số 1 - Trang 1-12 - 2013
Sónia P. M. Ventura1, Ana M.M. Gonçalves2,3, Tânia E. Sintra1, Joana Luísa Pereira3, Fernando Gonçalves3, João A. P. Coutinho1
1Departamento de Química, CICECO, Universidade de Aveiro, Campus Universitário de Santiago, Aveiro, Portugal
2Departamento das Ciências da Vida, Faculdade de Ciências e Tecnologia, IMAR-CMA (Instituto do Mar), Universidade de Coimbra, Coimbra, Portugal
3Departamento de Biologia & CESAM (Centro de Estudos do Ambiente e do Mar), Universidade de Aveiro, Aveiro, Portugal

Tóm tắt

Từ khóa


Tài liệu tham khảo

Allen DT, Shonnard DR (2002) Green engineering. Prentice Hall, Upper Saddle River

Arning J, Stolte S, Boschen A, Stock F, Pitner W-R, Welz-Biermann U, Jastorff B, Ranke J (2008) 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 10:47–58

ASTM (1980) Standard practice for conducting acute toxicity tests with fishes, macroinvertebrates and amphibians, E 729–80. American Society for Testing and Materials, Philadelphia

Austin RP, Barton P, Davis AM, Manners CN, Stansfield MC (1998) The effect of ionic strength on liposome-buffer and 1-octanol-buffer distribution coefficients. J Pharm Sci 87:599–607

Azur Environmental (1998) Microtox manual. Carlbad CA, USA

Baird DJ, Barber I, Bradley MC, Calow P, Soares AMVM (1989) The Daphnia bioassay: a critique. Hydrobiologia 188/189: 403–406

Beadham MG, Gathergood N (2012) Handbook of Green chemistry. In: Boethling R, Voutchkova A (eds) Designing safer chemicals—ionic liquids, Chap. 6, vol 9, 1st edn. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, pp 137–158

Bernot RJ, Brueseke MA, Evans-White MA, Lamberti GA (2005) Acute and chronic toxicity of imidazolium-based ionic liquids on Daphnia magna. Environ Toxicol Chem 24:87–92

Brennecke JF, Maginn EJ (2001) Ionic liquids: innovative fluids for chemical processing. AIChE J 47:2384–2389

Cho C-W, Jeon Y-C, Pham TPT, Vijayaraghavan K, Yun Y-S (2008a) The ecotoxicity of ionic liquids and traditional organic solvents on microalga Selenastrum capricornutum. Ecotoxicol Environ Saf 71:166–171

Cho C-W, Pham TPT, Jeon Y-C, Yun Y-S (2008b) Influence of anions on the toxic effects of ionic liquids to a phytoplankton Selenastrum capricornutum. Green Chem 10:67–72

Coleman D, Gathergood N (2010) Biodegradation studies of ionic liquids. Chem Soc Rev 39:600–637

Couling DJ, Bernot RJ, Docherty KM, Dixon JK, Maginn EJ (2006) Assessing the factors responsible for ionic liquid toxicity to aquatic organisms via quantitative structure–property relationship modeling. Green Chem 8:82–90

Cowgill UM, Milazzo DP (1991) The sensitivity of Ceriodaphnia dubia and Daphnia magna to seven chemicals utilizing the three-brood test. Arch Environ Contam Toxicol 20:211–217

Deetlefs M, Seddon KR (2006) Ionic liquids: fact and fiction. Chim Oggi Chem Today 24:16–23

Deetlefs M, Seddon KR (2010) Assessing the greenness of some typical laboratory ionic liquid preparations. Green Chem 12:17–30. doi: 10.1039/b915049h

Docherty KM, Kulpa CFJ (2005) Toxicity and antimicrobial activity of imidazolium and pyridinium ionic liquids. Green Chem 7:185–189

Earle MJ, Seddon KR (2000) Ionic liquids. Green solvents for the future. Pure Appl Chem 72:1391–1398

Earle MJ, Esperanca J, Gilea MA, Lopes JNC, Rebelo LPN, Magee JW, Seddon KR, Widegren JA (2006) The distillation and volatility of ionic liquids. Nature 439:831–834. doi: 10.1038/nature04451

EC (2002) European Commission Guidance document on aquatic ecotoxicology. Under Council directive 91/414/EEC. SANCO/3268/2001 Rev 4

EC (2006) http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:2006:396:0001:0849:EN:PDF . Accessed 14 Feb 2012

EPA (2002) Short-term methods for estimating the chronic toxicity of effluents and receiving waters to freshwater organisms, 4th edn. EPA-821-R-02-013

Finney DJ (1971) Probit Analysis. Cambridge University Press, Cambridge

Freire MG, Neves CMSS, Carvalho PJ, Gardas RL, Fernandes AM, Marrucho IM, Santos LMNBF, Coutinho JAP (2007a) Mutual solubilities of water and hydrophobic ionic liquids. J Phys Chem B 111:13082–13089

Freire MG, Santos LMNBF, Fernandes AM, Coutinho JAP, Marrucho IM (2007b) An overview of the mutual solubilities of water-imidazolium-based ionic liquids systems. Fluid Phase Equilib 261:449–454

Freire MG, Carvalho PJ, Gardas RL, Marrucho IM, Santos LMNBF, Coutinho JAP (2008a) Mutual solubilities of water and the [Cnmim][Tf2N] hydrophobic ionic liquids. J Phys Chem B 112:1604–1610

Freire MG, Carvalho PJ, Gardas RL, Santos LMNBF, Marrucho IM, Coutinho JAP (2008b) Solubility of water in tetradecyltrihexylphosphonium-based ionic liquids. J Chem Eng Data 53:2378–2382. doi: 10.1021/je8002805

Freire MG, Carvalho PJ, Silva AMS, Santos LMNBF, Rebelo LPN, Marrucho IM, Coutinho JAP (2009) Ion specific effects on the mutual solubilities of water and hydrophobic ionic liquids. J Phys Chem B 113:202–211

Freire MG, Neves CMSS, Marrucho IM, Coutinho JAP, Fernandes AM (2010) Hydrolysis of tetrafluoroborate and hexafluorophosphate counter ions in imidazolium-based ionic liquid. J Phys Chem A 114:3744–3749

Freire MG, Cláudio AFM, Araújo JMM, Coutinho JAP, Marrucho IM, Canongia Lopes JN, Rebelo LPN (2012) Aqueous Biphasic Systems: a boost brought about by using ionic liquids. Chem Soc Rev. 41:4966–4995

Garcia MT, Gathergood N, Scammells PJ (2005) Biodegradable ionic liquids Part II. Effect of the anion and toxicology. Green Chem 7:9–14

Gathergood N, Scammells PJ (2002) Design and preparation of room-temperature ionic liquids containing biodegradable side chains. Aust J Chem 55:557–560

Gathergood N, Scammells PJ, Garcia MT (2004) Biodegradable ionic liquids: Part I. Concept, preliminary targets and evaluation. Green Chem 6:166–175

Gathergood N, Scammells PJ, Garcia MT (2006) Biodegradable ionic liquids Part III. The first readily biodegradable ionic liquids. Green Chem 8:156–160

Gonçalves AMM, de Figueiredo DR, Pereira MJ (2005) A low-cost methodology for algal growth inhibition tests using three freshwater green algae. Fresenius Environ Bull 14:1192–1195

Gorman-Lewis DJ, Fein JB (2004) Experimental study of the adsorption of an ionic liquid onto bacterial and mineral surfaces. Environ Sci Technol 38:2491–2495

Kaiser KLE, Palabrica VS (1991) Photobacterium phosphoreum toxicity data index. Water Pollut Res J Can 26:361–431

Kaniewska- Prus M (1982) The effect of ammonia, chlorine and chloramines toxicity on the mortality of Daphnia magna Straus. Pol Arch Hydrobiol 29:607–624

Kragl U, Eckstein M, Kaftzik N (2002) Enzyme catalysis in ionic liquids. Curr Opin Biotechnol 13:565–571

Kulacki KJ, Lamberti GA (2008) Toxicity of imidazolium ionic liquids to freshwater algae. Green Chem 10:104–110

Latala A, Stepnowski P, Nedzi M, Mrozik W (2005) Marine toxicity assessment of imidazolium ionic liquids: acute effects on the Baltic algae Oocystis submarina and Cyclotella meneghiniana. Aquat Toxicol 73:91–98

Latala A, Nedzi M, Stepnowski P (2009a) Acute toxicity assessment of perfluorinated carboxylic acids towards the Baltic microalgae. Environ Toxicol Pharmacol 28:167–171

Latala A, Nedzi M, Stepnowski P (2009b) Toxicity of imidazolium and pyridinium based ionic liquids towards algae. Bacillaria paxillifer (a microphytobenthic diatom) and Geitlerinema amphibium (a microphytobenthic blue green alga). Green Chem 11:1371–1376

Latala A, Nedzi M, Stepnowski P (2009c) Toxicity of imidazolium and pyridinium based ionic liquids towards algae. Chlorella vulgaris, Oocystis submarina (green algae) and Cyclotella meneghiniana, Skeletonema marinoi (diatoms). Green Chem 11:580–588

Luo Y-R, Li X-Y, Chen X-X, Zhang B-J, Sun Z-J, Wang J-J (2008) The developmental toxicity of 1-methyl-3-octylimidazolium bromide on Daphnia magna. Environ Toxicol 23:736–744

Matzke M, Stolte S, Thiele K, Juffernholz T, Arning J, Ranke J, Welz-Biermann U, Jastorff B (2007) The influence of anion species on the toxicity of 1-alkyl-3-methylimidazolium ionic liquids observed in an (eco)toxicological test battery. Green Chem 9:1198–1207

Matzke M, Arning J, Ranke J, Jastorff B, Stolte S (2010) Design of inherently safer ionic liquids: toxicology and biodegradation. In: Handbook of green chemistry. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, pp 225–290. doi: 10.1002/9783527628698.hgc069

Microbics Corporation (1992) Microtox® manual—a toxicity testing handbook. Microbics Corporation, Carlsbad, pp 1–5

OECD (2004) Daphnia sp., acute immobilisation test—test guideline 202. Organization for the Economic Cooperation and Development, Paris

OECD (2008) Daphnia magna reproduction test–test guideline 211. Organization for the Economic Cooperation and Development, Paris

OECD (2011) Freshwater alga and cyanobacteria, growth inhibition test—test guideline 201. Organization for the Economic Cooperation and Development, Paris

Passino DRM, Smith SB (1987) Acute bioassays and hazard evaluation of representative contaminants detected in Great Lakes fish. Environ Toxicol Chem 6:901–907

Plechkova NV, Seddon KR (2007) Ionic liquids: “Designer” solvents for green chemistry, in methods and reagents for green chemistry, vol 38. John Wiley & Sons, Inc, pp 103–130

Plechkova NV, Seddon KR (2008) Applications of ionic liquids in the chemical industry. Chem Soc Rev 37:123–150

Pretti C, Chiappe C, Baldetti I, Brunini S, Monni G, Intorre L (2009) Acute toxicity of ionic liquids for three freshwater organisms: Pseudokirchneriella subcapitata, Daphnia magna and Danio rerio. Ecotoxicol Environ Saf 72:1170–1176

Ranke J, Molter K, Stock F, Bottin-Weber U, Poczobutt J, Hoffmann J, Ondruschka B, Filser J, Jastorff B (2004) Biological effects of imidazolium ionic liquids with varying chain lengths in acute Vibrio fischeri and WST-1 cell viability assays. Ecotoxicol Environ Saf 58:396–404

Ranke J, Muller A, Bottin-Weber U, Stock F, Stolte S, Arning J, Stormann R, Jastorff B (2007a) Lipophilicity parameters for ionic liquid cations and their correlation to in vitro cytotoxicity. Ecotoxicol Environ Saf 67:430–438. doi: 10.1016/j.ecoenv.2006.08.008

Ranke J, Stolte S, Stormann R, Arning J, Jastorff B (2007b) Design of sustainable chemical products the example of ionic liquids. Chem Rev 107:2183–2206. doi: 10.1021/cr050942s

Ranke J, Othman A, Fan P, Müller A (2009) Explaining ionic liquid water solubility in terms of cation and anion hydrophobicity. Int J Mol Sci 10:1271–1289

Romero A, Santos A, Tojo J, Rodríguez A (2008) Toxicity and biodegradability of imidazolium ionic liquids. J Hazard Mater 151:268–273

Salminen J, Papaiconomou N, Kumara A, Lee J-M, Kerr J, Newmana J, Prausnitz JM (2007) Physicochemical properties and toxicities of hydrophobic piperidinium and pyrrolidinium ionic liquids. Fluid Phase Equilib 261:421–426

Samorì C, Pasteris A, Galletti P, Tagliavini E (2007) Acute toxicity of oxygenated and nonoxygenated imidazolium-based ionic liquids to Daphnia magna and Vibrio fischeri. Environ Toxicol Chem 26:2379–2382

Sheldon R (2001) Catalytic reactions in ionic liquids. Chem Commun 2399–2407

Sheldon RA, Lau RM, Sorgedrager MJ, van Rantwijk FV, Seddon KR (2002) Biocatalysis in ionic liquids. Green Chem 4:147–151

Smith DG (2001) Pennak’s freshwater invertebrates of the United States: Porifera to Crustacea, 4th edn. Wiley, New York

Steinberg SM, Poziomek EJ, Engelmann WH, Rogers KR (1995) A review of environmental applications of bioluminescence measurements. Chemosphere 30:2155–2197

Stepnowski P, Zaleska A (2005) Comparison of different advanced oxidation processes for the degradation of room temperature ionic liquids. J Photochem Photobiol A 170:45–50

Stolte S, Arning J, Bottin-Weber U, Muller A, Pitner W-R, Welz-Biermann U, Jastorff B, Ranke J (2007) Effects of different head groups and functionalised side chains on the cytotoxicity of ionic liquids. Green Chem 9:760–767

van Rantwijk FV, Madeira Lau R, Sheldon RA (2003) Biocatalytic transformations in ionic liquids. Trends Biotechnol 21:131–138

Ventura SPM, Gonçalves AMM, Gonçalves F, Coutinho JAP (2010) Assessing the toxicity on [C3mim][Tf2N] to aquatic organisms of different trophic levels. Aquat Toxicol 96:290–297

Ventura SPM, Gardas RL, Gonçalves F, Coutinho JAP (2011) Ecotoxicological risk profile of ionic liquids: octanol–water distribution coefficients and toxicological data. J Chem Technol Biotechnol 86:957–963

Wasserscheid P, Welton T (2007) Ionic liquids in synthesis, 2nd edn. Wiley-VCH-Verlag, Weinheim

Wells AS, Coombe VT (2006) On the freshwater ecotoxicity and biodegradation properties of some common ionic liquids. Org Process Res Dev 10:794–798

Zhao H (2006) Innovative applications of ionic liquids as “green” engineering liquids. Chem Eng Commun 193:1660–1677