Impact of ionic liquids in environment and humans: An overview

Ionic liquids enclose a large number of molecular structures consisting of a cation and an anion. Their physical state and their chemical properties can be tuned by different combination of the ions and a large number of ionic liquids have already been reported. Toxicity of ionic liquids is a subject of great importance concerning their likely use as greener solvents and new materials for a broad number of potential applications. This review provides relevant toxicological data published so far about this topic and includes a large range of ionic liquids based on different cations (imidazolium, pyridinium, pyrrolidinium, quaternary ammonium, quaternary phosphonium and guanidinium) and anions (halogens-Br, Cl, bis (trifluoromethyl)sulfonylamide, tetrafluoroborate, hexafluorophosphate, dicyanamide, acesulfame and saccharin, amongst others). In general, toxicity of ionic liquids depends on both ions and the effect of the cation alkyl chain length is very pronounced although the type of anion also exerts impact on the overall toxicity.

[1]  E. Macedo,et al.  Ionic liquids as alternative co-solvents for laccase: study of enzyme activity and stability. , 2008, Biotechnology and bioengineering.

[2]  J. Fraser Stoddart,et al.  Inside Cover: A Molecular Solomon Link (Angew. Chem. Int. Ed. 1‐2/2007) , 2007 .

[3]  A. Latała,et al.  Toxicity of imidazolium ionic liquids towards algae. Influence of salinity variations , 2010 .

[4]  D. Armstrong,et al.  Dicationic ionic liquid stationary phase for GC-MS analysis of volatile compounds in herbal plants , 2007, Analytical and bioanalytical chemistry.

[5]  T. Jiang,et al.  Dynamic coating of a capillary with room-temperature ionic liquids for the separation of amino acids and acid drugs by capillary electrophoresis , 2006 .

[6]  B. Ondruschka,et al.  Biological effects of imidazolium ionic liquids with varying chain lengths in acute Vibrio fischeri and WST-1 cell viability assays. , 2004, Ecotoxicology and environmental safety.

[7]  A. Wells,et al.  On the Freshwater Ecotoxicity and Biodegradation Properties of Some Common Ionic Liquids , 2006 .

[8]  P. D. D. María "Nonsolvent" applications of ionic liquids in biotransformations and organocatalysis. , 2008 .

[9]  C. Afonso,et al.  Effect of ionic liquids on human colon carcinoma HT-29 and CaCo-2 cell lines , 2007 .

[10]  Andreas Tholey,et al.  Pyridinium-based ionic liquid matrices can improve the identification of proteins by peptide mass-fingerprint analysis with matrix-assisted laser desorption/ionization mass spectrometry , 2006, Analytical and bioanalytical chemistry.

[11]  Jingtian Hu,et al.  Use of ionic liquids for liquid-phase microextraction of polycyclic aromatic hydrocarbons. , 2003, Analytical chemistry.

[12]  Roger A. Sheldon,et al.  Biocatalysis in Ionic Liquids , 2007 .

[13]  T. Welton,et al.  Chiral ionic liquids as stationary phases in gas chromatography. , 2004, Analytical chemistry.

[14]  Zhaofu Fei,et al.  Cytotoxicity of ionic liquids and precursor compounds towards human cell line HeLa , 2007 .

[15]  S. Stolte,et al.  PAPER www.rsc.org/greenchem | Green Chemistry Effects , 2007 .

[16]  S. Stolte,et al.  Qualitative and quantitative structure activity relationships for the inhibitory effects of cationic head groups, functionalised side chains and anions of ionic liquids on acetylcholinesterase , 2008 .

[17]  Hua Zhao,et al.  INNOVATIVE APPLICATIONS OF IONIC LIQUIDS AS “GREEN” ENGINEERING LIQUIDS , 2006 .

[18]  Xiao-yu Li,et al.  Acute effects of 1-octyl-3-methylimidazolium bromide ionic liquid on the antioxidant enzyme system of mouse liver. , 2008, Ecotoxicology and environmental safety.

[19]  "Nonsolvent" applications of ionic liquids in biotransformations and organocatalysis. , 2008 .

[20]  Konrad J. Kulacki,et al.  Toxicity of imidazolium ionic liquids to freshwater algae , 2008 .

[21]  C. Pretti,et al.  Acute toxicity of ionic liquids to the zebrafish (Danio rerio) , 2006 .

[22]  P. Scammells,et al.  Biodegradable ionic liquids Part II. Effect of the anion and toxicology , 2005 .

[23]  Pedro M. P. Gois,et al.  Efficient catalyst reuse by simple dissolution in non-conventional media. , 2007, Chemical communications.

[24]  J. Iborra,et al.  Enzymatic Catalysis in Ionic Liquids and Supercritical Carbon Dioxide Biphasic Systems , 2009 .

[25]  Randall J. Bernot,et al.  Assessing the factors responsible for ionic liquid toxicity to aquatic organisms via quantitative structure–property relationship modeling , 2006 .

[26]  Xingguo Chen,et al.  Rapid and sensitive determination of anthraquinones in Chinese herb using 1-butyl-3-methylimidazolium-based ionic liquid with beta-cyclodextrin as modifier in capillary zone electrophoresis. , 2004, Journal of chromatography. A.

[27]  S. Stolte,et al.  The influence of anion species on the toxicity of 1-alkyl-3-methylimidazolium ionic liquids observed in an (eco)toxicological test battery , 2007 .

[28]  L. Yuan,et al.  (R)‐N,N,N‐Trimethyl‐2‐Aminobutanol‐Bis(Trifluoromethane‐Sulfon)Imidate Chiral Ionic Liquid Used as Chiral Selector in HPCE, HPLC, and CGC , 2006 .

[29]  Frauke Stock,et al.  Progress in evaluation of risk potential of ionic liquids—basis for an eco-design of sustainable products , 2005 .

[30]  K. R. Seddon,et al.  Applications of Ionic Liquids in the Chemical Industry , 2008 .

[31]  C. E. Evans,et al.  Retention characteristics of a new butylimidazolium-based stationary phase , 2005, Analytical and bioanalytical chemistry.

[32]  Colin R. Janssen,et al.  Choline saccharinate and choline acesulfamate: ionic liquids with low toxicities. , 2007, The journal of physical chemistry. B.

[33]  Alessandra Basso,et al.  Biocatalysis in Non-Conventional Media-Ionic Liquids, Supercritical Fluids and the Gas Phase , 2007 .

[34]  P. Stepnowski,et al.  AMP deaminase in vitro inhibition by xenobiotics A potential molecular method for risk assessment of synthetic nitro- and polycyclic musks, imidazolium ionic liquids and N-glucopyranosyl ammonium salts. , 2005, Environmental toxicology and pharmacology.

[35]  S. Stolte,et al.  Lipophilicity parameters for ionic liquid cations and their correlation to in vitro cytotoxicity. , 2007, Ecotoxicology and environmental safety.

[36]  T. Welton Room-Temperature Ionic Liquids. Solvents for Synthesis and Catalysis. , 1999, Chemical reviews.

[37]  S. Stolte,et al.  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 , 2008 .

[38]  Alessandra Basso,et al.  Biocatalysis in non-conventional media—ionic liquids, supercritical fluids and the gas phase , 2007 .

[39]  F. Zhao,et al.  Coupling of ionic liquid-based headspace single-drop microextraction with GC for sensitive detection of phenols. , 2008, Journal of separation science.

[40]  P. Stepnowski,et al.  Evaluating the cytotoxicity of ionic liquids using human cell line HeLa , 2004, Human & experimental toxicology.

[41]  B. Myasoedov,et al.  Application of ionic liquids for solid-phase extraction of trace elements. , 2008, Analytical sciences : the international journal of the Japan Society for Analytical Chemistry.

[42]  A. Latała,et al.  Marine toxicity assessment of imidazolium ionic liquids: acute effects on the Baltic algae Oocystis submarina and Cyclotella meneghiniana. , 2005, Aquatic toxicology.

[43]  Maykel Pérez González,et al.  Cytotoxicity of selected imidazolium-derived ionic liquids in the human Caco-2 cell line. Sub-structural toxicological interpretation through a QSAR study , 2008 .

[44]  U. Bornscheuer,et al.  Growth of Escherichia coli, Pichia pastoris and Bacillus cereus in the Presence of the Ionic Liquids [BMIM][BF4] and [BMIM][PF6] and Organic Solvents , 2006, Biotechnology Letters.

[45]  Weijian Xu,et al.  Use of 1-alkyl-3-methylimidazolium-based ionic liquids as background electrolytes in capillary electrophoresis for the analysis of inorganic anions. , 2008, Journal of separation science.

[46]  D. Armstrong,et al.  High-stability ionic liquids. A new class of stationary phases for gas chromatography. , 2003, Analytical chemistry.

[47]  S. Stolte,et al.  Ionic liquids in soils: effects of different anion species of imidazolium based ionic liquids on wheat (Triticum aestivum) as affected by different clay minerals and clay concentrations , 2009, Ecotoxicology.

[48]  J. Prausnitz,et al.  In vitro cytotoxicities of ionic liquids: Effect of cation rings, functional groups, and anions , 2009, Environmental toxicology.

[49]  P. Stepnowski,et al.  Assessing toxicity and biodegradation of novel, environmentally benign ionic liquids (1-alkoxymethyl-3-hydroxypyridinium chloride, saccharinate and acesulfamates) on cellular and molecular level. , 2008, Ecotoxicology and environmental safety.

[50]  Charles F. Kulpa,et al.  Toxicity and antimicrobial activity of imidazolium and pyridinium ionic liquids , 2005 .

[51]  P. Kulkarni,et al.  Toxicological evaluation on human colon carcinoma cell line (CaCo-2) of ionic liquids based on imidazolium, guanidinium, ammonium, phosphonium, pyridinium and pyrrolidinium cations , 2009 .

[52]  Chul-Woong Cho,et al.  Toxicity of imidazolium salt with anion bromide to a phytoplankton Selenastrum capricornutum: effect of alkyl-chain length. , 2007, Chemosphere.

[53]  H. Weingaertner Understanding Ionic Liquids at the Molecular Level: Facts, Problems, and Controversies , 2008 .

[54]  Chul-Woong Cho,et al.  The ecotoxicity of ionic liquids and traditional organic solvents on microalga Selenastrum capricornutum. , 2008, Ecotoxicology and environmental safety.

[55]  Woo-Jin Chang,et al.  Influence of ionic liquids on the growth ofEscherichia coli , 2005 .

[56]  D. Armstrong,et al.  Ionic Liquids in Separations , 2008 .

[57]  Xiao-yu Li,et al.  The toxic effects of ionic liquids on the activities of acetylcholinesterase and cellulase in earthworms. , 2009, Chemosphere.

[58]  Jairton Dupont,et al.  Ionic Liquid (Molten Salt) Phase Organometallic Catalysis , 2003 .