(Eco)toxicity and biodegradability of protic ionic liquids

Oliveira, Maria Vanessa Souza; Vidal, Bruna T.; Melo, Cláudia Moura de; Miranda, Rita de Cássia Mendonça de; Soares, Cleide Mara Faria; Coutinho, João A. P.; Ventura, Sónia P. M.; Mattedi, Silvana; Lima, Álvaro Silva

doi:10.1016/j.chemosphere.2015.11.016

Cited by 98 publications

(42 citation statements)

References 56 publications

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“…the ILs in this study were moderately toxic (decanoates and isostearates between 10–100 mg/L) or practically harmless (neodecanoates 100–1000 mg/L) according to their EC 50 values. Two EC 50 values, after 5 and 15 minutes incubation, are provided for reference purposes, since either of these incubation times is typically used in previous studies7131415161718192021222324252627282930313233343536373839 utilising V. fischeri bacteria. The toxic effect is time-dependent, particularly with relatively short incubation times (minutes time-scale).…”

Section: Resultsmentioning

confidence: 99%

Impact of Surface-Active Guanidinium-, Tetramethylguanidinium-, and Cholinium-Based Ionic Liquids on Vibrio Fischeri Cells and Dipalmitoylphosphatidylcholine Liposomes

Rantamäki

Ruokonen

Sklavounos

et al. 2017

Sci Rep

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We investigated the toxicological effect of seven novel cholinium, guanidinium, and tetramethylguanidinium carboxylate ionic liquids (ILs) from an ecotoxicological point of view. The emphasis was on the potential structure-toxicity dependency of these surface-active ILs in aqueous environment. The median effective concentrations (EC50) were defined for each IL using Vibrio (Aliivibrio) fischeri marine bacteria. Dipalmitoylphosphatidylcholine (DPPC) liposomes were used as biomimetic lipid membranes to study the interactions between the surface-active ILs and the liposomes. The interactions were investigated by following the change in the DPPC phase transition behaviour using differential scanning calorimetry (DSC). Critical micelle concentrations for the ILs were determined to clarify the analysis of the toxicity and the interaction results. Increasing anion alkyl chain length increased the toxicity, whereas branching of the chain decreased the toxicity of the ILs. The toxicity of the ILs in this study was mainly determined by the surface-active anions, while cations induced a minor impact on the toxicity. In the DSC experiments the same trend was observed for all the studied anions, whereas the cations seemed to induce more variable impact on the phase transition behaviour. Toxicity measurements combined with liposome interaction studies can provide a valuable tool for assessing the mechanism of toxicity.

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Section: Resultsmentioning

confidence: 99%

Impact of Surface-Active Guanidinium-, Tetramethylguanidinium-, and Cholinium-Based Ionic Liquids on Vibrio Fischeri Cells and Dipalmitoylphosphatidylcholine Liposomes

Rantamäki

Ruokonen

Sklavounos

et al. 2017

Sci Rep

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“…Based on TU values, the compounds can be classified into four categories: i) non-toxic: TU values < 1, ii) toxic: TU values from 1 to 10, iii) very toxic: TU values between 10 and 100, and iv) extremely toxic: TU values > 100 [33,35]. All analytical measurements were performed at least three times.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

“…Taking into account that bacterial luminescence (light emission) is directly related to cellular respiration, a drop in light emission is caused by a decrease in respiration due to the presence of toxic compounds to the bacteria. In this sense, EC50, i.e., the concentration of IL that reduces the luminescence of bacteria by 50% after 15 min of exposure, was calculated[33]. Additionally, the toxic units (TU) were determined after 15 min of contact time.…”

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confidence: 99%

Physicochemical, traction and tribofilm formation properties of three octanoate-, laurate- and palmitate-anion based ionic liquids

Battez

Rivera

Blanco

et al. 2019

Journal of Molecular Liquids

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Three new ionic liquids with different anions and the same cation were synthesized from fatty acids through a metathesis reaction. All the ionic liquids were identified via NMR and FTIR and several properties (density, viscosity, thermal, and environmental) were measured. Traction tests were performed under different entrainment speeds (10-2000 mm/s), at slide-roll ratio (SRR) of 50% and 30 N-load, and at different temperatures (40, 60, 80 and 100 ºC) using a mini-traction machine (MTM). Tribofilm formation tests were also made in the MTM at 50 N-load, 150 mm/s of entrainment speed, at SRR of 50% and temperature of 100 ºC, for 60 minutes. This work showed that the alkyl chain length in the anion affects properties such as viscosity, toxicity, biodegradability and lubrication. Viscosity decreased with increasing alkyl chain length but only below 60ºC, at higher temperatures the viscosity values of the ionic liquids converge. The toxicity and biodegradability increased with the alkyl chain length, but these novel ionic liquids are much better from both toxicity and biodegradability points of view than the [N8881][TFSI] ionic liquid, which contains the same cation and anion not coming from fatty acids. The ionic liquids at low temperature (40 ºC) performed under elastohydrodynamic lubrication and changed to mixed lubrication at higher temperatures and decreasing speeds, according to the alkyl chain length of each anion. All ionic liquids adsorbed on the steel surfaces, and the tribofilm thickness and the kinetics of formation were different.

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“…Because of this feature, many works in the past claimed that they were green solvents, but many ionic liquids are toxic (Latala et al, 2005) and effluents or spills could contaminate aquifers and consequently affect the flora and the fauna present in the enviroment. Studies indicate that ionic liquids based on imidazolium are more toxic than protic ionic liquids (PIL) based on amines and short -chain acids and that the toxicity is related to the hydrophilicity / lipophilicity of the ionic liquid (Peric et al, 2014, Oliveira et al 2016. They are formed by a Bronsted-Lowry acid-base reaction (Drummond and Kennedy, 2009) that, unlike aprotic ionic liquids, have labile protons and are able to form a hydrogen bond network.…”

Section: Introductionmentioning

confidence: 99%

Liquid-Liquid Equilibria Data of N-Methyl-2-Hydroxyethyl Ammonium Alkylates With Butanol+water and Pentanol+water at 293.15K, 313.15K and 333.15K

Amorim

Soares

Ganem

et al. 2018

Braz. J. Chem. Eng.

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Ionic liquids (ILs) are organic salts with low volatility and have different applications including organic synthesis, separation and extraction processes, fuel cell electrolyte, surfactants, among others. Protic ILs based on the N-methyl-2-hydroxyethyl ammonium cation and short chain carboxylic anions have simple synthesis and purification. However, as new substances few data are available for their thermodynamic properties and phase equilibria. In order to investigate the partition of these substances in alcohol-water, liquid-liquid equilibria data were determined experimentally for three ionic liquids (formed by the cation N-methyl-2-hydroxyethyl ammonium (m-2HEA) and the anions propionate (Pr), butanoate (B) and pentanoate (P)) with butanol and pentanol, at three different temperatures: 293.15K, 313.15K and 333.15K. The binodal curves are obtained by the turbidity method with gravimetric determination of all the components, curves are fitted using the Merchuk method. The tie-lines are also gravimetrically determined. The results confirm the high hydrophilicity of these ionic liquids, with partition coefficients of water-butanol and water-pentanol lower than 1. Data were correlated with UNIFAC.

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(Eco)toxicity and biodegradability of protic ionic liquids

Cited by 98 publications

References 56 publications

Impact of Surface-Active Guanidinium-, Tetramethylguanidinium-, and Cholinium-Based Ionic Liquids on Vibrio Fischeri Cells and Dipalmitoylphosphatidylcholine Liposomes

Impact of Surface-Active Guanidinium-, Tetramethylguanidinium-, and Cholinium-Based Ionic Liquids on Vibrio Fischeri Cells and Dipalmitoylphosphatidylcholine Liposomes

Physicochemical, traction and tribofilm formation properties of three octanoate-, laurate- and palmitate-anion based ionic liquids

Liquid-Liquid Equilibria Data of N-Methyl-2-Hydroxyethyl Ammonium Alkylates With Butanol+water and Pentanol+water at 293.15K, 313.15K and 333.15K

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