Persistence of selected ammonium- and phosphonium-based ionic liquids in urban park soil microcosms

Sydow, Mateusz; Szczepaniak, Zuzanna; Framski, Grzegorz; Staninska, J.; Owsianiak, Mikołaj; Szulc, Alicja; Piotrowska-Cyplik, Agnieszka; Zgoła‐Grześkowiak, Agnieszka; Wyrwas, Bogdan; Chrzanowski, Łukasz

doi:10.1016/j.ibiod.2015.04.019

Cited by 17 publications

(27 citation statements)

References 32 publications

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“…[92] Ammonium-and phosphonium-based ILs also demonstrate the ability to persist on soil for long periodso ft ime. [93] The length of the alkyl side chain is am ajor factor affecting the strength of binding of the ILs to the soil surface. [94] ILs with longera lkyl side chains are adsorbedt oahighere xtent than those with short or/and hydroxylated side chains in the cation.…”

Section: The Ability Of Ionic Liquidstoa Dsorbmentioning

confidence: 98%

“…have observed that after 40 days of contact between soil and [omim][BF 4 ] the concentration of the IL changes by no more than 5 % . Ammonium‐ and phosphonium‐based ILs also demonstrate the ability to persist on soil for long periods of time . The length of the alkyl side chain is a major factor affecting the strength of binding of the ILs to the soil surface .…”

Section: Degradation Of Ionic Liquidsmentioning

confidence: 99%

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Environmental Impact of Ionic Liquids: Recent Advances in (Eco)toxicology and (Bio)degradability

et al. 2017

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This Review aims to integrate the most recent and pertinent data available on the (bio)degradability and toxicity of ionic liquids for global and critical analysis and on the conscious use of these compounds on a large scale thereafter. The integrated data will enable focus on the recognition of toxicophores and on the way the community has been dealing with them, with the aim to obtain greener and safer ionic liquids. Also, an update of the most recent biotic and abiotic methods developed to overcome some of these challenging issues will be presented. The review structure aims to present a potential sequence of events that can occur upon discharging ionic liquids into the environment and the potential long-term consequences.

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Section: The Ability Of Ionic Liquidstoa Dsorbmentioning

confidence: 98%

Section: Degradation Of Ionic Liquidsmentioning

confidence: 99%

Environmental Impact of Ionic Liquids: Recent Advances in (Eco)toxicology and (Bio)degradability

et al. 2017

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“…Furthermore, the data from biodegradation studies carried out in the terrestrial environment with respect to based ILs are scarce, as the number of reports dedicated to this topic is limited (Modelli et al 2008;Pham et al 2010). The results obtained in our previous study showed that primary biodegradation of selected phosphonium-based ILs in urban park microcosms was low and reached 25 and 29% for [P 66614 ][Cl] and [P 66614 ][Tr], respectively (Sydow et al 2015).…”

Section: Introductionmentioning

confidence: 93%

“…The soil has document biodegradation potential toward other phosphonium-based ionic liquids (Sydow et al 2015). Yet, apart from [P 66614 ][Br], the studied ILs are antifungal agents and are expected to influence biodiversity mainly through ecotoxic effects of the attached anions (Walkiewicz et al 2010).…”

Section: Introductionmentioning

confidence: 99%

Biodiversity of soil bacteria exposed to sub-lethal concentrations of phosphonium-based ionic liquids: Effects of toxicity and biodegradation

Sydow

Owsianiak

Framski

et al. 2018

Ecotoxicology and Environmental Safety

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Little is known about the effect of ionic liquids (ILs) on the structure of soil microbial communities and resulting biodiversity. Therefore, we studied the influence of six trihexyl(tetradecyl)phosphonium ILs (with either bromide or various organic anions) at sublethal concentrations on the structure of microbial community present in an urban park soil in 100-day microcosm experiments. The biodiversity decreased in all samples (Shannon's index decreased from 1.75 down to 0.74 and OTU's number decreased from 1399 down to 965) with the largest decrease observed in the microcosms spiked with ILs where biodegradation extent was higher than 80%. (i.e. [P][Br] and [P][2,4,4]). Despite this general decrease in biodiversity, which can be explained by ecotoxic effect of the ILs, the microbial community in the microcosms was enriched with Gram-negative hydrocarbon-degrading genera e.g. Sphingomonas. It is hypothesized that, in addition to toxicity, the observed decrease in biodiversity and change in the microbial community structure may be explained by the primary biodegradation of the ILs or their metabolites by the mentioned genera, which outcompeted other microorganisms unable to degrade ILs or their metabolites. Thus, the introduction of phosphonium-based ILs into soils at sub-lethal concentrations may result not only in a decrease in biodiversity due to toxic effects, but also in enrichment with ILs-degrading bacteria.

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“…One of the most studied quaternary ammonium and phosphonium compounds are ionic liquids which persist for a long time in the environment and are toxic to different types of organisms [28]. They can be degraded by microorganisms [29], by physical [30] or chemical agents [31]. Morawski et al [30] observed that phosphonium salts are decomposed by photocatalysis more easily than ammonium salts.…”

Section: Introductionmentioning

confidence: 99%

Novel Phospholium‐Type Cationic Surfactants: Synthesis, Aggregation Properties and Antimicrobial Activity

Lukáč

Devı́nsky

Pisárčik

et al. 2016

J Surfact & Detergents

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A series of novel phospholium amphiphilic compounds with straight alkyl chains with different numbers of carbon atoms (12,14,15,16,17,18) were synthesized. The quaternary phosphorus, phosphonium cation, is incorporated into a five-membered heterocyclic ring. Their physicochemical properties were investigated by measurements of surface tension, conductivity and dynamic light scattering. The critical micelle concentration (c M ), the surface tension value at the c M (c cmc ), the surface area at the surface saturation per head group (A cmc ), the ionization degree of micelle (a), the free energy of micellization (DG°m ic ), and hydrodynamic diameter (d h ) were determined. Antimicrobial activity was tested against bacteria and yeast. The structure-activity relationship was determined. 3 J CP = 17.3 Hz, = C-CH 3 ) 22.5 (d, 1 J CP = 46.2 Hz, a CH 2 of alkyl chain), 22.6 (d, 2 J CP = 4.1 Hz, b CH 2 of alkyl chain), 22.7 (x CH 2 of alkyl chain), 29.1, 29.3, 29.4, 29.5, 29.6(0), 29.6(4), 29.7 (d-x-2 CH 2 of alkyl chain), 30.5 (d, 3 J CP = 15.6 Hz, c CH 2 of alkyl chain), 31.9 (x-1 CH 2 of alkyl chain), 113.6 (d, 1 J CP = 80.0 Hz, = CHP), 115.9 (d, 1 J CP = 83.9 Hz, Ph C 1 ), 130.0 (d, 3 J CP = 12.9 Hz, Ph C meta ), 133.6 (d, 2 J CP = 10.7 Hz, Ph C ortho ), 134.6 (d, 4 J CP = 3.0 Hz, Ph C para ), 163.2 (d, 2 J CP = 16.4 Hz, = C-CH 3 ); 31 P NMR (CDCl 3 , H 3 PO 4 ) d: 38.5; IR t max /cm -H NMR (CDCl 3 , TMS) d: 0.88 (t, 3 J H,H = 6.7 Hz, 3H, CH 3 of alkyl chain), 1.13-1.38 (m, 22H, 11 9 CH 2 of alkyl chain), 1.38-1.62 (m, 4H, b, c CH 2 of alkyl chain) 2.29 (s, 6H, 2 9 = C-CH 3 ), 3.08-3.22 (m, 2H, a CH 2 of alkyl chain), 7.08 (d, 2 J HP = 30.9 Hz, 2H, = CHP), 7.54-7.61 (m, 2H, Ph H meta ), 7.61-7.75 (m, 1H, Ph H para ), 8.15-8.23 (m, 2H, Ph H ortho ); 13 C NMR (CDCl 3 , TMS) d: 14.1 (CH 3 of alkyl chain), 18.5 (d, 3 J CP = 17.3 Hz, = C-CH 3 ) 22.5 (d, 1 J CP = 46.1 Hz, a CH 2 of alkyl chain), 22.6 (d, 2 J CP = 4.1 Hz, b CH 2 of alkyl chain), 22.7 (x CH 2 of alkyl chain), 29.1, 29.3, 29.4, 29.5, 29.6, 29.7 (d-x-2 CH 2 of alkyl chain), 30.5 (d, 3 J CP = 15.4 Hz, c CH 2 of alkyl chain), 31.9 (x-1 CH 2 of alkyl chain), 113.6 (d, 1 J CP = 80.0 Hz, = CHP), 115.8 (d, 1 J CP = 83.8 Hz, Ph C 1 ), 130.0 (d, 3 J CP = 12.9 Hz, Ph C meta ), 133.5 (d, 2 J CP = 10.4 Hz, Ph C ortho ), 134.7 (d, 4 J CP = 3.0 Hz, Ph C para ), 163.2 (d, 2 J CP = 16.5 Hz, = C-CH 3 ); 31 P NMR (CDCl 3 , H 3 PO 4 ) d: 38.5; IR t max /cm -

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Persistence of selected ammonium- and phosphonium-based ionic liquids in urban park soil microcosms

Cited by 17 publications

References 32 publications

Environmental Impact of Ionic Liquids: Recent Advances in (Eco)toxicology and (Bio)degradability

Environmental Impact of Ionic Liquids: Recent Advances in (Eco)toxicology and (Bio)degradability

Biodiversity of soil bacteria exposed to sub-lethal concentrations of phosphonium-based ionic liquids: Effects of toxicity and biodegradation

Novel Phospholium‐Type Cationic Surfactants: Synthesis, Aggregation Properties and Antimicrobial Activity

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