Sorption to Dissolved Humic Acid and Its Impacts on the Toxicity of Imidazolium Based Ionic Liquids

Zhang, Zhen; Liu, Jingfu; Cai, Xiaoqiang; Jiang, Weiwei; Luo, Wenru; Jiang, Guibin

doi:10.1021/es103514s

Cited by 39 publications

(23 citation statements)

References 56 publications

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“…The K DOC values of p,p′‐DDT (10 5.44 ), TCrP (10 5.31 ), and EHDPP (10 5.30 ) are quite close, probably due to their 3‐dimensional configuration that can hinder the interaction with the aromatic moieties in the humic matrix by the π electron association . The K DOC values of the 5 low‐ K OW OPEs to Aldrich humic acid (10 3.31 –10 4.29 ) are comparable to those of many nonpolar organic contaminants (10 3.50 –10 6.00 ) and a variety of organic cations (10 3.60 –10 5.65 ) .…”

Section: Resultsmentioning

confidence: 93%

Evaluating the sorption of organophosphate esters to different sourced humic acids and its effects on the toxicity to Daphnia magna

Pang

Liu

Yin

et al. 2013

Enviro Toxic and Chemistry

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Because of large usage as flame retardants and additives, organophosphate esters (OPEs) are widely detected in the environment and regarded as emerging contaminants. However, the sorption of OPEs to organic matter and its effects have scarcely been studied. In the present study, the sorption of 9 commonly used OPEs to 4 representative humic acids--Elliott Soil humic acid, Suwannee River humic acid, Aldrich humic acid, and Acros humic acid--in the range of 0 mg/L to 50 mg/L dissolved organic carbon (DOC), was evaluated with negligible-depletion solid-phase microextraction and verified by its impacts on the toxicity to the aquatic invertebrate Daphnia magna. Whereas OPEs with a high octanol/water partition coefficient (log K(OW)=4.51-6.64) were associated with humic acids mainly by hydrophobic interaction with DOC partition coefficient (K(DOC)) in the range of 10²·²² to 10⁵·³¹, the sorption of low-K(OW) OPEs (log K(OW)=-0.65 to 2.59) to humic acids was not hydrophobic interaction-dominant, with K(DOC) in the range of 10³·⁴⁷ to 10⁴·²⁹. These results were corroborated by the effects of humic acids on the acute toxicity of 3 high-K(OW) OPEs to D. magna. The sorption of OPEs to Suwannee River humic acid was weak and had negligible effects on the toxicity of high-K(OW) OPEs; the presence of terrestrial Acros humic acid (50 mg/L DOC), however, significantly decreased the toxicity by 53% to 60%. The results indicated that the strong sorption between high-K(OW) OPEs and terrestrial humic acid might affect their transportation and bioavailability.

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Section: Resultsmentioning

confidence: 93%

Evaluating the sorption of organophosphate esters to different sourced humic acids and its effects on the toxicity to Daphnia magna

Pang

Liu

Yin

et al. 2013

Enviro Toxic and Chemistry

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“…Water solubility is an important parameter for evaluating the environmental behavior of herbicides and is also determining factor for the environmental fate of ILs. 43 The solubilities of HILs in water were measured at different pH (5.0, 7.0, and 9.0) at room temperature, and the results are shown in Table 2. The results indicated that the solubility of mesotrione increased with increasing pH, while the solubilities of HILs were almost unaffected by pH changes.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Ionic Liquid Forms of Mesotrione with Enhanced Stability and Reduced Leaching Risk

WeiChen

Liang

Yang

et al. 2019

ACS Sustainable Chem. Eng.

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Mesotrione is one of the triketone herbicides that are widely used in corn fields to control broadleaf and some grass weeds because of its high herbicidal activity and crop safety. However, mesotrione is unstable during the progress of storage and application and can easily enter the groundwater to cause environmental pollution due to its high leakage in soil. In this study, 22 new salts based on mesotrione, most of which were defined as herbicidal ionic liquids (HILs), were synthesized by pairing with different structural cations to optimize the physicochemical properties for solving these problems of mesotrione. The results showed that the water solubilities of HILs were no longer limited by pH and could be decreased by selecting suitable paired cations. Also, HILs exhibited a higher thermal stability, lower surface tension, higher octanol−water partition coefficient, and better soil adsorption capacity and herbicidal activity than mesotrione. HIL-22 paired with cetylpyridinium could meet the requirements such as efficacy control, thermal stability, and reduction of environmental risk based on the physicochemical properties and biological activities. This study showed the novel HILs could make contributions to solve the problems existing in the practical applications and reduce the negative impact of herbicides on the environment.

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“…11 For soils it is affected most readily by organic matter content though Please do not adjust margins Please do not adjust margins clay content (especially presence of swelling clays) is also important. [12][13][14][15] For IL cations the length of alkyl substituent plays an important role. 11,16 In batch sorption tests, double layer sorption was observed resulting from surfactant-like properties of, especially long chain, ILs.…”

Section: Sorption and Transport In Soilsmentioning

confidence: 99%

Mobility and biodegradability of an imidazolium based ionic liquid in soil and soil amended with waste sewage sludge

Markiewicz

Jungnickel

Cho

et al. 2015

Environ. Sci.: Processes Impacts

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Sorption on solids and biodegradation are main phenomena that can mitigate the pollution of soil and water by ionic liquids (ILs). ILs sorbed on soil particles become immobilized (temporarily or permanently) which prevents them from spreading into deeper layers of soil or groundwater but which also makes them less bioavailable. In this study we attempt to examine if amendment of soil with waste sludge has a potential to mitigate the transport and enhance biodegradation of ILs using 1-methyl-3-octylimidazolium chloride ([OMIM][Cl]) as an example. We present the results of adsorption test (batch and column) and ultimate biodegradation of [OMIM][Cl] using microbial communities derived from soil. Finally, we combine all of these processes together to examine the fate of [OMIM][Cl] in a continuous column flow-through system in soil amended with waste sewage sludge. Addition of sludge serves two purposes: firstly increasing soil organic matter (formerly proved to facilitate retardation), and secondly augmenting soil with versatile microbial communities previously shown to successfully degrade ILs.

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Sorption to Dissolved Humic Acid and Its Impacts on the Toxicity of Imidazolium Based Ionic Liquids

Cited by 39 publications

References 56 publications

Evaluating the sorption of organophosphate esters to different sourced humic acids and its effects on the toxicity to Daphnia magna

Evaluating the sorption of organophosphate esters to different sourced humic acids and its effects on the toxicity to Daphnia magna

Ionic Liquid Forms of Mesotrione with Enhanced Stability and Reduced Leaching Risk

Mobility and biodegradability of an imidazolium based ionic liquid in soil and soil amended with waste sewage sludge

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