Ionic liquid biodegradability depends on specific wastewater microbial consortia

Docherty, Kathryn M.; Aiello, Steven; Buehler, Barbara; Jones, Stuart; Szymczyna, Blair R.; Walker, Katherine A.

doi:10.1016/j.chemosphere.2015.05.016

Cited by 34 publications

(17 citation statements)

References 38 publications

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“…After 42 days approximately 60% of compound (3a), and more than 75% of (2a) and IL (4) were biodegraded, demonstrating for (3a) inherent biodegradability and for the latter two compounds inherent, ultimate biodegradability. 29 In that study the specific IL caused a significant change in the microbial composition probably due to the selective growth of certain strains. 20,28 This indicates that the responsible bacteria Table 1 Biodegradation rates (average of duplicates) in % ThOD of the L-phenylalanine derived ILs and related non-ionic derivatives (expanded with "a") in the Closed Bottle tests (CBTs) after 28 and 42 days; grey boxes mark biodegradation values close to or over 60% needed more time than that given in the standardized OECD tests to reach a sufficient cell density which results in the biodegradation of a xenobiotic above 60%.…”

Section: Biodegradationmentioning

confidence: 84%

On the way to greener ionic liquids: identification of a fully mineralizable phenylalanine-based ionic liquid

et al. 2016

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Over the past few decades ionic liquids (ILs) are increasingly seen as an important building block of green chemistry because of their specific properties as solvents, such as their potential for high recyclability, low volatility, low flammability, low toxicity, and their potential for synthesis from renewable resources. However, avoiding persistent or toxic cation/anion fragments is also urgently needed. In the best case they should be fully mineralizable by microorganisms after their release into the aquatic environment. The fragments fostering this can be determined by biodegradation studies, and the employment of identified readily biodegradable building blocks presents an innovation in the targeted design of green environmentally friendly ILs. The aim of this study was to improve the data-platform for the design of completely mineralizable ILs. Therefore the ready biodegradability of seven phenylalanine-based ILs and three nonionic related compounds was investigated with a modified Closed Bottle test based on OECD guideline 301D. Liquid chromatography combined with high-resolution mass spectrometry (LC-HRMS) analysis was used to identify the chemical structures of products resulting from incomplete biodegradation and transformation. Two kinds of degradation pathways were observed: the hydrolysis of an ethyl ester group or the hydrolysis of an amide bond and biodegradation of the released phenylalanine ethyl ester. Both degradation pathways resulted in persistent transformation products (TPs) with the exception of IL (4), a pyridinium substituted phenylalanine derived IL and the non-ionic deanol derivative (2a). IL (4) was ultimately biodegraded in the CBT after 42 days without leaving any TP. The biodegradation of compound (2a) was 78% after 42 days but resulted in a TP, which was readily biodegradable in a further CBT after a lag phase of 3 weeks, respectively. Even if both compounds were not "readily biodegradable" in the sense of the OECD guideline, particularly IL (4) can be proposed as a basic structure for sustainable and green ILs (benign by design) with the aim of optimizing its degradation rate further. † Electronic supplementary information (ESI) available. See

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Section: Biodegradationmentioning

confidence: 84%

On the way to greener ionic liquids: identification of a fully mineralizable phenylalanine-based ionic liquid

et al. 2016

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“…[Br] was tested using communities from two wastewater treatment plants (WWTP) at three time points. 390 Results indicated that only the IL ring is metabolized in [OmPy] + case, and variations in location and time influence the biodegradability of [OmPy] + . In contrast, uniform results are observed for [Bmim] + and [BmPy] + using samples from both WWTP locations and across time.…”

Section: Biodegradability Of [Bmim][cl] [Bmpy]-[br] and [Ompy]mentioning

confidence: 99%

“…Biodegradation products are less toxic than the initial compound to a standard aquatic test organism, Daphnia magna , indicating that biodegradation in an aquatic environment can decrease toxicity hazards associated with the initial ILs. Biodegradability of [Bmim][Cl], [BmPy][Br], and [OmPy][Br] was tested using communities from two wastewater treatment plants (WWTP) at three time points . Results indicated that only the IL ring is metabolized in [OmPy] + case, and variations in location and time influence the biodegradability of [OmPy] + .…”

Section: Degradation Of Ionic Liquidsmentioning

confidence: 99%

Ionic-Liquid-Based CO₂ Capture Systems: Structure, Interaction and Process

et al. 2017

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The inherent structure tunability, good affinity with CO, and nonvolatility of ionic liquids (ILs) drive their exploration and exploitation in CO separation field, and has attracted remarkable interest from both industries and academia. The aim of this Review is to give a detailed overview on the recent advances on IL-based materials, including pure ILs, IL-based solvents, and IL-based membranes for CO capture and separation from the viewpoint of molecule to engineering. The effects of anions, cations and functional groups on CO solubility and selectivity of ILs, as well as the studies on degradability of ILs are reviewed, and the recent developments on functionalized ILs, IL-based solvents, and IL-based membranes are also discussed. CO separation mechanism with IL-based solvents and IL-based membranes are explained by combining molecular simulation and experimental characterization. Taking into consideration of the applications and industrialization, the recent achievements and developments on the transport properties of IL fluids and the process design of IL-based processes are highlighted. Finally, the future research challenges and perspectives of the commercialization of CO capture and separation with IL-based materials are posed.

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“…However, with longer substituents (C > 4), complete mineralization was observed, even for an alkyl-3-methylpyridinium core. Pyridinium bearing a butyl chain (Py1-4) was reported to be degradable in some works , but not in others. ,− Usually, homologues substituted with short chains are not degradable except when a particular bacterial strain is used − or functional groups promoting biodegradation are present . Similar to the imidazoliums’ presence of groups such as terminal hydroxyl, carboxyl, or ester, , degradability is often, but not always, increased.…”

Section: Design Of Ils With Greater Degradabilitymentioning

confidence: 99%

Toward the Proactive Design of Sustainable Chemicals: Ionic Liquids as a Prime Example

et al. 2021

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The tailorable and often unique properties of ionic liquids (ILs) drive their implementation into a broad variety of seminal technologies. The modular design of ILs allows in this context a proactive selection of structures that favor environmental sustainabilityideally without compromising their technological performance. To achieve this objective, the whole life cycle must be taken into account and various aspects considered simultaneously. In this review, we discuss how the structural design of ILs affects their environmental impacts throughout all stages of their life cycles and scrutinize the available data in order to point out knowledge gaps that need further research activities. The design of more sustainable ILs starts with the selection of the most beneficial precursors and synthesis routes, takes their technical properties and application specific performance into due account, and considers its environmental fate particularly in terms of their (eco)toxicity, biotic and abiotic degradability, mobility, and bioaccumulation potential. Special emphasis is placed on reported structure−activity relationships and suggested mechanisms on a molecular level that might rationalize the empirically found design criteria.

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Ionic liquid biodegradability depends on specific wastewater microbial consortia

Cited by 34 publications

References 38 publications

On the way to greener ionic liquids: identification of a fully mineralizable phenylalanine-based ionic liquid

On the way to greener ionic liquids: identification of a fully mineralizable phenylalanine-based ionic liquid

Ionic-Liquid-Based CO₂ Capture Systems: Structure, Interaction and Process

Toward the Proactive Design of Sustainable Chemicals: Ionic Liquids as a Prime Example

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Ionic liquid biodegradability depends on specific wastewater microbial consortia

Cited by 34 publications

References 38 publications

On the way to greener ionic liquids: identification of a fully mineralizable phenylalanine-based ionic liquid

On the way to greener ionic liquids: identification of a fully mineralizable phenylalanine-based ionic liquid

Ionic-Liquid-Based CO2 Capture Systems: Structure, Interaction and Process

Toward the Proactive Design of Sustainable Chemicals: Ionic Liquids as a Prime Example

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Ionic-Liquid-Based CO₂ Capture Systems: Structure, Interaction and Process