Biodegradation of ionic liquids – a critical review

Jordan, Andrew; Gathergood, Nicholas

doi:10.1039/c5cs00444f

Cited by 355 publications

(244 citation statements)

References 105 publications

(400 reference statements)

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“…A similar observation was made for the nicotinate IL 7 and DMAP derivative 8, although the decrease to 32% and 33% respectively is more significant. Pyridinium ILs substituted at the 3 position with ester groups are known to have good biodegradation properties 24,26 and our result is an exception to this trend. The C 2 symmetric imidazolium IL 11 was also shown to be recalcitrant to biodegradation with the lowest value (17%) recorded.…”

Section: Preliminary Biodegradation Studies Of Ionic Liquids and Tertcontrasting

confidence: 82%

Synthesis of a series of amino acid derived ionic liquids and tertiary amines: green chemistry metrics including microbial toxicity and preliminary biodegradation data analysis

Jordan

Haiß

Špulák³

et al. 2016

Green Chem.

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A series of L-phenylalanine ionic liquids (ILs), L-tyrosine ILs, tertiary amino analogues and proposed transformation products (PTPs) have been synthesised. Antimicrobial toxicity data, as part of the green chemistry metrics evaluation and to supplement preliminary biodegradation studies, was determined for ILs, tertiary amino analogues and PTPs. Good to very good overall yields (76 to 87%) for the synthesis of 6 ILs from L-phenylalanine were achieved. A C 2 -symmetric IL was prepared from TMS-imidazole in a one-pot two-step method in excellent yield (91%). Synthesis of the L-tyrosine IL derivatives utilised a simple protection group strategy by using an extra equivalent of the bromoacetyl bromide reagent. Improvements in the synthesis of the α-bromoamide alkylating reagent from L-phenylalanine were achieved, directed by green chemistry metric analysis. A solvent switch from dichloromethane to THF is described, however the yield was 15% lower. Antimicrobial activity testing of L-phenylalanine ILs, L-tyrosine ILs, tertiary amino analogues and PTPs, against 8 bacteria and 12 fungi strains, showed that no compound had a high antimicrobial activity, apart from an L-proline analogue. In this exceptional case, the highest toxicity (IC 95 = 125 and 250 µM) was observed towards the two Gram positive strains Staphylococcus aureus and Staphylococcus epidermidis respectively. High antimicrobial activity was not found for the other bacteria or fungi strains screened. The limitations of the antimicrobial activity study is discussed in relation to SAR studies. Preliminary analysis of biodegradation data (Closed Bottle Test, OECD 301D) is presented. The pyridinium IL derivative is the preferred green IL of the series based on synthesis, toxicity and biodegradation considerations. This work is a joint study with Kümmerer and co-workers and the PTPs were selected as target compounds based on concurrent biodegradation studies by the Kümmerer group. For the comprehensive biodegradation and transformation product analysis see the accompanying paper.

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Section: Preliminary Biodegradation Studies Of Ionic Liquids and Tertcontrasting

confidence: 82%

Synthesis of a series of amino acid derived ionic liquids and tertiary amines: green chemistry metrics including microbial toxicity and preliminary biodegradation data analysis

Jordan

Haiß

Špulák³

et al. 2016

Green Chem.

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“…Initially, ILs were applied almost exclusively as a substitution of the conventional volatile organic solvents, transforming dangerous processes in recyclable and environmental friendly [42]. Later on, the range of application fields was broadened to the use in polymerization, electrolytes in batteries and in the nanocomposites preparation.…”

Section: Ionic Liquids As Multifunctional Additives In Polymer-silicamentioning

confidence: 99%

Recent Applications of Ionic Liquids in the Sol-Gel Process for Polymer–Silica Nanocomposites with Ionic Interfaces

Donato

Matějka

Mauler

et al. 2017

Colloids and Interfaces

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Abstract:Understanding the organic-inorganic interphases of hybrid materials allows structure and properties control for obtaining new advanced materials. Lately, the use of ionic liquids (ILs) and poly(ionic liquids) (PILs) allowed structure control from the first sol-gel reaction steps due to their anisotropy and multiple bonding capacity. They also act as multifunctional compatibilizing agents that affect the interfacial interactions in a molecular structure-dependent manner. Thus, this review will explore the concepts and latest efforts to control silica morphology using processes such as the sol-gel, both in situ and ex situ of polymer matrices, pre-polymers or polymer precursors. It discusses how to control the polymer-filler interphase bonding, highlighting the last achievements in the interphase ionicity control and, consequently, how these affect the final nanocomposites providing materials with barrier, shape-memory and self-healing properties.

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“…It also offers attractive industrial forecasts in terms of sustainable and viable chemistry 30 . It has several advantages in terms of availability, low price, biodegradability and environmentally benign features [31][32][33] .…”

Section: Introductionmentioning

confidence: 99%

A choline hydroxide catalyzed synthesis of 2,3-dihydroquinazolin-4(1H)-ones in an aqueous medium

2016

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A simple, metal and ligand-free protocol for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones derivatives using choline hydroxide (ChOH) as an effective catalyst in an aqueous medium has been developed. The good to high yield of the desired product is obtained, with low environmental factor and high atom economy. The ChOH was found to be recyclable up to six consecutive runs without significant loss in its activity. The use of water as an environmentally benign solvent, ease of work up and efficient recyclability of the catalyst makes this process more advantageous and greener.

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Biodegradation of ionic liquids – a critical review

Cited by 355 publications

References 105 publications

Synthesis of a series of amino acid derived ionic liquids and tertiary amines: green chemistry metrics including microbial toxicity and preliminary biodegradation data analysis

Synthesis of a series of amino acid derived ionic liquids and tertiary amines: green chemistry metrics including microbial toxicity and preliminary biodegradation data analysis

Recent Applications of Ionic Liquids in the Sol-Gel Process for Polymer–Silica Nanocomposites with Ionic Interfaces

A choline hydroxide catalyzed synthesis of 2,3-dihydroquinazolin-4(1H)-ones in an aqueous medium

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