Insights into the levulinate-based ionic liquid class: synthesis, cellulose dissolution evaluation and ecotoxicity assessment

Mezzetta, Andrea; Becherini, Stefano; Pretti, Carlo; Monni, Gianfranca; Casu, Valentina; Chiappe, Cinzia; Guazzelli, Lorenzo

doi:10.1039/c9nj03239h

Cited by 34 publications

(36 citation statements)

References 68 publications

(73 reference statements)

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“…Therefore, ADIL 3 was synthesized in an overall 76% yield from 1-octylimidazole. 1 H-NMR, 13 C-NMR, and FTIR experiments confirmed the structures and the purities of compounds 1, 2, and 3. In particular, the presence of bis(trifluoromethane)sulfonimide anions in compound 3 was confirmed by the presence of a diagnostic quadruplet signal of CF 3 in the 13 C-NMR spectrum (125.0, 121.8, 118.6, and 115.4 ppm) and the well-known bands at 1347, 1178, and 1051 cm −1 in the FTIR spectrum.…”

Section: Resultsmentioning

confidence: 63%

“…In conclusion, we synthesized the ADIL 1-octyl-3-(3-(1-methylpyrrolidiniumyl)propyl)imidazolium bis(trifluoromethane)sulfonimide 3 in three steps in an excellent overall yield (76%). The final compound (3) and intermediates 1 and 2 were characterized by 1 H-NMR, 13 C-NMR, and FTIR to confirm their structure. The thermal stability of C 3 (C 8 Im) 2 /2 Tf 2 N (3) was ascertained by TGA analysis, which confirmed this ADIL as a suitable medium for high thermal stability applications.…”

Section: Resultsmentioning

confidence: 99%

“…ILs are considered designer solvents due to the fact that, through modifications of the cation and/or of the anion portion, their physicochemical properties can easily be fine-tuned. For this reason, ILs are used in various fields spanning from solvents [7] or catalysts [8,9] for organic reactions, to electrochemistry [10,11], from biopolymer dissolution [12,13] and modification [14], to their use as surfactant and dispersing agents [15,16].…”

Section: Introductionmentioning

confidence: 99%

“…The two different positively charged moieties, bearing a methyl and octyl alkyl chain, respectively, were linked through a propyl alkyl chain. The target ADIL and all the intermediates were characterized by 1 H-NMR, 13 C-NMR, and FTIR. Finally, solubility, density, and viscosity at 25 • C were measured, and the thermal properties of all prepared compounds were analyzed by differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA) to evaluate the operating range of these new set of ILs.…”

Section: Introductionmentioning

confidence: 99%

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1-Octyl-3-(3-(1-methylpyrrolidiniumyl)propyl)imidazolium Bis(trifluoromethane)sulfonimide

Mezzetta

Pomelli

D’Andrea

et al. 2019

Molbank

Self Cite

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The title compound 1-octyl-3-(3-(1-methylpyrrolidiniumyl)propyl)imidazolium bis(trifluoromethane)sulfonimide was prepared in three steps. This asymmetrical dicationic ionic liquid (ADIL) is composed of two different positively charged head groups (1-octylimidazolium and methylpyrrolidinium cations), which are linked through a propyl alkyl chain and by two bis(trifluoromethane)sulfonimide anions. The final ADIL was obtained by a simple metathesis reaction of the corresponding dibromide ionic liquid, in turn prepared by alkylation of 3-(3-bromopropyl)-1-propylimidazolium bromide. The ADIL structure and those of its precursors were confirmed through NMR and infrared spectroscopy, and the thermal properties of all compounds were evaluated by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). Density, solubility, and viscosity were measured for the prepared compounds.

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Section: Resultsmentioning

confidence: 63%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

1-Octyl-3-(3-(1-methylpyrrolidiniumyl)propyl)imidazolium Bis(trifluoromethane)sulfonimide

Mezzetta

Pomelli

D’Andrea

et al. 2019

Molbank

Self Cite

View full text Add to dashboard Cite

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“…Other works using PILs for cellulose dissolution have been published [ 4 ]. Guazzelli and co-workers [ 152 , 153 ] have produced new protic and aprotic ILs based in levulinic acid as an alternative to acetate. These ILs presented comparable cellulose dissolution ability to acetate-based ILs.…”

Section: Cellulosementioning

confidence: 99%

Use of Ionic Liquids and Deep Eutectic Solvents in Polysaccharides Dissolution and Extraction Processes towards Sustainable Biomass Valorization

et al. 2020

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A shift to a bioeconomy development model has been evolving, conducting the scientific community to investigate new ways of producing chemicals, materials and fuels from renewable resources, i.e., biomass. Specifically, technologies that provide high performance and maximal use of biomass feedstocks into commodities with reduced environmental impact have been highly pursued. A key example comprises the extraction and/or dissolution of polysaccharides, one of the most abundant fractions of biomass, which still need to be improved regarding these processes’ efficiency and selectivity parameters. In this context, the use of alternative solvents and the application of less energy-intensive processes in the extraction of polysaccharides might play an important role to reach higher efficiency and sustainability in biomass valorization. This review debates the latest achievements in sustainable processes for the extraction of polysaccharides from a myriad of biomass resources, including lignocellulosic materials and food residues. Particularly, the ability of ionic liquids (ILs) and deep eutectic solvents (DESs) to dissolve and extract the most abundant polysaccharides from natural sources, namely cellulose, chitin, starch, hemicelluloses and pectins, is scrutinized and the efficiencies between solvents are compared. The interaction mechanisms between solvent and polysaccharide are described, paving the way for the design of selective extraction processes. A detailed discussion of the work developed for each polysaccharide as well as the innovation degree and the development stage of dissolution and extraction technologies is presented. Their advantages and disadvantages are also identified, and possible synergies by integrating microwave- and ultrasound-assisted extraction (MAE and UAE) or a combination of both (UMAE) are briefly described. Overall, this review provides key information towards the design of more efficient, selective and sustainable extraction and dissolution processes of polysaccharides from biomass.

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A comprehensive study demonstrating the influence of the solvent composition on the phytotoxicity of compounds, as exemplified by 2,4‐D‐based ILs with a choline‐type cation

Niemczak

Stachowiak

Kaczmarek

et al. 2023

Pest Management Science

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BackgroundGrowing concern for the protection of the environment and existing ecosystems has resulted in increasing consideration of phytotoxicity tests as valid ecotoxicological indicators of the potential hazards of the use of ionic liquids (ILs) or any other chemical. The objective of this study was to gain a detailed understanding of the influence of the solvent composition of spray solutions on the phytotoxic effect of foliar application of ionic pairs with weak (choline 2,4‐dichlorophenoxyacetate, [Chol][2,4‐D]), medium (N‐hexylcholine 2,4‐dichlorophenoxyacetate, [C6Chol][2,4‐D]) and good (N‐dodecylcholine 2,4‐dichlorophenoxyacetate, [C12Chol][2,4‐D]) surface‐active properties.ResultsExperimental results unambiguously demonstrated that the biological activity of the test salt solutions, particularly [Chol][2,4‐D] and [C6Chol][2,4‐D], can be strongly affected by the addition of an organic solvent, such as methanol, ethanol, dimethylformamide (DMF) or dimethylsulfoxide (DMSO) compared to solutions in pure water. However, the observed tendency is less pronounced for the compound exhibiting good surface activity, [C12Chol][2,4‐D].ConclusionsThe collected findings show that caution is warranted in the exploitation or modification of methodologies for assessing phytotoxicity to ensure the reliable interpretation of obtained results for environmental risk assessment or building quantitative structure–activity relationship (QSAR) models. © 2023 Society of Chemical Industry.

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Insights into the levulinate-based ionic liquid class: synthesis, cellulose dissolution evaluation and ecotoxicity assessment

Abstract: New levulinate ionic liquids (ILs) were able to dissolve cellulose in high amounts. The ecotoxicity profiles of these new ILs were also assessed.

Cited by 34 publications

References 68 publications

1-Octyl-3-(3-(1-methylpyrrolidiniumyl)propyl)imidazolium Bis(trifluoromethane)sulfonimide

1-Octyl-3-(3-(1-methylpyrrolidiniumyl)propyl)imidazolium Bis(trifluoromethane)sulfonimide

Use of Ionic Liquids and Deep Eutectic Solvents in Polysaccharides Dissolution and Extraction Processes towards Sustainable Biomass Valorization

A comprehensive study demonstrating the influence of the solvent composition on the phytotoxicity of compounds, as exemplified by 2,4‐D‐based ILs with a choline‐type cation

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