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One-pot synthesis of symmetric imidazolium ionic liquids N,N-disubstituted with long alkyl chains.

ABSTRACT: The Debus-Radziszewski imidazole synthesis was adapted to directly yield long-chain imidazolium ionic liquids. Imidazolium acetate ionic liquids with side-chains up to sixteen carbon atoms were synthesised in excellent yields via an on-water, one-pot reaction. The imidazolium acetate ILs acted as surfactants when dissolved in various solvents. The imidazolium acetate ionic liquids were also derivatised via an acid metathesis to the chloride, nitrate, and hydrogen oxalate derivatives. The thermal behaviour of all the ionic liquids was determined via thermogravimetric and calorimetric analysis.

SUBMITTER: Damilano G

PROVIDER: S-EPMC9054310 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature

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One-pot synthesis of symmetric imidazolium ionic liquids N,N-disubstituted with long alkyl chains.

Damilano Giacomo G Kalebić Demian D Binnemans Koen K Dehaen Wim W

RSC advances 20200603 36

The Debus-Radziszewski imidazole synthesis was adapted to directly yield long-chain imidazolium ionic liquids. Imidazolium acetate ionic liquids with side-chains up to sixteen carbon atoms were synthesised in excellent yields via an on-water, one-pot reaction. The imidazolium acetate ILs acted as surfactants when dissolved in various solvents. The imidazolium acetate ionic liquids were also derivatised via an acid metathesis to the chloride, nitrate, and hydrogen oxalate derivative ...[more]

PMID: 35518762

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Project description:By mixing ionic liquids (ILs), it is possible to fine-tune their bulk and interfacial structure. This alters their physical properties and solvation behavior and is a simple way to prepare a collection of ILs whose properties can be tuned to optimize a specific application. In this study, mixtures of perfluorinated and alkylated ILs have been prepared, and links between composition, properties, and nanostructure have been investigated. These different classes of ILs vary substantially in the flexibility and polarizability of their chains. Thus, a range of useful structural and physical property variations are accessible through mixing that will expand the library of IL mixtures available in an area that to this point has received relatively little attention. In the experiments presented herein, the physical properties and bulk structure of mixtures of 1-methyl-3-octylimidazolium bis(trifluoromethylsulfonyl)imide [C8MIM][Tf2N] and 1-(1H,1H,2H,2H-perfluorooctyl)-3-methylimidazolium bis(trifluoromethylsulfonyl)imide [C8MIM-F13][Tf2N] have been prepared. The bulk liquid structure was investigated using a combination of small-angle X-ray and neutron scattering (SAXS and SANS, respectively) experiments in combination with atomistic molecular dynamics simulations and the measurement of density and viscosity. We observed that the addition of [C8MIM-F13][Tf2N] to [C8MIM][Tf2N] causes changes in the nanostructure of the IL mixtures that are dependent on composition so that variation in the characteristic short-range correlations is observed as a function of composition. Thus, while the length scales associated with the apolar regions (polar non-polar peak─PNPP) increase with the proportion of [C8MIM-F13][Tf2N] in the mixtures, perhaps surprisingly given the greater volume of the fluorocarbon chains, the length scale of the charge-ordering peak decreases. Interestingly, consideration of the contact peak shows that its origins are both in the direct anion···cation contact length scale and the nature (and hence volume) of the chains appended to the imidazolium cation.

Dataset Information

One-pot synthesis of symmetric imidazolium ionic liquids N,N-disubstituted with long alkyl chains.

Publications

One-pot synthesis of symmetric imidazolium ionic liquids <i>N</i>,<i>N</i>-disubstituted with long alkyl chains.

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