Room temperature ionic liquids as novel media for ‘clean’ liquid–liquid extraction

Huddleston, Jonathan G.; Willauer, Heather D.; Swatloski, Richard P.; Visser, Ann E.; Rogers, Robin D.

doi:10.1039/a803999b

Cited by 2,199 publications

(1,521 citation statements)

References 8 publications

(11 reference statements)

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“…34−36 These studies revealed that the nature of RTILs is more complicated than conventional solvents due to the presence of structural heterogeneity of the microenvironment in RTILs, which affects the solvation and rotational dynamics and other processes of the solute in RTILs. 16,29,33 Furthermore, molecular dynamics (MD) simulation studies have indicated that RTILs based on the 1-alkyl-3-methylimidazolium cation ([C n mim] + ) with alkyl chains C 4 and longer are spatially heterogeneous, 37−41 where two types of structural domains with alkyl chains of C 4 or longer in the ionic liquid were expected. Nonpolar domains arising from aggregation of the alkyl chains are formed mainly through the weak essentially van der Waals interactions, and polar domains arising from charge ordering of the anions and imidazolium rings of the cations are formed through the strong electrostatic interactions.…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic Evidence for Unusual Microviscosity in Imidazolium Ionic Liquid and Tetraethylene Glycol Dimethyl Ether Cosolvent Mixtures

Wang

et al. 2012

J. Phys. Chem. B

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The rotational dynamics of coumarin 153 (C153) in imidazolium-based ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim] [PF 6 ]) and tetraethylene glycol dimethyl ether (TEGDME) mixtures across all mole fractions have been investigated to determine the local viscosity of the microenvironment surrounding the probe molecules. The excimer-to-monomer fluorescence emission intensity ratio (I E /I M ) of a well-known microviscosity probe, 1,3-bis(1-pyrenyl)propane (BPP), is also employed to study the microviscosity of the mixtures as a complementary measurement. The rotational dynamics of C153 show that there are incompact and compact domains within the heterogeneous structural [bmim] [PF 6 ], resulting in fast and slow components of C153 rotational dynamics. The microviscosity in different structural domains of [bmim] [PF 6 ] before and after adding cosolvent TEGDME with different mole fractions is further investigated by studying the fluorescence anisotropy decay of probe molecules. The obtained average rotation time constants show that the microviscosity of [bmim] [PF 6 ] is enhanced after mixing with a certain amount of TEGDME, although the bulk viscosity of TEGDME itself is much lower than that of the ionic liquid. This unusual behavior of microviscosity enhancement is further proven by the steady state fluorescence measurement with the microviscosity probe of BPP. The microviscosity enhancement is reasonably demonstrated by the fast time constant of C153 rotational dynamics and the departure between the experimentally observed and calculated ratio of I E /I M of BPP, which shows that this effect is most pronounced at intermediate mole fractions of the [bmim] [PF 6 ] and TEGDME mixtures. The strengthening effects caused by the molecular interactions between TEGDME and structural heterogeneous ionic liquid [bmim] [PF 6 ] are proposed to interpret the unusual microviscosity behaviors.

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Section: Introductionmentioning

confidence: 99%

Spectroscopic Evidence for Unusual Microviscosity in Imidazolium Ionic Liquid and Tetraethylene Glycol Dimethyl Ether Cosolvent Mixtures

Wang

et al. 2012

J. Phys. Chem. B

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“…In the second approach, the IL was injected into a preheated aqueous sample. The 1-decyl-3-methylimidazolium tetrafluoroborate ([C 10 MIM + ][BF 4 − ]) IL was used in the extraction of the derivatized herbicide glyphosate (Gly-FMOC) and its major metabolite, aminomethylphosphonic acid (AMPA-FMOC) in real water samples. Although both methods exhibited enrichment factors above 50, recoveries between 92 and 99%, and RSD values below 7%, the second approach was 5 min faster due to preheating of the aqueous sample.…”

Section: Temperature-assisted Il-dllmementioning

confidence: 99%

Ionic liquids: solvents and sorbents in sample preparation

Clark

Emaus

Varona

et al. 2017

J of Separation Science

140

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The applications of ionic liquids (ILs) and IL-derived sorbents are rapidly expanding. By careful selection of the cation and anion components, the physicochemical properties of ILs can be altered to meet the requirements of specific applications. Reports of IL solvents possessing high selectivity for specific analytes are numerous and continue to motivate the development of new IL-based sample preparation methods that are faster, more selective, and environmentally benign compared to conventional organic solvents. The advantages of ILs have also been exploited in solid/polymer formats in which ordinarily nonspecific sorbents are functionalized with IL moieties in order to impart selectivity for an analyte or analyte class. Furthermore, new ILs that incorporate a paramagnetic component into the IL structure, known as magnetic ionic liquids (MILs), have emerged as useful solvents for bioanalytical applications. In this rapidly changing field, this Review focuses on the applications of ILs and IL-based sorbents in sample preparation with a special emphasis on liquid phase extraction techniques using ILs and MILs, IL-based solid-phase extraction, ILs in mass spectrometry, and biological applications. K E Y W O R D Salternative solvents, ionic liquids, magnetic ionic liquids, microextraction, sample preparation

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“…1-5 Such environmental-friendly properties make ILs relatively benign solvents for cleaner processes to minimize toxic chemical wastes which have become a priority for chemical industries. 6 Room temperature ILs have been used in various applications such as replacing conventional organic solvents in organic synthesis, 7 solvent extractions, 8 electrochemical reactions, 9,10 liquid-liquid extractions, 11 and in enzymatic reactions. 12 In addition, analytical applications of ILs such as their use as buffers in capillary electrophoresis, 13 as stationary phases in gas chromatography 14,15 as well as high performance liquid chromatography, 16 and enhancement of sensitivity in thermal lens measurement have also been investigated.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of novel chiral ionic liquids and investigation of their enantiomeric recognition properties

et al. 2007

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We report the synthesis and characterization of amino acid ester based chiral ionic liquids, derived from L-and D-alanine tert butyl ester chloride. The synthesis was accomplished via an anion metathesis reaction between commercially available L-and D-alanine tert butyl ester chloride using a variety of counterions such as lithium bis (trifluoromethane) sulfonimide, silver nitrate, silver lactate, and silver tetrafluoroborate. Both enantiomeric forms were obtained as confirmed by bands of opposite sign in the circular dichroism spectra. The L-and D-alanine tert butyl ester bis (trifluoromethane) sulfonimide were obtained as liquids at room temperature and intriguingly exhibited the highest thermal stability (up to 263°C). In addition, the ionic liquids demonstrated enantiomeric recognition ability as evidenced by splitting of racemic Mosher's sodium salt signal using a liquid state 19 F nuclear magnetic resonance (NMR) and fluorescence spectroscopy. The L-and D-alanine tert butyl ester chloride resulted in solid salts with nitrate, lactate, and tetrafluoroborate anions. This illustrates the previously observed tunability of ionic liquid synthesis, resulting in ionic liquids of varying properties as a function of varying the anion.

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Room temperature ionic liquids as novel media for ‘clean’ liquid–liquid extraction

Cited by 2,199 publications

References 8 publications

Spectroscopic Evidence for Unusual Microviscosity in Imidazolium Ionic Liquid and Tetraethylene Glycol Dimethyl Ether Cosolvent Mixtures

Spectroscopic Evidence for Unusual Microviscosity in Imidazolium Ionic Liquid and Tetraethylene Glycol Dimethyl Ether Cosolvent Mixtures

Ionic liquids: solvents and sorbents in sample preparation

Synthesis and characterization of novel chiral ionic liquids and investigation of their enantiomeric recognition properties

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