Solvatochromic Probes Absorbance Behavior in Mixtures of 2-Hydroxy Ethylammonium Formate with Methanol, Ethylene Glycol and Glycerol

Salari, Hadi; Harifi‐Mood, Ali Reza; Elahifard, Mohammad Reza; Gholami, Mohammad Reza

doi:10.1007/s10953-010-9596-8

Cited by 24 publications

(13 citation statements)

References 35 publications

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“…The Kamlet-Taft parameters were obtained from the literature. [51][52][53][54] Since no data were available for the 2mHEAPr, the Kamlet-Taft parameters for the 2-hydroxyethylammonium formate were used assuming that they are a good approximation to the protic IL parameters. 54 It can be observed that the ILs CH 4 /CO 2 and H 2 S/CH 4 selectivities present a similar trend to the Kamlet-Taft b parameter indicating that, as expected from the non-ideality analysis carried out above, the solubility of methane in the ILs is related to the ionic liquids' polarity, in particular to their hydrogen bond accepting ability.…”

Section: Co 2 /Ch 4 and H 2 S/ch 4 Selectivitiesmentioning

confidence: 99%

The polarity effect upon the methane solubility in ionic liquids: a contribution for the design of ionic liquids for enhanced CO2/CH4 and H2S/CH4 selectivities

Carvalho

Coutinho

2011

Energy Environ. Sci.

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Aiming at designing ionic liquids for the purification of natural gas, the solubility of methane in ionic liquids is investigated here through the measurement of the solubilities of methane in four ionic liquids (ILs), in a wide range of molar fractions, temperature and pressures. With the exception of the phosphonium-based IL, which behaves as an almost ideal solution, the other ionic liquids show strong positive deviations from ideality, resulting from non-favorable interactions between CH 4 and the ILs. The results indicate that the non-ideality of the solution increases, and the solubility decreases, with the polarity of the ionic liquid. The effect of the ionic liquid polarity on the CO 2 /CH 4 and H 2 S/CH 4 selectivities is evaluated here. The ionic liquids studied here present the largest CO 2 /CH 4 and H 2 S/CH 4 selectivities ever reported. The selectivity models previously proposed in the literature are tested against these new experimental data and are shown to fail. Furthermore, it is shown that describing the ILs' polarity using the Kamlet-Taft parameters, the CO 2 /CH 4 and H 2 S/CH 4 selectivities correlate well with the b-parameter providing a key to the design of ionic liquids with enhanced selectivities.

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Section: Co 2 /Ch 4 and H 2 S/ch 4 Selectivitiesmentioning

confidence: 99%

The polarity effect upon the methane solubility in ionic liquids: a contribution for the design of ionic liquids for enhanced CO2/CH4 and H2S/CH4 selectivities

Carvalho

Coutinho

2011

Energy Environ. Sci.

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“…Stirring of the solution was continued for 24 h at room temperature to obtain a colourless and viscous liquid. The ionic liquid was characterised via 1 H NMR spectroscopy as described elsewhere [23]. The ionic liquid was degassed for 2 h in vacuum (0.3 mbar at 80°C).…”

Section: Preparation Of the Ionic Liquid (2-hydroxyethylammonium Formmentioning

confidence: 99%

Investigation of Solvent Effects on the Reaction of 1-Fluoro-2,4-Dinitrobenzene with Aniline in Molecular-Molecular and Ionic Liquid–Molecular Solvent Mixtures

Harifi‐Mood

Faramarzi

Mehrabi

2015

Progress in Reaction Kinetics and Mechanism

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The solvent effects on the reaction of 1-fluoro-2,4-dinitrobenzene with aniline was studied in various compositions of molecular-molecular solvent mixtures and molecular solvent-2-hydroxyethylammonium formate mixtures as media containing an ionic liquid. A mounting trend with the mole fraction of water in aqueous solution of alcohols up to a maximum at a mole fraction of 0.9 with respect to water was found, but a mild decrease with the mole fraction of ethyl acetate in methanol-ethyl acetate mixtures. A similar increasing trend was observed with increasing methanol, ethanol, 2-propanol and dimethylsulfoxide content in the mixtures containing the ionic liquid. Solvent effect investigations based on linear free energy relationship confirm that polarity has a major effect in molecular-molecular solvent mixtures, whereas polarity and hydrogen-bond acceptor ability were the dominant factors on reaction rate in molecular-ionic solvent mixtures. A nonlinear free energy relationship based on the preferential solvation hypothesis showed differences between the microsphere solvation of the solute and the bulk composition of the solvents. In these mixtures, the intermediate of the reaction was preferentially solvated by the ionic liquid.

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“…8,9 This shows that both ionic character and hydrogen bonding are crucial for the PIL solvation capacity. In addition, recent observations that solvation environment can strongly be affected by cosolvents, [41][42][43][44] indicating the importance of competitive solvation between PIL and co-solvents. 43,45 The connection between a PIL and its corresponding precursors are often overlooked, and are treated as novel green solvents as opposed to mixtures of well-established acids and bases.…”

Section: Introductionmentioning

confidence: 97%

Connecting precursors to a protic ionic liquid: Effects of hydrogen bond synergy in acid-base binary mixtures on the solvent-solute interactions

Reid

Shimizu

Walker³

2020

Journal of Molecular Liquids

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How does the solvation behaviour of a protic ionic liquid (PIL) relate to their precursor Brønsted acid and base? By studying how the solvent-solute interactions in a binary mixture of a Brønsted acid and base changes with respect to composition, a rational connection between precursor and PIL can be made. Using acetic acid and N,N-dimethylethanolamine as model precursors, we demonstrate here that the change in solvent-solute interactions, as inferred from the Kamlet-Taft solvatochromic parameters, are drastically different from additivity approximation based on the simple sum of precursors. Indeed, the apparent hydrogen bond basicity of these mixtures can either be greater than or lesser than either precursor, and the apparent hydrogen bond acidity of these mixtures are dependent on the solvatochromic probe used. Nevertheless, the change in polarizability correlates well with the extent of proton transfer taking place, as inferred from infrared spectroscopy, and can be used as a measure for precursor non-additivity in PILs. Our findings shed light on how the solvation properties of PILs connect to their precursor materials and showcase a new strategy to expand the tuneability of the solvent properties in PIL-based systems. .

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Solvatochromic Probes Absorbance Behavior in Mixtures of 2-Hydroxy Ethylammonium Formate with Methanol, Ethylene Glycol and Glycerol

Cited by 24 publications

References 35 publications

The polarity effect upon the methane solubility in ionic liquids: a contribution for the design of ionic liquids for enhanced CO2/CH4 and H2S/CH4 selectivities

The polarity effect upon the methane solubility in ionic liquids: a contribution for the design of ionic liquids for enhanced CO2/CH4 and H2S/CH4 selectivities

Investigation of Solvent Effects on the Reaction of 1-Fluoro-2,4-Dinitrobenzene with Aniline in Molecular-Molecular and Ionic Liquid–Molecular Solvent Mixtures

Connecting precursors to a protic ionic liquid: Effects of hydrogen bond synergy in acid-base binary mixtures on the solvent-solute interactions

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