Thermochemical investigations of solute transfer into ionic liquid solvents: updated Abraham model equation coefficients for solute activity coefficient and partition coefficient predictions

Abstract

Experimental data have been compiled from the published chemical and engineering literature pertaining to the infinite dilution activity coefficients, gas solubilities and chromatographic retention factors for solutes dissolved in ionic liquid (IL) solvents. Included in the compilation are chromatographic retention factors for forty-five solutes on a 1-butyl-1-methylpyrrolidinium tricyanomethanide ionic liquid gas-liquid chromatographic stationary phase. The published experimental data were converted to gas-to-IL and water-to-IL partition coefficients, and correlated with the ion-specific equation coefficient version of the Abraham general solvation 2 model. Ion-specific equation coefficients were calculated for 40 different cations and 16 different anions. The calculated ion-specific equation coefficients describe the experimental gas-to-IL and water-to-IL partition coefficient data to within 0.123 and 0.149 log units, respectively.

Abraham model correlations for describing solute transfer into 2-butoxyethanol from both water and the gas phase at 298K

“…The model that we have been using in our studies has been the Abraham solvation parameter model [2,[21][22][23][24][25][26], which allows one to describe solute transfer between two condensed phases (a biphasic aqueous-organic or organic-organic system) or solute transfer to a condensed phase from the vapor phase. During the past five years we have published Abraham model correlations for 11 additional organic solvents (e.g., diisopropyl ether [27], tributyl phosphate [28], 2-hexadecene [29,30], 1,9-decadiene [29,30], sulfolane [31], benzonitrile [32], ethylbenzene [33], o-xylene [34], m-xylene [34], p-xylene [34], 2-ethoxyethanol [35], and propylene glycol [36]) and several ionic liquids [37][38][39][40][41][42][43][44][45][46][47], as well as updating our existing correlations for hexane [48], heptane [48], octane [48], decane [48], isooctane [49], toluene [33], tetrahydrofuran [50], and 1,4-dioxane [50].…”

Deduction of Physicochemical Properties from Solubilities: 2,4-Dihydroxybenzophenone, Biotin, and Caprolactam as Examples

“…3−8 Equation coefficients are available for partition from water and the gas phase into ionic liquids, 16,17 and solubilities in these ionic liquids can then easily be calculated. Coefficients are also available for equations related to various biological and environmental processes, 18−20 and it is a matter of simple arithmetic to obtain values for these processes.…”

Correlation of the Solubilizing Abilities of 1-Butyl-1-methyl-pyrrolidinium Tris(pentafluoroethyl)trifluorophosphate, 1-Butyl-1-methylpyrrolidinium Triflate and 1-Methoxyethyl-1-methylmorpholinium Tris(pentafluoroethyl)trifluorophosphate

“…The solvation parameter model, developed by Abraham and coworkers [10,11], has been successfully employed to evaluate the solubilizing properties of a large number of traditional organic solvents [12][13][14][15][16][17] and several classes of ILs [18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33]. The solvation parameter model is based on two liner free energy relationships (LFERs), the first relationship describes solute transfer between two condensed phases: log 10 P = c p + e p ·E + s p ·S + a p ·A + b p ·B + v p ·V (1) and the second relationship involves solute transfer from the gas phase to a condensed phase log 10 K = c k + e k ·E + s k ·S + a k ·A + b k ·B + l k ·L (2) where P and K refer to the solute's condensed phase-to-condensed phase partition coefficient (often water-to-organic solvent partition coefficient) and gas-to-condensed phase partition coefficient, respectively.…”