Study of Ether-, Alcohol-, or Cyano-Functionalized Ionic Liquids Using Inverse Gas Chromatography

Abstract

Activity coefficients of 52 organic compounds in four ionic liquids (ILs), 1,3-dimethoxyimidazolium bis((trifluoromethyl)sulfonyl)imide, 1-(methylethylether)-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide, 1-ethanol-3-methylimidazolium bis((trifluoromethyl)-sulfonyl)imide, and 1-(3-cyanopropyl)-3-methylimidazolium dicyanamide, were measured using inverse gas chromatography from (312 to 353) K. The retention data were also converted in gas-to-IL partition coefficients and water-to-IL partition coefficients using the corresponding gas-to-water partition coefficients. Both sets of partition coefficients were analyzed using the modified Abraham solvation parameter model. The derived equations correlated the experimental gas-to-IL and water-to-IL partition coefficient data to within (0.09 and 0.14) log units, respectively.

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

“…[24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39] The ion-specific equation coefficients can be combined to allow one to predict solute [40], were used to derive Abraham model log K and log P correlations at 298 K and 323 K. As part of the present study we have also updated the cation-specific and anion-specific equation coefficients published in our earlier papers. The last major revision of the numerical values of the coefficients occurred slightly more than three years ago and was based on a total of 1790 log K and 1760 log P values.…”

“…Each database has about doubled in size. Several of the more notable changes in the database include replacement of the log K and log P values for solutes dissolved in 1-(methylethylether)-3-methylimidazolium bis(trifluoromethylsulfonyl)imide at 298.15 K [27], addition of several more cations and anions, and the nearly doubling of experimental log P and log K through recently published activity coefficient, solubility and chromatographic retention data. There was a mathematical error in the computer program used to correct the measured gas-to-liquid partition coefficient for solutes dissolved in 1-(methylethyl-ether)-3-methylimidazolium bis(trifluoromethylsulfonyl)imide at 298.15 K back to 298 K. The corrected log K and log P values are given in Table 6.…”

“…[22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39] The basic model describes solute transfer to an IL solvent both from the gas phase (Eqns. 1 and 2):…”

Interactions between Organic Compounds and Ionic Liquids. Selectivity and Capacity Characteristics of Ionic Liquids

“…hexane/benzene, hexane/methanol, hexane/thiophene, cyclohexane/thiophene for ILs at T = 323.15 K. The selectivities and capacities were calculated using experimental activity coefficient at infinite dilution in 1-ethanol-3-methylimidazolium bis((trifluoromethyl)-imide, 1,3-dimethoxyimidazolium bis((trifluoromethyl)sulfonyl)imide, 1-(methylethylether)-3-methylimidazolium bis((trifluoromethyl)sulfonyl) sulfonyl)imide and 1-(3-cyanopropyl)-3-methylimidazolium dicyanamide, (Revelli et al, 2010b), 1-ethyl-3-methyl-imidazolium bis(trifluoromethylsulfonyl) imidate (Deenadayalu et al, 2005), 1-hexyloxymethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)-imide and 1,3-dihexyloxymethyl-imidazolium bis(trifluoromethylsulfonyl)-imide (Domańska & Marciniak, 2009b), 4-methyl-N-butylpyridinium bis(trifluoromethylsulfonyl)-imide (Domańska & Marciniak, 2009c), triethylsulphonium bis(trifluoromethylsulfonyl)imide (Domańska & Marciniak, 2009a), 1-hexyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide (Heintz et al, 2006), trihexyl(tetradecyl)phosphonium bis(trifluoromethylsulfonyl)imide (Revelli et al, 2009c), 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ( Krummen et al, 2002), 1-ethyl-3-methylimidazolium dicyanamide and trimethylhexylammonium bis((trifluoromethyl)sulfonyl)amide (Mutelet et al, 2010), 1-ethanol-3-methylimidazolium tetrafluoroborate, 1-ethanol-3-methylimidazolium hexafluorophosphate (Revelli et al, 2009a). The temperature is an important parameter on selectivity and capacity.…”

Infinite Dilution Activity Coefficients of Solutes Dissolved in Two Trihexyl(tetradecyl)phosphonium Ionic Liquids

“…We have furthered these efforts by measuring the infinite dilution activity coefficients (γ i ∞ ) and gas-to-IL partition coefficients (K L ) of organic solutes dissolved in a host of ILs: 1-propyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide, 6 1-butyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide, 6 1-pentyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide, 6 1-hexyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide, 7 1-octyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide, diethylphosphate, 12 trihexyl(tetradecyl)phosphonium bis-(trifluoromethylsulfonyl)imide, 13 1-butyl-3-methylimidazolium tetrafluoroborate, 14 1-hexadecyl-3-methylimidazolium tetrafluoroborate, 15 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, 15 1-butyl-3-methylimidazolium hexafluorophosphate, 15 1-butyl-3-methylimidazolium octylsulfate, 16 and 1-ethyl-3-methylimidazolium tosylate. 16 Results of this suite of experimental measurements were used to develop IL-specific Abraham model correlations for describing the logarithm of gasto-IL partition coefficients (log K L ) and the logarithm of waterto-IL partition coefficients (log P) of solutes dissolved in the given anhydrous IL solvent, 6−14 to determine cation-specific and anion-specific Abraham model equation coefficients, [6][7][8][9][10][11]13 and to calculate numerical fragment values for a group contribution version of the Abraham model. 17,18 This latter method contains provisions for estimating log K L and log P as a function of temperature.…”