Physical properties of phosphonium ionic liquid and its mixtures with dodecane and water (original) (raw)
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Viscosities and Densities of Phosphonium-Based Ionic Liquids Mixed with Dodecane
Zeitschrift für Physikalische Chemie, 2014
While phosphonium-based ionic liquids are good solvents for gases, they have high viscosities. Addition of a diluent like dodecane significantly lowers the viscosities of the ionic liquids. In the range 20–90 ℃, viscosities and densities were measured for binary mixtures of dodecane with one of five phosphonium-based ionic liquids: Tributylmethylphosphonium bis(2,4,4-trimethylpentyl)phosphinate [TMPP-PA], Tributyltetradecylphosphonium dodecylbenyzenesulfonate [TTDP-DB], Trimethyloctylphosphonium bis(2,4,4-trimethylpentyl)phosphinate [TMPP-TP], Trihexyltetradecylphosphonium dicyanamide [TTDP-DC], and Trihexyltetradecylphophonium bis(2,4,4-trimethylpentyl)phosphoniate [TTDP-PA]. For every one of these ionic liquids, addition of 10 wt. % dodecane very much reduces the viscosity but slightly reduces the density.
Ternary mixtures of phosphonium ionic liquids + organic solvents + water
Pure and Applied Chemistry, 2000
Ionic liquids (ILs) and water are both potentially green solvents that are useful in a variety of extraction processes. This report presents the ternary phase diagrams and tie-line data of trihexyl(tetradecyl)phosphonium dicyanamide [P 6,6,6,14 ][DCA], phosphonium bis(2,4,4-trimethylpentyl)phosphinate [P 6,6,6,14 ][((CH 3 ) 3 C 5 H 8 ) 2 PO 2 ], and 1-ethyl-3methylimidazolium ethylsulfate [emim][C 2 H 5 SO 4 ] ILs in organic solvents (ethanol, acetonitrile, toluene) and water. [P 6,6,6,14 ][DCA] and [P 6,6,6,14 ][((CH 3 ) 3 C 5 H 8 ) 2 PO 2 ] tended to yield emulsions when combined with water and ethanol, while [emim][C 2 H 5 SO 4 ] combined with toluene and water provided two clear phases of reasonable viscosity. The compositions of the ternary mixtures were determined to obtain the tie-lines. A noticeable difference was observed for the tie-lines of the same IL (e.g., [P 6,6,6,14 ][DCA]) with different organic solvents (ethanol and acetonitrile) and water mixtures. In all cases, the addition of ethanol eventually produced a single phase.
The Journal of Physical Chemistry B, 2008
Dynamic solvation of the dye coumarin 153 is studied in a phosphonium ionic liquid: hexadecyltributylphosphonium bromide, [(C4)3C16P+][Br-]. It forms micelles in water, and the bulk also exists as a liquid under our experimental conditions. This system permits a comparison with an imidazolium ionic liquid studied earlier, which also formed micelles in water (J. Phys. Chem. A 2006, 110, 10725−10730). We conclude that our analysis of the comparable situation in a phosphonium liquid is not as definitive as we had proposed earlier, i.e., that the majority of the early-time solvation arises from the organic cation. Part of the difficulty in performing this analysis is most likely due to the amount of water that is associated with the micelle. In the course of this work, we have focused on the calculation of the solvation correlation function, C(t), and investigated how it depends upon the methods with which the "zero-time" spectrum is constructed.
The Journal of Chemical Thermodynamics, 2011
In this work, the solubility of water in several tetradecyltrihexylphosphonium-based ionic liquids at 298.15 K, and densities and viscosities of both pure and water-saturated ionic liquids in a broad temperature range were measured. The selected ionic liquids comprise the common tetradecyltrihexylphosphonium cation combined with the following anions: bromide, chloride, bis(trifluoromethylsulfonyl)imide, decanoate, methanesulfonate, dicyanamide and bis(2,4,4-trimethylpentyl)phosphinate. The isobaric thermal expansion coefficients for pure and water-saturated ionic liquids were determined based on the density dependence with temperature. Taking into account that the excess molar volumes of the current hydrophobic water-saturated ionic liquids are negligible, the solubility of water was additionally estimated from the gathered density data and compared with the experimental solubilities obtained. Moreover, the experimental densities were compared with those predicted by the Gardas and Coutinho model while viscosity data were correlated using the Vogel-Tammann-Fulcher method.
Thermophysical properties of phosphonium-based ionic liquids
Fluid Phase Equilibria, 2015
Experimental data for density, viscosity, refractive index and surface tension of four phosphonium-based ionic liquids were measured in the temperature range between (288.15 and 353.15) K and at atmospheric pressure. The ionic liquids considered include tri(isobutyl) methylphosphonium tosylate, [P i 1 ][Tos], tri(butyl) methylphosphonium methylsulfate, [P 4441 ][CH 3 SO 4 ], tri(butyl) ethylphosphonium diethylphosphate, [P 4442 ][(C 2 H 5 O) 2 PO 2 ], and tetraoctylphosphonium bromide, [P 8888 ] [Br]. Additionally, derivative properties, such as the isobaric thermal expansion coefficient, the surface thermodynamic properties and the critical temperatures for the investigated ionic liquids were also estimated and are presented and discussed. Group contribution methods were evaluated and fitted to the density, viscosity and refractive index experimental data.
Solubility of Water in Tetradecyltrihexylphosphonium-Based Ionic Liquids
The solubility of water in tetradecyltrihexylphosphonium-based ionic liquids (ILs) with the bromide, bis(trifluoromethylsulfonyl)imide, bis(2,4,4-trimethylpentyl)phosphinate, chloride, decanoate, and dicyanimide anions was measured at temperatures between (288.15 and 318.15) K and atmospheric pressure. The effect of the nature of the IL anion, as well as the influence of temperature, are analyzed and discussed. From the experimental results, it was found that the anion-induced hydrophobicity increases from bis(2,4,4trimethylpentyl)phosphinate < decanoate < chloride < bromide < dicyanimide < bis(trifluoromethylsulfonyl)imide. COSMO-RS, a predictive method based on unimolecular quantum chemistry calculations, was used to predict the solubility of the water-IL binary systems. COSMO-RS was found to provide fine qualitative and quantitative predictions of the experimental data for extremely hydrophobic ILs. Less accurate predictions were observed with the increase of the anion hydrophilic character.
Density, Viscosity, and Conductivity of Tetraalkyl Phosphonium Ionic Liquids
ECS Transactions, 2006
The density, viscosity and conductivity of nine commercially available tetra-alkyl phosphonium ionic liquids (ILs) are presented. The effect of cation volume and symmetry, anion volume, and temperature are observed. The Vogel-Tamman-Fulcher (VTF) equation is used to calculate the theoretical glass transition temperature (T 0 ) and the activation energy of conductivity E a,Λ . The conductivity of three halo-aluminate ionic liquid systems for mole fractions up to 0.7 AlCl 3 is reported.
Intermolecular interactions in binary mixtures of phosphonium based ionic liquid and propanoic acid
2018
Thermophysical properties of binary systems containing trihexyltetradecylphosphonium chloride [P14, 6, 6, 6] [Cl ̶ ] ionic liquid (IL) and propanoic acid (PA), have been investigated. Measurements of densities , and speeds of sound have been made at p = 0.1 MPa and at varying temperatures ranging from 293.15 to 313.15 K. The computed excess properties which include excess molar volume , apparent molar volume ( , intermolecular free length (Lf), isentropic compressibility , apparent molar isentropic compressibility ( ) and deviation in isentropic compressibility ∆ have been computed from the experimental data of densities and speeds of sound. Based on the calculated derived properties, it is evident that the investigated IL and PA exhibit strong interactions across the entire mole fraction composition. Good correlation has been achieved with the Redlich-Kister equation.
Amphiphilic behavior of two phosphonium based ionic liquids
Solution and surface chemical behavior of two phosphonium based ionic liquids triisobutyl (methyl) phosphonium tosylate (IL-1) and trihexyl (tetradecyl) phosphonium bis 2,4,4-(trimethylpentyl)phosphinate (IL-2) have been studied. The polar IL-1 is surface active and water soluble, whereas the weakly polar IL-2 is more surface active with very low aqueous solubility. IL-1 does not form micelles but affects the micellization properties of ionic, nonionic, and zwitterionic surfactants more strongly than conventional electrolytes. IL-2 itself forms micelles and mixed micelles with Triton X-100 (TX-100) in aqueous solution. It also forms Langmuir monolayers of liquid expanded type, at the air/water interface. IL-1 can replace water in forming microemulsions with the oil isopropylmyristate (IPM), stabilized by IL-2 (surfactant) + isopropanol (IP as a co-surfactant) like the IL-1/IPM/(IL-2+IP) system. It produces a large monophasic zone in the pseudoternary phase diagram. The thermodynamics of formation of the microemulsions of IL-1 in oil (IPM) have been examined. The dimensions and the polydispersity of the dispersed nano-droplets in the microemulsions have been determined by DLS. The thermal stability of the microemulsion forming systems has also been studied. ILs studied against Sarcoma-180 cell lines have evidenced proficient anti-cancer activity of IL-1 and moderate activity of IL-2.