Experimental and theoretical excess molar properties of imidazolium based ionic liquids with isomers of butanol

doi:10.1016/j.tca.2016.03.026

Thermochimica Acta

Volume 634, 20 June 2016, Pages 38-47

https://doi.org/10.1016/j.tca.2016.03.026 Get rights and content

Highlights

•
Experimental density, speeds of sound and refractive index at temperatures 298.15, 308.15 and 318.15 K.
•
Volumetric, Acoustic and optical properties of binary mixtures involving ionic liquids and butanols.
•
Excess molar volume predicted through PFP and ERAS model.
•
Estimation of refractive index through several semi empirical equations.

Abstract

The experimental densities (ρ), speeds of sound (u), and refractive indices (n_D) of binary mixtures of 1-octyl-3-methylimidazolium tetrafluoroborate ([C₈mim][BF₄]) with isomers of butanol (1-butanol, 2-methyl-1-propanol, and 2-methyl-2-propanol) were measured at 0.1 MPa and at 298.15, 308.15 and 318.15 K. Excess molar volumes $(V_{m}^{E})$ , excess molar isentropic compressibilities $(K_{s, m}^{E})$ , and deviations in refractive index $(Δ_{ϕ} n_{D})$ were calculated from the experimental data and were fitted to the Redlich–Kister polynomial equation. The results have been interpreted in terms of interstitial accommodation, ion–dipole interactions, formation of the hydrogen bonds, and structural factors involved in the mixture of ionic liquid and molecular organic solvents. Various mixing rules were used to predict the refractive indices and the data have been compared with the experimental results. In addition, analysis of the present $V_{m}^{E}$ data were done through the Prigogine–Flory–Patterson (PFP) theory and the extended real associated solution (ERAS) model.

Graphical abstract

Introduction

Among the various classes of the ILs [1], [2], imidazolium based ILs are the most extensively studied and used. The ILs are used in various fields, including in catalysis, in electrochemistry, in preparation of highly efficient fuel and solar cells, in the column as the stationary phase in chromatography, in the synthesis of nano-materials and also in various industrial applications [1], [2], [3], [4], [5]. Several technological process used in the industries are designed and implemented successfully from the knowledge of the thermophysical properties of ILs solutions in organic solvents. Reliable and accessible reference data on the physical (density, speeds of sound and viscosity) and chemical properties of pure components (ILs) and their mixtures are very crucial for: several industrial process engineering, transportation and storage of fluids, equipment designing, to develop the models for process design and energy efficient processes, to qualify and quantify the energy efficiency. In the literature, the data pertaining to ILs (pure and mixture with organic solvents) are very limited as well as scattered, which makes them inaccessible to the industry. Furthermore, along with the physical properties, several derived properties are also important to characterize the compounds in their pure form as well as in the mixtures and provide the end user the best information about the behavioral changes occurred when the pure ILs is mixed with the organic solvents through the knowledge of molecular interaction.

Our laboratory is engaged in the systematic experimental and theoretical investigations of the thermodynamic, transport, acoustic, and optical properties of the binary mixtures involving ILs and molecular organic solvents as the functions of composition and temperature [6], [7], [8], [9], [10], [11], [12]. In the previous papers [12], [13], the thermophysical properties of the binary mixtures of imidazolium based ILs: [C₆mim][BF₄] and [C₈mim][BF₄] with the cyclic ethers and alkyl amines were reported. Alaknol as being highly polar H-bonding molecular solvents and used in many organic synthesis has been selected in the present work. Here we report the volumetric, acoustic and optical properties of binary mixtures; [C₈mim][BF₄] + isomers of butanol (1-butanol, 2-methyl-1-propanol and 2-methyl-2-propanol) at (298.15, 308.15 & 318.15) K and at 0.1 MPa pressure. The isomers of butanol were selected as one of the components in order to see the effect of different position of single bond OH and CH₃ groups in butanol molecule on the investigated thermophysical properties. Only the excess molar volumes $(V_{m}^{E})$ of [C₈mim][BF₄] + 1-butanol at 298.15 K have been reported in literature [14]. The results have been interpreted in terms of interstitial accommodation, ion–dipole interactions, H-bond formation and structural factors involved in the liquid components. Further, the refractive indices of the binary mixtures were correlated with Lorentz–Lorenz, Dale–Gladstone, Eykman, Arago–Boit, Newton, Oster, Heller, and Wiener mixing rules [15]. The PFP theory [16], [17], [18] and the ERAS model [17], [19], [20] were also used to analyse the $V_{m}^{E}$ data.

Section snippets

Materials

[C₈mim][BF₄] was synthesized in our laboratory following the two-step synthetic procedure [12], [13], [21], the formation of the halide intermediate followed by the anion exchange of the tetrafluoroborate anion. The purification procedure has been described in our previous publications [12], [13] and the purity was determined through the corresponding ¹H NMR spectra with cation and anion specific peak integrals. ¹H NMR of the synthesized IL (200 MHz, TMS, DMSO-d6, Fig. S1) 0.86 (3H, t, N single bond (CH₂)₅CH

Results and discussion

Isentropic compressibilities (k_S) and molar isentropic compressibilities (K_s,m) were obtained from Eqs. (1) and (2), respectively [48]. $κ_{s} = - V_{m}^{- 1} {(\partial V_{m} / \partial P)}_{S} = {(ρ u^{2})}^{- 1} = V_{m} {(M_{m} u^{2})}^{- 1}$ $K_{S, m} = - {(\partial V_{m} / \partial P)}_{S} = V_{m} κ_{S} = M_{m} / {(ρ u)}^{2}$ where V_m, M_m, ρ, and u are the molar volume, molar mass, density, and speed of sound of the mixture, respectiely. To have better agreement with the other thermodynamic quantities, here we have calculated the mole-intensive quantity K_s,m inplace of the volume-intensive κ_S [57].Measured densities,

Conclusions

Densities, speeds of sound, molar isentropic compressibilities, refractive indices, excess molar volume, excess molar isentropic compressibilities, and deviation in refractive indces for [C₈mim][BF₄] + 1-butanol, + 2-methyl-1-propanol, and + 2-methyl-2-propanol mixtures at 298.15, 308.15 and 318.15 K are reported. The $V_{m}^{E}$ and $K_{s, m}^{E}$ for all the mixtures are negative where as $Δ_{ϕ} n_{D}$ is positive at the most of compositions and at all the temperatures. Interstitial accommodation, formation of H-bonds and

Acknowledgements

Finacial assistance by SVNIT through Faculty Research Grant is acknowledged here. N.I.M. acknowledge Department of Science and Technology, New Delhi for providing the financial assistance through grants No. SR/FT/CS-014/2010 to carry out this work. Financial assistance by Council of Scientific and Industrial Research (CSIR), New Delhi through grant No. 01(2545)/11/EMR-II is also acknowledged. Maulana Azad National Fellowship, (MANF-2012-13-MUS-GUJ-10818) for a research fellowship to Z. Vaid and

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Experimental and theoretical excess molar properties of imidazolium based ionic liquids with isomers of butanol

Highlights

Abstract

Graphical abstract

Introduction

Section snippets

Materials

Results and discussion

Conclusions

Acknowledgements

J. Mol. Catal. A

Thermochim. Acta

Thermochim. Acta

Thermochim. Acta

J. Chem. Thermodyn.

J. Chem. Thermodyn.

Fluid Phase Equilib.

J. Chem. Thermodyn.

J. Chem. Thermodyn.

J. Mol. Liq.

Thermochim. Acta

J. Chem. Thermodyn.

J. Mol. Liq.

J. Chem. Thermodyn.

J. Chem. Thermodyn.

J. Chem. Thermodyn.

J. Chem. Thermodyn.

Chin. J. Chem. Eng.

Thermochim. Acta

J. Chem. Thermodyn.

Fluid Phase Equilib.

Fliud Phase Equilib.

J. Chem. Thermodyn.

Room-Temperature ionic liquids. solvents for synthesis and catalysis

Chem. Rev.

Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation

Green Chem.

Ionic liquids: innovative fluids for chemical processing

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J. Phys. Chem. B

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Excess molar properties for binary systems of CnMIM-BF4 ionic liquids with alkyl amines in the temperature range (298.15-318.15) K. Experimental results and theoretical model calculations

J. Chem. Eng. Data

Excess molar volumes and liquid–liquid equilibria of the ionic liquid 1-methyl-3-octyl-imidazolium tetrafluoroborate mixed with butan-1-ol and pentan-1-ol

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Excess molar properties for binary systems of C_nMIM-BF₄ ionic liquids with alkyl amines in the temperature range (298.15-318.15) K. Experimental results and theoretical model calculations