Volumetric properties of binary mixtures of 1-ethyl-3-methylimidazolium ethyl phosphonate + methanol or 2-propanol

Year 2019, Volume: 22 Issue: 3, 128 - 136, 01.09.2019

Farida Allal , Abdellah Dahmani Boubaker Saidat

https://doi.org/10.5541/ijot.532108

Cited By: 3

Abstract

The present study aimed to determine the refractive
indices at 293.15 K and density data at T= (283.15, 293.15, 303.15 and 313.15)
K of the binary mixtures of 1-ethyl-3-methylimidazolium ethylphosphonate + methanol or 2-propanol
under the atmospheric pressure. The excess molar volume, the apparent molar
volume, the partial molar and excess partial molar volumes of the components at
infinite dilution were calculated from the experimental values. The results of
excess molar volumes were fitted to a Redlich– Kister equation, leading thus to
obtain the coefficients and to estimate the standard deviations between the
experimental and the calculated quantities. Also, the results of excess molar
volumes of the two investigated binary mixtures showed negative deviations from
ideal behavior of the investigated binary systems which can be then discussed in
terms of ion-dipole interactions, formation of hydrogen bonds and structural
factors. Additionally, the refractive indices measurements and the deviations
of refractive index were determined.

Keywords

Ethylimidazolium ionic liquid, Density, Refractive index, Excess volumes, volumetric properties

Volumetric properties of binary mixtures of 1-ethyl-3-methylimidazolium ethyl phosphonate + methanol or 2-propanol

Abstract

La présente étude visait à déterminer les indices de réfraction à 293,15 K et les données de densité à T = (283,15, 293,15, 303,15 et 313,15) K des mélanges binaires de 1- éthyl - 3 - méthylimidazoliuméthylphosphonate + méthanol ou 2-propanol sous la pression atmosphérique. Le volume molaire en excès, le volume molaire apparent, les volumes molaires partiels et les volumes molaires partiels en excès des composants à dilution infinie ont été calculés à partir des valeurs expérimentales. Les résultats des volumes molaires en excès ont été ajustés à une équation de Redlich-Kister, conduisant ainsi à obtenir les coefficients et à estimer les écarts-types entre les quantités expérimentale et calculée. En outre, les résultats des volumes molaires en excès des deux mélanges binaires étudiés ont montré des écarts négatifs par rapport au comportement idéal des systèmes binaires étudiés, qui peuvent ensuite être discutés en termes d’interactions ion-dipôle, de formation de liaisons hydrogène et de facteurs structurels. . Additionally, the refractive indices measurements
and the deviations of refractive index were determined.

 

Keywords

Ethylphosphonate ionic liquid, Density, Refractive index, Excee volumes, Volumetric properties

References

• [1] ] R. Anantharaj, T. Banerjee, “COSMO-RS based predictions for the desulphurization of diesel oil using ionic liquids: Effect of cation and anion combination ». Fuel Process Technol, 92, 39,2011.
• [2] K.Kedra-Krolik, .; F.Mutelet,, F.; .Moise, J-C.; Jaubert, J-N.; Energy Fuels, , 25, 1559, 2011.
• [3] K. Kedra-Krolik, M. Fabrice, J.-N.Jaubert.; “Extraction of Thiophene or Pyridine from n-Heptane Using Ionic Liquids. Gasoline and Diesel Desulfurization ». Ind. Eng. Chem. Res, , 50, 2296–2306, 2011.
• [4] A. Seeberger, A. Jess.; “Desulfurization of diesel oil by selective oxidation and extraction of sulfur compounds by ionic liquids - A contribution to a competitive process design ». Green Chem., 12, 602–608, 2010. [5] F.Mutelet, P.Carré, A.Skrzypczak.;.;”Study of interaction between organic compounds and mono or dicationic oxygenated ionic liquids using gas chromatography ». Fluid Phase equilibria, 387, 59-72, 2015.
• [6] F.Mutelet, A.-L.Revelli, J.-N.Jaubert, L.M.Sprunger, W.E.Jr.Acree, G.A. Baker.; “Partition Coefficients of Organic Compounds in New Imidazolium and Tetralkylammonium Based Ionic Liquids Using Inverse Gas Chromatography”. J.Chem. Eng. Data, ,55, 234–242, 2009.
• [7] S. Keskin, D. Kayrak-Talay, U. Akman, O.A. Hortacsu,; “A review of ionic liquids towards supercritical fluid applications ». J. Supercrit. Fluids, 43, 150–180, 2007.
• [8] N. Deenadayalu, I. Bahadur, T. Hofman.; “Volumetric Properties for (Ionic Liquid + Methanol or Ethanol or 1-Propanol + Nitromethane) at 298.15 K and Atmospheric Pressure » J. Chem. Eng. Data, , 56, 1682–1686, 2011.
• [9] A. Kokorin.; Ionic Liquids: “Applications and Perspectives”, In Tech, Croatia, 2011.
• [10] F. Mutelet, J.-N.Jaubert, “Measurement of activity coefficients at infinite dilution in 1-hexadecyl-3-methylimidazolium tetrafluoroborate ionic liquid ». J. Chem. Thermodyn, , 39, 1144-1150, 2007.
• [11] P.Wasserscheid, T.Welton.; “Ionic Liquids in Synthesis”, Wiley-VCH, 2003.
• [12] A.L. Revelli, F. Mutelet, M. Turmine, R. Solimando, J.N. Jaubert.; “Activity Coefficients at Infinite Dilution of Organic Compounds in 1-Butyl-3-methylimidazolium Tetrafluoroborate Using Inverse Gas Chromatograph ». J. Chem. Eng.Data, , 54, 90–101, 2008.
• [13] A.B. Pereiro, J.M.M. Araújo, J.M.S.S. Esperança, I.M. Marrucho, L.P.N. Rebelo.; “Ionic liquids in separations of azeotropic systems – A review”. J.Chem. Thermodyn, 46, 2–28, 2012.
• [14] A. Heintz, D.V. Kulikov, S.P. Verevkin.; “Thermodynamic properties of mixtures containing ionic liquids. Activity coefficients at infinite dilution of polar solutes in 4-methyl- N-butyl-pyridinium tetrafluoroborate using gas–liquid chromatography ». J. Chem. Thermodyn, 34, 1314–1347, 2002.
• [15] Letcher, T.M.; Deenadayalu, N.; Soko, B.; Ramjugernath, D.; Nevines, A.; Naicker, P.K.; Activity Coefficients at Infinite Dilution of Organic Solutes in 1-Hexyl-3-methylimidazolium Hexafluorophosphate from Gas−Liquid Chromatography. J. Chem. Eng. Data, 48, 708–711, 2003.
• [16] T.V. Vasiltsova, S.P. Verevkin, E. Bich, A. Heintz, R. Bogel-Lukasisk, U.Domanska,; « Thermodynamic properties of mixtures containing ionic liquids. Activity coefficients of aldehydes and ketones in 1-methyl-3-ethyl-imidazolium bis (trifluoromethyl-sulphonyl) imide using the transpiration method ». J. Chem. Eng. Data, 50, 142–148, 2005.
• [17] T.M. Letcher, B. Soko, P. Reddy, N. Deenadayalu; “Determination of Activity Coefficients at Infinite Dilution of Solutes in the Ionic Liquid 1-Hexyl-3-methylimidazolium Tetrafluoroborate Using Gas−Liquid Chromatography at the Temperatures 298.15 K and 323.15 K”. J. Chem. Eng. Data, 48, 1587–159, 2003.
• [18] M. Radhamma, P. Venkatesu, M.V.P. Rao, M.J. Lee, H.M. Lin.; “Excess molar volumes and ultrasonic studies of dimethylsulphoxide with ketones at T = 303.15 K”. J. Chem. Thermodyn, 40, 492–497, 2008.
• [19] ] R.M. Pires, H.F. Costa, A.G.M. Ferreira, I.M.A. Fonseca; “Viscosity and Density of Water + Ethyl Acetate + Ethanol Mixtures at 298.15 and 318.15 K and Atmospheric Pressure”. J. Chem. Eng. Data, 52, 1240–1245, 2007.
• [20] F.Mutelet, A.-L.Revelli, J.-N.Jaubert, L.M.Sprunger, W.E.Jr.Acree, G.A. Baker.; “Partition Coefficients of Organic Compounds in New Imidazolium and Tetralkylammonium Based Ionic Liquids Using Inverse Gas Chromatography”. J.Chem. Eng. Data, 55, 234–242, 2010.
• [21] A.-L. Revelli, F.Mutelet, J.N-.Jaubert, M.Garcia-Martinez, L.M.Sprunger, W.E.Jr.Acree, J. A. Baker, J., J. A.; “Study of Ether-, Alcohol-, or Cyano-Functionalized Ionic Liquids Using Inverse Gas Chromatography”. J. Chem. Eng. Data, 55, 2434–2443, 2010.
• [22] A.-L.Revelli, F.Mutelet, J.-N.Jaubert.; “Prediction of Partition Coefficients of Organic Compounds in ionic liquids”. Ind. Eng. Chem. Res, 49, 3883–3892, 2010.
• [23] T.M. Letcher, U. Doman´ ska, M. Marciniak, A. Marciniak, A.; “Activity coefficients at infinite dilution measurements for organic solutes in the ionic liquid 1-butyl-3-methyl-imidazolium 2-(2-methoxyethoxy) ethyl sulfate using g.l.c. at T = (298.15, 303.15, and 308.15) K ». J. Chem. Thermody, 37, 587–593, 2005.
• [24] I. Bahadur, B.B. Govender, K. Osman, M.D. Williams-Wynn Nelson, W.M.P. Naidoo, D. Ramjugernat.; “Measurement of activity coefficients at infinite dilution of organic solutes in the ionic liquid 1-ethyl-3-methylimidazolium 2-(2-methoxyethoxy) ethylsulfate at T = (308.15, 313.15, 323.15 and 333.15) K using gas + liquid chromatography”. J. Chem. Thermodyn, 70, 245–252, 2005.
• [25] U. Domanska, G.G. Redhi, A. Marciniak.; “Activity coefficients at infinite dilution measurements for organic solutes and water in the ionic liquid 1-butyl-1-methylpyrrolidinium trifluoromethanesulfonate using GLC ». Fluid Phase Equilib. 278, 97–102, 2009.
• [26] U. Domanska, M.J. Laskowska, M.J.; “Effect of Temperature and Composition on the Density and Viscosity of Binary Mixtures of Ionic Liquid with Alcohols ». J. Chem. Thermodyn, 41, 645–650, 2009.
• [27] U. Domanska, A. Marciniak.; “Measurements of activity coefficients at infinite dilution of aromatic and aliphatic hydrocarbons, alcohols and water in new ionic liquid [EMIM][SCN] using GLC ». J. Chem. Thermodyn, 40, 860–866, 2008.
• [28] J.S. Dickmann, J.C. Hassler, E. Kiran.; “Modeling of the volumetric properties and estimation of the solubility parameters of ionic liquid + ethanol mixtures with the Sanchez–Lacombe and Simha–Somcynsky equations of state: [EMIM]Ac + ethanol and [EMIM]Cl + ethanol mixtures ». J. Supercrit. Fluids, 98, 86–101, 2015.
• [29] D. Matkowska, T. Hofman, T.; “Volumetric properties of the ionic liquids: [C6mim][MeSO4], [C6mim][EtSO4], [C4mim][EtSO4] and their mixtures with methanol or ethanol ». J. Mol. Liq, 177, 301–305, 2013.
• [30] N. Calvar, E.J. Gonzalez, A. Dominguez, E.A. Macedo.; “Acoustic, Volumetric and Osmotic Properties of Binary Mixtures Containing The Ionic Liquid 1-butyl-3-methylimidazolium dicyanamide Mixed with Primary and Secondary Alcohols”. J. Chem. Thermodyn. 50, 19–29, 2012.
• [31] Y. Deng, P. Husson, J. Jacquemin, T.G.A. Youngs, V.L. Kett, C. Hardacre, M.F.C.Gomes.; “Volumetric properties and enthalpies of solution of alcohols CkH2k+1OH (k=1, 2, 6) in 1-methyl-3-alkylimidazolium bis(trifluoromethylsulfonyl)imide {[C1CnIm][NTf2] n=2, 4, 6, 8, 10} ionic liquids”. J. Chem. Thermodyn. 43, 1708–1718, 2011.
• [32] N. Deenadayalu, I. Bahadur, T. Hofman,.;. “Volumetric Properties for (Ionic Liquid + Methanol or Ethanol or 1-Propanol + Nitromethane) at 298.15 K and Atmospheric Pressure ». J. Chem. Eng. Data, 56, 1682–1686, 2011.
• [33] U.Domanska, A.Pobudkowska, A. Wisniewska.; “Refractive Indices, Density and Derivative Properties OF Binary Mixtures Hydroxylic Solvents With Ionic Liquid (1-Ethyl-3-Methyl Imidazolium Ethylsulfate And 1-Methyl-3-Mmethylimidazolim Methylsulfate from 298.15 K TO 318.15 K”. J. Solution Chem, 35, 311–334, 2011.
• [34] E.R.E. Hassan, F. Mutelet, S. Pontvianne, J.C. Moise ; « Studies on the Dissolution of Glucose in Ionic Liquids and Extraction Using the Antisolvent Method ». Environ. Sci. Technol, 47 (6), 2809–2816, 2013.
• [35] A. Ayad, F.Mutelet, E.S.Abumandour, A. Negadi.; “Activity coefficients at infinite dilution of organic solutes in methylphosphonate based ionic liquids using gas-liquid chromatography ». J. Chem. Thermodyn. 86, 116–122, 2015.
• [36] F.Mutelet, J.-C. Moise, A. Skrzypczak.; “Evaluation of The Performance of Trigeminal Tricationic Ionic Liquids for Separation Problems”. J. Chem. Eng. Data, 57, 918–927, 2011.
• [37] F. Mutelet, J.N. Jaubert.; “Accurate measurements of thermodynamic properties of solutes in ionic liquids using inverse gas chromatography ». J. Chromatogr,. A, 1102, 256–267, 2006.
• [38] U. Domanska, E.V. Lukoshko, M. Krolikowski.; “Separation of thiophene from heptane with ionic liquids”. J. Chem. Thermodyn, 61, 126–131, 2013.[39] A. Marciniak.; “Influence of cation and anion structure of the ionic liquid on extraction processes based on activity coefficients at infinite dilution. A review ». Fluid Phase Equilib. 294, 213–233, 2010.
• [40] F.Allal, F.Mutelet, A.Dahmani, B.Saidat.; “Measurements of activity coefficients at infinite dilution of organic solutes in the ionic liquid 1-ethyl-3-methylimidazolium ethylphosphonate [EMIM][(EtO)(H)PO2] using gas-liquid chromatography ». J. Mol. Liq, 220, 243–247, 2016. [41] Ki-Sub. Kim, Byung Heung Park “Volumetric properties of solutions of choline chloride + glycerol deep eutectic solvent with water, methanol, ethanol, or iso-propanol ». J. Mol. Liq, 254, 272–279, 2018.
• [42] Q.Yang, H.Zhang, B.Su, Y.Yang, Q.Ren, H.Xing; “Volumetric Properties of Binary Mixtures of 1-Butyl-3-methylimidazolium Chloride + Water or Hydrophilic Solvents at Different Temperatures”. J.Chem.Eng.Data., 55, 1750-1754, 2010.[43] G.Gonfa, M.A.Bustam, N.Muhammad, S.Ullah,.: “Density and excess molar volume of binary mixture of thiocyanate-based ionic liquids and methanol at temperatures 293.15–323.15 K”. J.Mol.Liq, 211, 734-741, 2015.
• [44] C. Yang, H. Lai, Z. Liu, P. Ma. ; « Densities and Viscosities of Diethyl Carbonate + Toluene, + Methanol, and + 2-Propanol from (293.15 to 363.15) K ». J. Chem. Eng. Data, 51, 584–589, 2006.
• [45] F.M.Pang, C.E.Seng, T.T.Teng, M.H.Ibrahim.; « Densities and viscosities of aqueous solutions of 1-propanol and 2-propanol at temperatures from 293.15 K to 333.15 K ». J. Mol. Liq, 136, 71–78, 2007.
• [46] O. Ridlich, A.T. Kister.; “Algebraic Representation of Thermodynamic Properties and the Classification of Solutions ». Ind. Eng. Chem, 40, 345–348, 1948.
• [47] E. Vercher, A.V. Orchilles, P.J. Miguel, A. Martı_nez-Andreu.; “Volumetric and Ultrasonic Studies of 1-Ethyl-3-methylimidazolium Trifluoromethanesulfonate Ionic Liquid with Methanol, Ethanol, 1-Propanol, and Water at Several Temperatures”. J. Chem. Eng. Data, , 52, 1468-1482, 2007.
• [48] Y.-H. Gong, C. Shen, Y.-Z.Lu, H. Meng, C.-X. Li.; “Viscosity and Density Measurements for Six Binary Mixtures of Water (Methanol or Ethanol) with an Ionic Liquid ([BMIM][DMP] or [EMIM][DMP]) at Atmospheric Pressure in the Temperature Range of (293.15 to 333.15) K ». J. Chem. Eng. Data, 57, 33-39, 2012.
• [49] Y. Zhong, H. Wang, K. Diao.; “Densities and excess volumes of binary mixtures of the ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate with aromatic compound at T=(298.15 to 313.15)K”. J. Chem. Thermodyn. 39, 291-296, 2007.
• [50] M.S. Sandhya, C.N. Rao, K. Sivakumar, P. Bhanuprakash, P. Venkateswarlu.; “Effect of Temperature and Alkyl Chail Lengh on Molecular Interactions in The Binary Mixtures of 1-Ethyl-3_Methylimidazolium Methyl Sulphate with 1-Alkanols (C3-C6)”. J. Mol. Liq, 222, 981-987, 2016.
• [51] E.Vercher, A.V.Orchillés, F.J.Liopez, V.Gonzalez-Alfaro, A.Martinez-Audren.; “Ultrasonic and Volumetric Properties of 1-Ethyl-3-methylimidazolium Trifluoromethanesulfonate Ionic Liquid with 2-Propanol or Tetrahydrofuran at Several Temperatures”. J. Chem. Eng. Data, 56, 4633-4642, 2011.[52] S. Belic, N.Zec, M.Vranes, L.Grbovic, S.Podunavac-Kuzmanovic, S.Kovacevic, S.Gadsuric.; “Nature of the interactions in binary mixtures of 1-butyl-3-ethylimidazolium bromide ionic liquid with methanol and ethanol”. J. Mol. Liq, 229, 212-216, 2017.
• [53] A. Pineiro, P. Brocos, A. Amigo, M. Pintos, R.; “Prediction of Excess Volumes and Excess Surface Tensions from Experimental Refractive Indices ». Phys. Chem. Liq, , 38, 251–260, 2000.
• [54] P. Brocos, A. Pinerio, R. Bravo, A. Amigo.; “Refractive indices, molar volumes and molar refractions of binary liquid mixtures: concepts and correlations ». Phys. Chem. Chem. Phys, 5, 550–557, 2003.