Physicochemical studies of intermolecular interactions in 1-butyl-3-methylimidazolium tetrafluoroborate + benzonitrile binary mixtures at temperatures from 293.15 to 318.15 K

References

• Dupont J, de Souza RF, Suarez PA. Ionic liquid (molten salt) phase organometallic catalysis. Chem Rev. 2007;102:3667–3692.
   Google Scholar
• Requejo FP, González EJ, Macedo EA, et al. Effect of the temperature on the physical properties of the pure ionic liquid 1-ethyl-3-methylimidazolium ethylsulfate and characterization of its binary mixtures with alcohols. J Chem Thermodyn. 2014;74:193–200.
   Web of Science ®Google Scholar
• Ramdin M, Loos TWD, Vlugt TJH. State-of-the-art of CO2 capture with ionic liquids. Ind Eng Chem Res. 2012;51:8149–8177.
   Web of Science ®Google Scholar
• MacFarlane DR, Tachikawa N, Forsyth M, et al. Energy applications of ionic liquids. Energy Environ Sci. 2014;7:232–250.
   Web of Science ®Google Scholar
• EJB D, González EOC, Cortés YL, et al. Thermodynamic and transport properties of 1-allyl-3-methylimidazolium bis(trifluromethy lsulfonyl)imide + 1-propanol liquid mixtures: A molecular dynamics study. J Mol Liq. 2019;279:662–668.
   Web of Science ®Google Scholar
• Bourbigou HO, Magna L, Morvan D. Ionic liquids and catalysis: recent progress from knowledge to applications. Appl Catal A. 2010;373:1−56.
   Web of Science ®Google Scholar
• Earle MJ, Esperanca J, Gilea MA, et al. The distillation and volatility of ionic liquids. Nature. 2006;439:831−834.
   PubMed Web of Science ®Google Scholar
• Pauliukaite R, Doherty AP, Murnaghan KD, et al. Molecular dynamics simulations of imidazolium-based ionic liquid/water mixtures: alkyl side chain length and anion effects. Fluid Phase Equilib. 2010;294:148−156.
   Web of Science ®Google Scholar
• Lu X, Xie H, Lei Q, et al. Densities and viscosities of binary mixtures of 2,2-diethyl-1,1,3,3-tetramethylguanidinium bis(trifluoromethylsulfonyl)imide with methanol and ethanol. J Chem Thermodyn. 2019;136:44–53.
   Web of Science ®Google Scholar
• Marcus Y. Introduction to liquid state chemistry. New York: Wiley Interscience; 1977.
   Google Scholar
• Simons JK, Saxton MR. Benzoguanamine. Org Synth. 1953;33:13.
   Web of Science ®Google Scholar
• Wayland BB, Poszmik G, Mukerjee SL, et al. Living radical polymerization of acrylates by organocobalt porphyrin complexes. J Am Chem Soc. 1994;116:7943–7944.
   Web of Science ®Google Scholar
• Bulher DR, Reed DJ. Nitrogen and phosphorus solvents. Amsterdam (Netherlands): Elsevier Science Publishers B.V. (Biomedical Division); 1990.
   Google Scholar
• Riddick JA, Bunger WB, Sakano T. Organic solvents: physical properties and methods of purification. 4th ed. New York: Wiley Interscience; 1986.
   Google Scholar
• Scholz E. Karl Fischer titration. Berlin: Springer-Verlag.; 1984.
   Google Scholar
• Nezhaad GV, Vatani M, Asghari M, et al. Effect of temperature on the physical properties of 1-butyl-3-methylimidazolium based ionic liquids with thiocyanate and tetrafluoroborate anions, and 1-hexyl-3-methylimidazolium with tetrafluoroborate and hexafluorophosphate anions. J Chem Thermodyn. 2012;54:148–154.
   Web of Science ®Google Scholar
• Zhou Q, Wang L, Chen H. Densities and viscosities of 1-butyl-3-methylimidazolium tetrafluoroborate + H2O binary mixtures from (303.15 to 353.15) K. J Chem Eng Data. 2006;51:905–908.
   Web of Science ®Google Scholar
• Pal A, Kumar B. Volumetric and acoustic properties of binary mixtures of the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate [bmim][BF4] with alkoxyalkanols at different temperatures. J Chem Eng Data. 2012;57:688−695.
   Web of Science ®Google Scholar
• Taib MM, Murugesan T. Density, refractive index, and excess properties of 1-butyl-3-methylimidazolium tetrafluoroborate with water and monoethanolamine. J Chem Eng Data. 2012;57:120–126.
   Web of Science ®Google Scholar
• Moattar MTZ, Shekaari H. Application of Prigogine–Flory–Patterson theory to excess molar volume and speed of sound of 1-n-butyl-3-methylimidazolium hexafluorophosphate or 1-n-butyl-3-methylimidazolium tetrafluoroborate in methanol and acetonitrile. J Chem Thermodyn. 2006;38:1377–1384.
   Web of Science ®Google Scholar
• Kumar A. Estimates of internal pressure and molar refraction of imidazolium based ionic liquids as a function of temperature. J Solut Chem. 2008;37:203–214.
   Web of Science ®Google Scholar
• Ciocirlan O, Croitoru O, Iulian O. Density and refractive index of binary mixtures of two 1-alkyl-3-methylimidazolium ionic liquids with 1,4-dioxane and ethylene glycol. J Chem Eng Data. 2014;59:1165−1174.
   Web of Science ®Google Scholar
• Rilo E, Vila J, Garcia M, et al. Viscosity and electrical conductivity of binary mixtures of CnMIM-BF4 with ethanol at 288 K, 298 K, 308 K, and 318 K. J Chem Eng Data. 2010;55:5156–5163.
   Web of Science ®Google Scholar
• Tian S, Hou Y, Wu W, et al. Physical properties of 1-butyl-3-methylimidazolium tetrafluoroborate/N-methyl-2-pyrrolidone mixtures and the solubility of CO2 in the system at elevated pressures. J Chem Eng Data. 2012;57:756−763.
   Web of Science ®Google Scholar
• Vercher E, Llopis FJ, Alfaro VG, et al. Volumetric properties, viscosities and refractive indices of binary liquid mixtures of tetrafluoroborate-based ionic liquids with methanol at several temperatures. J Chem Thermodyn. 2015;90:174–184.
   Web of Science ®Google Scholar
• Krishna TS, Sankara MG, Nain AK, et al. Temperature dependent study of thermophysical and optical properties of binary mixtures of imidazolium based ionic liquids. Indian J Chem. 2016;55A:664–675.
   Google Scholar
• Li J, Zhu H, Peng C, et al. Densities and viscosities for ionic liquids [BMIM][BF4] and [BMIM][Cl] and their binary mixtures at various temperatures and atmospheric pressure. Chin J Chem Eng. DOI:10.1016/j.cjche.2019.04.016
   Web of Science ®Google Scholar
• Iglesias-Otero MA, Troncoso J, Carballo E, et al. Density and refractive index for binary systems of the ionic liquid [Bmim][BF4] with methanol,1,3-dichloropropane, and dimethyl carbonate. J Solut Chem. 2017;36:1219–1230.
   Google Scholar
• Xu W, Li L, Ma X, et al. Density, surface tension, and refractive index of ionic liquids homologue of 1-alkyl-3-methylimidazolium tetrafluoroborate [Cnmim][BF4] (n = 2,3,4,5,6). J Chem Eng Data. 2012;57:2177−2184.
   Web of Science ®Google Scholar
• Droliya P, Nain AK. Densities, speeds of sound and excess properties of (benzonitrile + methyl methacrylate, or + ethyl methacrylate, or + n-butyl methacrylate) binary mixtures at temperatures from 293.15 K to 318.15 K. J Chem Thermodyn. 2019;132:142–154.
   Web of Science ®Google Scholar
• Nikam PS, Kharat SJ. Excess molar volumes and deviations in viscosity of binary mixtures of N, N-dimethylformamide with aniline and benzonitrile at (298.15, 303.15, 308.15, and 313.15) K. J Chem Eng Data. 2003;48:972–976.
   Web of Science ®Google Scholar
• Shukla RK, Kumar A, Srivastava U, et al. Estimation of the surface tensions of benzonitrile, chlorobenzene, benzyl chloride and benzyl alcohol in mixtures with benzene by associated and non-associated processes at 298.15, 303.15 and 313.15 K. J Mol Liq. 2011;158:131–138.
   Web of Science ®Google Scholar
• Viswanathan S, Rao MA, Prashad DHJ. Densities and viscosities of binary liquid mixtures of anisole or methyl tert-butyl ether with benzene, chlorobenzene, benzonitrile, and nitrobenzene. J Chem Eng Data. 2000;45:764–770.
   Web of Science ®Google Scholar
• Wilhelm E, Egger W, Vencour M, et al. Thermodynamics of liquid mixtures consisting of a very polar and a non-polar aromatic: (benzonitrile + benzene, or toluene). J Chem Thermodyn. 1998;30:1509–1532.
   Web of Science ®Google Scholar
• Gill DS, Singh R, Anand H, et al. Compressibility studies of some copper (I) and tetraalkylammonium salts in binary mixtures of triethylphosphite with acetronitrile, benzonitrile and pyridine at 298.15 K. J Mol Liq. 2002;98:15–25.
   Web of Science ®Google Scholar
• Narendra K, Krishna TS, Sudhamsa B, et al. Compressibility studies of some copper (I) and tetraalkylammonium salts in binary mixtures of triethylphosphite with acetronitrile, benzonitrile and pyridine at 298.15 K. J Chem Thermodyn. 2016;103:17–29.
   Web of Science ®Google Scholar
• Durai S, Ramadoss P, Durai S, et al. Optical refractive index from ultrasonic velocity in binary liquid mixtures. Indian J Pure Appl Phys. 2004;42:334–337.
   Web of Science ®Google Scholar
• Shukla RK, Misra P, Sharma S, et al. Refractive index and molar refractivity of benzonitrile, chlorobenzene, benzyl chloride and benzyl alcohol with benzene at T = 298.15, 303.15, 308.15 and 313.15 K. J Iran Chem Soc. 2012;9:1033–1043.
   Web of Science ®Google Scholar
• Takagi T, Teranishi H. Ultrasonic speed in (benzonitrile + nitrobenzene) under high pressures. J Chem Eng Data. 1988;20:809–814.
   Google Scholar
• Chaudhary N, Nain AK. Densities, speeds of sound, refractive indices, excess and partial molar properties of polyethylene glycol 200 + methyl acrylate or ethyl acrylate or n-butyl acrylate binary mixtures at temperatures from 293.15 to 318.15 K. J Mol Liq. 2018;271:501–513.
   Web of Science ®Google Scholar
• Krishna TS, Narendra K, Gowrisankar M, et al. Physicochemical and spectroscopic studies of molecular interactions of 1-butyl-3-methylimidazolium hexafluorophosphate + 2-methoxyethanol or 2-ethoxyethanol binary mixtures at temperatures from 298.15 to 323.15 K. J Mol Liq. 2017;227:333–350.
   Web of Science ®Google Scholar
• Yadav A, Guha A, Pandey A, et al. Densities and dynamic viscosities of ionic liquids having 1-butyl-3-methylimidazolium cation with different anions and bis(trifluoromethylsulfonyl)imide anion with different cations in the temperature range (283.15 to 363.15) K. J Chem Thermodyn. 2018;116:67–75.
   Web of Science ®Google Scholar
• Douheret G, Davis MI, Reis JCR, et al. Isentropic compressibilities—experimental origin and the quest for their rigorous estimation in thermodynamically ideal liquid mixtures. Chem Phys Chem. 2001;2:148–161.
   Google Scholar
• Benson GC, Kiyohara O. Evaluation of excess isentropic compressibilities and isochoric heat capacities. J Chem Thermodyn. 1979;11:1061–1064.
   Web of Science ®Google Scholar
• Reid RC, Prausnitz JM, Poling BE. The properties of gases and liquids. 4th ed. New York: McGraw Hill Inc; 1987. p. 139.
   Google Scholar
• Redlich O, Kister AT. Algebraic representation of thermodynamic properties and the classification of solutions. J Ind Eng Chem. 1948;40:345–348.
   Web of Science ®Google Scholar
• Wang H, Liu W, Huang J. Densities and volumetric properties of a (xylene +- dimethyl sulfoxide) at temperature from (293.15 to 353.15) K. J Chem Thermodyn. 2004;36:743–752.
   Web of Science ®Google Scholar
• Hawrylak B, Gracie K, Palepu R. Thermodynamic properties of binary mixtures of butanediols with water. J Sol Chem. 1998;27:17–31.
   Web of Science ®Google Scholar
• Nain AK. Densities and volumetric properties of butyl acrylate + 1-butanol, or + 2 butanol, or + 2-methyl-l-propanol, or + 2-methyl-2-propanol binary mixtures at temperatures from 288.15 to 318.15 K. J Solut Chem. 2013;42:1404–1422.
   Web of Science ®Google Scholar
• Abe A, Flory PJ. The thermodynamic properties of mixtures of small, nonpolar molecules. J Am Chem Soc. 1965;87:1838–1846.
   Web of Science ®Google Scholar
• Flory PJ. Statistical thermodynamics of liquid mixtures. J Am Chem Soc. 1965;87:1833–1838.
   Web of Science ®Google Scholar
• Patterson D. Effects of molecular size and shape in solution thermodynamics. Pure Appl Chem. 1976;47:305–314.
   Web of Science ®Google Scholar
• Nain AK, Droliya PK. Temperature and concentration dependence of volumetric properties of (tetrahydrofuran + methyl acrylate, or + ethyl acrylate, or + n-butyl acrylate, or + tert-butyl acrylate) binary mixtures. J Chem Thermodyn. 2017;105:317–326.
   Web of Science ®Google Scholar
• Krishna TS, Nain AK, Chentilnath S, et al. Densities, ultrasonic speeds, refractive indices, excess and partial molar properties of binary mixtures of imidazolium based ionic liquid with pyrrolidin-2-one at temperatures from 298.15 to 323.15 K. J Chem Thermodyn. 2016;101:103–114.
   Web of Science ®Google Scholar
• Arago DFJ, Biot JB. Refractive properties of binary mixtures. Mem Acad Fr. 1806;15:7–11.
   Google Scholar
• Dale D, Gladstone F. Influence of temperature on refraction of light. Philos Trans Roy Soc Lond. 1858;148:887–890.
   Google Scholar
• Lorentz HA. Theory of electrons. Leipzig: B. G. Teubner; 1916.
   Google Scholar
• Gupta M, Vibhu I, Shukla JP. Refractive index, molar refraction deviation and excess molar volume of binary mixtures of 1,4-dioxane with carboxylic acids. Phys Chem Liq. 2010;48:415–427.
   Web of Science ®Google Scholar
• Eyring H, John MS. Significant liquid structures. New York: John Wiley; 1969.
   Google Scholar
• Prigogine I. Molecular theory of solutions. Amsterdam, Netherlands: North Holland Publishing Company; 1957.
   Google Scholar
• Weiner O. Refractive index mixing rule in higher alkanes and alkanol systems. Berichte (Leipzig). 1910;62:256–260.
   Google Scholar
• Garcia B, Alcalde R, Leal RM. Formamide-(C1–C5) alkan-1-ols solvent systems. J Chem Soc Faraday Trans. 1996;92:3347–3352.
   Google Scholar
• Assarson P, Eirich ER. Properties of amides in aqueous solution. I. Viscosity and density changes of amide-water systems. An analysis of volume deficiencies of mixtures based on molecular size differences (mixing of hard spheres). J Phys Chem. 1968;72:2710–2719.
   Web of Science ®Google Scholar
• Wang JJ, Zhao Y, Zhao AL. The physicochemical properties of some imidazolium-based ionic liquids and their binary mixtures. J Solut Chem. 2005;34:585–596.
   Web of Science ®Google Scholar
• Gao H, Qi F, Wang H. Densities and volumetric properties of binary mixtures of the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate with benzaldehyde at T = (298.15 to 313.15) K. J Chem Thermodyn. 2009;41:888–892.
   Web of Science ®Google Scholar
• Moattar MTZ, Shekaari H. Volumetric and speed of sound of ionic liquid, 1-butyl-3-methylimidazolium hexafluorophosphate with acetonitrile and methanol at T = (298.15 to 318.15) K. J Chem Eng Data. 2005;50:1694–1699.
   Web of Science ®Google Scholar
• Prakash O, Sinha S. Ultrasonic studies in binary mixtures of tetrahydrofuran with formamide, methyl formamide, dimethyl formamide and 2-methyl pyridine. Acustica. 1984;54:223–225.
   Google Scholar
• Kawaizumi F, Ohno M, Miyahara Y. Ultrasonic and volumetric investigation of aqueous solutions of amides. Bull Chem Soc Jpn. 1977;50:2229–2233.
   Web of Science ®Google Scholar
• Solimo HN, Riggio D, Davolio F, et al. Thermodynamic properties of binary liquid acid-base mixtures. Can J Chem. 1975;53:1258–1262.
   Web of Science ®Google Scholar
• Oswal S, Desai HS. Studies of viscosity and excess molar volume of binary mixtures: propylamine+ 1-alkanol mixtures at 303.15 and 313.15 K. Fluid Phase Equilib. 1998;149:359–376.
   Web of Science ®Google Scholar
• Pineiro A, Brocos P, Amigo A. Prediction of excess volumes and excess surface tensions from experimental refractive indices. Phys Chem Liq. 2000;38:251–260.
   Web of Science ®Google Scholar
• Brocos P, Pineiro A, Bravo R. Refractive indices, molar volumes and molar refractions of binary liquid mixtures: concepts and correlations. Phys Chem Chem Phys. 2003;5:550–557.
   Web of Science ®Google Scholar
• Desnoyers JE, Perron G. Treatment of excess thermodynamic quantities for liquid mixtures. J Solut Chem. 1997;26:749–755.
   Web of Science ®Google Scholar
• Hall L. The origin of ultrasonic absorption in water. Phys Rev. 1948;73:775–784.
   Web of Science ®Google Scholar
• Cipiciani A, Onori G, Savelli G. Structural properties of water-ethanol mixtures: a correlation with the formation of micellar aggregates. Chem Phys Lett. 1988;143:505–509.
   Web of Science ®Google Scholar