A Group Contribution Method for the Correlation of Static Dielectric Constant of Ionic Liquids

doi:10.1016/S1004-9541(14)60009-4

摘要/Abstract

摘要： Static dielectric constant is a key parameter to estimate the electro-viscous effect which plays important roles in the flow and convective heat transfer of fluids with ions in microfluidic devices such as micro reactors and heat exchangers. A group contribution method based on 27 groups is developed for the correlation of static dielectric constant of ionic liquids in this paper. The ionic liquids considered include imidazolium, pyridinium, pyrrolidinium, alkylammonium, alkylsulfonium, morpholinium and piperidinium cations and various anions. The data collected cover the temperature ranges of 278.15-343.15 K and static dielectric constant ranges of 9.4-85.6. The results of the method show a satisfactory agreement with the literature data with an average absolute relative deviation of 7.41%, which is generally of the same order of the experimental data accuracy. The method proposed in this paper provides a simple but reliable approach for the prediction of static dielectric constant of ionic liquids at different temperatures.

关键词: ionic liquid, static dielectric constant, group contribution method

Abstract: Static dielectric constant is a key parameter to estimate the electro-viscous effect which plays important roles in the flow and convective heat transfer of fluids with ions in microfluidic devices such as micro reactors and heat exchangers. A group contribution method based on 27 groups is developed for the correlation of static dielectric constant of ionic liquids in this paper. The ionic liquids considered include imidazolium, pyridinium, pyrrolidinium, alkylammonium, alkylsulfonium, morpholinium and piperidinium cations and various anions. The data collected cover the temperature ranges of 278.15-343.15 K and static dielectric constant ranges of 9.4-85.6. The results of the method show a satisfactory agreement with the literature data with an average absolute relative deviation of 7.41%, which is generally of the same order of the experimental data accuracy. The method proposed in this paper provides a simple but reliable approach for the prediction of static dielectric constant of ionic liquids at different temperatures.

Key words: ionic liquid, static dielectric constant, group contribution method

周颖, 林真, 吴可君, 徐国华, 何潮洪. A Group Contribution Method for the Correlation of Static Dielectric Constant of Ionic Liquids[J]. Chinese Journal of Chemical Engineering, 2014, 22(1): 79-88.

ZHOU Ying, LIN Zhen, WU Kejun, XU Guohua, HE Chaohong. A Group Contribution Method for the Correlation of Static Dielectric Constant of Ionic Liquids[J]. Chin.J.Chem.Eng., 2014, 22(1): 79-88.

参考文献

1 Huddleston, J.G., Visser, A.E., Reichert, W.M., Willauer, H.D., Broker, G.A., Rogers, R.D., "Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation", Green Chem., 3 (4), 156-164 (2001).

2 Valizadeh, H., Vaghefi, S., "One-pot Wittig and Knoevenagel reactions in ionic liquid as convenient methods for the synthesis of coumarin derivatives", Synthetic Commun., 39 (9), 1666-1678 (2009).

3 Wang, J.H., Cheng, D.H., Chen, X.W., Du, Z., Fang, Z.L., "Direct extraction of double-stranded DNA into ionic liquid 1-butyl-3- methylimidazolium hexafluorophosphate and its quantification", Anal. Chem., 79 (2), 620-625 (2007).

4 Parvulescu, V.I., Hardacre, C., "Catalysis in ionic liquids", Chem. Rev, 107 (6), 2615-2665 (2007).

5 Ma, Z., Yu, J.H., Dai, S., "Preparation of inorganic materials using ionic liquids", Adv. Mater, 22 (2), 261-285 (2010).

6 Orsini, M., Chiarotto, I., Elinson, M.N., Sotgiu, G., Inesi, A., "Benzoin condensation in 1,3-dialkylimidazolium ionic liquids via electrochemical generation of N-heterocyclic carbene", Electrochem. Commun., 11 (5), 1013-1017 (2009).

7 Holbrey, J.D., "Heat capacities of common ionic liquids-potential applications as thermal fluids?", Chim. Oggi., 25 (6), 24-26 (2007).

8 Wakai, C., Oleinikova, A., Ott, M., Weingartner, H., "How polar are ionic liquids? Determination of the static dielectric constant of an imidazolium-based ionic liquid by microwave dielectric spectroscopy", J. Phys. Chem. B, 109 (36), 17028-17030 (2005).

9 Li, D.Q., "Electro-viscous effects on pressure-driven liquid flow in microchannels", Colloid Surf. A, 195 (1), 35-57 (2001).

10 Ren, C.L., Li, D.Q., "Electroviscous effects on pressure-driven flow of dilute electrolyte solutions in small microchannels", J. Colloid. Interf. Sci., 274 (1), 319-330 (2004).

11 Bharti, R.P., Harvie, D.J.E., Davidson, M.R., "Steady flow of ionic liquid through a cylindrical microfluidic contraction-expansion pipe: Electroviscous effects and pressure drop", Chem. Eng. Sci., 63 (14), 3593-3604 (2008).

12 Huang, M.M., Jiang, Y.P., Sasisanker, P., Driver, G.W., Weingartner, H., "Static relative dielectric permittivities of iionic liquids at 25 degrees C", J. Chem. Eng. Data, 56 (4), 1494-1499 (2011).

13 Katritzky, A.R., Jain, R., Lomaka, A., Petrukhin, R., Karelson, M., Visser, A.E., Rogers, R.D., "Correlation of the melting points of potential ionic liquids (imidazolium bromides and benzimidazolium bromides) using the CODESSA program", J. Chem. Inf. Comp. Sci., 42 (2), 225-231 (2002).

14 Eiden, P., Bulut, S., Kochner, T., Friedrich, C., Schubert, T., Krossing, I., "In silico predictions of the temperature-dependent viscosities and electrical conductivities of functionalized and non-functionalized ionic liquids", J. Phys. Chem. B, 115 (2), 300-309 (2011).

15 Koddermann, T., Wertz, C., Heintz, A., Ludwig, R., "The association of water in ionic liquids: A reliable measure of polarity", Angew. Chem. Int. Ed., 45 (22), 3697-3702 (2006).

16 Dupont, J., de Souza, R.F., Suarez, P.A.Z., "Ionic liquid (molten salt) phase organometallic catalysis", Chem. Rev., 102 (10), 3667-3691 (2002).

17 Antonietti, M., Kuang, D.B., Smarsly, B., Yong, Z., "Ionic liquids for the convenient synthesis of functional nanoparticles and other inorganic nanostructures", Angew. Chem. Int. Ed., 43 (38), 4988-4992 (2004).

18 Schroder, U., Wadhawan, J.D., Compton, R.G., Marken, F., Suarez, P.A.Z., Consorti, C.S., de Souza, R.F., Dupont, J., "Water-induced accelerated ion diffusion: Voltammetric studies in 1-methyl3-[2,6-(S)- dimethylocten-2-yl]imidazolium tetrafluoroborate, 1-butyl-3- methylimidazolium tetrafluoroborate and hexafluorophosphate ionic liquids", New. J. Chem., 24 (12), 1009-1015 (2000).

19 Singh, T., Kumar, A., "Static dielectric constant of room temperature ionic liquids: Internal pressure and cohesive energy density approach", J. Phys. Chem. B, 112 (41), 12968-12972 (2008).

20 Izgorodina, E.I., Forsyth, M., MacFarlane, D.R., "On the components of the dielectric constants of ionic liquids: Ionic polarization?", Phys. Chem. Chem. Phys., 11 (14), 2452-2458 (2009).

21 Böttcher, C.J.F., Theory of Electric Polarization, Elsevier, Amsterdam (1973).

22 Kobrak, M.N., Li, H., "Electrostatic interactions in ionic liquids: The dangers of dipole and dielectric descriptions", Phys. Chem. Chem. Phys., 12 (8), 1922-1932 (2010).

23 Valderrama, J.O., Sanga, W.W., Lazzus, J.A., "Critical properties, normal boiling temperature, and acentric factor of another 200 ionic liquids", Ind. Eng. Chem. Res., 47 (4), 1318-1330 (2008).

24 Valderrama, J.O., Sanga, W.W., Lazzus, J.A., "Critical properties, normal boiling temperatures, and acentric factors of fifty ionic liquids", Ind. Eng. Chem. Res., 46 (4), 1338-1344 (2007).

25 Gardas, R.L., Coutinho, J.A.P., "Group contribution methods for the prediction of thermophysical and transport properties of ionic liquids", AIChE J., 55 (5), 1274-1290 (2009).

26 Gardas, R.L., Coutinho, J.A.P., "A group contribution method for viscosity estimation of ionic liquids", Fluid Phase Equilib., 266 (1), 195-201 (2008).

27 Nakamura, K., Shikata, T., "Systematic dielectric and NMR study of the ionic Liquid 1-alkyl-3-methyl imidazolium", Chemphyschem, 11 (1), 285-294 (2010).

28 Hunger, J., Stoppa, A., Schr dle, S., Hefter, G., Buchner, R., "Temperature dependence of the dielectric properties and dynamics of ionic liquids", Chemphyschem., 10 (4), 723-733 (2009).

29 Stoppa, A., Buchner, R., Hefter, G., "How ideal are binary mixtures of room-temperature ionic liquids?", J. Mol. Liq., 153 (1), 46-51 (2010).

30 Hunger, J., Stoppa, A., Buchner, R., Hefter, G., "From ionic liquid to electrolyte solution: Dynamics of 1-N-butyl-3-N-methylimidazolium tetrafluoroborate/dichloromethane mixtures", J. Phys. Chem. B, 112 (41), 12913-12919 (2008).

31 Weingartner, H., "The static dielectric constant of ionic liquids", Z Phys. Chem., 220 (10-11), 1395-1405 (2006).

32 Hunger, J., Stoppa, A., Buchner, R., Hefter, G., "Dipole correlations in the ionic liquid 1-N-ethyl-3-N-methylimidazolium ethylsulfate and its binary mixtures with dichloromethane", J. Phys. Chem. B, 113 (28), 9527-9537 (2009).

33 Daguenet, C., Dyson, P.J., Krossing, I., Oleinikova, A., Slattery, J., Wakai, C., Weingartner, H., "Dielectric response of imidazolium- based room-temperature ionic liquids", J. Phys. Chem. B, 110 (25), 12682-12688 (2006).

34 Weingartner, H., Sasisanker, P., Daguenet, C., Dyson, P.J., Krossing, I., Slattery, J.M., Schubert, T., "The dielectric response of room- temperature ionic liquids: Effect of cation variation", J. Phys. Chem. B, 111 (18), 4775-4780 (2007).

35 Stoppa, A., Hunger, J., Buchner, R., Hefter, G., Thoman, A., Helm, H., "Interactions and dynamics in ionic liquids", J. Phys. Chem. B, 112 (16), 4854-4858 (2008).

36 Huang, M.M., Weingartner, H., "Protic ionic liquids with unusually high dielectric permittivities", Chemphyschem., 9 (15), 2172-2173 (2008).

37 Aparicio, S., Alcalde, R., Atilhan, M., "Experimental and computational study on the properties of pure and water mixed 1-ethyl-3-methylimidazolium L-(+)-lactate ionic liquid", J. Phys. Chem. B, 114 (17), 5795-5809 (2010).

38 Stoppa, A., Zech, O., Kunz, W., Buchner, R., "The conductivity of imidazolium-based ionic liquids from (-35 to 195) degrees C. A. variation of cation’s alkyl chain", J. Chem. Eng. Data, 55 (5), 1768-1773 (2010).

39 Schreiner, C., Zugmann, S., Hartl, R., Gores, H.J., "Fractional walden rule for ionic liquids: Examples from recent measurements and a critique of the so-called ideal KCl line for the walden plot", J. Chem. Eng. Data, 55 (5), 1784-1788 (2010).

40 Malham, I.B., Turmine, M., "Viscosities and refractive indices of binary mixtures of 1-butyl-3-methylimidazolium tetrafluoroborate and 1-butyl-2,3-dimethylimidazolium tetrafluoroborate with water at 298 K", J. Chem. Thermodyn., 40 (4), 718-723 (2008).

41 Muhammad, A., Mutalib, M.I.A., Wilfred, C.D., Murugesan, T., Shafeeq, A., "Thermophysical properties of 1-hexyl-3-methyl imidazolium based ionic liquids with tetrafluoroborate, hexafluorophosphate and bis(trifluoromethylsulfonyl)imide anions", J. Chem. Thermodyn., 40 (9), 1433-1438 (2008).

42 Soriano, A.N., Doma, B.T., Li, M.H., "Measurements of the density and refractive index for 1-n-butyl-3-methylimidazolium-based ionic liquids", J. Chem. Thermodyn., 41 (3), 301-307 (2009).

43 Fan, W., Zhou, Q., Sun, J., Zhang, S.J., "Density, excess molar volume, and viscosity for the methyl methacrylate+1-butyl-3- methylimidazolium hexafluorophosphate ionic liquid binary system at atmospheric pressure", J. Chem. Eng. Data, 54 (8), 2307-2311 (2009).

44 Pereiro, A.B., Rodriguez, A., "A study on the liquid-liquid equilibria of 1-alkyl-3-methylimidazolium hexafluorophosphate with ethanol and alkanes", Fluid Phase Equilib., 270 (1-2), 23-29 (2008).

45 Fredlake, C.P., Crosthwaite, J.M., Hert, D.G., Aki, S.N.V.K., Brennecke, J. F., "Thermophysical properties of imidazolium-based ionic liquids", J. Chem. Eng. Data, 49 (4), 954-964 (2004).

46 Vercher, E., Llopis, F.J., Gonzalez-Alfaro, V., Martinez-Andreu, A., "Refractive indices and deviations in refractive indices for binary mixtures of 1-ethyl-3-methylimidazolium trifluoromethanesulfonate with methanol, ethanol, 1-propanol, and 2-propanol at several temperatures", J. Chem. Eng. Data, 55 (3), 1430-1433 (2010).

47 García-Miaja, G., Troncoso, J., Romaní, L., "Excess properties for binary systems ionic liquid + ethanol: Experimental results and theoretical description using the ERAS model", Fluid Phase Equilib., 274 (1-2), 59-67 (2008).

48 Wang, J.Y., Zhao, F.Y., Liu, R.J., Hu, Y.Q., "Thermophysical properties of 1-methyl-3-methylimidazolium dimethyl phosphate and 1-ethyl-3- methylimidazolium diethylphosphate", J. Chem. Thermodyn., 43 (1), 47-50 (2011).

49 Costa, A.J.L., Esperanca, J.M.S.S., Marrucho, I.M., Rebelo, L.P.N., "Densities and viscosities of 1-ethyl-3-methylimidazolium n-alkyl sulfates", J. Chem. Eng. Data, 56 (8), 3433-3441 (2011).

50 Esperana, J.M.S.S., Visak, Z.P., Plechkova, N.V., Seddon, K.R., Guedes, H.J.R., Rebelo, L.P.N., "Density, speed of sound, and derived thermodynamic properties of ionic liquids over an extended pressure range. 4.[C₃mim][NTf₂] and [C₅mim][NTf₂]", J. Chem. Eng. Data, 51 (6), 2009-2015 (2006).

51 Andreatta, A.E., Arce, A., Rodil, E., Soto, A., "Physico-chemical properties of binary and ternary mixtures of ethyl acetate plus ethanol + 1-butyl-3-methyl-imidazolium bis(trifluoromethylsulfonyl)imide at 298.15 K and atmospheric pressure", J. Solution Chem., 39 (3), 371-383 (2010).

52 Pereiro, A.B., Veiga, H.I.M., Esperanca, J.M.S.S., Rodriguez, A., "Effect of temperature on the physical properties of two ionic liquids", J. Chem. Thermodyn., 41 (12), 1419-1423 (2009).

53 Widegren, J.A., Magee, J.W., "Density, viscosity, speed of sound, and electrolytic conductivity for the ionic liquid 1-hexyl-3- methylimidazolium bis(trifluoromethylsulfonyl)imide and its mixtures with water", J. Chem. Eng. Data, 52 (6), 2331-2338 (2007).

54 Andreatta, A.E., Arce, A., Rodil, E., Soto, A., "Physical properties of binary and ternary mixtures of ethyl acetate, ethanol, and 1-octyl-3-methyl-imidazolium bis(trifluoromethylsulfonyl)imide at 298.15 K", J. Chem. Eng. Data, 54 (3), 1022-1028 (2009).

55 Heintz, A., Kulikov, D.V., Verevkin, S.P., "Thermodynamic properties of mixtures containing ionic liquids. 2. Activity coefficients at infinite dilution of hydrocarbons and polar solutes in 1-methyl-3- ethyl-imidazolium bis(trifluoromethyl-sulfonyl) amide and in 1,2-dimethyl-3-ethyl-imidazolium bis(trifluoromethyl-sulfonyl) amide using gas-liquid chromatography", J. Chem. Eng. Data, 47 (4), 894-899 (2002).

56 Tokuda, H., Tsuzuki, S., Susan, M.A.B.H., Hayamizu, K., Watanabe, M., "How ionic are room-temperature ionic liquids? An indicator of the physicochemical properties", J. Phys. Chem. B, 110 (39), 19593-19600 (2006).

57 Carvalho, P.J., Regueira, T., Santos, L.M.N.B.F., Fernandez, J., Coutinho, J.A.P., "Effect of water on the viscosities and densities of 1-butyl-3-methylimidazolium dicyanamide and 1-butyl-3- methylimidazolium tricyanomethane at atmospheric pressure", J. Chem. Eng. Data, 55 (2), 645-652 (2010).

58 Sanchez, L.G., Espel, J.R., Onink, F., Meindersma, G.W., Haan, A.B., "Density, viscosity, and surface tension of synthesis grade imidazolium, pyridinium, and pyrrolidinium based room temperature ionic liquids", J. Chem. Eng. Data, 54 (10), 2803-2812 (2009).

59 Wong, C.L., Soriano, A.N., Li, M.H., "Diffusion coefficients and molar conductivities in aqueous solutions of 1-ethyl-3-methylimidazolium-based ionic liquids", Fluid Phase Equilib., 271 (1-2), 43-52 (2008).

60 Klomfar, J., Souckova, M., Patek, J., "Temperature dependence of the surface tension and density at 0.1 MPa for 1-ethyl- and 1-butyl-3-methylimidazolium dicyanamide", J. Chem. Eng. Data, 56 (8), 3454-3462 (2011).

61 Yuan, X.L., Zhang, S.J., Lu, X.M., "Hydroxyl ammonium ionic liquids: Synthesis, properties, and solubility of SO₂", J. Chem. Eng. Data, 52 (2), 596-599 (2007).

62 Wang, J.Y., Jiang, H.C., Liu, Y.M., Hu, Y.Q., "Density and surface tension of pure 1-ethyl-3-methylimidazolium L-lactate ionic liquid and its binary mixtures with water", J. Chem. Thermodyn., 43 (5), 800-804 (2011).

63 Widegren, J.A., Magee, J.W., "Density, viscosity, speed of sound, and electrolytic conductivity for the ionic liquid 1-hexyl-3- methylimidazolium bis(trifluoromethylsulfonyl)imide and its mixtures with water", J. Chem. Eng. Data, 52 (6), 2331-2338 (2007).

64 Ye, C.F., Shreeve, J.M., "Rapid and accurate estimation of densities of room-temperature ionic liquids and salts", J. Phys. Chem. A, 111 (8), 1456-1461 (2007).

65 Preiss, U.P.R.M., Slattery, J.M., Krossing I., "In silico prediction of molecular volumes, heat capacities, and temperature-dependent densities of ionic liquids", J. Ind. Eng. Chem. Res., 48 (4), 2290-2296 (2009).

66 Gardas, R.L., Coutinho, J.A.P., "Extension of the Ye and Shreeve group contribution method for density estimation of ionic liquids in a wide range of temperatures and pressures", Fluid Phase Equilib., 263 (1), 26-32 (2008).

67 Qiao, Y., Ma, Y.G., Huo, Y., Ma, P.S., Xia, S.Q., "A group contribution method to estimate the densities of ionic liquids", J. Chem. Thermodyn., 42 (7), 852-855 (2010).

68 Paduszyński, K., Domanska, U M., "A new group contribution method for prediction of density of pure ionic liquids over a wide range of temperature and pressure", Ind. Eng. Chem. Res., 51 (1), 591-604 (2012).

69 Bulut, S., Klose, P., Huang, M.M., Weingartner, H., Duson, P.J., Laurenczy, H., Friedrich, C., Menz, J., Kummerer, K., Krossing, I., "Synthesis of room-temperature ionic liquids with the weakly coordinating [Al (OR^F)₄]^- Anion [R^F C(H)A (CF₃)₂] and the determination of their principal physical properties", Chem. Eur. J., 16 (44), 13139-13154 (2010).

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