2.2 Mixtures Containing 1,3-Dialkyl Imidazolium Ionic Liquids 761 Properties of 1-Hexyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide 2.2 Mixtures Containing 1,3-Dialkyl Imidazolium Ionic Liquids 02021-03001: imide Abbreviation: Molecular Formula: Molar Mass: Structure: 1-Hexyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl) [C6MIm][NTf2], [C6C1Im][Ntf2], [HMIM][BTI], [C6mim][Tf2N], [C6mim] [NTf2], [C6MIM][NTf2], [HMIM][NTf2], [hmim][Tf2N] C12H19F6N3O4S2 447.42 - + N N O N O S S CF 3 F 3C O O Binary Mixtures Mixture 1: CF4 (1) + [C6C1Im][Ntf2] (2) (1) Phase Equilibrium Ref. [224] T/K p/102 Pa KH/105 Pa CF4 (Partial Pressure of Solute is 0.1 Mpa) 303.42 1146.54 665.69 313.40 1184.57 721.00 323.44 1222.83 783.18 333.45 1260.93 849.06 343.44 1299.08 946.33 x1/103 dev % 1.50 1.39 1.28 1.18 1.06 +0.2 0.4 0.3 +0.8 0.4 # Springer Science+Business Media Dordrecht 2016 S. Zhang et al., Physicochemical Properties of Ionic Liquid Mixtures, DOI 10.1007/978-94-017-7573-1_63 761 762 Properties of 1-Hexyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide (2) Thermodynamic Properties Ref. [224] T/K ΔsolvG1/kJ mol1 CF4 in [C6C1Im][Ntf2] 303 313 323 333 343 ΔsolvH1/kJ mol1 ΔsolvS1/J mol1 K1 p0 = 0.1 MPa 5.38 6.38 7.48 8.68 9.99 16.38 17.11 17.88 18.68 19.52 71.8 75.1 78.5 82.2 86.0 Mixture 2: CH3CH(CH2)4CH2 (1) + [HMIM][BTI] (2) (1) Excess Molar Enthalpy Ref. [78] HE x1 (J mol1) 363.15 K, 1617 kPa 0.0612 192.0 0.1180 385.0 0.1708 553.3 0.2202 695.4 x1 HE (J mol1) x1 HE (J mol1) 0.2663 0.3096 0.3885 0.4586 735.3 723.4 643.7 569.3 0.5213 0.6288 0.7176 0.7922 502.5 394.6 302.1 219.8 x1 HE (J mol1) 0.8840 112.5 (2) Activity Coefficient at Infinite Dilution Ref. [78] Solvent [HMIM][BTI] γ 11 303.15 K 6.83 313.15 K 6.59 323.15 K 6.30 333.15 K 6.06 Mixture 3: C8H18 (1) + [HMIM][BTI] (2) (1) Excess Molar Enthalpy Ref. [78] HE x1 (J mol1) 363.15 K, 1548 kPa 0.0486 203.6 0.0950 369.2 0.1392 449.8 0.1814 483.5 x1 HE (J mol1) x1 HE (J mol1) 0.2217 0.2603 0.3327 0.3993 462.9 443.1 401.1 367.0 0.4608 0.5707 0.6660 0.7495 331.0 266.3 202.2 160.8 x1 HE (J mol1) 0.8568 95.1 2.2 Mixtures Containing 1,3-Dialkyl Imidazolium Ionic Liquids 763 (2) Activity Coefficient at Infinite Dilution and Partial Molar Excess Enthalpy at Infinite Dilution Ref. [4] Solute (1) n-Octane γ 11 (dilutor technique) 303.15 K 313.15 K 14.4 14.1 323.15 K 13.1 333.15 K 12.8 γ 11 (gas-liquid chromatography) 303.15 K 313.15 K 15.2 14.3 323.15 K 13.5 333.15 K 13. 0 Ref. [4] Solute (1) n-Octane Ref. [4] H12E,1/kJ mol1 4.031 Solute (1) n-Octane Mixture 4: C6H5CH3 (1) + [HMIM][BTI] (2) (1) Activity Coefficient at Infinite Dilution and Partial Molar Excess Enthalpy at Infinite Dilution Ref. [78] Solvent [HMIM][BTI] γ 11 303.15 K 0.85 313.15 K 0.95 323.15 K 1.05 333.15 K 1.14 Ref. [4] Solute (1) Toluene γ 11 (gas-liquid chromatography) 303.15 K 313.15 K 1.01 1.03 323.15 K 1.05 333.15 K 1.08 Ref. [4] H12E,1/kJ mol1 1.843 Solute (1) Toluene (2) Excess Molar Enthalpy Ref. [50] HE x1 (J mol1) 363.15 K 0.0501 91.4 0.1001 184.4 0.1501 269.7 x1 HE (J mol1) x1 HE (J mol1) x1 HE (J mol1) 0.2002 0.3002 0.4503 362.2 523.1 707.4 0.6003 0.7002 0.8002 765.4 685.5 487.4 0.8501 0.9001 0.9501 363.0 239.0 120.3 764 Properties of 1-Hexyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide Mixture 5: H2O (1) + [C6mim][Tf2N] (2) (1) Solubility Ref. [45] T/K 288.15 293.15 298.15 303.15 308.15 313.15 318.15 a Standard deviation. x1 σa 0.1906 0.1978 0.2076 0.2187 0.2303 0.2424 0.2556 0.0006 0.0006 0.0006 0.0005 0.0006 0.0006 0.0007 104 (x2 σ) 8.90 0.03 8.96 0.07 9.56 0.02 9.73 0.01 10.2 0.1 11.7 0.2 13.2 0.2 a 22.969 0.004 298.15 K 6.0 1.5 Standard deviation. (ΔsolGm0 σa)/ kJ mol1 (ΔsolHm0 σa)/ kJ mol1 Ref. [45] 56.8 5.1 (ΔsolSm0 σa)/ J K1 mol1 (2) Thermodynamic Properties 167.0 6.2 (ΔsvtHm0 σa)/ kJ mol1 (ΔsvtSm0 σa)/ J K1 mol1 58.830 0.004 363 21 (ΔsvtGm0 σa)/ kJ mol1 164.8 6.2 (ΔsvtHm* σa)/ kJ mol1 76.738 0.004 (ΔsvtGm* σa)/ kJ mol1 295 21 (ΔsvtSm* σa)/ J K1 mol1 2.2 Mixtures Containing 1,3-Dialkyl Imidazolium Ionic Liquids 765 766 Properties of 1-Hexyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide (3) Phase Equilibrium Ref. [50] x1 353.15 K 0.1016 0.3997 P (kPa) x1 P (kPa) x1 P (kPa) x1 P (kPa) 12.18 43.08 0.1708 20.02 0.2122 24.66 0.2971 33.32 Mixture 6: [C6mim]Cl (1) + [C6mim][NTf2] (2) (1) Thermal Conductivity Ref. [82] These physicochemical properties data are listed in a mixture 3 of IL 02021-01001. [978-94-017-7573-1_60] Mixture 7: C6H14 (1) + [HMIM][BTI] (2) (1) Phase Equilibrium Ref. [50] x1 353.15 K 0.0112 0.0243 P (kPa) x1 P (kPa) x1 P (kPa) x1 P (kPa) 9.561 20.22 0.0436 0.0578 35.92 46.98 0.0839 0.1380 66.92 102.6 0.1944 133.0 (2) Excess Molar Enthalpy Ref. [50] HE x1 (J mol1) 363.15 K 0.0200 51.9 0.0501 146.3 0.1002 305.4 0.1503 434.2 x1 HE (J mol1) x1 HE (J mol1) 0.2003 0.3003 0.4004 0.5004 516.7 527.0 446.9 367.2 0.6004 0.7003 0.8002 0.9001 297.4 213.8 137.3 65.7 x1 HE (J mol1) 0.9501 33.5 (3) Activity Coefficient at Infinite Dilution and Partial Molar Excess Enthalpy at Infinite Dilution Ref. [4] Solute (1) n-Hexane γ 11 (dilutor technique) 303.15 K 313.15 K 7.82 7.55 323.15 K 6.96 333.15 K 6.55 2.2 Mixtures Containing 1,3-Dialkyl Imidazolium Ionic Liquids 767 Ref. [4] γ 11 (gas-liquid chromatography) 303.15 K 313.15 K 8.23 7.82 Solute (1) n-Hexane 323.15 K 7.48 333.15 K 7.27 Ref. [4] H12E,1/kJ mol1 3.525 Solute (1) n-Hexane Mixture 8: 1-C8H16 (1) + [HMIM][BTI] (2) (1) Excess Molar Enthalpy Ref. [50] x1 413.15 K 0.0504 0.0982 0.1437 0.1869 HE (J mol1) x1 HE (J mol1) x1 HE (J mol1) 168.9 305.1 426.9 546.7 0.2281 0.2675 0.3409 0.4082 596.1 588.4 543.0 484.4 0.4700 0.5797 0.6742 0.7563 429.5 341.0 258.2 197.3 x1 HE (J mol1) 0.8613 114.0 x1 HE (J mol1) 0.9161 0.9704 285.6 88.75 Mixture 9: C6H6 (1) + [HMIM][BTI] (2) (1) Excess Molar Enthalpy Ref. [50] x1 363.15 K 0.0854 0.1608 0.2279 0.2880 HE (J mol1) x1 HE (J mol1) x1 HE (J mol1) 158.1 291.9 415.3 502.8 0.3421 0.3912 0.4765 0.5482 593.2 681.3 798.2 879.4 0.6094 0.7082 0.7845 0.8452 897.3 862.1 765.5 576.2 (2) Activity Coefficient at Infinite Dilution and Partial Molar Excess Enthalpy at Infinite Dilution Ref. [4] Solute (1) Benzene γ 11 (gas-liquid chromatography) 303.15 K 313.15 K 0.75 0.76 323.15 K 0.78 333.15 K 0.79 Ref. [4] Solute (1) Benzene H12E,1/kJ mol1 1.511 768 Properties of 1-Hexyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide Mixture 10: C2H5OH (1) + [HMIM][BTI] (2) (1) Excess Molar Enthalpy Ref. [50] HE x1 (J mol1) 353.15 K 0.0506 270.9 0.1012 551.5 x1 HE (J mol1) x1 HE (J mol1) x1 HE (J mol1) 0.1517 0.2022 846.3 1127 0.4534 0.6033 2133 2305 0.9012 0.9506 1074 577.8 (2) Volumetric Properties Ref. [225] x2 0.1 MPa 0.0354 0.1970 0.3950 0.4977 0.5942 0.7946 0.0998 0.1480 0.2232 0.3009 0.6939 0.4330 106 VE/m3 mol1 293.15 K 106 VE/m3 mol1 298.15 K 106 VE/m3 mol1 303.15 K 0.23 0.34 0.24 0.18 0.12 0.04 0.33 0.34 0.31 0.28 0.06 0.22 0.24 0.35 0.24 0.17 0.11 0.04 0.34 0.34 0.32 0.28 0.05 0.22 0.24 0.35 0.24 0.17 0.11 0.04 0.35 0.35 0.32 0.28 0.05 0.22 (3) Phase Equilibrium Ref. [4] x1 353.16 K 0.062 0.118 0.168 0.214 0.260 0.375 0.476 P/kPa x1 P/kPa x1 P/kPa x1 P/kPa 9.01 16.55 23.12 29.23 34.96 48.83 60.49 0.568 0.650 0.725 0.784 0.810 0.828 0.845 70.33 78.62 85.67 90.87 93.34 94.54 96.15 0.860 0.878 0.885 0.908 0.933 0.954 0.969 97.19 98.68 99.21 100.89 102.76 104.26 105.38 0.980 0.988 0.994 0.996 0.998 0.999 1.000 106.21 106.86 107.35 107.58 107.72 107.81 107.91 2.2 Mixtures Containing 1,3-Dialkyl Imidazolium Ionic Liquids 769 (4) Activity Coefficient at Infinite Dilution and Partial Molar Excess Enthalpy at Infinite Dilution Ref. [4] γ 11 (gas-liquid chromatography) 303.15 K 313.15 K 1.60 1.47 Solute (1) Ethanol 323.15 K 1.36 333.15 K 1.27 Ref. [4] H12E,1/kJ mol1 6.478 Solute (1) Ethanol Mixture 11: CH3COCH3 (1) + [HMIM][BTI] (2) (1) Excess Molar Enthalpy Ref. [50] x1 353.15 K 0.0200 0.0499 0.0999 0.1498 HE (J mol1) x1 HE (J mol1) x1 HE (J mol1) 44.80 105.9 214.4 332.8 0.1998 0.2997 0.3996 0.4996 444.3 661.3 846.2 998.5 0.5996 0.6997 0.7998 0.8999 1088 1123 1045 760.3 x1 HE (J mol1) 0.9499 488.6 (2) Activity Coefficient at Infinite Dilution and Partial Molar Excess Enthalpy at Infinite Dilution Ref. [4] γ 11 (dilutor technique) 303.15 K 313.15 K 0.31 0.32 Solute (1) Acetone 323.15 K 0.34 333.15 K 0.34 Ref. [4] H12E,1/kJ mol1 2.665 Solute (1) Acetone Mixture 12: 2-CH3COC2H5 (1) + [HMIM][BTI] (2) (1) Excess Molar Enthalpy Ref. [50] x1 353.15 K 0.0200 0.0500 0.1000 0.1500 HE (J mol1) x1 HE (J mol1) x1 HE (J mol1) 52.4 123.8 242.0 377.5 0.2001 0.3001 0.4001 0.5001 502.0 713.3 900.3 1047 0.6001 0.7001 0.8001 0.9000 1145 1165 1067 757.6 x1 HE (J mol1) 0.9500 478.5 770 Properties of 1-Hexyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide (2) Activity Coefficient at Infinite Dilution Ref. [4] Solute (1) 2-Butanone γ 11 (gas-liquid chromatography) 303.15 K 313.15 K 0.41 0.42 323.15 K 0.44 333.15 K 0.44 Mixture 13: 3-C2H5COC2H5 (1) + [HMIM][BTI] (2) (1) Excess Molar Enthalpy Ref. [50] x1 353.15 K 0.0503 0.1005 0.1507 HE (J mol1) x1 HE (J mol1) x1 HE (J mol1) x1 HE (J mol1) 103.5 220.5 332.4 0.2009 0.3011 0.4013 448.2 653.9 829.0 0.5013 0.6013 0.7011 1006 1113 1155 0.8009 0.9005 0.9503 1042 741.5 454.8 Mixture 14: NH(CH2)5C = O (1) + [HMIM][NTf2] (2) (1) Saturation Temperatures, Activity Coefficient, Molar Enthalpies of Mixing for the Solute and Vapor Pressure Ref. [226] TSLE/K xSLE 1 Caprolactam 342.2a 1.00 331.9 0.8867 320.4 0.7756 315.4 0.7475 311.9 0.7117 305.9 0.6520 303.8 0.6457 298.4 0.5911 281.4 0.4389 264.1b 0.312b [C6MIm][NTf2] 264.1b 0.312b 265.6 0.2692 267.2 0.1934 269.3 0.1034 272.0a 0.00 γ SLE (exp tl) i γ SLE (calcd) i Δc ΔmixHm,j(Ttp,i)/kJ mol1 1.00 0.95 0.89 0.84 0.83 0.82 0.79 0.78 0.76 0.76 1 0.93 0.87 0.85 0.83 0.81 0.81 0.79 0.76 0.76 0.0 2.1 2.2 1.2 0.0 1.2 2.5 1.3 0.0 0.0 6.9 1.01 1.02 0.99 0.98 1.00 1.01 1.00 1.00 1.00 1.00 0.0 2.0 1.0 2.0 0.0 0.1 Triple-point temperature of the pure solute. Extrapolated values, eutectic point. c Δ = 100∙(γ iSLE (exptl) -γ iSLE(calcd))/ (γ iSLE (exptl)) a b 2.2 Mixtures Containing 1,3-Dialkyl Imidazolium Ionic Liquids 771 Ref. [226] x1 pexptl/ Pa pNRTL/ Pa γ NRTL 1 315.3 K 1.00 2.86 2.86 0.748 (1.82a) 1.80 0.682 0.623 0.569 0.548 0.458 0.397 0.349 0.223 0.193 0.121 0.00 a 1.52 1.36 1.27 1.23 0.94 0.81 0.61 0.36 0.30 0.15 1.58 1.41 1.25 1.19 0.94 0.77 0.65 0.34 0.28 0.15 x1 1.00 0.84 (0.85a) 0.81 0.79 0.77 0.76 0.72 0.68 0.65 0.54 0.51 0.42 0.24 pexptl/ Pa pNRTL/ Pa γ NRTL 1 320.3 K 1.00 4.42 4.42 0.776 (3.05a) 2.98 0.718 0.652 0.488 0.262 0.228 0.193 0.154 0.139 0.081 0.061 0.00 2.72 2.48 1.71 0.70 0.60 0.49 0.38 0.29 0.17 0.10 1.00 0.88 (0.87a) 0.87 0.85 0.80 0.65 0.62 0.58 0.53 0.51 0.42 0.39 0.28 2.76 2.45 1.73 0.75 0.62 0.49 0.36 0.31 0.15 0.11 x1 pexptl/ Pa 331.9 K 1 11.44 0.887 (9.44a) 0.853 0.796 0.723 0.595 0.453 0.421 0.171 0.124 0.066 0.038 0 9.25 9.19 7.74 6.46 4.94 4.41 1.17 0.82 0.40 0.22 pNRTL/ Pa 11.44 9.96 γ NRTL 1 1.00 0.98 (0.93a) 0.98 0.98 0.97 0.94 0.89 0.88 0.66 0.6 0.51 0.46 0.40 9.56 8.92 8.02 6.40 4.61 4.24 1.29 0.85 0.39 0.20 Vapor pressure was calculated as pexptl ¼ γ SLE CL P0 xCL . (2) Activity Coefficient at Infinite Dilution, Partial Molar Excess Enthalpies at Infinite Dilution and The Excess Partial Molar Heat Capacity at Infinite Dilution Ref. [226] E, 1 substance T/K γ1 <T>/K Hi NH(CH2)5CO 427.5 0.49 ðhT iÞ/kJ mol1 E, 1 Cp, m, i ðhT iÞ/J K mol1 Mixture 15: CH2(CH2)3CH2C = NOH (1) + [HMIM][NTf2] (2) (1) Saturation Temperatures, Activity Coefficient and Molar Enthalpies of Mixing for the Solute Ref. [226] TSLE/K xSLE 1 γ SLE 1 (exp tl) γ SLE 1 (calcd) Δc ΔmixHm,1(Ttp,i)/kJ mol1 310.0 338.2 362.5a 0.2127 0.4087 1.0 2.50 1.84 1.00 2.73 1.50 1.00 9.1 18.1 0.0 16.4 a Triple-point temperature of the pure cyclohexanone oxime. (exptl)) c Δ = 100∙(γ iSLE (exptl) -γ iSLE(calcd))/ (γ iSLE (2) Activity Coefficient at Infinite Dilution, Partial Molar Excess Enthalpies at Infinite Dilution and Excess Partial Molar Heat Capacity at Infinite Dilution Ref. [226] substance cyclohexanone oxime T/K 364.9 γ1 2.61 <T>/ K 403.3 E, 1 Hi ðhT iÞ/ kJ mol1 E, 1 Cp, m, i ðhT iÞ/ J K mol1 13.3 0.3 175 29 (continued) 772 Properties of 1-Hexyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide substance γ1 2.41 2.22 2.03 1.84 1.67 1.61 1.51 1.28 T/K 375.4 386.0 396.5 407.0 417.1 417.6 427.5 438.0 <T>/ K E, 1 Hi ðhT iÞ/ kJ mol1 E, 1 Cp, m, i ðhT iÞ/ J K mol1 Mixture 16: 1-C6H13OH (1) + [C6MIM][NTf2] (2) (1) Cloud Point Ref. [164] w2 0.0568 0.0633 0.1331 0.1656 0.2224 0.2675 T/K 288.19 289.30 299.83 302.40 304.54 305.33 w2 0.2764 0.2764 0.3832 0.3956 0.3956 0.4629 T/K 305.46 305.46 305.94 306.06 306.06 306.08 w2 0.5254 0.5816 0.6175 0.6325 0.6663 T/K 305.75 305.00 304.22 303.78 302.20 w2 0.7114 0.7424 0.7770 0.8185 0.8279 T/K 299.71 297.28 293.61 286.77 285.39 T/K x2 w2 T/K 306.21 306.30 306.32a 306.33 306.15 305.84 305.11 0.29698 0.34941 0.37049 0.40548 0.47827 0.55978 0.64909 0.70164 0.72044 0.74915 0.80056 0.84774 303.35 300.33 299.17 295.76 290.24 281.78 (2) Phase Equilibrium Ref. [225] x2 w2 T/K x2 0.01188 0.02489 0.03031 0.03868 0.05384 0.07020 0.08838 0.05001 0.10054 0.12040 0.14980 0.19947 0.24844 0.29801 288.41 297.40 299.50 301.76 303.79 304.99 305.75 0.10888 0.12973 0.15293 0.15745 0.18893 0.21692 0.25160 a w2 0.1 MPa 0.34853 0.39494 0.44150 0.45003 0.50495 0.54811 0.59548 Values obtained from extrapolation of T = f ( p) to p = 0.1 MPa. Ref. [225] w2 0.44150 x2 0.15293 p/MPa 10.055 14.881 20.176 24.967 30.110 T/K 306.53 306.65 306.84 306.85 307.01 T/K ( p = 0.1 MPa) 306.32 dT/dp (K/MPa) 0.023 (continued) 2.2 Mixtures Containing 1,3-Dialkyl Imidazolium Ionic Liquids w2 x2 p/MPa 35.077 40.046 45.079 49.926 55.067 773 T/K ( p = 0.1 MPa) T/K 307.18 307.25 307.36 307.46 307.56 dT/dp (K/MPa) (3) Excess Molar Partial Enthalpies Ref. [227] HE1/ (J mol1) x1 298.15 K 0.0152 8719 0.0226 8540 0.0299 8372 x1 HE1/ (J mol1) 0.0371 0.0444 0.0512 8099 8106 8078 x1 HE1/ (J mol1) x1 HE1/ (J mol1) 0.0549 0.0652 0.0752 7847 7410 7253 0.0851 0.0947 0.1041 7175 7051 6663 (4) Activity Coefficient at Infinite Dilution and Partial Molar Excess Enthalpies at Infinite Dilution Ref. [227] T/K 333.4 343.9 354.4 364.8 375.2 386.0 396.0 γ 11 (298 K)b HE/11 / (kJ mol1) a Number of moles of the stationary phase component on the column/103 mol 2.01 2.01 3.36 3.36 3.36 7.61 5.83 (32%)a (32%)a (48%)a (48%)a (48%)a (48%)a (60%)a 2.57 2.32 2.25 2.37 2.03 1.98 2.13 2.18 2.15 2.14 2.19 1.83 1.80 1.97 1.97 1.95 1.95 1.99 1.67 1.80 1.82 1.77 1.82 1.85 1.67 1.67 1.69 1.70 1.56 4.21 4.22 3.79 3.91 4.05 3.67 3.90 11.2 11.6 8.9 9.3 10.0 8.5 9.1 Weight per cent IL of the mass of support material. b Extrapolated to T = 298.15 K. Ref. [227] Solute 1-Hexanol a Derived from g.l.c. data. HE/11/(kJ mol1) at T = 298.15 K Calorimetric 9.04 0.07 (9.8 0.8)a From γ 11 12.1a 774 Properties of 1-Hexyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide Mixture 17: 1-C3H7OH (1) + [C6mim][NTf2] (2) (1) Volumetric Properties Ref. [225] x2 0.1 MPa 0.1769 0.3724 0.4923 0.5971 0.7899 0.2008 0.6764 106 VE/m3 mol1 293.15 K 106 VE/m3 mol1 298.15 K 106 VE/m3 mol1 303.15 K 0.14 0.08 0.00 0.04 0.05 0.14 0.04 0.135 0.068 0.003 0.053 0.052 0.134 0.046 0.135 0.064 0.005 0.056 0.053 0.134 0.050 (2) Activity Coefficient at Infinite Dilution and Partial Molar Excess Enthalpy at Infinite Dilution Ref. [4] γ 11 (gas-liquid chromatography) 303.15 K 313.15 K 1.90 1.71 Solute (1) 1-Propanol 323.15 K 1.57 333.15 K 1.45 Ref. [4] H12E,1/kJ mol1 7.536 Solute (1) 1-Propanol Mixture 18: 1-C4H9OH (1) + [C6MIm][NTf2] (2) (1) Volumetric Properties Ref. [225] x2 0.1 MPa 0.2003 0.3968 0.5031 0.5963 0.7693 0.0511 0.1023 0.1523 0.3013 0.6851 106 VE/m3 mol1 293.15 K 106 VE/m3 mol1 298.15 K 106 VE/m3 mol1 303.15 K 0.01 0.06 0.10 0.11 0.11 0.06 0.05 0.03 0.03 0.11 0.01 0.07 0.11 0.12 0.11 0.06 0.05 0.03 0.04 0.12 0.01 0.08 0.11 0.12 0.12 0.06 0.05 0.03 0.05 0.12 2.2 Mixtures Containing 1,3-Dialkyl Imidazolium Ionic Liquids 775 (2) Phase Equilibrium Ref. [225] x2 0.1 MPa 0.01829 0.02813 0.03987 0.05236 0.06599 a w2 T/K x2 w2 T/K x2 w2 T/K 0.10107 0.14872 0.20039 0.25011 0.29898 260.11 264.52 266.93 267.97 268.69 0.08011 0.09883 0.10685 0.11947 0.14224 0.34453 0.39830 0.41931 0.45024 0.50024 269.20 269.44 269.45a 269.46 269.30 0.16393 0.19937 0.23802 0.27730 0.32046 0.54202 0.60048 0.65343 0.69843 0.74002 269.01 268.17 266.90 265.04 262.00 Values obtained from extrapolation of T = f ( p) to p = 0.1 MPa. Ref. [225] w2 0.41931 x2 0.10685 p/MPa 10.129 20.101 30.054 40.026 50.258 T/K ( p = 0.1 MPa) 269.45 T/K 269.16 268.90 268.66 268.36 268.06 dT/dp (K/MPa) 0.027 (3) Excess Molar Partial Enthalpies Ref. [227] x1 298.15 K 0.0132 0.0197 0.0260 0.0276 0.0323 0.0365 HE1/ (J mol1) 9141 9063 9034 8962 8901 8851 x1 HE1/ (J mol1) 0.0386 0.0447 0.0452 0.0508 0.0538 8893 8782 8730 8706 8654 x1 HE1/ (J mol1) x1 HE1/ (J mol1) 0.0567 0.0622 0.0626 0.0685 0.0705 8659 8560 8558 8459 8453 0.0742 0.0786 0.0799 0.0856 0.0866 8436 8359 8325 8254 8236 (4) Activity Coefficient at Infinite Dilution and Partial Molar Excess Enthalpies at Infinite Dilution Ref. [227] T/K 323.1 333.5 344.0 354.5 364.9 375.4 386.1 Number of moles of the stationary phase component on the column/103 mol 2.01 2.01 3.36 3.36 3.36 7.61 5.83 (32%)a (32%)a (48%)a (48%)a (48%)a (48%)a (60%)a 1.99 1.98 1.99 2.06 1.99 1.78 1.77 1.78 1.83 1.78 1.87 1.60 1.57 1.60 1.67 1.61 1.60 1.68 1.45 1.42 1.45 1.53 1.46 1.46 1.52 1.34 1.30 1.34 1.32 1.32 1.37 1.23 1.23 1.23 1.28 1.14 (continued) 776 Properties of 1-Hexyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide Number of moles of the stationary phase component on the column/103 mol 2.01 2.01 3.36 3.36 3.36 7.61 5.83 (32%)a (32%)a (48%)a (48%)a (48%)a (48%)a (60%)a 2.73 2.69 2.65 2.70 2.68 2.59 2.82 T/K γ 11 (298 K)b HE/11/ (kJ mol1) 10.8 9.9 9.3 9.0 9.6 9.0 9.6 Weight per cent IL of the mass of support material. b Extrapolated to T = 298.15 K. a Ref. [227] HE/11/(kJ mol1) Calorimetric 9.32 0.01 Solute 1-Butanol (9.6 0.8) From γ 1i 9.8b a b a This work. Derived from g.l.c. data. Mixture 19: 1-C5H11OH (1) + [C6mim][NTf2] (2) (1) Volumetric Properties Ref. [225] x2 0.1 MPa 0.1011 0.2010 0.4967 0.3987 0.5988 0.7995 106 VE/m3 mol1 293.15 K 106 VE/m3 mol1 298.15 K 106 VE/m3 mol1 303.15 K 0.03 0.08 0.20 0.18 0.20 0.16 0.03 0.09 0.21 0.19 0.21 0.16 0.03 0.09 0.21 0.20 0.21 0.16 (2) Phase Equilibrium Ref. [225] x2 0.1 MPa 0.01142 0.02147 0.02724 0.03372 0.04706 0.06095 0.07807 a w2 T/K x2 w2 T/K x2 w2 T/K 0.05536 0.10018 0.12444 0.15047 0.20040 0.24781 0.30061 272.94 281.13 283.31 285.08 287.30 288.49 289.10 0.09594 0.11610 0.11622 0.13966 0.16444 0.19134 0.19400 0.35006 0.40000 0.40028 0.45172 0.49972 0.54564 0.54989 289.44 289.62 289.62a 289.64 289.52 289.20 288.94a 0.22635 0.26737 0.31615 0.34027 0.37491 0.44041 0.59758 0.64940 0.70117 0.72359 0.75273 0.79978 288.46 287.04 284.50 282.94 280.58 275.02 Values obtained from extrapolation of T = f ( p) to p = 0.1 MPa. 2.2 Mixtures Containing 1,3-Dialkyl Imidazolium Ionic Liquids 777 Ref. [225] w2 0.40028 x2 0.11622 0.54989 0.19400 p/MPa 10.148 20.089 24.965 30.055 39.508 49.981 10.240 20.316 30.245 40.251 50.141 T/K 289.67 289.70 289.72 289.74 289.76 289.83 288.96 289.01 289.09 289.18 289.24 T/K ( p = 0.1 MPa) 289.62 dT/dp (K/MPa) 0.004 288.94 0.007 Mixture 20: 1-C8H17OH (1) + [C6MIm][NTf2] (2) (1) Phase Equilibrium Ref. [225] x2 0.1 MPa 0.01488 0.03134 0.04779 0.06762 0.08787 0.10969 w2 T/K x2 w2 T/K x2 w2 T/K 0.04933 0.10003 0.14707 0.19945 0.24865 0.29739 316.25 325.97 329.66 331.91 332.86 333.32 0.13627 0.16148 0.19309 0.22455 0.26092 0.30860 0.35149 0.39816 0.45118 0.49871 0.54809 0.60528 333.50 333.62 333.46 333.14 332.48 331.23 0.34523 0.40333 0.47166 0.62114 0.71942 0.64431 0.69900 0.75411 0.84923 0.89805 329.32 325.95 321.33 305.79 287.75 Mixture 21: CH2(CH2)4CH2 (1) + [HMIM][BTI] (2) (1) Phase Equilibrium Ref. [4] x1 353.23 K 0.0310 0.0641 0.0951 P/kPa x1 P/kPa x1 P/kPa x1 P/kPa 9.94 21.92 34.51 0.1252 0.1502 0.2165 47.12 57.12 79.44 0.2939 0.6908 0.7408 97.39 99.72 99.83 0.7903 0.9993 1.0000 99.97 99.81 99.58 (2) Activity Coefficient at Infinite Dilution and Partial Molar Excess Enthalpy at Infinite Dilution Ref. [4] Solute (1) Cyclohexane γ 11 (dilutor technique) 303.15 K 313.15 K 5.29 5.01 323.15 K 4.78 333.15 K 4.68 778 Properties of 1-Hexyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide γ 11 (gas-liquid chromatography) 303.15 K 313.15 K 5.48 5.15 Solute (1) Cyclohexane 323.15 K 4.90 333.15 K 4.75 Ref. [4] H12E,1/kJ mol1 3.751 Solute (1) Cyclohexane Mixture 22: CH = CHCH2CH2CH2CH2 (1) + [HMIM][BTI] (2) (1) Phase Equilibrium Ref. [4] x1 353.41 K 0.0432 0.0624 0.0821 0.102 0.139 0.228 0.309 P/kPa x1 P/kPa x1 P/kPa x1 P/kPa 10.81 16.67 22.36 28.19 38.15 59.54 76.27 0.394 0.485 0.576 0.653 0.717 0.768 0.818 89.84 94.21 94.21 94.13 94.03 93.93 93.99 0.856 0.890 0.920 0.945 0.963 0.976 0.986 94.01 94.02 94.03 94.04 94.05 94.05 94.06 0.993 0.996 0.998 0.999 0.999 1.000 94.07 94.07 94.07 94.07 94.06 94.04 (2) Activity Coefficient at Infinite Dilution and Partial Molar Excess Enthalpy at Infinite Dilution Ref. [4] Solute (1) Cyclohexene γ 11 (dilutor technique) 303.15 K 313.15 K 3.20 3.15 323.15 K 3.07 333.15 K 3.01 γ 11 (gas-liquid chromatography) 303.15 K 313.15 K 3.42 3.28 323.15 K 3.18 333.15 K 3.14 Ref. [4] Solute (1) Cyclohexene Ref. [4] Solute (1) Cyclohexene H12E,1/kJ mol1 0.440 2.2 Mixtures Containing 1,3-Dialkyl Imidazolium Ionic Liquids 779 Mixture 23: CH3OH (1) + [HMIM][BTI] (2) (1) Phase Equilibrium Ref. [4] x1 P/kPa x1 0.136 0.232 0.306 0.373 0.422 0.529 0.613 0.685 20.72 38.03 51.92 65.10 75.05 96.18 112.05 125.68 0.749 0.803 0.847 0.860 0.860 0.860 0.879 0.887 P/kPa x1 353.11 K 137.10 0.902 146.63 0.912 154.18 0.920 155.85 0.920 155.84 0.934 155.84 0.952 159.48 0.967 160.36 P/kPa x1 P/kPa 163.43 164.46 166.42 166.41 168.13 171.27 173.85 0.978 0.986 0.992 0.996 0.998 0.999 1.000 175.78 177.07 178.15 179.10 179.50 179.79 179.93 (2) Excess Molar Partial Enthalpies Ref. [227] x1 298.15 K 0.0242 0.0359 0.0473 0.0584 HE1/ (J mol1) 7200 6941 6939 6732 x1 HE1/ (J mol1) 0.0693 0.0799 0.0903 0.1004 6550 6609 6454 6298 x1 HE1/ (J mol1) x1 HE1/ (J mol1) 0.1104 0.1201 0.1296 0.1389 6231 6103 6091 5875 0.1480 0.1569 0.1656 0.1741 5802 5722 5651 5573 (3) Activity Coefficient at Infinite Dilution and Partial Molar Excess Enthalpies at Infinite Dilution Ref. [227] T/K 301.8 312.4 322.9 333.2 344.0 354.3 γ 11(298 K)c HE/11 /(kJ mol1) a Number of moles of the stationary phase component on the column/103 mol 2.01 (32%)a 2.01 (32%)a 3.36 (48%)a 5.83 (60%)a (30%)b 1.43 1.50 1.46 1.46 1.34 (298.2)b 1.27 1.35 1.34 1.29 1.17 (313.2)b 1.15 1.25 1.22 1.15 1.05 1.17 1.10 1.07 1.00 (333.2)b 1.02 0.99 0.98 0.87 0.93 0.90 1.49 1.53 1.53 1.50 1.34 8.4 6.4 7.8 8.4 6.9 Weight per cent IL of the mass of support material. b Derived from data. c Extrapolated to T = 298.15 K. Ref. [227] HiE,1/(kJ mol1) Calorimetric 7.38 0.03 Solute Methanol a b c (7.8 1.0) a This work. Derived from g.l.c. data. Derived from dilutor technique data. From γ 1i 6.9b, 6.8b,4.3c, 780 Properties of 1-Hexyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide Ref. [4] Solute (1) Methanol γ 11 (dilutor technique) 303.15 K 313.15 K 1.16 323.15 K 1.14 333.15 K 1.05 γ 11 (gas-liquid chromatography) 303.15 K 313.15 K 1.30 1.19 323.15 K 1.10 333.15 K 1.02 Ref. [4] Solute (1) Methanol Ref. [4] H12E,1/kJ mol1 6.208 Solute (1) Methanol Mixture 24: [C6mim][NTf2] (1) + [C10mim][NTf2] (2) (1) Volumetric Properties Ref. [57] x1 1 0.836 0.660 0.556 0.463 0.246 0 V (pure component) or VE/cm3 mol1 T = 298.15 K 326.222 (326.2) 0.053 0.091 0.110 0.159 0.071 404.021 (404.0) T = 333.15 K 334.058 (334.1) 0.061 0.093 0.115 0.111 0.106 413.736 (413.5) Mixture 25: C5H12 (1) + [HMIM][BTI] (2) (1) Activity Coefficient at Infinite Dilution and Partial Molar Excess Enthalpy at Infinite Dilution Ref. [4] Solute (1) n-Pentane γ 11 (dilutor technique) 303.15 K 313.15 K 5.93 5.67 323.15 K 5.48 333.15 K 5.27 γ 11 (gas-liquid chromatography) 303.15 K 313.15 K 5.95 5.76 323.15 K 5.65 333.15 K 5.52 Ref. [4] Solute (1) n-Pentane 2.2 Mixtures Containing 1,3-Dialkyl Imidazolium Ionic Liquids 781 Ref. [4] H12E,1/kJ mol1 2.663 Solute (1) n-Pentane Mixture 26: C7H16 (1) + [HMIM][BTI] (2) (1) Activity Coefficient at Infinite Dilution and Partial Molar Excess Enthalpy at Infinite Dilution Ref. [4] Solute (1) n-Heptane γ 11 (dilutor technique) 303.15 K 313.15 K 11.0 10.6 323.15 K 10.1 333.15 K 9.77 γ 11 (gas-liquid chromatography) 303.15 K 313.15 K 11.2 10.6 323.15 K 10. 0 333.15 K 9.67 Ref. [4] Solute (1) n-Heptane Ref. [4] H12E,1/kJ mol1 3.844 Solute (1) n-Heptane Mixture 27: 1-C5H10 (1) + [HMIM][BTI] (2) (1) Activity Coefficient at Infinite Dilution and Partial Molar Excess Enthalpy at Infinite Dilution Ref. [4] Solute (1) 1-Pentene γ 11 (dilutor technique) 303.15 K 313.15 K 3.36 3.33 323.15 K 3.30 333.15 K 3.23 γ 11 (gas-liquid chromatography) 303.15 K 313.15 K 3.47 3.40 323.15 K 3.30 333.15 K 3.31 Ref. [4] Solute (1) 1-Pentene Ref. [4] Solute (1) 1-Pentene H12E,1/kJ mol1 1.220 782 Properties of 1-Hexyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide Mixture 28: 1-C6H12 (1) + [HMIM][BTI] (2) (1) Activity Coefficient at Infinite Dilution and Partial Molar Excess Enthalpy at Infinite Dilution Ref. [4] Solute (1) 1-Hexene γ 11 (dilutor technique) 303.15 K 313.15 K 4.64 4.56 323.15 K 4.48 333.15 K 4.39 γ 11 (gas-liquid chromatography) 303.15 K 313.15 K 4.71 4.61 323.15 K 4.48 333.15 K 4.44 Ref. [4] Solute (1) 1-Hexene Ref. [4] H12E,1/kJ mol1 1.672 Solute (1) 1-Hexene Mixture 29: 1-C7H14 (1) + [HMIM][BTI] (2) (1) Activity Coefficient at Infinite Dilution and Partial Molar Excess Enthalpy at Infinite Dilution Ref. [4] Solute (1) 1-Heptene γ 11 (dilutor technique) 303.15 K 313.15 K 6.28 6.12 323.15 K 5.96 333.15 K 5.86 γ 11 (gas-liquid chromatography) 303.15 K 313.15 K 6.46 6.28 323.15 K 6.09 333.15 K 5.96 Ref. [4] Solute (1) 1-Heptene Ref. [4] H12E,1/kJ mol1 2.133 Solute (1) 1-Heptene Mixture 30: 1-C8H16 (1) + [HMIM][BTI] (2) (1) Activity Coefficient at Infinite Dilution and Partial Molar Excess Enthalpy at Infinite Dilution Ref. [4] Solute (1) 1-Octene γ 11 (dilutor technique) 303.15 K 313.15 K 8.28 8.08 323.15 K 7.92 333.15 K 7.77 2.2 Mixtures Containing 1,3-Dialkyl Imidazolium Ionic Liquids 783 Ref. [4] Solute (1) 1-Octene γ 11 (gas-liquid chromatography) 303.15 K 313.15 K 8.81 8.47 323.15 K 8.18 333.15 K 7.90 Ref. [4] H12E,1/kJ mol1 2.369 Solute (1) 1-Octene Mixture 31: CH2(CH2)3CH2 (1) + [HMIM][BTI] (2) (1) Activity Coefficient at Infinite Dilution and Partial Molar Excess Enthalpy at Infinite Dilution Ref. [4] Solute (1) Cyclopentane γ 11 (dilutor technique) 303.15 K 313.15 K 3.64 3.48 323.15 K 3.27 333.15 K 3.26 Ref. [4] H12E,1/kJ mol1 3.393 Solute (1) Cyclopentane Mixture 32: m-C6H4(CH3)2 (1) + [HMIM][BTI] (2) (1) Activity Coefficient at Infinite Dilution and Partial Molar Excess Enthalpy at Infinite Dilution Ref. [4] Solute (1) m-Xylene γ 11 (gas-liquid chromatography) 303.15 K 313.15 K 1.40 1.41 323.15 K 1.46 333.15 K 1.50 Ref. [4] H12E,1/kJ mol1 1.649 Solute (1) m-Xylene Mixture 33: p-C6H4(CH3)2 (1) + [HMIM][BTI] (2) (1) Activity Coefficient at Infinite Dilution and Partial Molar Excess Enthalpy at Infinite Dilution Ref. [4] Solute (1) p-Xylene γ 11 (gas-liquid chromatography) 303.15 K 313.15 K 1.42 1.42 323.15 K 1.48 333.15 K 1.51 784 Properties of 1-Hexyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide Ref. [4] H12E,1/kJ mol1 2.020 Solute (1) p-Xylene Mixture 34: 2-CH3COC3H7 (1) + [HMIM][BTI] (2) (1) Activity Coefficient at Infinite Dilution and Partial Molar Excess Enthalpy at Infinite Dilution Ref. [4] Solute (1) 2-Pentanone γ 11 (gas-liquid chromatography) 303.15 K 313.15 K 0.51 0.52 323.15 K 0.54 333.15 K 0.55 Ref. [4] H12E,1/kJ mol1 2.338 Solute (1) 2-Pentanone Mixture 35: 2-CH3CHCH3OH (1) + [HMIM][BTI] (2) (1) Activity Coefficient at Infinite Dilution and Partial Molar Excess Enthalpy at Infinite Dilution Ref. [4] Solute (1) 2-Propanol γ 11 (dilutor technique) 303.15 K 313.15 K 1.72 1.48 323.15 K 1.37 333.15 K 1.23 γ 11 (gas-liquid chromatography) 303.15 K 313.15 K 1.71 1.55 323.15 K 1.44 333.15 K 1.33 Ref. [4] Solute (1) 2-Propanol Ref. [4] H12E,1/kJ mol1 8.071 Solute (1) 2-Propanol Mixture 36: OCH2CH2CH2CH2 (1) + [HMIM][BTI] (2) (1) Activity Coefficient at Infinite Dilution and Partial Molar Excess Enthalpy at Infinite Dilution Ref. [4] Solute (1) Tetrahydrofuran γ 11 (gas-liquid chromatography) 303.15 K 313.15 K 0.49 0.51 323.15 K 0.53 333.15 K 0.55 2.2 Mixtures Containing 1,3-Dialkyl Imidazolium Ionic Liquids 785 Ref. [4] H12E,1/kJ mol1 3.149 Solute (1) Tetrahydrofuran Mixture 37: (CH3)2CHOCH(CH3)2 (1) + [HMIM][BTI] (2) (1) Activity Coefficient at Infinite Dilution Ref. [4] Solute (1) Diisopropyl ether γ 11 (gas-liquid chromatography) 303.15 K 313.15 K 2.76 2.82 323.15 K 2.85 333.15 K 2.92 Mixture 38: (CH3)3COC2H5 (1) + [HMIM][BTI] (2) (1) Activity Coefficient at Infinite Dilution and Partial Molar Excess Enthalpy at Infinite Dilution Ref. [4] Solute (1) Ethyl tert-butyl ether γ 11 (gas-liquid chromatography) 303.15 K 313.15 K 2.69 2.74 323.15 K 2.76 333.15 K 2.82 Ref. [4] H12E,1/kJ mol1 1.333 Solute (1) Ethyl tert-butyl ether Mixture 39: CH3OC(CH3)2C2H5 (1) + [HMIM][BTI] (2) (1) Activity Coefficient at Infinite Dilution and Partial Molar Excess Enthalpy at Infinite Dilution Ref. [4] Solute (1) Methyl tert-amyl ether γ 11 (gas-liquid chromatography) 303.15 K 313.15 K 1.83 1.90 323.15 K 1.94 333.15 K 2.02 Ref. [4] H12E,1/kJ mol1 2.657 Solute (1) Methyl tert-amyl ether Mixture 40: SO2 (1) + [hmim][Tf2N] (2) (1) Solubility Ref. [228] T/K 283.2 282.4 P/MPa 0.0107 0.0503 100x1 17.1 51.2 (continued) 786 Properties of 1-Hexyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide T/K 283.5 282.8 283.3 283.4 283.5 298.1 298.1 298.1 298.2 298.1 298.1 298.1 298.1 298.1 298.1 298.2 298.1 298.1 298.1 298.1 323.1 323.1 323.1 323.1 323.1 323.1 323.2 323.1 348.2 348.1 348.1 348.1 348.2 348.2 348.1 348.1 a Desorption measurements. P/MPa 0.0753 0.1002 0.1252 0.1501 0.1750 0.0109 0.0505 0.0753 0.1003 0.1504 0.2004 0.2502 0.3002 0.2505 0.2005 0.1503 0.1004 0.0761 0.0502 0.0111 0.0109 0.0505 0.0754 0.1003 0.1502 0.2001 0.2503 0.3002 0.0110 0.0504 0.0756 0.1003 0.1508 0.2003 0.2500 0.3003 100x1 61.6 70.6 76.7 82.5 87.5 12.4 37.7 47.7 55.3 66.7 75.2 82.0 88.1 82.1a 75.5a 67.0a 55.5a 48.1a 37.9a 12.9a 4.9 19.2 26.6 32.9 43.1 51.3 58.1 63.9 3.7 12.4 16.9 21.0 28.0 34.3 40.1 45.7 2.2 Mixtures Containing 1,3-Dialkyl Imidazolium Ionic Liquids 787 Mixture 41: 1,1,1,2-C2H2F4 (1) + [HMIm][Tf2N] (2) (1) Phase Equilibrium Ref. [221] T(K) 298.15 323.15 348.15 a P(bar) 0.42 0.75 1.17 1.81 2.51 3.46 4.02 4.55 5.23 5.86 0.53 1.04 1.55 2.13 2.86 3.92 5.06 6.12 7.48 8.66 9.72 10.62 11.43 11.92 5.02 8.74 12.11 15.59 18.78 22.92a 43.2b x1 0.0247 0.0761 0.1442 0.2360 0.3416 0.4609 0.5264 0.5893 0.6724 0.7578 0.0282 0.0652 0.1100 0.1604 0.2123 0.2860 0.3577 0.4223 0.5019 0.5702 0.6267 0.6807 0.7334 0.7642 0.2429 0.3916 0.5145 0.6205 0.7157 0.9107 0.9600 0.0019 0.0017 0.0015 0.0012 0.0009 0.0006 0.0005 0.0004 0.0002 0.0001 0.0014 0.0013 0.0012 0.0011 0.0010 0.0008 0.0007 0.0006 0.0005 0.0004 0.0003 0.0003 0.0002 0.0002 0.0044 0.0033 0.0025 0.0019 0.0013 0.0010 0.0010 ΔV/V0 0.0007 0.0006 0.0085 0.0006 0.0273 0.0006 0.0569 0.0006 0.1060 0.0006 0.1812 0.0006 0.2414 0.0007 0.3219 0.0007 0.4668 0.0007 0.7304 0.0008 0.0015 0.0005 0.0093 0.0005 0.0194 0.0005 0.0346 0.0005 0.0537 0.0005 0.0839 0.0005 0.1225 0.0006 0.1649 0.0006 0.2329 0.0006 0.3109 0.0006 0.3981 0.0006 0.5119 0.0007 0.6685 0.0007 0.7894 0.0008 0.050 0.002 0.113 0.002 0.189 0.002 0.310 0.002 0.498 0.002 VL(cm3/mol) 335.48 0.14 320.28 0.13 302.21 0.12 277.58 0.11 250.29 0.09 218.88 0.08 202.09 0.07 186.60 0.06 165.19 0.05 144.08 0.03 336.77 0.12 326.46 0.12 313.96 0.11 300.56 0.11 287.21 0.10 267.80 0.09 249.48 0.08 232.85 0.07 212.50 0.06 194.98 0.06 180.57 0.05 167.04 0.04 153.94 0.03 146.01 0.03 293.7 0.3 250.1 0.2 213.3 0.2 183.7 0.2 157.3 0.1 vapor–liquid–liquid equilibrium points for the IL-rich phase. b mixture critical point. 788 Properties of 1-Hexyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide Ternary Mixtures Mixture 1: CH3CH(CH2)4CH2 (1) + C6H5CH3 (2) + [HMIM][BTI] (3) (1) Selectivities and capacities at infinite dilution γ 11 for the separation of methylcyclohexane from toluene for ionic liquids Ref. [78] Separation problem Methylcyclohexane (1)/toluene (2) [C6MIm][NTf2] S112 8.07 6.97 6.03 5.34 T (K) 303.15 313.15 323.15 333.15 k12 1.18 1.06 0.96 0.88 (2) Phase Equilibrium Separation Factors Ref. [78] 80 mol% IL; 324.95 K x1,corr. y1 0.0556 0.3558 0.0873 0.4578 0.1840 0.6397 0.2773 0.7541 0.3722 0.8169 0.4745 0.8686 0.5844 0.9109 0.6816 0.9369 0.8329 0.9782 α12 9.38 8.83 7.88 7.99 7.53 7.32 7.27 6.94 9.00 90 mol% IL; 324.95 K x1,corr. y1 0.0559 0.3718 0.1072 0.5241 0.1149 0.5449 0.1743 0.6507 0.2313 0.7253 0.2630 0.7550 0.3285 0.8066 0.3734 0.8334 0.4292 0.8631 0.4669 0.8777 0.5746 0.9164 0.6694 0.9421 0.7740 0.9647 0.9205 0.9894 α12 10.00 9.18 9.22 8.82 8.77 8.63 8.52 8.40 8.38 8.19 8.12 8.04 7.98 8.04 80 mol% IL; 333.65 K x1,corr. y1 0.0454 0.2947 0.0932 0.4614 0.1364 0.5565 0.1804 0.6279 0.2989 0.7584 0.2731 0.7352 0.3351 0.7763 0.3687 0.8059 0.4218 0.8358 0.4747 0.8624 0.5631 0.8956 0.6670 0.9282 0.7792 0.9571 0.8711 0.9781 α12 8.79 8.33 7.95 7.67 7.37 7.39 6.89 7.11 6.98 6.93 6.65 6.46 6.32 6.60 Mixture 2: 1-C8H16 (1) + C8H18 (2) + [HMIM][BTI](3) (1) Phase Equilibrium Separation Factors Ref. [78] x1,corr. 95 mol%[C6MIm][NTf2] 342.45 K 0.0725 0.0846 0.1846 0.2100 0.3297 y1 1/α12 0.0609 0.0754 0.1513 0.1706 0.2715 1.21 1.33 1.27 1.29 1.32 (continued) 2.2 Mixtures Containing 1,3-Dialkyl Imidazolium Ionic Liquids x1,corr. 0.4229 0.4995 0.6081 0.7079 0.7891 0.8978 789 y1 0.3501 0.4231 0.5266 0.6302 0.7208 0.8511 1/α12 1.36 1.36 1.39 1.42 1.45 1.54 Mixture 3: H2O (1) + 1-C4H9OH (2) + [hmim][Tf2N] (3) (1) Distribution Ratio and Selectivity Ref. [166] H2O-rich phase w1 w2 298.15 K 0.9342 0.0658 0.9370 0.0630 0.9301 0.0699 0.9282 0.0718 0.9389 0.0611 0.9292 0.0708 0.9290 0.0710 0.9294 0.0706 0.9403 0.0598 0.9258 0.0742 0.9276 0.0724 0.9502 0.0498 0.9349 0.0651 0.9629 0.0371 0.9638 0.0362 0.7993 0.2007 0.9390 0.0610 0.9239 0.0761 w3 [hmim][Tf2N]-rich phase w1 w2 w3 S βBuOH 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0997 0.0518 0.1239 0.1419 0.1102 0.1292 0.1299 0.1643 0.1084 0.1585 0.1238 0.1362 0.1311 0.1208 0.2054 0.0522 0.3560 0.8728 75.27 67.27 48.81 47.59 47.42 47.23 45.93 40.55 36.52 33.43 32.84 25.97 25.30 14.00 7.42 6.03 1.56 0.63 8.04 3.72 6.50 7.28 5.56 6.57 6.42 7.17 4.21 5.72 4.38 3.72 3.55 1.75 1.58 0.39 0.59 0.59 0.5286 0.2341 0.4545 0.5227 0.3399 0.4649 0.4555 0.5060 0.2516 0.4243 0.3172 0.1853 0.2310 0.0651 0.0573 0.0790 0.0360 0.0452 0.3717 0.7141 0.4216 0.3353 0.5499 0.4059 0.4146 0.3297 0.6400 0.4173 0.5589 0.6784 0.6379 0.8141 0.7373 0.8689 0.6080 0.0821 Mixture 4: CO2 (1) + SO2 (2) + [hmim][Tf2N] (3) (1) Phase Equilibrium Ref. [228] feed feed feed [hmim] CO2/ SO2/ [Tf2N]/ mol % mol % mol % T/K 8.15 66.73 25.13 295.2 6.62 54.25 39.13 296.7 P/ MPa 0.143 0.115 liquid SO2 calculated/ mol % 60.2 50.0 liquid [hmim] [Tf2N] calculated/ mol % 38.8 49.1 vapor SO2 calculated/ mol % 78.7 71.2 vapor SO2 measured/ mol % 79.0a 71.7a (continued) 790 Properties of 1-Hexyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide feed feed [hmim] feed CO2/ SO2/ [Tf2N]/ mol % mol % mol % 6.03 51.83 42.13 4.51 43.67 51.81 8.15 66.73 25.13 6.62 54.25 39.13 6.03 51.83 42.13 42.20 42.63 15.18 32.81 33.14 34.05 27.78 28.06 44.16 7.99 8.08 83.93 27.78 28.06 44.16 7.99 8.08 83.93 76.06 6.80 17.14 62.26 5.57 32.17 47.40 4.24 48.36 34.42 3.08 62.50 22.49 2.01 75.50 76.06 6.80 17.14 62.26 5.57 32.17 47.40 4.24 48.36 34.42 3.08 62.50 22.49 2.01 75.50 T/K 294.8 294.5 322.1 322.1 322.1 295.7 294.7 295.2 295.3 320.6 320.6 296.0 296.0 296.0 296.0 296.1 321.5 321.5 321.1 320.2 320.1 P/ MPa 0.132 0.105 0.172 0.168 0.201 0.391 0.263 0.253 0.119 0.298 0.132 0.384 0.363 0.358 0.356 0.350 0.413 0.398 0.377 0.412 0.419 liquid SO2 calculated/ mol % 50.7 42.8 44.1 41.9 45.0 59.3 40.5 32.9 8.2 29.1 7.8 14.9 9.6 6.0 3.8 2.2 10.1 7.4 5.1 3.5 2.2 liquid [hmim] [Tf2N] calculated/ mol % 47.8 55.9 55.4 57.4 54.1 35.8 54.9 62.0 88.0 67.3 89.8 74.5 79.5 82.6 84.5 86.0 82.3 84.9 87.3 87.8 88.8 vapor SO2 calculated/ mol % 59.9 54.7 85.5 80.6 75.9 30.4 21.1 16.2 6.3 26.1 12.4 4.4 2.8 1.8 1.1 0.7 5.9 4.4 3.1 2.0 1.2 vapor SO2 measured/ mol % 62.3a 52.9a 86.1a 80.2a 75.1a 31.0b 20.0b 16.0b 6.0b 27.1b 12.4b 4.3c 2.8c 2.3c 1.6c 1.0c 7.0c 5.0c 3.9c 2.4c 1.2c a CO2/SO2 gas mixture: (9.4/90.6) mole %; b (49.7/50.3) mole %; c (91.8/8.2) mole %). Liquid CO2 mole% = (100 - Liquid SO2 mole%- Liquid [hmim][Tf2N] mole %). Vapor CO2 mole % = (100 Vapor SO2 mole %, and Vapor [hmim][Tf2N] = 0 mol %). Symbols and abbreviations Short Form (CH3)2CHOCH(CH3)2 (CH3)3COC2H5 ΔsvtG0m ΔsvtH0m ΔsvtS0m E, 1 C p, m, i ðT Þ H1E,,21 or HEi , 1 HE Full Form diisopropyl ether ethyl tert-butyl ether the standard molar Gibbs energy of solvation the standard molar enthalpy of solvation the standard molar entropy of solvation the excess partial molar heat capacity at infinite dilution partial molar excess enthalpy at infinite dilution excess enthalpy/excess molar enthalpy (continued) 2.2 Mixtures Containing 1,3-Dialkyl Imidazolium Ionic Liquids 791 Short Form KH Full Form Henry's law constant S1 ij selectivity at infinite dilution L V ex V the liquid molar volume E or V or Vo k1 j VEm or V exc excess molar volume molar volume of the pure component or k 1 capacity at infinite dilution α21 the relative volatility [C10mim][NTf2] 1-decyl-3-methylimidazolium bis ((trifluoromethyl)sulfonyl)imide 1-hexyl-3-methylimidazolium bis ((trifluoromethyl)sulfonyl)imide [C6MIm][NTf2], [C6C1Im][Ntf2], [HMIM][BTI], [C6mim][Tf2N], [C6mim][NTf2], [C6MIM][NTf2], [HMIM][NTf2], [hmim][Tf2N] [C6mim]Cl ΔHmix 1,1,1,2-C2H2F4 1-C3H7OH 1-C4H9OH 1-C5H10 1-C5H11OH 1-C6H12 1-C6H13OH 1-C7H14 1-C8H16 1-C8H17OH 2-CH3CHCH3OH 2-CH3COC2H5 2-CH3COC3H7 3-C2H5COC2H5 c C2H5OH C5H12 C6H14 C6H5CH3 C6H6 C7H16 C8H18 CF4 CH = CHCH2CH2CH2CH2 CH2(CH2)3CH2 CH2(CH2)3CH2C = NOH CH2(CH2)4CH2 1-hexyl-3-methylimidazolium chloride the heat of mixing per mole of solution 1,1,1,2-tetrafluoroethane 1-propanol 1-butanol 1-pentene 1-pentanol 1-hexene 1-hexanol 1-heptene 1-octene 1-octanol 2-propanol 2-butanone 2-pentanone pentan-3-one molarity ethanol n-pentane n-hexane toluene benzene n-heptane n-octane perfluoromethane cyclohexene cyclopentane cyclohexanone oxime cyclohexane (continued) 792 Properties of 1-Hexyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide Short Form CH3CH(CH2)4CH2 CH3COCH3 CH3OC(CH3)2C2H5 CH3OH CO2 H2O IL 02021-01001 Δsol H0m Full Form methylcyclohexane acetone methyl-1,1-dimethylpropyl ether methanol carbon dioxide water 1-hexyl-3-methylimidazolium chloride m-Xylene caprolactam tetrahydrofuran pressure p-xylene selectivity sulfur dioxide observed molar volume mass fraction mole fraction of liquid phase mole fraction of vapor phase distribution ratio activity coefficient at infinite dilution the standard molar Gibbs energy of solution the standard molar enthalpy of solution Δsvt Hm Δsvt Sm the Gibbs energy of solvation the enthalpy of solvation the entropy of solvation the local molar Gibbs energy of solvation the local molar enthalpy of solvation the local molar entropy of salvation m-C6H4(CH3)2 NH(CH2)5C = O OCH2CH2CH2CH2 P p-C6H4(CH3)2 S SO2 V w x y β, D2 γ1 Δsol G0m Δsol S0m Δsolv G1 or ΔsolvG Δsolv H1 or ΔsolvH Δsolv S1 or ΔsolvS Δsvt Gm the standard molar entropy of solution References 4. Kato R, Gmehling J (2005) Systems with ionic liquids: Measurement of VLE and γ 1 data and prediction of their thermodynamic behavior using original UNIFAC, mod. UNIFAC(Do) and COSMO-RS(Ol). The Journal of Chemical Thermodynamics 37 (6): 603-619. 45. Freire MG, Carvalho PJ, Gardas RL, Marrucho IM, Santos LMNBF, Coutinho JAP (2008) Mutual solubilities of water and the [Cnmim][Tf2N] hydrophobic ionic liquids. The Journal of Physical Chemistry B 112 (6): 1604-1610. References 793 50. Nebig S, Bölts R, Gmehling J (2007) Measurement of vapor–liquid equilibria (VLE) and excess enthalpies (HE) of binary systems with 1-alkyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide and prediction of these properties and γ 1 using modified UNIFAC (Dortmund). Fluid Phase Equilibria 258 (2): 168-178. 57. Canongia Lopes JN, Cordeiro TC, Esperanca JM, Guedes HJ, Huq S, Rebelo LP, Seddon KR (2005) Deviations from ideality in mixtures of two ionic liquids containing a common ion. The Journal of Physical Chemistry B 109 (8): 3519-3525. 78. Liebert V, Nebig S, Gmehling J (2008) Experimental and predicted phase equilibria and excess properties for systems with ionic liquids. Fluid Phase Equilibria 268 (1-2): 14-20. 82. Ge R, Hardacre C, Nancarrow P, Rooney DW (2007) Thermal conductivities of ionic liquids over the temperature range from 293 K to 353 K. Journal of Chemical & Engineering Data 52 (5): 1819-1823. 164. Wertz C, Tschersich A, Lehmann JK, Heintz A (2007) Liquid–liquid equilibria and liquid–liquid interfacial tension measurements of mixtures containing ionic liquids. Journal of Molecular Liquids 131-132:2-6. 166. Davis SE, Morton SA (2008) Investigation of ionic liquids for the separation of butanol and water. Separation Science and Technology 43 (9-10): 2460-2472. 221. Ren W, Scurto AM (2009) Phase equilibria of imidazolium ionic liquids and the refrigerant gas, 1,1,1,2-tetrafluoroethane (R-134a). Fluid Phase Equilibria 286 (1): 1-7. 224. Pison L, Canongia Lopes JN, Rebelo LPN, Padua AAH, Costa Gomes MF (2008) Interactions of fluorinated gases with ionic liquids: solubility of CF4, C2F6, and C3F8 in trihexyltetradecylphosphonium bis(trifluoromethylsulfonyl)amide. The Journal of Physical Chemistry B 112 (39): 12394-12400. 225. Lachwa J, Morgado P, Esperança JMSS, Guedes HJR, Canongia Lopes JN, Rebelo LPN (2006) Fluid-phase behavior of {1-hexyl-3-methylimidazolium bis(trifluoromethylsulfonyl) imide, [C6mim][NTf2], + C2-C8 n-alcohol} mixtures: Liquid-liquid equilibrium and excess volumes. Journal of Chemical & Engineering Data 51 (6): 2215-2221. 226. Shevelyova MP, Zaitsau DH, Paulechka YU, Blokhin AV, Kabo GJ, Verevkin SP, Heintz A (2007) Solid-liquid equilibrium and activity coefficients for caprolactam + 1-hexyl-3methylimidazolium bis(trifluoromethylsulfonyl)imide and cyclohexanone oxime + 1-hexyl3-methylimidazolium bis(trifluoromethylsulfonyl)imide. Journal of Chemical & Engineering Data 52 (4): 1360-1365. 227. Heintz A, Verevkin SP, Lehmann JK, Vasiltsova TV, Ondo D (2007) Activity coefficients at infinite dilution and enthalpies of solution of methanol, 1-butanol, and 1-hexanol in 1-hexyl3-methyl-imidazolium bis(trifluoromethyl-sulfonyl) imide. The Journal of Chemical Thermodynamics 39 (2): 268-274. 228. Yokozeki A, Shiflett MB (2009) Separation of carbon dioxide and sulfur dioxide gases using room-temperature ionic liquid [hmim][Tf2N]. Energy & Fuels 23 (9): 4701-4708.
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