978-94-017-7573-1 63

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
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Mutual solubilities of water and the [Cnmim][Tf2N] hydrophobic ionic liquids. The Journal
of Physical Chemistry B 112 (6): 1604-1610.
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