2
0
2011
gar
lar
0
journal
Original
Garcia, S.[Silvia]
Larriba, M.[Marcos]
Garcia, J.[Julian]
Torrecilla, J. S.[Jose S.]
Rodriguez, F.[Francisco]
J. Chem. Eng. Data
2011
2020-09-29
Liquid-Liquid Extraction of Toluene from Heptane Using 1-Alkyl-3-methylimidazolium Bis(trifluoromethylsulfonyl)imide Ionic Liquids
The good stability and suitable polarity of the 1-alkyl-3-methyl bis(trifluoromethylsulfonyl)imide ionic liquids have prompted their use as solvents for the extraction of mixtures of aromatic and aliphatic hydrocarbons. In this paper, aiming to extend the study of these ionic liquids, the liquid-liquid equilibrium for the systems toluene + heptane + [mmim][Tf2N], [emim][Tf2N], [bmim][Tf2N], or [hmim][Tf2N] at T = 313.2 K were determined. The experiments with [mmim][Tf2N] and [emim]Tf2N have shown good results in the separation of toluene from heptane compared with the distribution ratio and separation factor of sulfolane in the whole range of composition. The degree of consistency of the experimental LLE data was ascertained by applying the Othmer-Tobias correlation. The phase diagrams for the ternary systems were plotted, and the tie lines correlated with the NRTL model compare satisfactorily with the experimental data.
10.1021/je100982h
1
56
113-118
1
InChI=1S/C7H16/c1-3-5-7-6-4-2/h3-7H2,1-2H3
IMNFDUFMRHMDMM-UHFFFAOYSA-N
heptane
n-heptane
C7H16
1
Commercial source
1
99.5
3
Stated by supplier
2
0.005
1
Estimated by the compiler
2
InChI=1S/C7H8/c1-7-5-3-2-4-6-7/h2-6H,1H3
YXFVVABEGXRONW-UHFFFAOYSA-N
toluene
methylbenzene
C7H8
1
Commercial source
1
99.7
3
Stated by supplier
2
0.005
1
Estimated by the compiler
3
InChI=1S/C5H9N2.C2F6NO4S2/c1-6-3-4-7(2)5-6;3-1(4,5)14(10,11)9-15(12,13)2(6,7)8/h3-5H,1-2H3;/q+1;-1
SAYMDKMGIAANGQ-UHFFFAOYSA-N
1,3-dimethylimidazolium bis((trifluoromethyl)sulfonyl)amide
1,3-dimethyl-1H-imidazolium bis((trifluoromethyl)sulfonyl)amide
C7H9F6N3O4S2
1
Commercial source
1
99
2
Stated by supplier
2
0.01
1
Estimated by the compiler
3
0.01
1
Estimated by the compiler
4
InChI=1S/C6H11N2.C2F6NO4S2/c1-3-8-5-4-7(2)6-8;3-1(4,5)14(10,11)9-15(12,13)2(6,7)8/h4-6H,3H2,1-2H3;/q+1;-1
LRESCJAINPKJTO-UHFFFAOYSA-N
1-ethyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide
1-ethyl-3-methylimidazolium 1,1,1-trifluoro-N-[(trifluoromethyl)sulfonyl]methanesulfonamide
1-ethyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)amide
1-ethyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide [EMIM][NTf2]
1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide
C8H11F6N3O4S2
1
Commercial source
1
99
2
Stated by supplier
2
0.01
1
Estimated by the compiler
3
0.01
1
Estimated by the compiler
5
InChI=1S/C8H15N2.C2F6NO4S2/c1-3-4-5-10-7-6-9(2)8-10;3-1(4,5)14(10,11)9-15(12,13)2(6,7)8/h6-8H,3-5H2,1-2H3;/q+1;-1
INDFXCHYORWHLQ-UHFFFAOYSA-N
1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide
1-butyl-3-methyl-1H-imidazolium bis((trifluoromethyl)sulfonyl)amide
1-butyl-3-methylimidazolium 1,1,1-trifluoro-N-[(trifluoromethyl)sulfonyl]methanesulfonamide
1-butyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)amide
1-butyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide
1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide [BMIM][NTf2]
C10H15F6N3O4S2
1
Commercial source
1
99
2
Stated by supplier
2
0.01
1
Estimated by the compiler
3
0.01
1
Estimated by the compiler
6
InChI=1S/C10H19N2.C2F6NO4S2/c1-3-4-5-6-7-12-9-8-11(2)10-12;3-1(4,5)14(10,11)9-15(12,13)2(6,7)8/h8-10H,3-7H2,1-2H3;/q+1;-1
RCNFOZUBFOFJKZ-UHFFFAOYSA-N
1-hexyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide
1-hexyl-3-methylimidazolium 1,1,1-trifluoro-N-[(trifluoromethyl)sulfonyl]methanesulfonamide
1-hexyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide
1-hexyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]amide
1-hexyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide [HMIM][NTf2]
[c6mim][ntf2]
C12H19F6N3O4S2
1
Commercial source
1
99
2
Stated by supplier
2
0.01
1
Estimated by the compiler
3
0.01
1
Estimated by the compiler
1
1
1
3
1
Principal objective of the work
RDC
XXX
1/24/2011
1
Mole fraction
Chromatography
3
Liquid mixture 2
Direct value, X
Liquid mixture 2
Liquid mixture 1
1
Temperature, K
Liquid mixture 2
2
Pressure, kPa
Liquid mixture 2
1
313.2
4
2
101
3
1
0
2
2
1
1
3
1
Principal objective of the work
RDC
XXX
1/24/2011
1
Mole fraction
Chromatography
1
Liquid mixture 2
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid mixture 2
Liquid mixture 1
1
Temperature, K
Liquid mixture 2
2
Pressure, kPa
Liquid mixture 2
1
313.2
4
2
101.3
2
1
0.0178
3
1
0.002
3
2
1
3
1
Principal objective of the work
RDC
XXX
1/24/2011
1
Mole fraction
Chromatography
3
Liquid mixture 2
Direct value, X
Liquid mixture 2
Liquid mixture 1
1
Temperature, K
Liquid mixture 2
2
Pressure, kPa
Liquid mixture 2
1
313.2
4
2
101
3
1
0
2
4
2
1
3
1
Principal objective of the work
RDC
XXX
1/24/2011
1
Mole fraction
Chromatography
2
Liquid mixture 2
Direct value, X
Liquid mixture 2
Liquid mixture 1
1
Pressure, kPa
Liquid mixture 2
2
Temperature, K
Liquid mixture 2
1
101.3
2
2
313.2
4
1
0.5891
4
5
1
1
4
1
Principal objective of the work
RDC
XXX
1/24/2011
1
Mole fraction
Chromatography
4
Liquid mixture 2
Direct value, X
Liquid mixture 2
Liquid mixture 1
1
Temperature, K
Liquid mixture 2
2
Pressure, kPa
Liquid mixture 2
1
313.2
4
2
101
3
1
0
2
6
1
1
4
1
Principal objective of the work
RDC
XXX
1/24/2011
1
Mole fraction
Chromatography
1
Liquid mixture 2
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid mixture 2
Liquid mixture 1
1
Temperature, K
Liquid mixture 2
2
Pressure, kPa
Liquid mixture 2
1
313.2
4
2
101.33
3
1
0.0251
3
1
0.002
7
2
1
4
1
Principal objective of the work
RDC
XXX
1/24/2011
1
Mole fraction
Chromatography
4
Liquid mixture 2
Direct value, X
Liquid mixture 2
Liquid mixture 1
1
Temperature, K
Liquid mixture 2
2
Pressure, kPa
Liquid mixture 2
1
313.2
4
2
101
3
1
0
2
8
2
1
4
1
Principal objective of the work
RDC
XXX
1/24/2011
1
Mole fraction
Chromatography
2
Liquid mixture 2
Direct value, X
Liquid mixture 2
Liquid mixture 1
1
Pressure, kPa
Liquid mixture 2
2
Temperature, K
Liquid mixture 2
1
101.33
3
2
313.2
4
1
0.6341
4
9
1
1
5
1
Principal objective of the work
RDC
XXX
1/24/2011
1
Mole fraction
Chromatography
5
Liquid mixture 2
Direct value, X
Liquid mixture 2
Liquid mixture 1
1
Temperature, K
Liquid mixture 2
2
Pressure, kPa
Liquid mixture 2
1
313.2
4
2
101
3
1
0
2
10
1
1
5
1
Principal objective of the work
RDC
XXX
1/24/2011
1
Mole fraction
Chromatography
1
Liquid mixture 2
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid mixture 2
Liquid mixture 1
1
Temperature, K
Liquid mixture 2
2
Pressure, kPa
Liquid mixture 2
1
313.2
4
2
101.33
3
1
0.054
3
1
0.002
11
2
1
5
1
Principal objective of the work
RDC
XXX
1/24/2011
1
Mole fraction
Chromatography
5
Liquid mixture 2
Direct value, X
Liquid mixture 2
Liquid mixture 1
1
Temperature, K
Liquid mixture 2
2
Pressure, kPa
Liquid mixture 2
1
313.2
4
2
101
3
1
0
2
12
2
1
5
1
Principal objective of the work
RDC
XXX
1/24/2011
1
Mole fraction
Chromatography
2
Liquid mixture 2
Direct value, X
Liquid mixture 2
Liquid mixture 1
1
Pressure, kPa
Liquid mixture 2
2
Temperature, K
Liquid mixture 2
1
101.33
3
2
313.2
4
1
0.7273
4
13
1
1
6
1
Principal objective of the work
RDC
XXX
1/24/2011
1
Mole fraction
Chromatography
6
Liquid mixture 2
Direct value, X
Liquid mixture 2
Liquid mixture 1
1
Temperature, K
Liquid mixture 2
2
Pressure, kPa
Liquid mixture 2
1
313.2
4
2
101
3
1
0
2
14
1
1
6
1
Principal objective of the work
RDC
XXX
1/24/2011
1
Mole fraction
Chromatography
1
Liquid mixture 2
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid mixture 2
Liquid mixture 1
1
Temperature, K
Liquid mixture 2
2
Pressure, kPa
Liquid mixture 2
1
313.2
4
2
101.33
3
1
0.1375
4
1
0.0061
15
2
1
6
1
Principal objective of the work
RDC
XXX
1/24/2011
1
Mole fraction
Chromatography
6
Liquid mixture 2
Direct value, X
Liquid mixture 2
Liquid mixture 1
1
Temperature, K
Liquid mixture 2
2
Pressure, kPa
Liquid mixture 2
1
313.2
4
2
101
3
1
0
2
16
2
1
6
1
Principal objective of the work
RDC
XXX
1/24/2011
1
Mole fraction
Chromatography
2
Liquid mixture 2
Direct value, X
Liquid mixture 2
Liquid mixture 1
1
Pressure, kPa
Liquid mixture 2
2
Temperature, K
Liquid mixture 2
1
101.33
3
2
313.2
4
1
0.8068
4
17
2
1
1
1
3
1
Principal objective of the work
RDC
XXX
1/24/2011
1
Mole fraction
Chromatography
1
Liquid mixture 1
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
2
Mole fraction
Chromatography
1
Liquid mixture 2
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
3
Mole fraction
Chromatography
2
Liquid mixture 2
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid mixture 1
Liquid mixture 2
1
Temperature, K
Liquid mixture 2
313.2
4
2
Pressure, kPa
Liquid mixture 2
101.3
2
1
Mole fraction
2
Liquid mixture 1
1
0
2
1
1
5
2
0.0178
3
1
0.002
3
0
2
1
0.0297
3
1
0.9703
4
1
0.0028
2
0.0186
3
1
0.002
3
0.0214
3
1
0.0657
3
1
0.9343
4
1
0.0029
2
0.0162
3
1
0.002
3
0.0454
3
1
0.1364
4
1
0.8636
4
1
0.003
2
0.0174
3
1
0.002
3
0.0947
3
1
0.2174
4
1
0.7826
4
1
0.0032
2
0.0164
3
1
0.002
3
0.1428
4
1
0.3421
4
1
0.6579
4
1
0.0037
2
0.0154
3
1
0.002
3
0.2205
4
1
0.4674
4
1
0.5326
4
1
0.0044
2
0.0147
3
1
0.002
3
0.2847
4
1
0.5264
4
1
0.4736
4
1
0.0044
2
0.0151
3
1
0.002
3
0.3252
4
1
0.6324
4
1
0.3676
4
1
0.0038
2
0.0129
3
1
0.002
3
0.3921
4
1
0.7442
4
1
0.2558
4
1
0.0034
2
0.0124
3
1
0.002
3
0.445
4
1
0.834
4
1
0.166
4
1
0.0031
2
0.0107
3
1
0.002
3
0.5019
4
1
1
5
1
0
2
2
0
2
3
0.5891
4
18
2
1
1
1
4
1
Principal objective of the work
RDC
XXX
1/24/2011
1
Mole fraction
Chromatography
1
Liquid mixture 1
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
2
Mole fraction
Chromatography
1
Liquid mixture 2
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
3
Mole fraction
Chromatography
2
Liquid mixture 2
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid mixture 1
Liquid mixture 2
1
Temperature, K
Liquid mixture 2
313.2
4
2
Pressure, kPa
Liquid mixture 2
101.33
3
1
Mole fraction
2
Liquid mixture 1
1
0
2
1
1
5
2
0.0251
3
1
0.002
3
0
2
1
0.0288
3
1
0.9712
4
1
0.0028
2
0.0299
3
1
0.002
3
0.0269
3
1
0.0615
3
1
0.9385
4
1
0.0029
2
0.0256
3
1
0.002
3
0.0501
3
1
0.1297
4
1
0.8703
4
1
0.003
2
0.0261
3
1
0.002
3
0.1051
4
1
0.217
4
1
0.783
4
1
0.0032
2
0.0266
3
1
0.002
3
0.1706
4
1
0.3419
4
1
0.6581
4
1
0.0037
2
0.0252
3
1
0.002
3
0.2494
4
1
0.4303
4
1
0.5697
4
1
0.0042
2
0.0246
3
1
0.002
3
0.3111
4
1
0.5095
4
1
0.4905
4
1
0.0045
2
0.0236
3
1
0.002
3
0.3558
4
1
0.6163
4
1
0.3837
4
1
0.0039
2
0.0227
3
1
0.002
3
0.424
4
1
0.7322
4
1
0.2678
4
1
0.0034
2
0.0197
3
1
0.002
3
0.4802
4
1
0.8334
4
1
0.1666
4
1
0.0031
2
0.0144
3
1
0.002
3
0.5258
4
1
1
5
1
0
2
2
0
2
3
0.6341
4
19
2
1
1
1
5
1
Principal objective of the work
RDC
XXX
1/24/2011
1
Mole fraction
Chromatography
1
Liquid mixture 1
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
2
Mole fraction
Chromatography
1
Liquid mixture 2
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
3
Mole fraction
Chromatography
2
Liquid mixture 2
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid mixture 1
Liquid mixture 2
1
Temperature, K
Liquid mixture 2
313.2
4
2
Pressure, kPa
Liquid mixture 2
101.33
3
1
Mole fraction
2
Liquid mixture 1
1
0
2
1
1
5
2
0.054
3
1
0.002
3
0
2
1
0.026
3
1
0.974
4
1
0.0028
2
0.0584
3
1
0.002
3
0.0312
3
1
0.0527
3
1
0.9473
4
1
0.0029
2
0.0538
3
1
0.002
3
0.0581
3
1
0.1133
4
1
0.8867
4
1
0.0029
2
0.0509
3
1
0.002
3
0.1199
4
1
0.1881
4
1
0.8119
4
1
0.0031
2
0.0537
3
1
0.002
3
0.1901
4
1
0.3051
4
1
0.6949
4
1
0.0036
2
0.0531
3
1
0.002
3
0.2905
4
1
0.3913
4
1
0.6087
4
1
0.004
2
0.0481
3
1
0.002
3
0.3464
4
1
0.4776
4
1
0.5224
4
1
0.0044
2
0.0492
3
1
0.002
3
0.4126
4
1
0.591
4
1
0.409
4
1
0.004
2
0.0477
3
1
0.002
3
0.4757
4
1
0.7126
4
1
0.2874
4
1
0.0035
2
0.0407
3
1
0.002
3
0.541
4
1
0.816
4
1
0.184
4
1
0.0031
2
0.0332
3
1
0.0021
3
0.6416
4
1
1
5
1
0
2
2
0
2
3
0.7273
4
20
2
1
1
1
6
1
Principal objective of the work
RDC
XXX
1/24/2011
1
Mole fraction
Chromatography
1
Liquid mixture 1
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
2
Mole fraction
Chromatography
1
Liquid mixture 2
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
3
Mole fraction
Chromatography
2
Liquid mixture 2
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid mixture 1
Liquid mixture 2
1
Temperature, K
Liquid mixture 2
313.2
4
2
Pressure, kPa
Liquid mixture 2
101.33
3
1
Mole fraction
2
Liquid mixture 1
1
0
2
1
1
5
2
0.1375
4
1
0.0061
3
0
2
1
0.0228
3
1
0.9772
4
1
0.0028
2
0.1161
4
1
0.0061
3
0.0335
3
1
0.047
3
1
0.953
4
1
0.0028
2
0.1211
4
1
0.0061
3
0.0623
3
1
0.0949
3
1
0.9051
4
1
0.0029
2
0.1153
4
1
0.0061
3
0.1328
4
1
0.1594
4
1
0.8406
4
1
0.003
2
0.1047
4
1
0.006
3
0.1984
4
1
0.2692
4
1
0.7308
4
1
0.0034
2
0.1036
4
1
0.006
3
0.3115
4
1
0.3578
4
1
0.6422
4
1
0.0038
2
0.0969
3
1
0.006
3
0.3809
4
1
0.4814
4
1
0.5186
4
1
0.0044
2
0.0852
3
1
0.006
3
0.4588
4
1
0.551
4
1
0.449
4
1
0.0043
2
0.0864
3
1
0.006
3
0.511
4
1
0.6982
4
1
0.3018
4
1
0.0035
2
0.0744
3
1
0.006
3
0.5971
4
1
0.8121
4
1
0.1879
4
1
0.0031
2
0.0552
3
1
0.0061
3
0.6685
4
1
1
5
1
0
2
2
0
2
3
0.8068
4