2
0
2019
orc
ver
0
journal
Original
Orchilles, A. Vicent
Vercher, Ernesto
Miguel, Pablo J.
Gonzalez-Alfaro, Vicenta
Llopis, Francisco J.
J. Chem. Thermodyn.
2019
2020-09-29
Isobaric vapor-liquid equilibria for the extractive distillation of tert-butyl alcohol + water mixtures using 1-ethyl-3-methylimidazolium dicyanamide ionic liquid
Isobaric vapor-liquid equilibria for the binary systems tert-butyl alcohol + water, and tert-butyl alcohol + 1-ethyl-3-methylimidazolium dicyanamide ([emim][DCA]), as well as the vapor-liquid equilibria for the tert-butyl alcohol + water + [emim][DCA] ternary system, have been obtained at 100 kPa using a recirculating still. The electrolyte nonrandom two-liquid (e-NRTL) model was successfully used for fitting the experimental data. The effect of [emim][DCA] on the tert-butyl alcohol + water system has been compared with that produced by other ionic liquids reported in the literature. From the results, [emim][DCA] appears as a good entrainer for the extractive distillation of this solvent mixture, causing the azeotrope to disappear at 100 kPa when the ionic liquid mole fraction is greater than0.095.
Extractive distillation
Isobaric VLE
Ionic liquids
1-Ethyl-3-methylimidazolium dicyanamide
tert-Butyl alcohol
Water
10.1016/j.jct.2019.07.008
139
105866
1
InChI=1S/C4H10O/c1-4(2,3)5/h5H,1-3H3
DKGAVHZHDRPRBM-UHFFFAOYSA-N
2-methylpropan-2-ol
2-methyl-2-propanol
tert-butanol
tert-butyl alcohol
C4H10O
1
Commercial source
1
99.5
3
Stated by supplier
2
Molecular sieve treatment
3
0.05
1
Karl Fischer titration
2
InChI=1S/H2O/h1H2
XLYOFNOQVPJJNP-UHFFFAOYSA-N
water
H2O
1
Commercial source
1
Fractional distillation
2
99.8
3
Estimated by the compiler
3
InChI=1S/C6H11N2.C2N3/c1-3-8-5-4-7(2)6-8;3-1-5-2-4/h4-6H,3H2,1-2H3;/q+1;-1
MKHFCTXNDRMIDR-UHFFFAOYSA-N
1-ethyl-3-methylimidazolium dicyanamide
C8H11N5
1
Commercial source
1
98
2
Stated by supplier
2
Dried by vacuum heating
3
0.08
1
Karl Fischer titration
1
1
1
Principal objective of the work
AB
TRC
1/24/2020
1
Vapor or sublimation pressure, kPa
Ebulliometric method (Recirculating still)
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Gas
1
Temperature, K
Liquid
1
355.2
4
1
100
1
1
2
2
2
1
Principal objective of the work
AB
TRC
1/24/2020
1
Vapor or sublimation pressure, kPa
Ebulliometric method (Recirculating still)
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Gas
1
Temperature, K
Liquid
1
372.8
4
1
100
1
1
2
3
1
1
2
1
Principal objective of the work
AB
TRC
1/24/2020
1
Boiling temperature at pressure P, K
Ebulliometric method (Recirculating still)
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Gas
1
Pressure, kPa
Liquid
100
1
1
Mole fraction
1
Liquid
1
0
4
1
372.8
4
1
0.4
1
0.001
1
1
371.1
4
1
0.4
1
0.002
1
1
369.3
4
1
0.4
1
0.004
1
1
367
4
1
0.4
1
0.007
1
1
364.2
4
1
0.4
1
0.013
2
1
361
4
1
0.4
1
0.021
2
1
357.9
4
1
0.4
1
0.033
2
1
355.5
4
1
0.4
1
0.049
2
1
354.3
4
1
0.4
1
0.068
2
1
354.1
4
1
0.4
1
0.091
2
1
353.9
4
1
0.4
1
0.106
3
1
353.9
4
1
0.4
1
0.149
3
1
353.8
4
1
0.4
1
0.183
3
1
353.8
4
1
0.4
1
0.22
3
1
353.7
4
1
0.4
1
0.26
3
1
353.6
4
1
0.4
1
0.303
3
1
353.5
4
1
0.4
1
0.344
3
1
353.3
4
1
0.4
1
0.389
3
1
353.2
4
1
0.4
1
0.43
3
1
353
4
1
0.4
1
0.483
3
1
352.9
4
1
0.4
1
0.526
3
1
352.8
4
1
0.4
1
0.581
3
1
352.7
4
1
0.4
1
0.647
3
1
352.6
4
1
0.4
1
0.705
3
1
352.7
4
1
0.4
1
0.773
3
1
352.9
4
1
0.4
1
0.847
3
1
353.3
4
1
0.4
1
0.899
3
1
353.8
4
1
0.4
1
0.954
3
1
354.5
4
1
0.4
1
0.978
3
1
354.8
4
1
0.4
1
1
4
1
355.2
4
1
0.4
4
1
1
2
1
Principal objective of the work
AB
TRC
1/24/2020
1
Mole fraction
Chromatography
1
Gas
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Gas
Liquid
1
Pressure, kPa
Liquid
100
1
1
Mole fraction
1
Liquid
1
0
4
1
0
4
1
0.001
1
1
0.046
2
1
0.002
1
0.002
1
1
0.098
2
1
0.002
1
0.004
1
1
0.176
3
1
0.003
1
0.007
1
1
0.27
3
1
0.003
1
0.013
2
1
0.376
3
1
0.004
1
0.021
2
1
0.444
3
1
0.004
1
0.033
2
1
0.493
3
1
0.005
1
0.049
2
1
0.522
3
1
0.005
1
0.068
2
1
0.528
3
1
0.005
1
0.091
2
1
0.53
3
1
0.005
1
0.106
3
1
0.531
3
1
0.005
1
0.149
3
1
0.533
3
1
0.005
1
0.183
3
1
0.534
3
1
0.005
1
0.22
3
1
0.537
3
1
0.005
1
0.26
3
1
0.539
3
1
0.005
1
0.303
3
1
0.542
3
1
0.005
1
0.344
3
1
0.548
3
1
0.005
1
0.389
3
1
0.556
3
1
0.004
1
0.43
3
1
0.565
3
1
0.004
1
0.483
3
1
0.577
3
1
0.004
1
0.526
3
1
0.592
3
1
0.004
1
0.581
3
1
0.614
3
1
0.004
1
0.647
3
1
0.647
3
1
0.004
1
0.705
3
1
0.682
3
1
0.004
1
0.773
3
1
0.737
3
1
0.003
1
0.847
3
1
0.807
3
1
0.003
1
0.899
3
1
0.863
3
1
0.002
1
0.954
3
1
0.933
3
1
0.002
1
0.978
3
1
0.967
3
1
0.002
1
1
4
1
1
4
5
1
1
3
1
Principal objective of the work
AB
TRC
1/24/2020
1
Boiling temperature at pressure P, K
Ebulliometric method (Recirculating still)
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Gas
1
Pressure, kPa
Liquid
100
1
1
Mole fraction
3
Liquid
1
0
4
1
355.2
4
1
0.4
1
0.023
2
1
355.5
4
1
0.4
1
0.036
2
1
355.6
4
1
0.4
1
0.051
2
1
355.7
4
1
0.4
1
0.067
2
1
355.9
4
1
0.4
1
0.082
2
1
356
4
1
0.4
1
0.099
2
1
356.4
4
1
0.4
1
0.114
3
1
356.6
4
1
0.4
1
0.129
3
1
357
4
1
0.4
1
0.146
3
1
357.3
4
1
0.4
1
0.162
3
1
357.9
4
1
0.4
1
0.178
3
1
358.3
4
1
0.4
1
0.185
3
1
358.5
4
1
0.4
1
0.197
3
1
358.9
4
1
0.4
1
0.206
3
1
359.3
4
1
0.4
1
0.221
3
1
359.7
4
1
0.4
1
0.241
3
1
360.4
4
1
0.4
1
0.265
3
1
361.1
4
1
0.4
1
0.273
3
1
361.3
4
1
0.4
1
0.284
3
1
361.8
4
1
0.4
1
0.305
3
1
362.6
4
1
0.4
1
0.32
3
1
362.8
4
1
0.4
1
0.336
3
1
363.5
4
1
0.4
1
0.356
3
1
364.3
4
1
0.4
1
0.364
3
1
364.6
4
1
0.4
1
0.375
3
1
365.1
4
1
0.4
1
0.384
3
1
365.5
4
1
0.4
1
0.393
3
1
365.6
4
1
0.4
1
0.398
3
1
365.7
4
1
0.4
1
0.098
2
1
356.4
4
1
0.4
1
0.23
3
1
359.8
4
1
0.4
6
1
1
3
1
2
1
Principal objective of the work
AB
TRC
1/24/2020
1
Mole fraction
Chromatography
2
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
2
Mole fraction
Chromatography
2
Gas
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
3
Mole fraction
Chromatography
1
Gas
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Gas
1
Pressure, kPa
Liquid
100
1
1
Temperature, K
Liquid
2
Mole fraction
1
Liquid
1
374.6
4
2
0
4
1
0.946
3
1
0.002
2
1
4
3
0
4
1
371.1
4
2
0.005
1
1
0.942
3
1
0.002
2
0.9
3
1
0.002
3
0.1
3
1
366.4
4
2
0.016
2
1
0.931
3
1
0.002
2
0.762
3
1
0.003
3
0.238
3
1
361.9
4
2
0.037
2
1
0.91
3
1
0.002
2
0.619
3
1
0.004
3
0.381
3
1
358.4
4
2
0.066
2
1
0.881
3
1
0.002
2
0.525
3
1
0.005
3
0.475
3
1
355.9
4
2
0.103
3
1
0.843
3
1
0.002
2
0.481
3
1
0.005
3
0.519
3
1
355
4
2
0.154
3
1
0.791
3
1
0.003
2
0.458
3
1
0.005
3
0.542
3
1
354.3
4
2
0.219
3
1
0.726
3
1
0.003
2
0.439
3
1
0.004
3
0.561
3
1
353.9
4
2
0.293
3
1
0.652
3
1
0.003
2
0.417
3
1
0.004
3
0.583
3
1
353.6
4
2
0.366
3
1
0.578
3
1
0.004
2
0.393
3
1
0.004
3
0.607
3
1
353.6
4
2
0.442
3
1
0.5
3
1
0.004
2
0.362
3
1
0.004
3
0.638
3
1
353.6
4
2
0.532
3
1
0.41
3
1
0.004
2
0.325
3
1
0.004
3
0.675
3
1
353.8
4
2
0.617
3
1
0.324
3
1
0.003
2
0.279
3
1
0.003
3
0.721
3
1
354
4
2
0.7
3
1
0.242
3
1
0.003
2
0.228
3
1
0.003
3
0.772
3
1
354.3
4
2
0.764
3
1
0.178
3
1
0.002
2
0.179
3
1
0.003
3
0.821
3
1
354.6
4
2
0.824
3
1
0.122
3
1
0.002
2
0.131
3
1
0.002
3
0.869
3
1
355
4
2
0.872
3
1
0.073
2
1
0.002
2
0.081
2
1
0.002
3
0.919
3
1
355.5
4
2
0.897
3
1
0.038
2
1
0.002
2
0.043
2
1
0.002
3
0.957
3
1
355.7
4
2
0.949
3
1
0
4
2
0
4
3
1
4
1
376.6
4
2
0
4
1
0.902
3
1
0.002
2
1
4
3
0
4
1
374.1
4
2
0.005
1
1
0.897
3
1
0.002
2
0.914
3
1
0.002
3
0.086
2
1
369.8
4
2
0.017
2
1
0.885
3
1
0.002
2
0.806
3
1
0.003
3
0.194
3
1
364.8
4
2
0.042
2
1
0.86
3
1
0.002
2
0.643
3
1
0.004
3
0.357
3
1
360.3
4
2
0.085
2
1
0.816
3
1
0.002
2
0.527
3
1
0.005
3
0.473
3
1
357.3
4
2
0.133
3
1
0.767
3
1
0.003
2
0.468
3
1
0.005
3
0.532
3
1
356.2
4
2
0.191
3
1
0.708
3
1
0.003
2
0.429
3
1
0.004
3
0.571
3
1
355.4
4
2
0.272
3
1
0.627
3
1
0.003
2
0.391
3
1
0.004
3
0.609
3
1
354.9
4
2
0.36
3
1
0.539
3
1
0.004
2
0.358
3
1
0.004
3
0.642
3
1
354.6
4
2
0.437
3
1
0.461
3
1
0.004
2
0.321
3
1
0.003
3
0.679
3
1
354.8
4
2
0.519
3
1
0.379
3
1
0.003
2
0.283
3
1
0.003
3
0.717
3
1
355
4
2
0.593
3
1
0.305
3
1
0.003
2
0.241
3
1
0.003
3
0.759
3
1
355.2
4
2
0.663
3
1
0.235
3
1
0.003
2
0.201
3
1
0.003
3
0.799
3
1
355.4
4
2
0.716
3
1
0.181
3
1
0.002
2
0.163
3
1
0.002
3
0.837
3
1
355.6
4
2
0.761
3
1
0.136
3
1
0.002
2
0.124
3
1
0.002
3
0.876
3
1
355.8
4
2
0.793
3
1
0.102
3
1
0.002
2
0.095
2
1
0.002
3
0.905
3
1
356
4
2
0.822
3
1
0.072
2
1
0.002
2
0.068
2
1
0.002
3
0.932
3
1
356.3
4
2
0.847
3
1
0.047
2
1
0.002
2
0.044
2
1
0.002
3
0.956
3
1
356.4
4
2
0.902
3
1
0
4
2
0
4
3
1
4
1
380.3
4
2
0
4
1
0.834
3
1
0.002
2
1
4
3
0
4
1
376.4
4
2
0.002
1
1
0.839
3
1
0.002
2
0.917
3
1
0.002
3
0.083
2
1
373.1
4
2
0.015
2
1
0.824
3
1
0.002
2
0.797
3
1
0.003
3
0.203
3
1
369.2
4
2
0.043
2
1
0.789
3
1
0.003
2
0.672
3
1
0.004
3
0.328
3
1
365.2
4
2
0.073
2
1
0.755
3
1
0.003
2
0.563
3
1
0.004
3
0.437
3
1
360.7
4
2
0.134
3
1
0.692
3
1
0.003
2
0.458
3
1
0.005
3
0.542
3
1
358.5
4
2
0.207
3
1
0.624
3
1
0.004
2
0.388
3
1
0.004
3
0.612
3
1
357.1
4
2
0.275
3
1
0.558
3
1
0.004
2
0.346
3
1
0.004
3
0.654
3
1
356.8
4
2
0.332
3
1
0.494
3
1
0.004
2
0.311
3
1
0.003
3
0.689
3
1
357
4
2
0.399
3
1
0.425
3
1
0.004
2
0.274
3
1
0.003
3
0.726
3
1
357.2
4
2
0.469
3
1
0.351
3
1
0.003
2
0.235
3
1
0.003
3
0.765
3
1
357.3
4
2
0.531
3
1
0.287
3
1
0.003
2
0.2
3
1
0.003
3
0.8
3
1
357.4
4
2
0.588
3
1
0.231
3
1
0.003
2
0.165
3
1
0.003
3
0.835
3
1
357.7
4
2
0.636
3
1
0.181
3
1
0.002
2
0.134
3
1
0.002
3
0.866
3
1
357.8
4
2
0.68
3
1
0.143
3
1
0.002
2
0.109
3
1
0.002
3
0.891
3
1
357.8
4
2
0.714
3
1
0.106
3
1
0.002
2
0.082
2
1
0.002
3
0.918
3
1
358
4
2
0.752
3
1
0.073
2
1
0.002
2
0.058
2
1
0.002
3
0.942
3
1
358.1
4
2
0.779
3
1
0.05
2
1
0.002
2
0.04
2
1
0.002
3
0.96
3
1
358.3
4
2
0.822
3
1
0
4
2
0
4
3
1
4
1
384.2
4
2
0
4
1
0.776
3
1
0.003
2
1
4
3
0
4
1
381.8
4
2
0.01
2
1
0.771
3
1
0.003
2
0.929
3
1
0.002
3
0.071
2
1
378.3
4
2
0.024
2
1
0.744
3
1
0.003
2
0.822
3
1
0.003
3
0.178
3
1
374.9
4
2
0.044
2
1
0.724
3
1
0.003
2
0.691
3
1
0.003
3
0.309
3
1
369.9
4
2
0.074
2
1
0.696
3
1
0.003
2
0.566
3
1
0.004
3
0.434
3
1
366.1
4
2
0.112
3
1
0.655
3
1
0.003
2
0.481
3
1
0.005
3
0.519
3
1
362.9
4
2
0.171
3
1
0.602
3
1
0.004
2
0.392
3
1
0.004
3
0.608
3
1
360
4
2
0.243
3
1
0.536
3
1
0.004
2
0.332
3
1
0.004
3
0.668
3
1
359.7
4
2
0.302
3
1
0.474
3
1
0.004
2
0.295
3
1
0.003
3
0.705
3
1
359.8
4
2
0.349
3
1
0.42
3
1
0.004
2
0.259
3
1
0.003
3
0.741
3
1
359.8
4
2
0.406
3
1
0.358
3
1
0.003
2
0.224
3
1
0.003
3
0.776
3
1
360
4
2
0.452
3
1
0.302
3
1
0.003
2
0.194
3
1
0.003
3
0.806
3
1
359.9
4
2
0.517
3
1
0.242
3
1
0.003
2
0.158
3
1
0.002
3
0.842
3
1
360
4
2
0.564
3
1
0.194
3
1
0.002
2
0.128
3
1
0.002
3
0.872
3
1
360.1
4
2
0.608
3
1
0.153
3
1
0.002
2
0.102
3
1
0.002
3
0.898
3
1
360.2
4
2
0.65
3
1
0.113
3
1
0.002
2
0.077
2
1
0.002
3
0.923
3
1
360.1
4
2
0.693
3
1
0.074
2
1
0.002
2
0.052
2
1
0.002
3
0.948
3
1
359.8
4
2
0.733
3
1
0.048
2
1
0.002
2
0.035
2
1
0.002
3
0.965
3
1
359.8
4
2
0.77
3
1
0
4
2
0
4
3
1
4
1
388.8
4
2
0
4
1
0.724
3
1
0.003
2
1
4
3
0
4
1
386.3
4
2
0.008
1
1
0.719
3
1
0.003
2
0.948
3
1
0.002
3
0.052
2
1
383.3
4
2
0.017
2
1
0.714
3
1
0.003
2
0.851
3
1
0.002
3
0.149
3
1
379.6
4
2
0.033
2
1
0.697
3
1
0.003
2
0.717
3
1
0.003
3
0.283
3
1
376
4
2
0.057
2
1
0.665
3
1
0.003
2
0.621
3
1
0.004
3
0.379
3
1
373.4
4
2
0.082
2
1
0.635
3
1
0.004
2
0.529
3
1
0.005
3
0.471
3
1
371
4
2
0.104
3
1
0.6
3
1
0.004
2
0.466
3
1
0.005
3
0.534
3
1
368.2
4
2
0.148
3
1
0.552
3
1
0.004
2
0.388
3
1
0.004
3
0.612
3
1
366.7
4
2
0.192
3
1
0.501
3
1
0.004
2
0.332
3
1
0.004
3
0.668
3
1
364.1
4
2
0.25
3
1
0.445
3
1
0.004
2
0.277
3
1
0.003
3
0.723
3
1
363.4
4
2
0.315
3
1
0.386
3
1
0.004
2
0.233
3
1
0.003
3
0.767
3
1
363.1
4
2
0.354
3
1
0.338
3
1
0.003
2
0.199
3
1
0.003
3
0.801
3
1
362.8
4
2
0.408
3
1
0.283
3
1
0.003
2
0.166
3
1
0.003
3
0.834
3
1
362.6
4
2
0.463
3
1
0.232
3
1
0.003
2
0.139
3
1
0.002
3
0.861
3
1
363.1
4
2
0.493
3
1
0.188
3
1
0.002
2
0.109
3
1
0.002
3
0.891
3
1
363.3
4
2
0.546
3
1
0.14
3
1
0.002
2
0.079
2
1
0.002
3
0.921
3
1
363.3
4
2
0.596
3
1
0.091
2
1
0.002
2
0.055
2
1
0.002
3
0.945
3
1
363.5
4
2
0.63
3
1
0.058
2
1
0.002
2
0.032
2
1
0.002
3
0.968
3
1
362.6
4
2
0.695
3
1
0
4
2
0
4
3
1
4
7
3
1
2
1
Principal objective of the work
AB
TRC
1/24/2020
1
Boiling temperature at pressure P, K
Ebulliometric method (Recirculating still)
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Gas
1
Pressure, kPa
Liquid
100
1
1
Mole fraction
2
Liquid
1
0.946
3
1
374.6
4
1
0.6
1
0.902
3
1
376.6
4
1
0.6
1
0.834
3
1
380.3
4
1
0.6
1
0.776
3
1
384.2
4
1
0.6
1
0.724
3
1
388.8
4
1
0.6