Liquid-Liquid Equilibria in Ternary Systems of Aromatic Hydrocarbons (Toluene or Ethylbenzene) + Phenols + Water Antje Martin, Mandy Klauck, Klaus Taubert, Annett Precht, René Meinhardt and Jürgen Schmelzer* Department of Chemical Engineering, Hochschule für Technik und Wirtschaft Dresden – University of Applied Sciences, Friedrich-List-Platz 1, 01069 Dresden, Germany *Corresponding author: Tel.: +49-351-462-2777. Fax: +49-351-462-3228. E-mail:
[email protected]
Supporting Information Table 1. Experimental and literature values of pure component densities. ............................................ 2 Table 2. Solubility of water (1) in ethylbenzene (2) or in phenol (2) at atmospheric pressure............... 2 Table 3. LLE of the toluene(1) + phenol(2) + water(3) system at atmospheric pressure....................... 3 Table 4. LLE of the toluene(1) + 2-cresol(2) + water(3) system at atmospheric pressure..................... 4 Table 5. LLE of the toluene(1) + 3-cresol(2) + water(3) system at atmospheric pressure..................... 5 Table 6. LLE of the toluene(1) + 4-cresol(2) + water(3) system at atmospheric pressure..................... 6 Table 7. LLE of the ethylbenzene(1) + phenol(2) + water(3) system at atmospheric pressure. ............. 7 Table 8. LLE of the ethylbenzene(1) + 2-cresol(2) + water(3) system at atmospheric pressure............ 8 Table 9. LLE of the ethylbenzene(1) + 3-cresol(2) + water(3) system at atmospheric pressure............ 9 Table 10. LLE of the ethylbenzene(1) + 4-cresol(2) + water(3) system at atmospheric pressure........ 10
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Table 1. Experimental and literature values of pure component densities.
ρ g ⋅ cm 3
T K substance
exptl.
lit.a
phenol
313.15
1.05830
1.0587b
2-cresol
308.15
1.03273
1.0327
3-cresol
293.15
1.03385
1.0339
4-cresol
313.15
1.01880
1.0185
toluene
293.15
0,86678
0.8668
ethylbenzene
298.15
0.86259
0.8626
a
b
Lide, D.R.; Frederike, H. P. R. CRC Handbook of chemistry and physics on CD-ROM; CRC Press: Boca Raton, FL, 2004. Riddick, J. A.; Bunger, W. B.; Sakano, T.K. Organic solvents – physical properties and methods of purification; Wiley: New York 1986.
Table 2. Solubility of water (1) in ethylbenzene (2) or in phenol (2) at atmospheric pressure. water (1) + ethylbenzene (2)
water (1) + phenol (2)
T K
x1′′
T K
x1′′
313.15
0.004550
298.15
0.6877
318.15
0.005251
313.15
0.7245
323.15
0.005894
318.15
0.7400
328.15
0.006652
323.15
0.7580
333.15
0.007467
328.15
0.7835
338.15
0.008717
333.15
0.8068
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Table 3. LLE of the toluene(1) + phenol(2) + water(3) system at atmospheric pressure. T K = 298.15
T K = 313.15
x1
x2
x3
x1
x2
x3
0.0000
0.3123
0.6877
0.0000
0.2755
0.7245
0.0520
0.3946
0.5534
0.0519
0.3709
0.5772
0.1003
0.4208
0.4789
0.1012
0.3987
0.5001
0.1583
0.4268
0.4149
0.1423
0.4128
0.4449
0.2041
0.4282
0.3677
0.1965
0.4085
0.3950
0.2691
0.4141
0.3168
0.2356
0.4064
0.3580
0.3894
0.3779
0.2327
0.3068
0.3976
0.2956
0.3894
0.3779
0.2327
0.4004
0.3723
0.2273
0.4767
0.3389
0.1844
0.4666
0.3470
0.1864
0.5371
0.3103
0.1526
0.5537
0.2956
0.1507
0.6338
0.2561
0.1101
0.5940
0.2665
0.1396
0.6809
0.2295
0.0896
0.7656
0.1752
0.0592
0.8772
0.0895
0.0333
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Table 4. LLE of the toluene(1) + 2-cresol(2) + water(3) system at atmospheric pressure.
x1
T K = 298.15 x2
x3
x1
T K = 323.15 x2
x3
0.0000
0.5093
0.4907
0.0000
0.4917
0.5083
0.0375
0.5160
0.4465
0.0459
0.5004
0.4537
0.0992
0.5158
0.3850
0.0996
0.4967
0.4037
0.1003
0.5216
0.3781
0.2034
0.4784
0.3182
0.1166
0.5197
0.3637
0.3252
0.4345
0.2403
0.1177
0.5247
0.3576
0.3007
0.4432
0.2561
0.1718
0.5072
0.3210
0.9933
0.0000
0.0068
0.1728
0.5100
0.3172
0.2114
0.4972
0.2914
0.2121
0.4988
0.2891
0.2694
0.4686
0.2620
0.2721
0.4732
0.2547
0.3105
0.4534
0.2361
0.3245
0.4486
0.2269
0.3273
0.4524
0.2203
0.3731
0.4293
0.1976
0.3732
0.4294
0.1974
0.4604
0.3847
0.1549
0.5984
0.3021
0.0995
0.6010
0.3034
0.0956
0.6748
0.2468
0.0784
0.6794
0.2484
0.0722
0.9964
0.0000
0.0036
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Table 5. LLE of the toluene(1) + 3-cresol(2) + water(3) system at atmospheric pressure.
x1
T K = 298.15 x2
x3
x1
T K = 323.15 x2
x3
0.0000
0.5184
0.4816
0.0000
0.4742
0.5258
0.1358
0.5087
0.3555
0.0724
0.4826
0.4451
0.1776
0.4952
0.3272
0.1182
0.4801
0.4017
0.2195
0.4835
0.2970
0.1615
0.4696
0.3689
0.2867
0.4565
0.2568
0.1774
0.4692
0.3534
0.3295
0.4375
0.2329
0.2037
0.4668
0.3294
0.4116
0.3983
0.1902
0.2133
0.4547
0.3240
0.5338
0.3300
0.1361
0.2756
0.4362
0.2882
0.5791
0.3022
0.1186
0.3409
0.4118
0.2473
0.6960
0.2252
0.0788
0.4912
0.3408
0.1682
0.5216
0.3241
0.1544
0.5891
0.2847
0.1262
0.7168
0.2009
0.0823
0.7527
0.1692
0.0781
0.7735
0.1672
0.0594
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Table 6. LLE of the toluene(1) + 4-cresol(2) + water(3) system at atmospheric pressure.
x1
T K = 298.15 x2
x3
x1
T K = 323.15 x2
x3
0.0000
0.4814
0.5186
0.0000
0.4380
0.5620
0.0194
0.4861
0.4944
0.0830
0.4589
0.4581
0.0707
0.4941
0.4352
0.0944
0.4621
0.4435
0.1586
0.4849
0.3564
0.1968
0.4490
0.3542
0.1820
0.4810
0.3370
0.2197
0.4440
0.3363
0.2970
0.4427
0.2603
0.2318
0.4407
0.3275
0.4438
0.3687
0.1875
0.3668
0.3942
0.2390
0.4851
0.3554
0.1595
0.4401
0.3606
0.1993
0.5339
0.3267
0.1394
0.5201
0.3184
0.1615
0.7025
0.2218
0.0757
0.6205
0.2626
0.1169
0.7095
0.2094
0.0811
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Table 7. LLE of the ethylbenzene(1) + phenol(2) + water(3) system at atmospheric pressure.
x1
T K = 298.15 x2
x3
x1
T K = 323.15 x2
x3
0.0000
0.3123
0.6877
0.0000
0.2420
0.7580
0.1331
0.4343
0.4326
0.0411
0.3553
0.6036
0.1625
0.4249
0.4081
0.0525
0.3670
0.5806
0.2312
0.4333
0.3355
0.0592
0.3721
0.5687
0.3106
0.4078
0.2816
0.1189
0.4121
0.4690
0.3321
0.4002
0.2677
0.1463
0.4150
0.4387
0.3508
0.3912
0.2580
0.1613
0.4179
0.4208
0.4985
0.3291
0.1724
0.1624
0.4144
0.4232
0.5822
0.2823
0.1355
0.1850
0.4145
0.4005
0.5930
0.2789
0.1281
0.2131
0.4125
0.3744
0.6696
0.2240
0.1064
0.2491
0.4100
0.3409
0.6886
0.2251
0.0863
0.2882
0.4040
0.3078
0.9239
0.0226
0.0536
0.2892
0.4040
0.3068
0.3644
0.3790
0.2566
0.5030
0.3186
0.1784
0.7504
0.1736
0.0760
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Table 8. LLE of the ethylbenzene(1) + 2-cresol(2) + water(3) system at atmospheric pressure.
x1
T K = 298.15 x2
x3
x1
T K = 323.15 x2
x3
0.0000
0.5093
0.4907
0.0000
0.4917
0.5083
0.0156
0.5288
0.4556
0.0150
0.5095
0.4754
0.0369
0.5353
0.4278
0.0358
0.5181
0.4461
0.0620
0.5379
0.4002
0.0598
0.5190
0.4212
0.1162
0.5361
0.3477
0.1301
0.5221
0.3478
0.1719
0.5244
0.3037
0.1878
0.5086
0.3037
0.2347
0.5062
0.2591
0.2738
0.4747
0.2515
0.2976
0.4810
0.2214
0.3776
0.4282
0.1942
0.3539
0.4568
0.1893
0.4626
0.3817
0.1557
0.4137
0.4207
0.1656
0.5198
0.3504
0.1298
0.4729
0.3887
0.1384
0.5789
0.3140
0.1071
0.5296
0.3533
0.1171
0.6503
0.2681
0.0816
0.5890
0.3152
0.0958
0.6997
0.2383
0.0620
0.6540
0.2718
0.0742
0.7531
0.2044
0.0425
0.7153
0.2292
0.0555
0.8221
0.1523
0.0256
0.7562
0.1988
0.0451
0.8052
0.1613
0.0335
0.8716
0.1077
0.0207
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Table 9. LLE of the ethylbenzene(1) + 3-cresol(2) + water(3) system at atmospheric pressure.
x1
T K = 298.15 x2
x3
x1
T K = 323.15 x2
x3
0.0000
0.5184
0.4816
0.0000
0.4742
0.5258
0.1277
0.5183
0.3539
0.2312
0.4653
0.3035
0.1811
0.5057
0.3132
0.2317
0.4614
0.3069
0.2488
0.4811
0.2701
0.2904
0.4412
0.2684
0.2690
0.4719
0.2591
0.3105
0.4362
0.2533
0.3045
0.4572
0.2383
0.3485
0.4209
0.2307
0.3461
0.4377
0.2163
0.3545
0.4123
0.2332
0.3783
0.4219
0.1998
0.4498
0.3694
0.1807
0.6007
0.2947
0.1046
0.5024
0.3454
0.1522
0.6136
0.2848
0.1017
0.5152
0.3318
0.1530
0.6336
0.2733
0.0941
0.5288
0.3257
0.1455
0.7265
0.2140
0.0595
0.5595
0.3083
0.1322
0.8141
0.1485
0.0374
0.8379
0.1278
0.0342
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Table 10. LLE of the ethylbenzene(1) + 4-cresol(2) + water(3) system at atmospheric pressure.
x1
T K = 298.15 x2
x3
x1
T K = 323.15 x2
x3
0.0000
0.4814
0.5186
0.0000
0.4380
0.5620
0.0432
0.4929
0.4639
0.0282
0.4539
0.5179
0.0979
0.4947
0.4074
0.0491
0.4595
0.4914
0.1465
0.4900
0.3635
0.0858
0.4680
0.4462
0.2133
0.4759
0.3108
0.1435
0.4599
0.3966
0.2841
0.4503
0.2625
0.2091
0.4448
0.3461
0.3868
0.4019
0.2113
0.2725
0.4274
0.3001
0.4907
0.3650
0.1443
0.3207
0.4075
0.2718
0.5862
0.3016
0.1122
0.3884
0.3811
0.2305
0.6845
0.2315
0.0840
0.4935
0.3313
0.1752
0.8153
0.1406
0.0441
0.5192
0.3030
0.1778
0.6425
0.2522
0.1053
0.7969
0.1527
0.0504
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