2
0
2017
li
wan
1
journal
Original
Li, H.[Hengde]
Wan, L.[Li]
Chu, G.[Guoqiang]
Tan, W.[Wei]
Liu, B.[Baoyu]
Qin, Y.[Yanlin]
Feng, Y.[Yuqing]
Sun, D.[Dalei]
Fang, Y.[Yanxiong]
J. Chem. Thermodyn.
2017
2020-09-29
(Liquid + liquid) extraction of phenols from aqueous solutions with cineole
As an eco-friendly compound and good solvent, cineole (1,8-cineole, eucalyptol) has been evaluated for the extraction property of phenols (phenol or p-cresol) from aqueous solutions. This paper presents experimental (liquid + liquid) equilibrium (LLE) data for the ternary (water + phenol + cineole) and (water + p-cresol + cineole) mixtures from high concentration to low concentration of phenols-water solution. The mutual solubility of the binary (water + cineole) and (water + phenol or p-cresol) systems, and the LLE results for the ternary systems were determined with a tie-line method at T = (283.15, 298.15, and 313.15) K under atmospheric pressure. The experiment LLE results showed that cineole as a good extractant exhibited high extraction ability for phenol or p-cresol from aqueous solutions. The influence of temperature on the (liquid + liquid) phase equilibria was studied. The well-known Hand and Bachman equations were used to test the reliability of the experimental values. Moreover, the experimental LLE results were satisfactorily correlated by the NRTL and UNIQUAC models.
Phenols
Cineole (1,8-cineole)
LLE
Phenolic wastewater
Extraction property
10.1016/j.jct.2016.12.018
107
95-103
1
InChI=1S/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3
WEEGYLXZBRQIMU-UHFFFAOYSA-N
1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane
1,8-cineole
1,8-epoxy-p-menthane
2-oxabicyclo[2.2.2]octane, 1,3,3-trimethyl-
cineol
eucalyptol
p-menthane, 1,8-epoxy-
C10H18O
1
Commercial source
1
99
2
Gas chromatography
2
InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H
ISWSIDIOOBJBQZ-UHFFFAOYSA-N
phenol
benzenol
hydroxybenzene
phenyl hydroxide
C6H6O
1
Commercial source
1
99.5
3
Gas chromatography
3
InChI=1S/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3
IWDCLRJOBJJRNH-UHFFFAOYSA-N
4-methylphenol
1-hydroxy-4-methylbenzene
p-cresol
p-hydroxytoluene
para-cresol
para-hydroxytoluene
C7H8O
1
Commercial source
1
99
2
Gas chromatography
4
InChI=1S/H2O/h1H2
XLYOFNOQVPJJNP-UHFFFAOYSA-N
water
H2O
1
Commercial source
1
Fractional distillation
2
99.8
3
Estimated by the compiler
1
1
1
Principal objective of the work
AB
TRC
8/17/2017
1
Mass density, kg/m3
Vibrating tube method
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
1
Pressure, kPa
Liquid
2
Temperature, K
Liquid
1
100
1
2
293.15
5
1
924.84
5
1
2.02
2
1
1
Principal objective of the work
AB
TRC
8/17/2017
1
Refractive index (Na D-line)
Standard Abbe refractometry
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
1
Pressure, kPa
Liquid
2
Temperature, K
Liquid
1
100
1
2
293.15
5
1
1.45756
6
1
0.00107
3
4
1
Principal objective of the work
AB
TRC
8/17/2017
1
Mass density, kg/m3
Vibrating tube method
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
1
Pressure, kPa
Liquid
2
Temperature, K
Liquid
1
100
1
2
293.15
5
1
998.15
5
1
2.01
4
4
1
Principal objective of the work
AB
TRC
8/17/2017
1
Refractive index (Na D-line)
Standard Abbe refractometry
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
1
Pressure, kPa
Liquid
2
Temperature, K
Liquid
1
100
1
2
293.15
5
1
1.33299
6
1
0.00105
5
2
1
4
1
Principal objective of the work
AB
TRC
8/17/2017
1
Mole fraction
Chromatography
2
Liquid mixture 1
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid mixture 1
Liquid mixture 2
1
Pressure, kPa
Liquid mixture 1
100
1
1
Temperature, K
Liquid mixture 1
1
283.15
5
1
0.0156
3
1
0.0008
1
298.15
5
1
0.0174
3
1
0.0008
1
313.15
5
1
0.0214
3
1
0.0008
6
2
1
4
1
Principal objective of the work
AB
TRC
8/17/2017
1
Mole fraction
Chromatography
4
Liquid mixture 2
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid mixture 2
Liquid mixture 1
1
Pressure, kPa
Liquid mixture 1
100
1
1
Temperature, K
Liquid mixture 1
1
283.15
5
1
0.6301
4
1
0.0066
1
298.15
5
1
0.6731
4
1
0.0065
1
313.15
5
1
0.7244
4
1
0.0063
7
3
1
4
1
Principal objective of the work
AB
TRC
8/17/2017
1
Mole fraction
Chromatography
3
Liquid mixture 1
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid mixture 1
Liquid mixture 2
1
Pressure, kPa
Liquid mixture 1
100
1
1
Temperature, K
Liquid mixture 1
1
283.15
5
1
0.00348
3
1
0.0001
1
298.15
5
1
0.00365
3
1
0.0001
1
313.15
5
1
0.00403
3
1
0.0001
8
3
1
4
1
Principal objective of the work
AB
TRC
8/17/2017
1
Mole fraction
Chromatography
4
Liquid mixture 2
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid mixture 2
Liquid mixture 1
1
Pressure, kPa
Liquid mixture 1
100
1
1
Temperature, K
Liquid mixture 1
1
283.15
5
1
0.482
4
1
0.0069
1
298.15
5
1
0.5202
4
1
0.0069
1
313.15
5
1
0.5562
4
1
0.0068
9
1
1
4
1
Principal objective of the work
AB
TRC
8/17/2017
1
Mole fraction
Chromatography
1
Liquid mixture 1
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid mixture 1
Liquid mixture 2
1
Pressure, kPa
Liquid mixture 1
100
1
1
Temperature, K
Liquid mixture 1
1
283.15
5
1
0.00053
2
1
1e-05
1
298.15
5
1
0.00037
2
1
1e-05
1
313.15
5
1
0.00024
2
1
1e-05
10
1
1
4
1
Principal objective of the work
AB
TRC
8/17/2017
1
Mole fraction
Chromatography
4
Liquid mixture 2
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid mixture 2
Liquid mixture 1
1
Pressure, kPa
Liquid mixture 1
100
1
1
Temperature, K
Liquid mixture 1
1
283.15
5
1
0.0605
3
1
0.006
1
298.15
5
1
0.0648
3
1
0.006
1
313.15
5
1
0.0685
3
1
0.006
11
2
1
1
1
4
1
Principal objective of the work
AB
TRC
8/17/2017
1
Mole fraction
Chromatography
2
Liquid mixture 2
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
2
Mole fraction
Chromatography
1
Liquid mixture 1
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
3
Mole fraction
Chromatography
2
Liquid mixture 1
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid mixture 2
Liquid mixture 1
1
Pressure, kPa
Liquid mixture 2
100
1
1
Temperature, K
Liquid mixture 1
2
Mole fraction
4
Liquid mixture 2
1
283.15
5
2
0.0615
3
1
0.00057
2
1
0.00057
2
0.0005033
4
1
1.66e-05
3
1.28e-06
3
1
283.15
5
2
0.0605
3
1
0
1
2
0.00053
2
1
2e-05
3
0
1
1
283.15
5
2
0.0625
3
1
0.00235
3
1
0.00235
2
0.0005014
4
1
1.66e-05
3
5.18e-06
3
1
283.15
5
2
0.0658
3
1
0.00943
3
1
0.00943
2
0.0005003
4
1
1.68e-05
3
2.01e-05
3
1
283.15
5
2
0.0715
3
1
0.0189
3
1
0.0128
2
0.0004979
4
1
1.84e-05
3
4.04e-05
3
1
283.15
5
2
0.0803
3
1
0.0359
3
1
0.0152
2
0.0004899
4
1
1.67e-05
3
8.06e-05
3
1
283.15
5
2
0.0937
3
1
0.0703
3
1
0.0138
2
0.0004814
4
1
1.66e-05
3
0.0001709
4
1
283.15
5
2
0.1118
4
1
0.1019
4
1
0.0119
2
0.0004708
4
1
1.73e-05
3
0.0002652
4
1
283.15
5
2
0.12614
5
1
0.1256
4
1
0.0116
2
0.0004256
4
1
1.87e-05
3
0.0003451
4
1
283.15
5
2
0.6301
4
1
0.3699
4
1
0.0072
2
0
1
3
0.0156
3
1
298.15
5
2
0.6731
4
1
0.3269
4
1
0.0069
2
0
1
3
0.0174
3
1
298.15
5
2
0.0667
3
1
0.00226
3
1
0.00226
2
0.0003147
4
1
1.67e-05
3
6.65e-06
3
1
298.15
5
2
0.0648
3
1
0
1
2
0.00037
2
1
2e-05
3
0
1
1
298.15
5
2
0.0696
3
1
0.00924
3
1
0.00924
2
0.0003043
4
1
1.96e-05
3
2.61e-05
3
1
298.15
5
2
0.0769
3
1
0.0183
3
1
0.0116
2
0.0002978
4
1
2.09e-05
3
5.12e-05
3
1
298.15
5
2
0.0853
3
1
0.035
3
1
0.016
2
0.0002942
4
1
1.63e-05
3
0.000103
4
1
298.15
5
2
0.0951
3
1
0.0628
3
1
0.0135
2
0.0002937
4
1
1.64e-05
3
0.0002036
4
1
298.15
5
2
0.1139
4
1
0.095
3
1
0.012
2
0.0002911
4
1
1.64e-05
3
0.0003385
4
1
298.15
5
2
0.1297
4
1
0.1223
4
1
0.0121
2
0.0002606
4
1
1.63e-05
3
0.0004702
4
1
298.15
5
2
0.0646
3
1
0.00054
2
1
0.00054
2
0.0003401
4
1
1.64e-05
3
1.61e-06
3
1
313.15
5
2
0.1169
4
1
0.093
3
1
0.0118
2
0.0002019
4
1
1.61e-05
3
0.0004969
4
1
313.15
5
2
0.7244
4
1
0.2756
4
1
0.0066
2
0
1
3
0.0214
3
1
313.15
5
2
0.1338
4
1
0.1203
4
1
0.0114
2
0.0001888
4
1
1.61e-05
3
0.0007063
4
1
313.15
5
2
0.0685
3
1
0
1
2
0.00024
2
1
2e-05
3
0
1
1
313.15
5
2
0.0697
3
1
0.00223
3
1
0.00223
2
0.000226
4
1
1.62e-05
3
9.83e-06
3
1
313.15
5
2
0.0739
3
1
0.00885
3
1
0.00885
2
0.0002233
4
1
1.63e-05
3
3.72e-05
3
1
313.15
5
2
0.0676
3
1
0.00053
2
1
0.00053
2
0.0002263
4
1
1.61e-05
3
2.36e-06
3
1
313.15
5
2
0.081
3
1
0.0161
3
1
0.0107
2
0.00022
4
1
1.64e-05
3
6.62e-05
3
1
313.15
5
2
0.0892
3
1
0.0313
3
1
0.0164
2
0.0002142
4
1
1.61e-05
3
0.0001351
4
1
313.15
5
2
0.0989
3
1
0.0612
3
1
0.0143
2
0.0002039
4
1
1.61e-05
3
0.0002896
4
12
3
1
1
1
4
1
Principal objective of the work
AB
TRC
8/17/2017
1
Mole fraction
Chromatography
4
Liquid mixture 2
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
2
Mole fraction
Chromatography
1
Liquid mixture 1
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
3
Mole fraction
Chromatography
3
Liquid mixture 1
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid mixture 2
Liquid mixture 1
1
Pressure, kPa
Liquid mixture 2
100
1
1
Temperature, K
Liquid mixture 1
2
Mole fraction
3
Liquid mixture 2
1
283.15
5
2
0.0004
2
1
0.0614
3
1
0.006
2
0.0005345
4
1
1.66e-05
3
4.27e-07
3
1
283.15
5
2
0.00082
2
1
0.0617
3
1
0.006
2
0.0005306
4
1
1.66e-05
3
8.37e-07
3
1
283.15
5
2
0.00156
3
1
0.0621
3
1
0.006
2
0.0005252
4
1
1.66e-05
3
1.53e-06
3
1
283.15
5
2
0.00332
3
1
0.0626
3
1
0.0061
2
0.0005222
4
1
1.67e-05
3
3.24e-06
3
1
283.15
5
2
0.00641
3
1
0.0639
3
1
0.0064
2
0.0005116
4
1
1.66e-05
3
6.47e-06
3
1
283.15
5
2
0.0144
3
1
0.0666
3
1
0.0062
2
0.0005082
4
1
1.71e-05
3
1.592e-05
4
1
283.15
5
2
0.0275
3
1
0.0696
3
1
0.0062
2
0.0005034
4
1
1.71e-05
3
3.391e-05
4
1
283.15
5
2
0
1
1
0.0605
3
1
0.006
2
0.00053
2
1
2e-05
3
0
1
1
283.15
5
2
0.518
4
1
0.482
4
1
0.0086
2
0
1
3
0.00348
3
1
298.15
5
2
0.4798
4
1
0.5202
4
1
0.0091
2
0
1
3
0.00365
3
1
298.15
5
2
0.00042
2
1
0.0649
3
1
0.006
2
0.000365
4
1
1.63e-05
3
4.68e-07
3
1
298.15
5
2
0.00083
2
1
0.065
3
1
0.006
2
0.0003547
4
1
1.64e-05
3
9.09e-07
3
1
298.15
5
2
0.00156
3
1
0.0652
3
1
0.006
2
0.0003523
4
1
1.65e-05
3
1.69e-06
3
1
298.15
5
2
0.00309
3
1
0.0661
3
1
0.0063
2
0.00035
4
1
1.72e-05
3
3.28e-06
3
1
298.15
5
2
0.00605
3
1
0.0675
3
1
0.0064
2
0.0003419
4
1
2e-05
3
6.59e-06
3
1
298.15
5
2
0.0137
3
1
0.0699
3
1
0.0061
2
0.0003306
4
1
2.77e-05
3
1.604e-05
4
1
298.15
5
2
0.0268
3
1
0.0719
3
1
0.0061
2
0.0003217
4
1
2.08e-05
3
3.436e-05
4
1
298.15
5
2
0
1
1
0.0648
3
1
0.006
2
0.00037
2
1
2e-05
3
0
1
1
313.15
5
2
0
1
1
0.0685
3
1
0.006
2
0.00024
2
1
2e-05
3
0
1
1
313.15
5
2
0.4438
4
1
0.5562
4
1
0.0097
2
0
1
3
0.00403
3
1
313.15
5
2
0.0004
2
1
0.0696
3
1
0.006
2
0.0002351
4
1
1.62e-05
3
4.82e-07
3
1
313.15
5
2
0.00077
2
1
0.0697
3
1
0.006
2
0.0002319
4
1
1.62e-05
3
9.15e-07
3
1
313.15
5
2
0.00148
3
1
0.0702
3
1
0.006
2
0.000231
4
1
1.62e-05
3
1.7e-06
3
1
313.15
5
2
0.00299
3
1
0.0709
3
1
0.0061
2
0.0002253
4
1
1.63e-05
3
3.45e-06
3
1
313.15
5
2
0.00581
3
1
0.0718
3
1
0.0061
2
0.000222
4
1
1.65e-05
3
6.84e-06
3
1
313.15
5
2
0.0134
3
1
0.0732
3
1
0.0061
2
0.0002115
4
1
1.97e-05
3
1.673e-05
4
1
313.15
5
2
0.0265
3
1
0.0745
3
1
0.0061
2
0.0002094
4
1
1.62e-05
3
3.59e-05
4