2
0
2017
ces
can
0
journal
Original
Cesari, L.[Laetitia]
Canabady-Rochelle, L.[Laetitia]
Mutelet, F.[Fabrice]
Fluid Phase Equilib.
2017
2020-09-29
Extraction of phenolic compounds from aqueous solution using choline bis(trifluoromethylsulfonyl)imide
The efficiency of choline bis(trifluoromethylsulfonyl)imide [choline][NTf2] was evaluated as extractant media for the extraction of phenolic compounds from aqueous solution. Solid-liquid and liquid-liquid equilibria of the ternary mixtures {water + phenolic compounds (phenol, guaiacol, syringol or pyrocatechol) + ionic liquid} were first measured at 295.15 K at atmospheric pressure. The selectivity and the solute distribution ratio values calculated from experimental data indicate that [choline][NTf2] is suitable for the extraction of phenolic compounds. Thermodynamic data of ternary mixtures were used to regress the parameters of the NRTL and UNIQUAC thermodynamic models. The influence of experimental conditions on the extraction of phenolic compounds from aqueous solutions using [choline][NTf2] were evaluated. Process design shows that phenol, guaiacol and syringol are easily extractable with few amount of solvent, number of theoretical steps and energy.
Ternary diagrams
Extraction
Phenolic compounds
Process design.
10.1016/j.fluid.2017.04.022
446
28-35
1
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
Stated by supplier
2
InChI=1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3
LHGVFZTZFXWLCP-UHFFFAOYSA-N
2-methoxyphenol
guaiacol
o-hydroxyanisole
o-methoxyphenol
phenol, 2-methoxy-
C7H8O2
1
Commercial source
1
99
2
Stated by supplier
3
InChI=1S/C8H10O3/c1-10-6-4-3-5-7(11-2)8(6)9/h3-5,9H,1-2H3
KLIDCXVFHGNTTM-UHFFFAOYSA-N
1,3-dimethoxy-2-hydroxybenzene
1,3-dimethyl ether pyrogallol
2,6-dimethoxyphenol
2-hydroxy-1,3-dimethoxybenzene
syringol
C8H10O3
1
Commercial source
1
99
2
Stated by supplier
4
InChI=1S/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H
YCIMNLLNPGFGHC-UHFFFAOYSA-N
1,2-benzenediol
1,2-dihydroxybenzene
2-hydroxyphenol
benzene, 1,2-dihydroxy-
catechol
o-benzenediol
o-dihydroxybenzene
pyrocatechol
C6H6O2
1
Commercial source
1
99
2
Stated by supplier
5
InChI=1S/C5H14NO.C2F6NO4S2/c1-6(2,3)4-5-7;3-1(4,5)14(10,11)9-15(12,13)2(6,7)8/h7H,4-5H2,1-3H3;/q+1;-1
XFXJXURAALDGSW-UHFFFAOYSA-N
choline bis(trifluoromethylsulfonyl)imide
(2-hydroxyethyl)trimethylammonium bis(trifluoromethylsulfonyl)imide
2-hydroxyethyl-N,N,N-trimethylammonium bis(trifluoromethylsulfonyl)imide
C7H14F6N2O5S2
1
Commercial source
1
99
2
Stated by supplier
2
0.0061
2
Karl Fischer titration
6
InChI=1S/H2O/h1H2
XLYOFNOQVPJJNP-UHFFFAOYSA-N
water
H2O
1
Commercial source
1
99.8
3
Estimated by the compiler
1
1
1
6
1
5
1
Principal objective of the work
MPG
MPG
4/27/2017
1
Mole fraction
Chromatography
5
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
1
1
Temperature, K
Liquid
298.15
5
2
Pressure, kPa
Liquid
101
3
1
Mole fraction
1
Liquid
1
0.774
3
1
0.226
3
1
0.01
1
0.776
3
1
0.194
3
1
0.01
1
0.771
3
1
0.17
3
1
0.01
1
0.762
3
1
0.14
3
1
0.01
1
0.764
3
1
0.096
2
1
0.01
1
0.763
3
1
0.06
2
1
0.01
1
0.779
3
1
0.024
2
1
0.01
1
0.786
3
1
0.007
1
1
0.007
1
0.803
3
1
0
4
2
2
1
6
1
5
1
Principal objective of the work
MPG
MPG
4/18/2017
1
Mole fraction
Chromatography
5
Liquid mixture 2
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
2
Mole fraction
Chromatography
5
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
Temperature, K
Liquid mixture 2
298.15
5
2
Pressure, kPa
Liquid mixture 2
101
3
1
Mole fraction
2
Liquid mixture 2
1
0
1
1
0.29
2
1
0.01
2
0.006
1
1
0.006
3
0
1
1
0.083
2
1
0.292
3
1
0.011
2
0.006
1
1
0.006
3
0.0005
1
1
0.295
3
1
0.201
3
1
0.011
2
0.0045
2
1
0.0045
3
0.0025
2
1
0.383
3
1
0.173
3
1
0.011
2
0.004
1
1
0.004
3
0.0034
2
1
0.522
3
1
0.103
3
1
0.011
2
0.002
1
1
0.002
3
0.006
1
1
0.592
3
1
0.07
1
1
0.01
2
0.002
1
1
0.002
3
0.007
1
1
0.655
3
1
0.02
1
1
0.01
2
0.001
1
1
0.001
3
0.011
2
1
0.752
3
1
0
1
2
0
1
3
0.003
1
3
3
1
6
1
5
1
Principal objective of the work
MPG
MPG
4/18/2017
1
Mole fraction
Chromatography
5
Liquid mixture 2
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
2
Mole fraction
Chromatography
3
Liquid mixture 1
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
3
Mole fraction
Chromatography
5
Liquid mixture 1
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
298.15
5
2
Pressure, kPa
Liquid mixture 2
101
3
1
Mole fraction
3
Liquid mixture 2
1
0
1
1
0.29
2
1
0.01
2
0
1
3
0.006
1
1
0.109
3
1
0.278
3
1
0.011
2
0.0005
1
1
0.0005
3
0.006
1
1
0.191
3
1
0.236
3
1
0.012
2
0.001
1
1
0.001
3
0.005
1
1
0.294
3
1
0.151
3
1
0.013
2
0.002
1
1
0.002
3
0.004
1
1
0.32
2
1
0.121
3
1
0.014
2
0.003
1
1
0.003
3
0.004
1
1
0.337
3
1
0.109
3
1
0.023
2
0.003
1
1
0.003
3
0.003
1
1
0.368
3
1
0.027
2
1
0.027
2
0.004
1
1
0.004
3
0.001
1
1
1
1
1
0
1
2
0.003
1
1
0.003
3
0
1
4
3
1
6
1
5
1
Principal objective of the work
MPG
MPG
4/27/2017
1
Mole fraction
Chromatography
5
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
3
1
Temperature, K
Liquid
298.15
5
2
Pressure, kPa
Liquid
101
3
1
Mole fraction
3
Liquid
1
0.705
3
1
0.295
3
1
0.02
1
0.668
3
1
0.231
3
1
0.015
1
0.605
3
1
0.175
3
1
0.022
1
0.592
3
1
0.149
3
1
0.015
1
0.552
3
1
0.115
3
1
0.012
1
0.467
3
1
0.071
2
1
0.011
1
0.41
3
1
0.052
2
1
0.011
5
4
1
6
1
5
1
Principal objective of the work
MPG
MPG
4/18/2017
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
5
Liquid mixture 1
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
3
Mole fraction
Chromatography
4
Liquid mixture 1
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
298.15
5
2
Pressure, kPa
Liquid mixture 2
101
3
1
Mole fraction
5
Liquid mixture 2
1
0.29
2
1
0
1
2
0.006
1
1
0.006
3
0
1
1
0.248
3
1
0.048
2
1
0.015
2
0.006
1
1
0.006
3
0.004
1
1
0.236
3
1
0.06
1
1
0.02
2
0.007
1
1
0.007
3
0.006
1
1
0.226
3
1
0.073
2
1
0.014
2
0.008
1
1
0.008
3
0.008
1
1
0.21
2
1
0.087
2
1
0.012
2
0.009
1
1
0.009
3
0.01
1
1
0.178
3
1
0.108
3
1
0.011
2
0.011
2
1
0.01
3
0.017
2
1
0.122
3
1
0.127
3
1
0.01
2
0.015
2
1
0.01
3
0.03
1
1
0.071
2
1
0.087
2
1
0.013
2
0.024
2
1
0.01
3
0.042
2
6
4
1
6
1
5
1
Principal objective of the work
MPG
MPG
4/27/2017
1
Mole fraction
Chromatography
5
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
4
1
Temperature, K
Liquid
298.15
5
2
Pressure, kPa
Liquid
101
3
1
Mole fraction
4
Liquid
1
0.123
3
1
0
4
1
0.157
3
1
0.01
2
1
0.01
1
0.216
3
1
0.057
2
1
0.015
1
0.227
3
1
0.069
2
1
0.013
1
0.246
3
1
0.082
2
1
0.017
1
0.265
3
1
0.121
3
1
0.024
1
0.299
3
1
0.197
3
1
0.034
1
0.319
3
1
0.303
3
1
0.06
1
0.325
3
1
0.364
3
1
0.06
1
0.348
3
1
0.487
3
1
0.026
1
0.41
3
1
0.59
3
1
0.019
7
6
1
5
1
Principal objective of the work
MPG
MPG
4/18/2017
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
298.15
5
2
101
3
1
0.29
2
8
6
1
5
1
Principal objective of the work
MPG
MPG
4/18/2017
1
Mole fraction
Chromatography
5
Liquid mixture 1
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
2
Pressure, kPa
Liquid mixture 2
1
298.15
5
2
101
3
1
0.006
1
1
0.006
9
1
1
6
1
Principal objective of the work
MPG
MPG
4/18/2017
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
298.15
5
2
101
3
1
0.328
3
1
0.01
10
1
1
6
1
Principal objective of the work
MPG
MPG
4/18/2017
1
Mole fraction
Chromatography
1
Liquid mixture 1
Direct value, X
Liquid mixture 1
Liquid mixture 2
1
Temperature, K
Liquid mixture 2
298.15
5
2
Pressure, kPa
Liquid mixture 2
101
3
1
0.016
2
1
0.017
2
11
1
1
6
1
Principal objective of the work
MPG
MPG
4/27/2017
1
Mole fraction
Chromatography
1
Liquid
Direct value, X
Liquid
Crystal
1
1
Temperature, K
Liquid
2
Pressure, kPa
Liquid
1
298.15
5
2
101
3
1
0.803
3
12
1
1
5
1
Principal objective of the work
MPG
MPG
4/27/2017
1
Mole fraction
Chromatography
5
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
1
1
Temperature, K
Liquid
2
Pressure, kPa
Liquid
1
298.15
5
2
101
3
1
0.226
3
1
0.01
13
2
1
6
1
Principal objective of the work
MPG
MPG
4/18/2017
1
Mole fraction
Chromatography
2
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
298.15
5
2
101
3
1
0.752
3
14
2
1
6
1
Principal objective of the work
MPG
MPG
4/18/2017
1
Mole fraction
Chromatography
2
Liquid mixture 1
Direct value, X
Liquid mixture 1
Liquid mixture 2
1
Temperature, K
Liquid mixture 2
2
Pressure, kPa
Liquid mixture 2
1
298.15
5
2
101
3
1
0.003
1
15
3
1
6
1
Principal objective of the work
MPG
MPG
4/18/2017
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
Temperature, K
Liquid mixture 2
2
Pressure, kPa
Liquid mixture 2
1
298.15
5
2
101
3
1
0.003
1
1
0.003
16
3
1
5
1
Principal objective of the work
MPG
MPG
4/27/2017
1
Mole fraction
Chromatography
5
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
3
1
Temperature, K
Liquid
2
Pressure, kPa
Liquid
1
298.15
5
2
101
3
1
0.295
3
1
0.02
17
4
1
6
1
Principal objective of the work
MPG
MPG
4/27/2017
1
Mole fraction
Chromatography
4
Liquid
Direct value, X
Liquid
Crystal
4
1
Temperature, K
Liquid
2
Pressure, kPa
Liquid
1
298.15
5
2
101
3
1
0.123
3
18
4
1
5
1
Principal objective of the work
MPG
MPG
4/27/2017
1
Mole fraction
Chromatography
5
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
4
1
Temperature, K
Liquid
2
Pressure, kPa
Liquid
1
298.15
5
2
101
3
1
0.59
3
1
0.019