2
0
2017
joa
tom
0
journal
Original
Joao, K. G.[Karen G.]
Tome, L. C.[Liliana C.]
Gouveia, A. S. L.[Andreia S.L.]
Marrucho, I. M.[Isabel M.]
J. Chem. Eng. Data
2017
2020-09-29
Aqueous Biphasic Systems of Pyrrolidinium Ionic Liquids with Organic Acid-Derived Anions and K3PO4
Aqueous biphasic systems based on ionic liquids (ILs) have been researched as promising extraction and purification routes for a huge diversity of compounds. The inherent tunability offered by ILs combined with the large variety of salts available underlines the reliable phase equilibrium data. In this vein, this work presents novel aqueous biphasic systems based on the 1-butyl-1-methylpyrrolidinium cation combined with anions derived from organic acids, such as acetate, trifluoroacetate, hexanoate, adipate, and one halogenated anion, bromide, in the presence of a powerful salting out species, the inorganic salt K3PO4. The capacity of these ILs to undergo phase separation is discussed in regard to the chemical structure of the IL anion. The results here obtained were compared with those determined for poly(ionic liquid) analogues, and it was observed that while in ILs the hydrophobicity of the anion has the major role in phase splitting, in poly(ionic liquid)s that role is played by the polymer molecular weight. The effect of temperature on the phase equilibria is addressed.
10.1021/acs.jced.6b00487
4
62
1182-1188
1
InChI=1S/3K.H3O4P/c;;;1-5(2,3)4/h;;;(H3,1,2,3,4)/q3*+1;/p-3
LWIHDJKSTIGBAC-UHFFFAOYSA-K
tripotassium phosphate
phosphoric acid, potassium salt (1:3)
potassium phosphate
K3O4P
1
Commercial source
1
98
2
Stated by supplier
2
InChI=1S/H2O/h1H2
XLYOFNOQVPJJNP-UHFFFAOYSA-N
water
H2O
1
Commercial source
1
99.9
3
Estimated by the compiler
2
Fractional distillation
3
InChI=1S/C7H16N.C2H4O2/c1-3-8(2)6-4-5-7-8;1-2(3)4/h3-7H2,1-2H3;1H3,(H,3,4)/q+1;/p-1
SAVPWWJXFDHTAZ-UHFFFAOYSA-M
1-ethyl-1-methylpyrrolidinium acetate
C9H19NO2
1
Synthesized by the authors
1
95
2
NMR (proton)
2
Dried by vacuum heating
4
InChI=1S/C7H16N.C2HF3O2/c1-3-8(2)6-4-5-7-8;3-2(4,5)1(6)7/h3-7H2,1-2H3;(H,6,7)/q+1;/p-1
CXBGOFKDJHIOHB-UHFFFAOYSA-M
1-ethyl-1-methylpyrrolidinium trifluoroacetate
C9H16F3NO2
1
Synthesized by the authors
1
98.4
3
NMR (proton)
2
Dried by vacuum heating
5
InChI=1S/C7H16N.C6H12O2/c1-3-8(2)6-4-5-7-8;1-2-3-4-5-6(7)8/h3-7H2,1-2H3;2-5H2,1H3,(H,7,8)/q+1;/p-1
BOIQWQPNXSYONN-UHFFFAOYSA-M
1-ethyl-1-methylpyrrolidinium hexanoate
C13H27NO2
1
Synthesized by the authors
1
97.3
3
NMR (proton)
2
Dried by vacuum heating
6
InChI=1S/C7H16N.C6H10O4/c1-3-8(2)6-4-5-7-8;7-5(8)3-1-2-4-6(9)10/h3-7H2,1-2H3;1-4H2,(H,7,8)(H,9,10)/q+1;/p-1
ZAUICVLVBVJIHD-UHFFFAOYSA-M
1-ethyl-1-methylpyrrolidinium hydrogen adipate
C13H25NO4
1
Synthesized by the authors
1
97.3
3
NMR (proton)
2
Dried by vacuum heating
7
InChI=1S/C7H16N.BrH/c1-3-8(2)6-4-5-7-8;/h3-7H2,1-2H3;1H/q+1;/p-1
KHJQQUGSPDBDRM-UHFFFAOYSA-M
1-ethyl-1-methylpyrrolidinium bromide
N-Ethyl-N-methylpyrrolidinium bromide
C7H16BrN
1
Commercial source
1
99
2
Stated by supplier
1
2
1
1
1
3
1
Principal objective of the work
EP
EP
2/13/2017
1
Mass fraction
Titration method
1
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 1
298.15
5
2
Pressure, kPa
Liquid mixture 1
100
1
1
Mass fraction
3
Liquid mixture 1
1
0.38332
5
1
0.030456
5
1
0.000945
1
0.33187
5
1
0.044348
5
1
0.001376
1
0.28684
5
1
0.068323
5
1
0.00212
1
0.24904
5
1
0.091178
5
1
0.002828
1
0.22329
5
1
0.10748
5
1
0.00333
1
0.2063
5
1
0.12141
5
1
0.00377
1
0.19063
5
1
0.13494
5
1
0.00419
1
0.15482
5
1
0.17072
5
1
0.00529
1
0.13802
5
1
0.18966
5
1
0.00588
1
0.13115
5
1
0.1961
5
1
0.00608
1
0.11746
5
1
0.21112
5
1
0.00655
1
0.10406
5
1
0.22634
5
1
0.00702
1
0.090923
5
1
0.24148
5
1
0.00749
1
0.078101
5
1
0.25699
5
1
0.00797
1
0.072644
5
1
0.26406
5
1
0.00819
1
0.06625
5
1
0.27219
5
1
0.00844
1
0.061842
5
1
0.27821
5
1
0.00862
1
0.055091
5
1
0.28793
5
1
0.00893
1
0.042799
5
1
0.30765
5
1
0.00954
2
2
1
1
1
4
1
Principal objective of the work
EP
EP
2/13/2017
1
Mass fraction
Titration method
1
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 1
298.15
5
2
Pressure, kPa
Liquid mixture 1
100
1
1
Mass fraction
4
Liquid mixture 1
1
0.40291
5
1
0.045621
5
1
0.001415
1
0.373
5
1
0.055847
5
1
0.001732
1
0.34567
5
1
0.06919
5
1
0.002145
1
0.32315
5
1
0.076593
5
1
0.002374
1
0.30711
5
1
0.083884
5
1
0.002601
1
0.28101
5
1
0.097145
5
1
0.003012
1
0.26441
5
1
0.10668
5
1
0.00331
1
0.25095
5
1
0.11377
5
1
0.00353
1
0.23802
5
1
0.1207
5
1
0.00374
1
0.22522
5
1
0.12826
5
1
0.00398
1
0.20876
5
1
0.13873
5
1
0.0043
1
0.18963
5
1
0.15032
5
1
0.00466
1
0.17069
5
1
0.1622
5
1
0.00503
1
0.15752
5
1
0.17038
5
1
0.00528
1
0.14784
5
1
0.17671
5
1
0.00548
1
0.13689
5
1
0.18464
5
1
0.00572
1
0.12441
5
1
0.19301
5
1
0.00598
1
0.11051
5
1
0.20305
5
1
0.00629
1
0.093586
5
1
0.2178
5
1
0.00675
1
0.082512
5
1
0.22577
5
1
0.007
1
0.073104
5
1
0.23473
5
1
0.00728
1
0.064221
5
1
0.24465
5
1
0.00758
1
0.057318
5
1
0.25175
5
1
0.0078
1
0.050871
5
1
0.25961
5
1
0.00805
1
0.045232
5
1
0.26683
5
1
0.00827
1
0.039586
5
1
0.27538
5
1
0.00854
1
0.034278
5
1
0.28411
5
1
0.00881
1
0.028691
5
1
0.29502
5
1
0.00915
1
0.023408
5
1
0.30611
5
1
0.00949
3
5
1
2
1
1
1
Principal objective of the work
EP
EP
2/13/2017
1
Mass fraction
Titration method
1
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 1
298.15
5
2
Pressure, kPa
Liquid mixture 1
100
1
1
Mass fraction
5
Liquid mixture 1
1
0.28649
5
1
0.083344
5
1
0.002585
1
0.26282
5
1
0.096315
5
1
0.002986
1
0.24291
5
1
0.1079
5
1
0.00335
1
0.22558
5
1
0.11849
5
1
0.00367
1
0.20897
5
1
0.13009
5
1
0.00403
1
0.19597
5
1
0.13649
5
1
0.00423
1
0.17768
5
1
0.15011
5
1
0.00465
1
0.16263
5
1
0.16087
5
1
0.00499
1
0.14975
5
1
0.16957
5
1
0.00526
1
0.13778
5
1
0.17848
5
1
0.00553
1
0.12585
5
1
0.18788
5
1
0.00582
1
0.11492
5
1
0.19601
5
1
0.00608
1
0.10683
5
1
0.20313
5
1
0.0063
1
0.099859
5
1
0.20784
5
1
0.00644
1
0.087156
5
1
0.2185
5
1
0.00677
1
0.068198
5
1
0.2353
5
1
0.00729
1
0.058006
5
1
0.24538
5
1
0.00761
1
0.048197
5
1
0.25541
5
1
0.00792
1
0.040234
5
1
0.26506
5
1
0.00822
1
0.030915
5
1
0.27782
5
1
0.00861
1
0.019686
5
1
0.29731
5
1
0.00922
4
6
1
2
1
1
1
Principal objective of the work
EP
EP
2/13/2017
1
Mass fraction
Titration method
1
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 1
298.15
5
2
Pressure, kPa
Liquid mixture 1
100
1
1
Mass fraction
6
Liquid mixture 1
1
0.11489
5
1
0.24009
5
1
0.00744
1
0.081561
5
1
0.26489
5
1
0.00821
1
0.053787
5
1
0.2919
5
1
0.00905
1
0.049149
5
1
0.2969
5
1
0.0092
1
0.04463
5
1
0.30253
5
1
0.00938
1
0.034368
5
1
0.31535
5
1
0.00978
1
0.019734
5
1
0.34181
5
1
0.0106
5
2
1
1
1
7
1
Principal objective of the work
EP
EP
2/13/2017
1
Mass fraction
Titration method
1
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 1
298.15
5
2
Pressure, kPa
Liquid mixture 1
100
1
1
Mass fraction
7
Liquid mixture 1
1
0.49123
5
1
0.018282
5
1
0.000569
1
0.45408
5
1
0.027722
5
1
0.000861
1
0.42713
5
1
0.036519
5
1
0.001133
1
0.39421
5
1
0.042278
5
1
0.001311
1
0.37439
5
1
0.048571
5
1
0.001507
1
0.35786
5
1
0.05504
5
1
0.001708
1
0.32721
5
1
0.068963
5
1
0.002139
1
0.30032
5
1
0.080657
5
1
0.002501
1
0.27596
5
1
0.092994
5
1
0.002883
1
0.25785
5
1
0.10271
5
1
0.00318
1
0.23142
5
1
0.11928
5
1
0.0037
1
0.19859
5
1
0.13066
5
1
0.00405
1
0.18427
5
1
0.1409
5
1
0.00437
1
0.17227
5
1
0.15885
5
1
0.00493
1
0.16126
5
1
0.16535
5
1
0.00512
1
0.14854
5
1
0.17438
5
1
0.0054
1
0.13105
5
1
0.18755
5
1
0.00581
1
0.11209
5
1
0.20321
5
1
0.0063
1
0.093554
5
1
0.21915
5
1
0.00679
1
0.076332
5
1
0.23642
5
1
0.00733
1
0.058792
5
1
0.25762
5
1
0.00799
1
0.041761
5
1
0.2832
5
1
0.00878
1
0.022968
5
1
0.32339
5
1
0.01003