2
0
2017
wu
zha
0
journal
Original
Wu, Y.[Yufang]
Zhang, X.[Xiaolu]
Di, Y.[Yanchao]
Zhang, Y.[Yanting]
J. Chem. Thermodyn.
2017
2020-09-29
Solubility determination and modelling of 4-nitro-1,2-phenylenediamine in eleven organic solvents from T = (283.15 to 318.15) K and thermodynamic properties of solutions
By the isothermal saturation method, the solid-liquid equilibrium of 4-nitro-1,2-phenylenediamine in eleven organic solvents (methanol, ethanol, n-propanol, isopropanol, acetone, 2-butanone, acetonitrile, ethyl acetate, n-butanol, toluene and 1,4-dioxane) was obtained experimentally within temperature range from (283.15 to 318.15) K under atmospheric pressure, and the solubility values of 4-nitro-1,2- phenylenediamine in these solvents were determined by a high-performance liquid chromatography (HPLC). Within this temperature range, the mole fraction solubility of 4-nitro-1,2-phenylenediamine in selected organic solvents increased with increasing temperature. The descending order of the solubility values was as follows: acetone greater than 2-butanone greater than 1,4-dioxane greater than ethyl acetate greater than acetonitrile greater than methanol greater than ethanol greater than isopropanol greater than n-propanol greater than n-butanol greater than toluene. The solubility values for 4-nitro-1,2-phenylenediamine in the selected solvents were correlated and calculated by using the modified Apelblat equation, kh equation, Wilson model and NRTL model. Results showed that the largest values of RAD and RMSD obtained by the four models were 1.53% and 0.83 10 4, respectively. The modified Apelblat equation can correlate the experimental results best according to the result of AIC analysis. Moreover, the mixing properties including the mixing Gibbs energy, mixing enthalpy, mixing entropy, activity coefficient at infinitesimal concentration oc1 1 P and reduced excess enthalpy oHE;1 1 P were calculated. The solution process of 4-nitro-1,2-phenylenediamine is spontaneous and favourable in the selected solvents. Knowledge of solubility and associated thermodynamic studies are important in optimizing the purification process of 4-nitro-1,2-phenylenediamine.
4-Nitro-1,2-phenylenediamine
Solubility
Thermodynamic model
Mixing property
10.1016/j.jct.2016.11.014
106
22-35
1
InChI=1S/C6H7N3O2/c7-5-2-1-4(9(10)11)3-6(5)8/h1-3H,7-8H2
RAUWPNXIALNKQM-UHFFFAOYSA-N
4-nitro-1,2-benzenediamine
(2-amino-4-nitrophenyl)amine
1,2-diamino-4-nitrobenzene
2-amino-4-nitroaniline
4-nitro-1,2-phenylenediamine
p-nitro-o-phenylenediamine
C6H7N3O2
1
Commercial source
1
98.2
3
Stated by supplier
2
Crystallization from solution
3
99.7
3
HPLC
2
InChI=1S/CH4O/c1-2/h2H,1H3
OKKJLVBELUTLKV-UHFFFAOYSA-N
methanol
methyl alcohol
CH4O
1
Commercial source
1
99.6
3
Gas chromatography
3
InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N
ethanol
ethyl alcohol
C2H6O
1
Commercial source
1
99.5
3
Gas chromatography
4
InChI=1S/C3H8O/c1-2-3-4/h4H,2-3H2,1H3
BDERNNFJNOPAEC-UHFFFAOYSA-N
propan-1-ol
1-propanol
n-propanol
n-propyl alcohol
C3H8O
1
Commercial source
1
99.5
3
Gas chromatography
5
InChI=1S/C3H8O/c1-3(2)4/h3-4H,1-2H3
KFZMGEQAYNKOFK-UHFFFAOYSA-N
propan-2-ol
2-propanol
isopropanol
isopropyl alcohol
sec-propyl alcohol
C3H8O
1
Commercial source
1
99.5
3
Gas chromatography
6
InChI=1S/C3H6O/c1-3(2)4/h1-2H3
CSCPPACGZOOCGX-UHFFFAOYSA-N
acetone
2-propanone
dimethyl ketone
propan-2-one
propanone
pyroacetic ether
C3H6O
1
Commercial source
1
99.4
3
Gas chromatography
7
InChI=1S/C4H8O/c1-3-4(2)5/h3H2,1-2H3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N
butanone
2-butanone
butan-2-one
ethyl methyl ketone
methyl ethyl ketone
C4H8O
1
Commercial source
1
99.6
3
Gas chromatography
8
InChI=1S/C2H3N/c1-2-3/h1H3
WEVYAHXRMPXWCK-UHFFFAOYSA-N
acetonitrile
cyanomethane
ethanenitrile
ethanonitrile
methanecarbonitrile
methyl cyanide
C2H3N
1
Commercial source
1
99.4
3
Gas chromatography
9
InChI=1S/C4H8O2/c1-3-6-4(2)5/h3H2,1-2H3
XEKOWRVHYACXOJ-UHFFFAOYSA-N
ethyl acetate
ethyl ethanoate
C4H8O2
1
Commercial source
1
99.5
3
Gas chromatography
10
InChI=1S/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3
LRHPLDYGYMQRHN-UHFFFAOYSA-N
butan-1-ol
1-butanol
n-butanol
n-butyl alcohol
C4H10O
1
Commercial source
1
99.3
3
Gas chromatography
11
InChI=1S/C7H8/c1-7-5-3-2-4-6-7/h2-6H,1H3
YXFVVABEGXRONW-UHFFFAOYSA-N
toluene
methylbenzene
C7H8
1
Commercial source
1
99.4
3
Gas chromatography
12
InChI=1S/C4H8O2/c1-2-6-4-3-5-1/h1-4H2
RYHBNJHYFVUHQT-UHFFFAOYSA-N
1,4-dioxane
1,4-dioxacyclohexane
dioxane
p-dioxane
tetrahydro-1,4-dioxin
C4H8O2
1
Commercial source
1
99.5
3
Gas chromatography
1
1
1
Principal objective of the work
AB
TRC
6/24/2017
1
Normal melting temperature, K
DTA
Crystal
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Crystal
Liquid
Air at 1 atmosphere
1
472.4
5
1
1.06
2
1
1
Principal objective of the work
AB
TRC
6/24/2017
1
Molar enthalpy of transition or fusion, kJ/mol
DSC
Crystal
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Crystal
Liquid
Air at 1 atmosphere
1
36.28
4
1
1.07
3
2
1
1
1
Principal objective of the work
AB
TRC
6/24/2017
1
Mole fraction
Chromatography
1
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
1
1
Pressure, kPa
Liquid
101.2
4
1
Temperature, K
Liquid
1
283.15
5
1
0.001109
4
1
4.4e-05
1
285.65
5
1
0.0012
4
1
4.8e-05
1
288.15
5
1
0.001301
4
1
5.2e-05
1
290.65
5
1
0.001415
4
1
5.7e-05
1
293.15
5
1
0.001527
4
1
6.1e-05
1
295.65
5
1
0.001667
4
1
6.7e-05
1
298.15
5
1
0.0018
4
1
7.2e-05
1
300.65
5
1
0.00194
4
1
7.8e-05
1
303.15
5
1
0.002079
4
1
8.3e-05
1
305.65
5
1
0.002233
4
1
8.9e-05
1
308.15
5
1
0.002376
4
1
9.5e-05
1
310.65
5
1
0.002538
4
1
0.000102
1
313.15
5
1
0.002693
4
1
0.000108
1
315.65
5
1
0.002874
4
1
0.000115
1
318.15
5
1
0.003085
4
1
0.000124
4
3
1
1
1
Principal objective of the work
AB
TRC
6/24/2017
1
Mole fraction
Chromatography
1
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
1
1
Pressure, kPa
Liquid
101.2
4
1
Temperature, K
Liquid
1
283.15
5
1
0.0008707
4
1
3.49e-05
1
285.65
5
1
0.0009465
4
1
3.79e-05
1
288.15
5
1
0.00102
4
1
4.1e-05
1
290.65
5
1
0.001111
4
1
4.5e-05
1
293.15
5
1
0.00119
4
1
4.8e-05
1
295.65
5
1
0.001285
4
1
5.1e-05
1
298.15
5
1
0.001388
4
1
5.6e-05
1
300.65
5
1
0.001488
4
1
6e-05
1
303.15
5
1
0.001599
4
1
6.4e-05
1
305.65
5
1
0.001709
4
1
6.8e-05
1
308.15
5
1
0.001823
4
1
7.3e-05
1
310.65
5
1
0.001948
4
1
7.8e-05
1
313.15
5
1
0.002093
4
1
8.4e-05
1
315.65
5
1
0.002233
4
1
8.9e-05
1
318.15
5
1
0.002422
4
1
9.7e-05
5
4
1
1
1
Principal objective of the work
AB
TRC
6/24/2017
1
Mole fraction
Chromatography
1
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
1
1
Pressure, kPa
Liquid
101.2
4
1
Temperature, K
Liquid
1
283.15
5
1
0.0005697
4
1
2.28e-05
1
285.65
5
1
0.0006244
4
1
2.5e-05
1
288.15
5
1
0.0006791
4
1
2.72e-05
1
290.65
5
1
0.0007453
4
1
2.99e-05
1
293.15
5
1
0.0008109
4
1
3.25e-05
1
295.65
5
1
0.0008886
4
1
3.56e-05
1
298.15
5
1
0.0009701
4
1
3.89e-05
1
300.65
5
1
0.00105
4
1
4.2e-05
1
303.15
5
1
0.001151
4
1
4.6e-05
1
305.65
5
1
0.001257
4
1
5e-05
1
308.15
5
1
0.001363
4
1
5.5e-05
1
310.65
5
1
0.001486
4
1
6e-05
1
313.15
5
1
0.001618
4
1
6.5e-05
1
315.65
5
1
0.00175
4
1
7e-05
1
318.15
5
1
0.001889
4
1
7.6e-05
6
5
1
1
1
Principal objective of the work
AB
TRC
6/24/2017
1
Mole fraction
Chromatography
1
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
1
1
Pressure, kPa
Liquid
101.2
4
1
Temperature, K
Liquid
1
283.15
5
1
0.0006756
4
1
2.71e-05
1
285.65
5
1
0.0007328
4
1
2.94e-05
1
288.15
5
1
0.0008001
4
1
3.21e-05
1
290.65
5
1
0.0008629
4
1
3.46e-05
1
293.15
5
1
0.0009333
4
1
3.74e-05
1
295.65
5
1
0.001006
4
1
4e-05
1
298.15
5
1
0.001086
4
1
4.4e-05
1
300.65
5
1
0.001169
4
1
4.7e-05
1
303.15
5
1
0.001271
4
1
5.1e-05
1
305.65
5
1
0.001378
4
1
5.5e-05
1
308.15
5
1
0.00148
4
1
5.9e-05
1
310.65
5
1
0.001593
4
1
6.4e-05
1
313.15
5
1
0.001725
4
1
6.9e-05
1
315.65
5
1
0.001871
4
1
7.5e-05
1
318.15
5
1
0.00202
4
1
8.1e-05
7
6
1
1
1
Principal objective of the work
AB
TRC
6/24/2017
1
Mole fraction
Chromatography
1
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
1
1
Pressure, kPa
Liquid
101.2
4
1
Temperature, K
Liquid
1
283.15
5
1
0.02575
4
1
0.00103
1
285.65
5
1
0.02637
4
1
0.00106
1
288.15
5
1
0.027
4
1
0.00108
1
290.65
5
1
0.02777
4
1
0.00111
1
293.15
5
1
0.02844
4
1
0.00114
1
295.65
5
1
0.02916
4
1
0.00117
1
298.15
5
1
0.02993
4
1
0.0012
1
300.65
5
1
0.03062
4
1
0.00123
1
303.15
5
1
0.03146
4
1
0.00126
1
305.65
5
1
0.03223
4
1
0.00129
1
308.15
5
1
0.03305
4
1
0.00132
1
310.65
5
1
0.03391
4
1
0.00136
1
313.15
5
1
0.03474
4
1
0.00139
1
315.65
5
1
0.03564
4
1
0.00143
1
318.15
5
1
0.03655
4
1
0.00146
8
7
1
1
1
Principal objective of the work
AB
TRC
6/24/2017
1
Mole fraction
Chromatography
1
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
1
1
Pressure, kPa
Liquid
101.2
4
1
Temperature, K
Liquid
1
283.15
5
1
0.02131
4
1
0.00085
1
285.65
5
1
0.02191
4
1
0.00088
1
288.15
5
1
0.02253
4
1
0.0009
1
290.65
5
1
0.02316
4
1
0.00093
1
293.15
5
1
0.02381
4
1
0.00095
1
295.65
5
1
0.02451
4
1
0.00098
1
298.15
5
1
0.02523
4
1
0.00101
1
300.65
5
1
0.02599
4
1
0.00104
1
303.15
5
1
0.02675
4
1
0.00107
1
305.65
5
1
0.02755
4
1
0.0011
1
308.15
5
1
0.02837
4
1
0.00114
1
310.65
5
1
0.02921
4
1
0.00117
1
313.15
5
1
0.03009
4
1
0.00121
1
315.65
5
1
0.03103
4
1
0.00124
1
318.15
5
1
0.03196
4
1
0.00128
9
8
1
1
1
Principal objective of the work
AB
TRC
6/24/2017
1
Mole fraction
Chromatography
1
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
1
1
Pressure, kPa
Liquid
101.2
4
1
Temperature, K
Liquid
1
283.15
5
1
0.002443
4
1
9.8e-05
1
285.65
5
1
0.002628
4
1
0.000105
1
288.15
5
1
0.002859
4
1
0.000115
1
290.65
5
1
0.003139
4
1
0.000126
1
293.15
5
1
0.003434
4
1
0.000138
1
295.65
5
1
0.003743
4
1
0.00015
1
298.15
5
1
0.00408
4
1
0.000164
1
300.65
5
1
0.004422
4
1
0.000177
1
303.15
5
1
0.004797
4
1
0.000192
1
305.65
5
1
0.005195
4
1
0.000208
1
308.15
5
1
0.005631
4
1
0.000226
1
310.65
5
1
0.006097
4
1
0.000244
1
313.15
5
1
0.006608
4
1
0.000265
1
315.65
5
1
0.007187
4
1
0.000288
1
318.15
5
1
0.007806
4
1
0.000313
10
1
1
9
1
Principal objective of the work
AB
TRC
6/24/2017
1
Mole fraction
Chromatography
1
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
1
1
Pressure, kPa
Liquid
101.2
4
1
Temperature, K
Liquid
1
283.15
5
1
0.00379
4
1
0.000152
1
285.65
5
1
0.004084
4
1
0.000164
1
288.15
5
1
0.004359
4
1
0.000175
1
290.65
5
1
0.004683
4
1
0.000188
1
293.15
5
1
0.005014
4
1
0.000201
1
295.65
5
1
0.005349
4
1
0.000214
1
298.15
5
1
0.005731
4
1
0.00023
1
300.65
5
1
0.006178
4
1
0.000248
1
303.15
5
1
0.006646
4
1
0.000266
1
305.65
5
1
0.007082
4
1
0.000284
1
308.15
5
1
0.007544
4
1
0.000302
1
310.65
5
1
0.00808
4
1
0.000324
1
313.15
5
1
0.008653
4
1
0.000347
1
315.65
5
1
0.009192
4
1
0.000368
1
318.15
5
1
0.009789
4
1
0.000392
11
10
1
1
1
Principal objective of the work
AB
TRC
6/24/2017
1
Mole fraction
Chromatography
1
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
1
1
Pressure, kPa
Liquid
101.2
4
1
Temperature, K
Liquid
1
283.15
5
1
0.0004478
4
1
1.8e-05
1
285.65
5
1
0.0005045
4
1
2.02e-05
1
288.15
5
1
0.0005677
4
1
2.28e-05
1
290.65
5
1
0.0006328
4
1
2.54e-05
1
293.15
5
1
0.000703
4
1
2.82e-05
1
295.65
5
1
0.0007786
4
1
3.12e-05
1
298.15
5
1
0.0008652
4
1
3.47e-05
1
300.65
5
1
0.0009493
4
1
3.81e-05
1
303.15
5
1
0.001041
4
1
4.2e-05
1
305.65
5
1
0.001141
4
1
4.6e-05
1
308.15
5
1
0.001248
4
1
5e-05
1
310.65
5
1
0.001353
4
1
5.4e-05
1
313.15
5
1
0.001481
4
1
5.9e-05
1
315.65
5
1
0.001613
4
1
6.5e-05
1
318.15
5
1
0.001769
4
1
7.1e-05
12
1
1
11
1
Principal objective of the work
AB
TRC
6/24/2017
1
Mole fraction
Chromatography
1
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
1
1
Pressure, kPa
Liquid
101.2
4
1
Temperature, K
Liquid
1
283.15
5
1
3.312e-05
4
1
1.33e-06
1
285.65
5
1
3.885e-05
4
1
1.56e-06
1
288.15
5
1
4.569e-05
4
1
1.83e-06
1
290.65
5
1
5.292e-05
4
1
2.12e-06
1
293.15
5
1
6.042e-05
4
1
2.42e-06
1
295.65
5
1
6.915e-05
4
1
2.77e-06
1
298.15
5
1
7.866e-05
4
1
3.15e-06
1
300.65
5
1
8.923e-05
4
1
3.58e-06
1
303.15
5
1
0.0001008
4
1
4e-06
1
305.65
5
1
0.000113
4
1
4.5e-06
1
308.15
5
1
0.0001258
4
1
5e-06
1
310.65
5
1
0.0001409
4
1
5.7e-06
1
313.15
5
1
0.0001587
4
1
6.4e-06
1
315.65
5
1
0.0001772
4
1
7.1e-06
1
318.15
5
1
0.0001989
4
1
8e-06
13
1
1
12
1
Principal objective of the work
AB
TRC
6/24/2017
1
Mole fraction
Chromatography
1
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
1
1
Pressure, kPa
Liquid
101.2
4
1
Temperature, K
Liquid
1
283.15
5
1
0.005448
4
1
0.000218
1
285.65
5
1
0.006027
4
1
0.000242
1
288.15
5
1
0.006637
4
1
0.000266
1
290.65
5
1
0.007212
4
1
0.000289
1
293.15
5
1
0.007888
4
1
0.000316
1
295.65
5
1
0.008618
4
1
0.000345
1
298.15
5
1
0.009429
4
1
0.000378
1
300.65
5
1
0.01022
4
1
0.00041
1
303.15
5
1
0.0112
4
1
0.00045
1
305.65
5
1
0.01224
4
1
0.00049
1
308.15
5
1
0.0133
4
1
0.00053
1
310.65
5
1
0.01446
4
1
0.00058
1
313.15
5
1
0.01571
4
1
0.00063
1
315.65
5
1
0.01694
4
1
0.00068
1
318.15
5
1
0.01867
4
1
0.00075