2
0
2019
wu
wan
4
journal
Original
Wu, J.[Jiaxin]
Wang, J.[Jian]
Farajtabar, A.[Ali]
Zhao, H.[Hongkun]
J. Chem. Eng. Data
2019
2020-09-29
Solubility and Solution Thermodynamics of 2,6-Dichloro-4-nitroaniline in 12 Pure Solvents at Temperatures from 278.15 to 323.15 K
Through the shake-flask method, the solubility of 2,6-dichloro-4-nitroaniline (DCNA) in twelve pure solvents of n-butanol, n-propanol, methanol, ethylene glycol (EG),ethanol, isopropanol, acetonitrile, cyclohexane, 1,4-dioxoane, ethyl acetate, water and N-methyl pyrrolidone (NMP) was achieved over the temperatures from 278.15 to 323.15 K at ambient pressure of p = 101.2 kPa. The mole fraction solubility of DCNA in above solvents increased as the temperature increased and ranked as: NMP greater than 1,4-dioxoane greater than ethyl acetate greater than acetonitrile greater than n-butanol greater than n-propanol greater than ethanol greater than EG greater than isopropanol greater than methanol greater than cyclohexane greater than water. The solvent-solvent and solvent-solute interactions upon the DCNA solubility were investigated using the linear solvation energy relationship on the basis of the solvent descriptors. The acquired solubility was correlated using the NRTL model, h equation, modified Apelblat equation and Wilson model. The obtained maximum relative average deviation and root-mean-square deviation through the four models were 6.53x10-2 and 13.73x10-4, respectively. In general, the relative average deviation values achieved through the modified Apelblat equation were lower than those with the other three equations for a certain solvent. In addition, the mixing properties, reduced excess enthalpy and activity coefficient under infinitesimal concentration were derived based on the Wilson model.
10.1021/acs.jced.9b00778
12
64
5869-5877
1
InChI=1S/C6H4Cl2N2O2/c7-4-1-3(10(11)12)2-5(8)6(4)9/h1-2H,9H2
BIXZHMJUSMUDOQ-UHFFFAOYSA-N
1-amino-2,6-dichloro-4-nitrobenzene
2,6-dichloro-4-nitroaniline
2,6-dichloro-4-nitrobenzenamine
2,6-dichloro-p-nitroaniline
4-nitro-2,6-dichloroaniline
aniline, 2,6-dichloro-4-nitro-
benzenamine, 2,6-dichloro-4-nitro-
dichloran
dicloran
C6H4Cl2N2O2
1
Commercial source
1
95
3
Stated by supplier
2
Crystallization from solution
3
99.4
3
HPLC
2
InChI=1S/CH4O/c1-2/h2H,1H3
OKKJLVBELUTLKV-UHFFFAOYSA-N
methanol
methyl alcohol
CH4O
1
Commercial source
1
99.5
3
Stated by supplier
3
InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N
ethanol
ethyl alcohol
C2H6O
1
Commercial source
1
99.7
3
Stated by supplier
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
99.4
3
Stated by supplier
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
99.7
3
Stated by supplier
6
InChI=1S/C2H6O2/c3-1-2-4/h3-4H,1-2H2
LYCAIKOWRPUZTN-UHFFFAOYSA-N
1,2-ethanediol
1,2-dihydroxyethane
ethane-1,2-diol
ethylene glycol
C2H6O2
1
Commercial source
1
99.5
3
Stated by supplier
7
InChI=1S/C2H3N/c1-2-3/h1H3
WEVYAHXRMPXWCK-UHFFFAOYSA-N
acetonitrile
cyanomethane
ethanenitrile
ethanonitrile
methanecarbonitrile
methyl cyanide
C2H3N
1
Commercial source
1
99.7
3
Stated by supplier
8
InChI=1S/C6H12/c1-2-4-6-5-3-1/h1-6H2
XDTMQSROBMDMFD-UHFFFAOYSA-N
cyclohexane
C6H12
1
Commercial source
1
99.4
3
Stated by supplier
9
InChI=1S/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3
SECXISVLQFMRJM-UHFFFAOYSA-N
N-methylpyrrolidone
1-methyl-2-pyrrolidinone
1-methyl-2-pyrrolidone
1-methyl-5-pyrrolidinone
1-methylazacyclopentan-2-one
1-methylpyrrolidin-2-one
1-methylpyrrolidone
N-methyl-.alpha.-pyrrolidinone
N-methyl-.alpha.-pyrrolidone
N-methyl-.gamma.-butyrolactam
N-methyl-2-pyrrolidinone
N-methyl-2-pyrrolidone
N-methylpyrrolidin-2-one
NMP
C5H9NO
1
Commercial source
1
99.5
3
Stated by supplier
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
99.6
3
Stated by supplier
11
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
Stated by supplier
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
Stated by supplier
13
InChI=1S/H2O/h1H2
XLYOFNOQVPJJNP-UHFFFAOYSA-N
water
H2O
1
Commercial source
1
99.9
3
Estimated by the compiler
1
1
1
13
1
Principal objective of the work
EP
EP
9/30/2019
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
278.15
5
1
1.881e-06
4
1
1.17e-07
1
283.15
5
1
2.527e-06
4
1
1.57e-07
1
288.15
5
1
3.426e-06
4
1
2.13e-07
1
293.15
5
1
4.76e-06
4
1
2.96e-07
1
298.15
5
1
6.431e-06
4
1
3.99e-07
1
303.15
5
1
8.305e-06
4
1
5.15e-07
1
308.15
5
1
1.061e-05
4
1
6.6e-07
1
313.15
5
1
1.369e-05
4
1
8.5e-07
1
318.15
5
1
1.723e-05
4
1
1.07e-06
1
323.15
5
1
2.18e-05
4
1
1.35e-06
2
1
1
2
1
Principal objective of the work
EP
EP
9/30/2019
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
278.15
5
1
0.0007054
4
1
4.38e-05
1
283.15
5
1
0.0008142
4
1
5.05e-05
1
288.15
5
1
0.0009867
4
1
6.12e-05
1
293.15
5
1
0.00121
4
1
7.5e-05
1
298.15
5
1
0.001498
4
1
9.3e-05
1
303.15
5
1
0.001818
4
1
0.000113
1
308.15
5
1
0.002237
4
1
0.000139
1
313.15
5
1
0.002675
4
1
0.000166
1
318.15
5
1
0.003139
4
1
0.000195
1
323.15
5
1
0.003772
4
1
0.000234
3
1
1
3
1
Principal objective of the work
EP
EP
9/30/2019
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
278.15
5
1
0.0008791
4
1
5.45e-05
1
283.15
5
1
0.001018
4
1
6.3e-05
1
288.15
5
1
0.001232
4
1
7.6e-05
1
293.15
5
1
0.001487
4
1
9.2e-05
1
298.15
5
1
0.001831
4
1
0.000114
1
303.15
5
1
0.002221
4
1
0.000138
1
308.15
5
1
0.002677
4
1
0.000166
1
313.15
5
1
0.00325
4
1
0.000202
1
318.15
5
1
0.003839
4
1
0.000238
1
323.15
5
1
0.004552
4
1
0.000282
4
1
1
4
1
Principal objective of the work
EP
EP
9/30/2019
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
278.15
5
1
0.001017
4
1
6.3e-05
1
283.15
5
1
0.001227
4
1
7.6e-05
1
288.15
5
1
0.001464
4
1
9.1e-05
1
293.15
5
1
0.001759
4
1
0.000109
1
298.15
5
1
0.002159
4
1
0.000134
1
303.15
5
1
0.002575
4
1
0.00016
1
308.15
5
1
0.003073
4
1
0.000191
1
313.15
5
1
0.003643
4
1
0.000226
1
318.15
5
1
0.004412
4
1
0.000274
1
323.15
5
1
0.005459
4
1
0.000339
5
1
1
5
1
Principal objective of the work
EP
EP
9/30/2019
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
0.0009301
4
1
5.77e-05
1
288.15
5
1
0.001107
4
1
6.9e-05
1
293.15
5
1
0.001326
4
1
8.2e-05
1
298.15
5
1
0.001617
4
1
0.0001
1
303.15
5
1
0.001952
4
1
0.000121
1
308.15
5
1
0.00234
4
1
0.000145
1
313.15
5
1
0.002808
4
1
0.000174
1
318.15
5
1
0.003381
4
1
0.00021
1
323.15
5
1
0.004126
4
1
0.000256
6
1
1
10
1
Principal objective of the work
EP
EP
9/30/2019
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
278.15
5
1
0.00121
4
1
7.5e-05
1
283.15
5
1
0.001477
4
1
9.2e-05
1
288.15
5
1
0.001723
4
1
0.000107
1
293.15
5
1
0.002158
4
1
0.000134
1
298.15
5
1
0.002597
4
1
0.000161
1
303.15
5
1
0.003081
4
1
0.000191
1
308.15
5
1
0.003782
4
1
0.000235
1
313.15
5
1
0.004459
4
1
0.000277
1
318.15
5
1
0.005425
4
1
0.000337
1
323.15
5
1
0.006383
4
1
0.000396
7
1
1
6
1
Principal objective of the work
EP
EP
9/30/2019
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
278.15
5
1
0.0008145
4
1
5.05e-05
1
283.15
5
1
0.0009688
4
1
6.01e-05
1
288.15
5
1
0.001165
4
1
7.2e-05
1
293.15
5
1
0.001387
4
1
8.6e-05
1
298.15
5
1
0.00167
4
1
0.000104
1
303.15
5
1
0.001954
4
1
0.000121
1
308.15
5
1
0.002362
4
1
0.000147
1
313.15
5
1
0.002805
4
1
0.000174
1
318.15
5
1
0.003381
4
1
0.00021
1
323.15
5
1
0.004124
4
1
0.000256
8
1
1
7
1
Principal objective of the work
EP
EP
9/30/2019
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
278.15
5
1
0.001519
4
1
9.4e-05
1
283.15
5
1
0.001758
4
1
0.000109
1
288.15
5
1
0.002111
4
1
0.000131
1
293.15
5
1
0.002494
4
1
0.000155
1
298.15
5
1
0.00293
4
1
0.000182
1
303.15
5
1
0.003525
4
1
0.000219
1
308.15
5
1
0.004106
4
1
0.000255
1
313.15
5
1
0.004871
4
1
0.000302
1
318.15
5
1
0.005769
4
1
0.000358
1
323.15
5
1
0.006653
4
1
0.000413
9
1
1
8
1
Principal objective of the work
EP
EP
9/30/2019
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
278.15
5
1
0.0001194
4
1
7.4e-06
1
283.15
5
1
0.0001474
4
1
9.1e-06
1
288.15
5
1
0.0001849
4
1
1.15e-05
1
293.15
5
1
0.0002361
4
1
1.47e-05
1
298.15
5
1
0.0003013
4
1
1.87e-05
1
303.15
5
1
0.0003894
4
1
2.42e-05
1
308.15
5
1
0.0005006
4
1
3.11e-05
1
313.15
5
1
0.0006168
4
1
3.83e-05
1
318.15
5
1
0.0007396
4
1
4.59e-05
1
323.15
5
1
0.0009056
4
1
5.62e-05
10
1
1
12
1
Principal objective of the work
EP
EP
9/30/2019
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
293.15
5
1
0.02513
4
1
0.00156
1
298.15
5
1
0.02923
4
1
0.00181
1
303.15
5
1
0.03369
4
1
0.00209
1
308.15
5
1
0.03894
4
1
0.00242
1
313.15
5
1
0.0447
4
1
0.00277
1
318.15
5
1
0.05133
4
1
0.00318
1
323.15
5
1
0.05979
4
1
0.00371
11
1
1
11
1
Principal objective of the work
EP
EP
9/30/2019
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
278.15
5
1
0.008496
4
1
0.000527
1
283.15
5
1
0.009381
4
1
0.000582
1
288.15
5
1
0.0109
4
1
0.00068
1
293.15
5
1
0.01263
4
1
0.00078
1
298.15
5
1
0.01529
4
1
0.00095
1
303.15
5
1
0.01774
4
1
0.0011
1
308.15
5
1
0.02079
4
1
0.00129
1
313.15
5
1
0.02501
4
1
0.00155
1
318.15
5
1
0.02914
4
1
0.00181
1
323.15
5
1
0.03363
4
1
0.00209
12
1
1
9
1
Principal objective of the work
EP
EP
9/30/2019
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
278.15
5
1
0.1347
4
1
0.0084
1
283.15
5
1
0.1415
4
1
0.0088
1
288.15
5
1
0.1493
4
1
0.0093
1
293.15
5
1
0.1591
4
1
0.0099
1
298.15
5
1
0.1689
4
1
0.0105
1
303.15
5
1
0.1789
4
1
0.0111
1
308.15
5
1
0.1888
4
1
0.0117
1
313.15
5
1
0.1992
4
1
0.0124
1
318.15
5
1
0.2113
4
1
0.0131
1
323.15
5
1
0.2271
4
1
0.0141