2
0
2017
che
con
0
journal
Original
Cheng, C.[Chao]
Cong, Y.[Yang]
Du, C.[Cunbin]
Wang, J.[Jian]
Zhao, H.[Hongkun]
J. Chem. Thermodyn.
2017
2020-09-29
Thermodynamic modelling for solubility of 4-nitrobenzaldehyde in different solvents at temperature range from (273.15 to 313.15) K and mixing properties of solutions
In this work, the solubility of 4-nitrobenzaldehyde in methanol, ethanol, isopropanol, n-butanol, acetone, ethyl acetate, acetonitrile, 2-butanone, N,N-dimethylformamide, n-propanol and toluene was determined with the isothermal saturation method at the temperatures ranging from (273.15 to 313.15) K under atmosphere pressure. The mole fraction solubility increased with increasing temperature and obeyed the following order from high to low in the selected solvents except for acetonitrile: N,N-dimethylformamide greater than acetone greater than 2-butanone greater than ethyl acetate greater than methanol greater than toluene greater than ethanol greater than npropanol greater than n-butanol greater than isopropanol. The results correlated with four models, which corresponded to the Apelblat equation, kh equation, Wilson model and NRTL model. The largest value of root-meansquare deviation (RMSD) was 11.53*10-4, and relative average deviation (RAD), 2.36%. The four thermodynamic models could all be employed to correlate the mole fraction solubility of 4-nitrobenzaldehyde in the selected solvents under studied conditions. In addition, the mixing Gibbs energy, mixing enthalpy, mixing entropy, activity coefficient at infinitesimal concentration (c1 1 ) and reduced excess enthalpy (HE;1 1 ) were computed. The mixing process of 4-nitrobenzaldehyde in the solvents was spontaneous and endothermic. The acquired solubility and thermodynamic studies would be very helpful for optimizing the purification process and further study of 4-nitrobenzaldehyde.
4-Nitrobenzaldehyde
Solubility
Thermodynamic model
Mixing property
10.1016/j.jct.2016.09.012
104
50-60
1
InChI=1S/C7H5NO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5H
BXRFQSNOROATLV-UHFFFAOYSA-N
4-nitrobenzaldehyde
benzaldehyde, 4-nitro-
p-nitrobenzaldehyde
C7H5NO3
1
Commercial source
1
98.2
3
Stated by supplier
2
Crystallization from solution
3
99.6
3
HPLC
2
InChI=1S/CH4O/c1-2/h2H,1H3
OKKJLVBELUTLKV-UHFFFAOYSA-N
methanol
methyl alcohol
CH4O
1
Commercial source
1
99.7
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/c1-3(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
99.4
3
Gas chromatography
5
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
99.5
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/C4H8O2/c1-3-6-4(2)5/h3H2,1-2H3
XEKOWRVHYACXOJ-UHFFFAOYSA-N
ethyl acetate
ethyl ethanoate
C4H8O2
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
99.6
3
Gas chromatography
9
InChI=1S/C7H8/c1-7-5-3-2-4-6-7/h2-6H,1H3
YXFVVABEGXRONW-UHFFFAOYSA-N
toluene
methylbenzene
C7H8
1
Commercial source
1
99.3
3
Gas chromatography
10
InChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3
ZMXDDKWLCZADIW-UHFFFAOYSA-N
dimethylformamide
DMF
DMFA
N,N-dimethylformamide
N,N-dimethylmethanamide
dimethylformamide (DMF)
C3H7NO
1
Commercial source
1
99.4
3
Gas chromatography
11
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
99.3
3
Gas chromatography
12
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
99.5
3
Gas chromatography
1
1
1
Principal objective of the work
AB
TRC
3/30/2017
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
380.35
5
1
1.06
2
1
1
Principal objective of the work
AB
TRC
3/30/2017
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
25.1
4
1
1.04
3
2
1
1
1
Principal objective of the work
AB
TRC
3/30/2017
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
101.1
4
1
Temperature, K
Liquid
1
273.15
5
1
0.02629
4
1
0.00126
1
278.15
5
1
0.03229
4
1
0.00155
1
283.15
5
1
0.03983
4
1
0.00191
1
288.15
5
1
0.04885
4
1
0.00235
1
293.15
5
1
0.05962
4
1
0.00287
1
298.15
5
1
0.07308
4
1
0.00351
1
303.15
5
1
0.08837
4
1
0.00425
1
308.15
5
1
0.1076
4
1
0.0052
1
313.15
5
1
0.1304
4
1
0.0063
4
3
1
1
1
Principal objective of the work
AB
TRC
3/30/2017
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
101.1
4
1
Temperature, K
Liquid
1
273.15
5
1
0.0151
4
1
0.00073
1
278.15
5
1
0.01767
4
1
0.00085
1
283.15
5
1
0.01993
4
1
0.00096
1
288.15
5
1
0.0232
4
1
0.00112
1
293.15
5
1
0.02649
4
1
0.00127
1
298.15
5
1
0.03101
4
1
0.00149
1
303.15
5
1
0.03656
4
1
0.00176
1
308.15
5
1
0.04221
4
1
0.00203
1
313.15
5
1
0.0498
4
1
0.00239
5
4
1
1
1
Principal objective of the work
AB
TRC
3/30/2017
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
101.1
4
1
Temperature, K
Liquid
1
273.15
5
1
0.003263
4
1
0.000157
1
278.15
5
1
0.003989
4
1
0.000192
1
283.15
5
1
0.004512
4
1
0.000217
1
288.15
5
1
0.005001
4
1
0.00024
1
293.15
5
1
0.005889
4
1
0.000283
1
298.15
5
1
0.007031
4
1
0.000338
1
303.15
5
1
0.008435
4
1
0.000405
1
308.15
5
1
0.009289
4
1
0.000446
1
313.15
5
1
0.01108
4
1
0.00053
6
5
1
1
1
Principal objective of the work
AB
TRC
3/30/2017
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
101.1
4
1
Temperature, K
Liquid
1
273.15
5
1
0.01181
4
1
0.00057
1
278.15
5
1
0.01284
4
1
0.00062
1
283.15
5
1
0.01438
4
1
0.00069
1
288.15
5
1
0.01613
4
1
0.00078
1
293.15
5
1
0.01798
4
1
0.00086
1
298.15
5
1
0.02003
4
1
0.00096
1
303.15
5
1
0.02247
4
1
0.00108
1
308.15
5
1
0.02515
4
1
0.00121
1
313.15
5
1
0.02834
4
1
0.00136
7
6
1
1
1
Principal objective of the work
AB
TRC
3/30/2017
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
101.1
4
1
Temperature, K
Liquid
1
273.15
5
1
0.03891
4
1
0.00187
1
278.15
5
1
0.05095
4
1
0.00245
1
283.15
5
1
0.06622
4
1
0.00318
1
288.15
5
1
0.08509
4
1
0.00409
1
293.15
5
1
0.1075
4
1
0.0052
1
298.15
5
1
0.1344
4
1
0.0065
1
303.15
5
1
0.1661
4
1
0.008
1
308.15
5
1
0.2024
4
1
0.0097
1
313.15
5
1
0.2441
4
1
0.0117
8
7
1
1
1
Principal objective of the work
AB
TRC
3/30/2017
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
101.1
4
1
Temperature, K
Liquid
1
273.15
5
1
0.03212
4
1
0.00154
1
278.15
5
1
0.04005
4
1
0.00193
1
283.15
5
1
0.04877
4
1
0.00234
1
288.15
5
1
0.05912
4
1
0.00284
1
293.15
5
1
0.07195
4
1
0.00346
1
298.15
5
1
0.08697
4
1
0.00418
1
303.15
5
1
0.1056
4
1
0.0051
1
308.15
5
1
0.1263
4
1
0.0061
1
313.15
5
1
0.1511
4
1
0.0073
9
8
1
1
1
Principal objective of the work
AB
TRC
3/30/2017
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
101.1
4
1
Temperature, K
Liquid
1
273.15
5
1
0.02616
4
1
0.00126
1
278.15
5
1
0.03507
4
1
0.00169
1
283.15
5
1
0.04705
4
1
0.00226
1
288.15
5
1
0.06142
4
1
0.00295
1
293.15
5
1
0.08007
4
1
0.00385
1
298.15
5
1
0.1025
4
1
0.0049
1
303.15
5
1
0.1297
4
1
0.0062
1
308.15
5
1
0.161
4
1
0.0077
1
313.15
5
1
0.1989
4
1
0.0096
10
9
1
1
1
Principal objective of the work
AB
TRC
3/30/2017
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
101.1
4
1
Temperature, K
Liquid
1
273.15
5
1
0.01911
4
1
0.00092
1
278.15
5
1
0.02386
4
1
0.00115
1
283.15
5
1
0.02974
4
1
0.00143
1
288.15
5
1
0.03662
4
1
0.00176
1
293.15
5
1
0.04489
4
1
0.00216
1
298.15
5
1
0.05467
4
1
0.00263
1
303.15
5
1
0.06568
4
1
0.00316
1
308.15
5
1
0.08017
4
1
0.00385
1
313.15
5
1
0.09685
4
1
0.00466
11
12
1
1
1
Principal objective of the work
AB
TRC
3/30/2017
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
101.1
4
1
Temperature, K
Liquid
1
273.15
5
1
0.03673
4
1
0.00177
1
278.15
5
1
0.04586
4
1
0.0022
1
283.15
5
1
0.05672
4
1
0.00273
1
288.15
5
1
0.06892
4
1
0.00331
1
293.15
5
1
0.0836
4
1
0.00402
1
298.15
5
1
0.1018
4
1
0.0049
1
303.15
5
1
0.1223
4
1
0.0059
1
308.15
5
1
0.147
4
1
0.0071
1
313.15
5
1
0.1744
4
1
0.0084
12
10
1
1
1
Principal objective of the work
AB
TRC
3/30/2017
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
101.1
4
1
Temperature, K
Liquid
1
273.15
5
1
0.104
4
1
0.005
1
278.15
5
1
0.1186
4
1
0.0057
1
283.15
5
1
0.135
4
1
0.0065
1
288.15
5
1
0.1521
4
1
0.0073
1
293.15
5
1
0.1703
4
1
0.0082
1
298.15
5
1
0.1917
4
1
0.0092
1
303.15
5
1
0.2135
4
1
0.0103
1
308.15
5
1
0.2374
4
1
0.0114
1
313.15
5
1
0.2617
4
1
0.0126
13
11
1
1
1
Principal objective of the work
AB
TRC
3/30/2017
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
101.1
4
1
Temperature, K
Liquid
1
273.15
5
1
0.01396
4
1
0.00067
1
278.15
5
1
0.01521
4
1
0.00073
1
283.15
5
1
0.01684
4
1
0.00081
1
288.15
5
1
0.019
4
1
0.00091
1
293.15
5
1
0.02156
4
1
0.00104
1
298.15
5
1
0.0243
4
1
0.00117
1
303.15
5
1
0.02723
4
1
0.00131
1
308.15
5
1
0.03122
4
1
0.0015
1
313.15
5
1
0.03615
4
1
0.00174