2
0
2017
wan
xu
2
journal
Original
Wang, J.[Jian]
Xu, R.[Renjie]
Xu, A.[Anli]
J. Chem. Thermodyn.
2017
2020-09-29
Solubility determination and thermodynamic functions of 2-chlorophenothiazine in nine organic solvents from T = 283.15 K to T = 318.15 K and mixing properties of solutions
Solubility of 2-chlorophenothiazine in nine organic solvents including methanol, ethanol, isopropanol, npropanol, ethyl acetate, acetone, acetonitrile, 1-butanol and 2-butanone was determined experimentally by the isothermal saturation method over a temperature range from T = 283.15 K to T = 318.15 K under 101.1 kPa. Within the studied temperature range, the mole fraction solubility of 2-chlorophenothiazine in these solvents increased with a rise of temperature. Except for the solvent of acetonitrile, they follow the order of 2-butanone greater than (acetone, ethyl acetate) greater than methanol greater than ethanol greater than n-propanol greater than isopropanol greater than 1- butanol. The solubility in ethyl acetate and acetonitrile had the strongest positive dependency on temperature. The determined solubility of 2-chlorophenothiazine in the solvents studied was correlated by using the modified Apelblat equation, Buchowski Ksiazaczak kh equation, Wilson model and NRTL model. The maximum values of root-mean-square deviation (RMSD) and relative average deviation (RAD) were 2.77*10-4 and 0.59%, respectively. In general, the four thermodynamic models were all satisfactory for describing the solubility of 2-chlorophenothiazine, and the Wilson model can correlate the experimental solubility best based on the result of Akaike Information Criterion analysis. Furthermore, the mixing properties including 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 findings will be very useful in optimizing the purification process of 2-chlorophenothiazine.
2-Chlorophenothiazine
Solubility
Thermodynamic model
Mixing property
10.1016/j.jct.2016.11.029
106
132-144
1
InChI=1S/C12H8ClNS/c13-8-5-6-12-10(7-8)14-9-3-1-2-4-11(9)15-12/h1-7,14H
KFZGLJSYQXZIGP-UHFFFAOYSA-N
2-chlorophenothiazine
2-chloro-10H-phenothiazine
C12H8ClNS
1
Commercial source
1
98.3
3
Stated by supplier
2
Crystallization from solution
3
99.5
3
HPLC
2
InChI=1S/CH4O/c1-2/h2H,1H3
OKKJLVBELUTLKV-UHFFFAOYSA-N
methanol
methyl alcohol
CH4O
1
Commercial source
1
None used
2
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
None used
2
99.4
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
None used
2
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
None used
2
99.4
3
Gas chromatography
6
InChI=1S/C4H8O2/c1-3-6-4(2)5/h3H2,1-2H3
XEKOWRVHYACXOJ-UHFFFAOYSA-N
ethyl acetate
ethyl ethanoate
C4H8O2
1
Commercial source
1
None used
2
99.5
3
Gas chromatography
7
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
None used
2
99.5
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
None used
2
99.5
3
Gas chromatography
9
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
None used
2
99.6
3
Gas chromatography
10
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
None used
2
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
472.95
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
21.59
4
1
0.92
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
101.1
4
1
Temperature, K
Liquid
1
283.15
5
1
0.004648
4
1
0.000242
1
285.65
5
1
0.004832
4
1
0.000251
1
288.15
5
1
0.005016
4
1
0.000261
1
290.65
5
1
0.005248
4
1
0.000273
1
293.15
5
1
0.005451
4
1
0.000284
1
295.65
5
1
0.005697
4
1
0.000297
1
298.15
5
1
0.005942
4
1
0.000309
1
300.65
5
1
0.006198
4
1
0.000323
1
303.15
5
1
0.006469
4
1
0.000337
1
305.65
5
1
0.006732
4
1
0.00035
1
308.15
5
1
0.007006
4
1
0.000365
1
310.65
5
1
0.007283
4
1
0.000379
1
313.15
5
1
0.007581
4
1
0.000395
1
315.65
5
1
0.007862
4
1
0.000409
1
318.15
5
1
0.008189
4
1
0.000426
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
101.1
4
1
Temperature, K
Liquid
1
283.15
5
1
0.00431
4
1
0.000224
1
285.65
5
1
0.00446
4
1
0.000232
1
288.15
5
1
0.00465
4
1
0.000242
1
290.65
5
1
0.00486
4
1
0.000253
1
293.15
5
1
0.00505
4
1
0.000263
1
295.65
5
1
0.00525
4
1
0.000273
1
298.15
5
1
0.00546
4
1
0.000284
1
300.65
5
1
0.00569
4
1
0.000296
1
303.15
5
1
0.00592
4
1
0.000308
1
305.65
5
1
0.00617
4
1
0.000321
1
308.15
5
1
0.00641
4
1
0.000334
1
310.65
5
1
0.00667
4
1
0.000347
1
313.15
5
1
0.00695
4
1
0.000362
1
315.65
5
1
0.00723
4
1
0.000376
1
318.15
5
1
0.00756
4
1
0.000393
5
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
101.1
4
1
Temperature, K
Liquid
1
283.15
5
1
0.003541
4
1
0.000184
1
285.65
5
1
0.003778
4
1
0.000197
1
288.15
5
1
0.004064
4
1
0.000212
1
290.65
5
1
0.004354
4
1
0.000227
1
293.15
5
1
0.004666
4
1
0.000243
1
295.65
5
1
0.004977
4
1
0.000259
1
298.15
5
1
0.005321
4
1
0.000277
1
300.65
5
1
0.005639
4
1
0.000294
1
303.15
5
1
0.006003
4
1
0.000312
1
305.65
5
1
0.006331
4
1
0.00033
1
308.15
5
1
0.006717
4
1
0.00035
1
310.65
5
1
0.0071
4
1
0.00037
1
313.15
5
1
0.007555
4
1
0.000393
1
315.65
5
1
0.007953
4
1
0.000414
1
318.15
5
1
0.008368
4
1
0.000436
6
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
101.1
4
1
Temperature, K
Liquid
1
283.15
5
1
0.0041
4
1
0.000213
1
285.65
5
1
0.004255
4
1
0.000221
1
288.15
5
1
0.004457
4
1
0.000232
1
290.65
5
1
0.004664
4
1
0.000243
1
293.15
5
1
0.00487
4
1
0.000253
1
295.65
5
1
0.005085
4
1
0.000265
1
298.15
5
1
0.005303
4
1
0.000276
1
300.65
5
1
0.00552
4
1
0.000287
1
303.15
5
1
0.005753
4
1
0.000299
1
305.65
5
1
0.006005
4
1
0.000313
1
308.15
5
1
0.006222
4
1
0.000324
1
310.65
5
1
0.006489
4
1
0.000338
1
313.15
5
1
0.006776
4
1
0.000353
1
315.65
5
1
0.00705
4
1
0.000367
1
318.15
5
1
0.007365
4
1
0.000383
7
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
101.1
4
1
Temperature, K
Liquid
1
283.15
5
1
0.003799
4
1
0.000198
1
285.65
5
1
0.003972
4
1
0.000207
1
288.15
5
1
0.00415
4
1
0.000216
1
290.65
5
1
0.004332
4
1
0.000225
1
293.15
5
1
0.004538
4
1
0.000236
1
295.65
5
1
0.004726
4
1
0.000246
1
298.15
5
1
0.004933
4
1
0.000257
1
300.65
5
1
0.005129
4
1
0.000267
1
303.15
5
1
0.005358
4
1
0.000279
1
305.65
5
1
0.00556
4
1
0.000289
1
308.15
5
1
0.005801
4
1
0.000302
1
310.65
5
1
0.006052
4
1
0.000315
1
313.15
5
1
0.0063
4
1
0.000328
1
315.65
5
1
0.006572
4
1
0.000342
1
318.15
5
1
0.00687
4
1
0.000358
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
101.1
4
1
Temperature, K
Liquid
1
283.15
5
1
0.02677
4
1
0.00139
1
285.65
5
1
0.02814
4
1
0.00146
1
288.15
5
1
0.03001
4
1
0.00156
1
290.65
5
1
0.03172
4
1
0.00165
1
293.15
5
1
0.03364
4
1
0.00175
1
295.65
5
1
0.03557
4
1
0.00185
1
298.15
5
1
0.03779
4
1
0.00197
1
300.65
5
1
0.03986
4
1
0.00207
1
303.15
5
1
0.04209
4
1
0.00219
1
305.65
5
1
0.04428
4
1
0.0023
1
308.15
5
1
0.04695
4
1
0.00244
1
310.65
5
1
0.04929
4
1
0.00257
1
313.15
5
1
0.05183
4
1
0.0027
1
315.65
5
1
0.05436
4
1
0.00283
1
318.15
5
1
0.05753
4
1
0.00299
9
1
1
6
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
101.1
4
1
Temperature, K
Liquid
1
283.15
5
1
0.01563
4
1
0.00081
1
285.65
5
1
0.01734
4
1
0.0009
1
288.15
5
1
0.01942
4
1
0.00101
1
290.65
5
1
0.02159
4
1
0.00112
1
293.15
5
1
0.02396
4
1
0.00125
1
295.65
5
1
0.02653
4
1
0.00138
1
298.15
5
1
0.02914
4
1
0.00152
1
300.65
5
1
0.03228
4
1
0.00168
1
303.15
5
1
0.03571
4
1
0.00186
1
305.65
5
1
0.0397
4
1
0.00207
1
308.15
5
1
0.04351
4
1
0.00227
1
310.65
5
1
0.04837
4
1
0.00252
1
313.15
5
1
0.05278
4
1
0.00275
1
315.65
5
1
0.05755
4
1
0.003
1
318.15
5
1
0.06249
4
1
0.00325
10
9
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
101.1
4
1
Temperature, K
Liquid
1
283.15
5
1
0.003277
4
1
0.000171
1
285.65
5
1
0.003439
4
1
0.000179
1
288.15
5
1
0.003609
4
1
0.000188
1
290.65
5
1
0.003809
4
1
0.000198
1
293.15
5
1
0.004009
4
1
0.000209
1
295.65
5
1
0.004217
4
1
0.000219
1
298.15
5
1
0.004447
4
1
0.000231
1
300.65
5
1
0.004681
4
1
0.000244
1
303.15
5
1
0.004922
4
1
0.000256
1
305.65
5
1
0.005181
4
1
0.00027
1
308.15
5
1
0.005428
4
1
0.000283
1
310.65
5
1
0.005701
4
1
0.000297
1
313.15
5
1
0.005964
4
1
0.00031
1
315.65
5
1
0.006243
4
1
0.000325
1
318.15
5
1
0.006529
4
1
0.00034
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
101.1
4
1
Temperature, K
Liquid
1
283.15
5
1
0.03372
4
1
0.00176
1
285.65
5
1
0.03559
4
1
0.00185
1
288.15
5
1
0.03777
4
1
0.00197
1
290.65
5
1
0.04016
4
1
0.00209
1
293.15
5
1
0.04265
4
1
0.00222
1
295.65
5
1
0.04553
4
1
0.00237
1
298.15
5
1
0.04838
4
1
0.00252
1
300.65
5
1
0.05128
4
1
0.00267
1
303.15
5
1
0.05459
4
1
0.00284
1
305.65
5
1
0.05785
4
1
0.00301
1
308.15
5
1
0.06115
4
1
0.00318
1
310.65
5
1
0.06461
4
1
0.00336
1
313.15
5
1
0.06826
4
1
0.00355
1
315.65
5
1
0.07265
4
1
0.00378
1
318.15
5
1
0.07713
4
1
0.00401