2
0
2016
yan
yan
0
journal
Original
Yang, Y.[Yaoyao]
Yang, P.[Peng]
Du, S.[Shichao]
Li, K.[Kangli]
Zhao, K.[Kaifei]
Xu, S.[Shijie]
Hou, B.[Baohong]
Gong, J.[Junbo]
J. Chem. Thermodyn.
2016
2020-09-29
Solubility determination and thermodynamic modelling of allisartan isoproxil in different binary solvent mixtures from T = (278.15 to 313.15) K and mixing properties of solutions
In this work, the solubility of allisartan isoproxil in binary solvent mixtures, including (acetone + water), (acetonitrile + water) and (methanol + water), was determined by a gravimetric method with the temperature ranging from (278.15 to 313.15) K at atmospheric pressure (p = 0.1 MPa). The solubility of allisartan isoproxil in three binary solvent mixtures all increased with the rising of temperature at a constant solvent composition. For the binary solvent mixtures of (methanol + water), the solubility increased with the increasing of methanol fraction, while it appeared maximum value at a certain solvent composition in the other two binary solvent mixtures (acetone + water and acetonitrile + water). Based on the theory of solubility parameter, Fedors method and two mixing rules were employed to calculate the solubility parameters, by which the proximity of solubility parameters between allisartan isoproxil and binary solvent mixtures explained the co-solvent phenomenon. Additionally, the modified Apelblat equation, CNIBS/R-K model and Jouyban-Acree model were used to correlate the solubility data in binary solvent mixtures, and it turned out that all the three correlation models could give a satisfactory result. Furthermore, the mixing thermodynamic properties were calculated based on NRTL model, which indicated that the mixing process was spontaneous and exothermic.
Allisartan isoproxil
Solubility
Solubility parameter
Thermodynamic models
10.1016/j.jct.2016.08.035
103
432-445
1
InChI=1S/C27H29ClN6O5/c1-4-5-10-22-29-24(28)23(26(35)37-16-38-27(36)39-17(2)3)34(22)15-18-11-13-19(14-12-18)20-8-6-7-9-21(20)25-30-32-33-31-25/h6-9,11-14,17H,4-5,10,15-16H2,1-3H3,(H,30,31,32,33)
XMHJQQAKXRUCHI-UHFFFAOYSA-N
Allisartan isoproxil
((isopropoxycarbonyl)oxy)methyl 1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-butyl-4-chloro-1H-imidazole-5-carboxylate
C27H29ClN6O5
1
Commercial source
1
99.5
3
Stated by supplier
2
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
99.5
3
Stated by supplier
3
InChI=1S/C2H3N/c1-2-3/h1H3
WEVYAHXRMPXWCK-UHFFFAOYSA-N
acetonitrile
cyanomethane
ethanenitrile
ethanonitrile
methanecarbonitrile
methyl cyanide
C2H3N
1
Commercial source
1
99.5
3
Stated by supplier
4
InChI=1S/CH4O/c1-2/h2H,1H3
OKKJLVBELUTLKV-UHFFFAOYSA-N
methanol
methyl alcohol
CH4O
1
Commercial source
1
99.5
3
Stated by supplier
5
InChI=1S/H2O/h1H2
XLYOFNOQVPJJNP-UHFFFAOYSA-N
water
H2O
1
Commercial source
1
99.5
3
Estimation
1
1
1
Principal objective of the work
AB
TRC
2/2/2017
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
424.26
5
1
0.61
2
1
1
Principal objective of the work
AB
TRC
2/2/2017
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
42.78
4
1
1.43
3
2
1
5
1
1
1
Principal objective of the work
AB
TRC
2/2/2017
1
Mole fraction
Gravimetric analysis
1
Liquid
Direct value, X
2
5
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
1
1
Pressure, kPa
Liquid
100
1
1
Temperature, K
Liquid
2
Solvent: Mole fraction
2
Liquid
1
278.15
5
2
0.3
2
1
0.000144
3
1
1.5e-05
1
278.15
5
2
0.4
2
1
0.000688
3
1
6.9e-05
1
278.15
5
2
0.5
2
1
0.00212
3
1
0.00021
1
278.15
5
2
0.6
2
1
0.00428
3
1
0.00043
1
278.15
5
2
0.7
2
1
0.00735
3
1
0.00074
1
278.15
5
2
0.8
2
1
0.0107
4
1
0.00107
1
278.15
5
2
0.9
2
1
0.01231
4
1
0.00123
1
278.15
5
2
1
3
1
0.00987
3
1
0.00099
1
283.15
5
2
0.3
2
1
0.000209
3
1
2.1e-05
1
283.15
5
2
0.4
2
1
0.000912
3
1
9.3e-05
1
283.15
5
2
0.5
2
1
0.00249
3
1
0.00025
1
283.15
5
2
0.6
2
1
0.00514
3
1
0.00052
1
283.15
5
2
0.7
2
1
0.00855
3
1
0.00086
1
283.15
5
2
0.8
2
1
0.01205
4
1
0.00121
1
283.15
5
2
0.9
2
1
0.01335
4
1
0.00134
1
283.15
5
2
1
3
1
0.0112
4
1
0.00112
1
288.15
5
2
0.3
2
1
0.000267
3
1
2.8e-05
1
288.15
5
2
0.4
2
1
0.00131
3
1
0.00013
1
288.15
5
2
0.5
2
1
0.00318
3
1
0.00032
1
288.15
5
2
0.6
2
1
0.00615
3
1
0.00062
1
288.15
5
2
0.7
2
1
0.0102
4
1
0.00102
1
288.15
5
2
0.8
2
1
0.01414
4
1
0.00142
1
288.15
5
2
0.9
2
1
0.01619
4
1
0.00162
1
288.15
5
2
1
3
1
0.0132
4
1
0.00132
1
293.15
5
2
0.3
2
1
0.000344
3
1
3.6e-05
1
293.15
5
2
0.4
2
1
0.00177
3
1
0.00018
1
293.15
5
2
0.5
2
1
0.00407
3
1
0.00041
1
293.15
5
2
0.6
2
1
0.00757
3
1
0.00076
1
293.15
5
2
0.7
2
1
0.01199
4
1
0.0012
1
293.15
5
2
0.8
2
1
0.01652
4
1
0.00166
1
293.15
5
2
0.9
2
1
0.01907
4
1
0.00191
1
293.15
5
2
1
3
1
0.01554
4
1
0.00156
1
298.15
5
2
0.3
2
1
0.000482
3
1
5e-05
1
298.15
5
2
0.4
2
1
0.00229
3
1
0.00023
1
298.15
5
2
0.5
2
1
0.00502
3
1
0.00051
1
298.15
5
2
0.6
2
1
0.00925
3
1
0.00093
1
298.15
5
2
0.7
2
1
0.01457
4
1
0.00146
1
298.15
5
2
0.8
2
1
0.01985
4
1
0.00199
1
298.15
5
2
0.9
2
1
0.0227
4
1
0.00228
1
298.15
5
2
1
3
1
0.01903
4
1
0.00191
1
303.15
5
2
0.3
2
1
0.000664
3
1
6.8e-05
1
303.15
5
2
0.4
2
1
0.0029
3
1
0.00029
1
303.15
5
2
0.5
2
1
0.0065
3
1
0.00066
1
303.15
5
2
0.6
2
1
0.01175
4
1
0.00118
1
303.15
5
2
0.7
2
1
0.01824
4
1
0.00184
1
303.15
5
2
0.8
2
1
0.02451
4
1
0.00246
1
303.15
5
2
0.9
2
1
0.02737
4
1
0.00275
1
303.15
5
2
1
3
1
0.02345
4
1
0.00236
1
308.15
5
2
0.3
2
1
0.000871
3
1
8.9e-05
1
308.15
5
2
0.4
2
1
0.00387
3
1
0.00039
1
308.15
5
2
0.5
2
1
0.00916
3
1
0.00092
1
308.15
5
2
0.6
2
1
0.01607
4
1
0.00162
1
308.15
5
2
0.7
2
1
0.0243
4
1
0.00244
1
308.15
5
2
0.8
2
1
0.03143
4
1
0.00315
1
308.15
5
2
0.9
2
1
0.03405
4
1
0.00341
1
308.15
5
2
1
3
1
0.02991
4
1
0.003
1
313.15
5
2
0.3
2
1
0.00112
3
1
0.00011
1
313.15
5
2
0.4
2
1
0.00495
3
1
0.0005
1
313.15
5
2
0.5
2
1
0.01164
4
1
0.00117
1
313.15
5
2
0.6
2
1
0.02085
4
1
0.0021
1
313.15
5
2
0.7
2
1
0.03032
4
1
0.00304
1
313.15
5
2
0.8
2
1
0.03739
4
1
0.00374
1
313.15
5
2
0.9
2
1
0.03957
4
1
0.00396
1
313.15
5
2
1
3
1
0.03637
4
1
0.00365
4
3
1
5
1
1
1
Principal objective of the work
AB
TRC
2/2/2017
1
Mole fraction
Gravimetric analysis
1
Liquid
Direct value, X
3
5
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
1
1
Pressure, kPa
Liquid
100
1
1
Temperature, K
Liquid
2
Solvent: Mole fraction
3
Liquid
1
278.15
5
2
0.3
2
1
0.000137
3
1
1.4e-05
1
278.15
5
2
0.4
2
1
0.000393
3
1
3.9e-05
1
278.15
5
2
0.5
2
1
0.000758
3
1
7.6e-05
1
278.15
5
2
0.6
2
1
0.00125
3
1
0.00013
1
278.15
5
2
0.7
2
1
0.00194
3
1
0.00019
1
278.15
5
2
0.8
2
1
0.0027
3
1
0.00027
1
278.15
5
2
0.9
2
1
0.0025
3
1
0.00025
1
278.15
5
2
1
3
1
0.00131
3
1
0.00013
1
283.15
5
2
0.3
2
1
0.000148
3
1
1.5e-05
1
283.15
5
2
0.4
2
1
0.000434
3
1
4.4e-05
1
283.15
5
2
0.5
2
1
0.000862
3
1
8.7e-05
1
283.15
5
2
0.6
2
1
0.00144
3
1
0.00014
1
283.15
5
2
0.7
2
1
0.00226
3
1
0.00023
1
283.15
5
2
0.8
2
1
0.00309
3
1
0.00031
1
283.15
5
2
0.9
2
1
0.00286
3
1
0.00029
1
283.15
5
2
1
3
1
0.00154
3
1
0.00015
1
288.15
5
2
0.3
2
1
0.000184
3
1
1.9e-05
1
288.15
5
2
0.4
2
1
0.00054
3
1
5.4e-05
1
288.15
5
2
0.5
2
1
0.00109
3
1
0.00011
1
288.15
5
2
0.6
2
1
0.00182
3
1
0.00018
1
288.15
5
2
0.7
2
1
0.00287
3
1
0.00029
1
288.15
5
2
0.8
2
1
0.00381
3
1
0.00038
1
288.15
5
2
0.9
2
1
0.00354
3
1
0.00036
1
288.15
5
2
1
3
1
0.00195
3
1
0.0002
1
293.15
5
2
0.3
2
1
0.000231
3
1
2.3e-05
1
293.15
5
2
0.4
2
1
0.000672
3
1
6.8e-05
1
293.15
5
2
0.5
2
1
0.00138
3
1
0.00014
1
293.15
5
2
0.6
2
1
0.0023
3
1
0.00023
1
293.15
5
2
0.7
2
1
0.00375
3
1
0.00038
1
293.15
5
2
0.8
2
1
0.00498
3
1
0.0005
1
293.15
5
2
0.9
2
1
0.00464
3
1
0.00047
1
293.15
5
2
1
3
1
0.00247
3
1
0.00025
1
298.15
5
2
0.3
2
1
0.000309
3
1
3.1e-05
1
298.15
5
2
0.4
2
1
0.000923
3
1
9.3e-05
1
298.15
5
2
0.5
2
1
0.00189
3
1
0.00019
1
298.15
5
2
0.6
2
1
0.00302
3
1
0.0003
1
298.15
5
2
0.7
2
1
0.00505
3
1
0.00051
1
298.15
5
2
0.8
2
1
0.00662
3
1
0.00067
1
298.15
5
2
0.9
2
1
0.00613
3
1
0.00062
1
298.15
5
2
1
3
1
0.00326
3
1
0.00033
1
303.15
5
2
0.3
2
1
0.000336
3
1
3.4e-05
1
303.15
5
2
0.4
2
1
0.0011
3
1
0.00011
1
303.15
5
2
0.5
2
1
0.00232
3
1
0.00023
1
303.15
5
2
0.6
2
1
0.0041
3
1
0.00041
1
303.15
5
2
0.7
2
1
0.00647
3
1
0.00065
1
303.15
5
2
0.8
2
1
0.00839
3
1
0.00084
1
303.15
5
2
0.9
2
1
0.00775
3
1
0.00078
1
303.15
5
2
1
3
1
0.00445
3
1
0.00045
1
308.15
5
2
0.3
2
1
0.000484
3
1
4.9e-05
1
308.15
5
2
0.4
2
1
0.00147
3
1
0.00015
1
308.15
5
2
0.5
2
1
0.00302
3
1
0.0003
1
308.15
5
2
0.6
2
1
0.0056
3
1
0.00056
1
308.15
5
2
0.7
2
1
0.00867
3
1
0.00087
1
308.15
5
2
0.8
2
1
0.01111
4
1
0.00112
1
308.15
5
2
0.9
2
1
0.01032
4
1
0.00104
1
308.15
5
2
1
3
1
0.00597
3
1
0.0006
1
313.15
5
2
0.3
2
1
0.000573
3
1
5.8e-05
1
313.15
5
2
0.4
2
1
0.00184
3
1
0.00019
1
313.15
5
2
0.5
2
1
0.0041
3
1
0.00041
1
313.15
5
2
0.6
2
1
0.00735
3
1
0.00074
1
313.15
5
2
0.7
2
1
0.01173
4
1
0.00118
1
313.15
5
2
0.8
2
1
0.01458
4
1
0.00146
1
313.15
5
2
0.9
2
1
0.01321
4
1
0.00132
1
313.15
5
2
1
3
1
0.00816
3
1
0.00082
5
4
1
5
1
1
1
Principal objective of the work
AB
TRC
2/2/2017
1
Mole fraction
Gravimetric analysis
1
Liquid
Direct value, X
4
5
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
1
1
Pressure, kPa
Liquid
100
1
1
Temperature, K
Liquid
2
Solvent: Mole fraction
4
Liquid
1
278.15
5
2
0.5
2
1
1.66e-05
3
1
3.4e-06
1
278.15
5
2
0.6
2
1
5.76e-05
3
1
5.8e-06
1
278.15
5
2
0.7
2
1
0.000147
3
1
1.5e-05
1
278.15
5
2
0.8
2
1
0.000325
3
1
3.3e-05
1
278.15
5
2
0.9
2
1
0.000608
3
1
6.1e-05
1
278.15
5
2
1
3
1
0.00111
3
1
0.00011
1
283.15
5
2
0.5
2
1
2.08e-05
3
1
3.8e-06
1
283.15
5
2
0.6
2
1
7.03e-05
3
1
7.1e-06
1
283.15
5
2
0.7
2
1
0.000178
3
1
1.8e-05
1
283.15
5
2
0.8
2
1
0.000367
3
1
3.7e-05
1
283.15
5
2
0.9
2
1
0.000753
3
1
7.6e-05
1
283.15
5
2
1
3
1
0.00128
3
1
0.00013
1
288.15
5
2
0.5
2
1
2.64e-05
3
1
3.8e-06
1
288.15
5
2
0.6
2
1
8.68e-05
3
1
8.8e-06
1
288.15
5
2
0.7
2
1
0.000214
3
1
2.2e-05
1
288.15
5
2
0.8
2
1
0.000523
3
1
5.3e-05
1
288.15
5
2
0.9
2
1
0.00099
3
1
0.0001
1
288.15
5
2
1
3
1
0.00156
3
1
0.00016
1
293.15
5
2
0.5
2
1
3.76e-05
3
1
3.9e-06
1
293.15
5
2
0.6
2
1
0.000124
3
1
1.3e-05
1
293.15
5
2
0.7
2
1
0.000319
3
1
3.2e-05
1
293.15
5
2
0.8
2
1
0.000703
3
1
7.1e-05
1
293.15
5
2
0.9
2
1
0.00133
3
1
0.00013
1
293.15
5
2
1
3
1
0.00209
3
1
0.00021
1
298.15
5
2
0.5
2
1
5.58e-05
3
1
5.8e-06
1
298.15
5
2
0.6
2
1
0.000179
3
1
1.8e-05
1
298.15
5
2
0.7
2
1
0.000434
3
1
4.4e-05
1
298.15
5
2
0.8
2
1
0.000914
3
1
9.2e-05
1
298.15
5
2
0.9
2
1
0.00181
3
1
0.00018
1
298.15
5
2
1
3
1
0.00277
3
1
0.00028
1
303.15
5
2
0.5
2
1
8.1e-05
3
1
8.3e-06
1
303.15
5
2
0.6
2
1
0.00025
3
1
2.5e-05
1
303.15
5
2
0.7
2
1
0.00056
3
1
5.6e-05
1
303.15
5
2
0.8
2
1
0.0012
3
1
0.00012
1
303.15
5
2
0.9
2
1
0.00226
3
1
0.00023
1
303.15
5
2
1
3
1
0.00361
3
1
0.00036
1
308.15
5
2
0.5
2
1
0.000112
3
1
1.2e-05
1
308.15
5
2
0.6
2
1
0.00032
3
1
3.2e-05
1
308.15
5
2
0.7
2
1
0.00077
3
1
7.8e-05
1
308.15
5
2
0.8
2
1
0.00168
3
1
0.00017
1
308.15
5
2
0.9
2
1
0.00325
3
1
0.00033
1
308.15
5
2
1
3
1
0.00508
3
1
0.00051
1
313.15
5
2
0.5
2
1
0.000161
3
1
1.6e-05
1
313.15
5
2
0.6
2
1
0.000444
3
1
4.6e-05
1
313.15
5
2
0.7
2
1
0.00106
3
1
0.00011
1
313.15
5
2
0.8
2
1
0.00227
3
1
0.00023
1
313.15
5
2
0.9
2
1
0.00437
3
1
0.00044
1
313.15
5
2
1
3
1
0.00772
3
1
0.00078
6
2
1
1
1
Principal objective of the work
AB
TRC
2/2/2017
1
Mole fraction
Gravimetric analysis
1
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
1
1
Pressure, kPa
Liquid
100
1
1
Temperature, K
Liquid
1
278.15
5
1
0.00987
3
1
0.00099
1
283.15
5
1
0.0112
4
1
0.00112
1
288.15
5
1
0.0132
4
1
0.00132
1
293.15
5
1
0.01554
4
1
0.00156
1
298.15
5
1
0.01903
4
1
0.00191
1
303.15
5
1
0.02345
4
1
0.00236
1
308.15
5
1
0.02991
4
1
0.003
1
313.15
5
1
0.03637
4
1
0.00365
7
3
1
1
1
Principal objective of the work
AB
TRC
2/2/2017
1
Mole fraction
Gravimetric analysis
1
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
1
1
Pressure, kPa
Liquid
100
1
1
Temperature, K
Liquid
1
278.15
5
1
0.00131
3
1
0.00013
1
283.15
5
1
0.00154
3
1
0.00015
1
288.15
5
1
0.00195
3
1
0.0002
1
293.15
5
1
0.00247
3
1
0.00025
1
298.15
5
1
0.00326
3
1
0.00033
1
303.15
5
1
0.00445
3
1
0.00045
1
308.15
5
1
0.00597
3
1
0.0006
1
313.15
5
1
0.00816
3
1
0.00082
8
4
1
1
1
Principal objective of the work
AB
TRC
2/2/2017
1
Mole fraction
Gravimetric analysis
1
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
1
1
Pressure, kPa
Liquid
100
1
1
Temperature, K
Liquid
1
278.15
5
1
0.00111
3
1
0.00011
1
283.15
5
1
0.00128
3
1
0.00013
1
288.15
5
1
0.00156
3
1
0.00016
1
293.15
5
1
0.00209
3
1
0.00021
1
298.15
5
1
0.00277
3
1
0.00028
1
303.15
5
1
0.00361
3
1
0.00036
1
308.15
5
1
0.00508
3
1
0.00051
1
313.15
5
1
0.00772
3
1
0.00078