2
0
2019
zha
han
1
journal
Original
Zhao, X.[Xi]
Han, G.[Gui]
Zhao, H.[Hongkun]
J. Chem. Eng. Data
2019
2020-09-29
Thermodynamic Solubility and Mixing Properties of Phenformin in 14 Pure Solvents at Temperatures Ranging from 278.15 to 323.15 K
The equilibrium solubility of phenformin in 14 solvents of N,N-dimethylformamide (DMF), N-methyl-2-pyrrolidinone (NMP), dimethyl sulfoxide (DMSO), methanol, isopropanol, ethanol, n-propanol, 1,4-dioxane, n-butanol, isobutanol, acetonitrile, ethyl acetate, ethylene glycol (EG), and water was gained using the saturation shake-flask method over a temperature range of 278.15 to 323.15 K under pressure p = 101.2 kPa. The mole fraction solubility of phenformin in the above neat solvents increased as the temperature increased and had a variation trend in the different solvents: DMF greater than DMSO greater than NMP greater than EG greater than methanol greater than ethanol greater than ethyl acetate greater than n-propanol greater than isopropanol greater than n-butanol greater than isobutanol greater than water greater than acetonitrile greater than 1,4-dioxane. It was correlated using the nonrandom two-liquid model, modified Apelblat equation, h equation, and the Wilson model. The obtained values of maximum root-mean-square deviation and relative average deviation gained via the four models were, respectively, 29.14 * 10 4 and 4.46 * 10 2. Also, the reduced excess enthalpy, activity coefficient under infinitesimal concentration, and mixing properties were derived based on the determined solubility data.
10.1021/acs.jced.9b00844
12
64
6009-6019
1
InChI=1S/C10H15N5/c11-9(12)15-10(13)14-7-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H6,11,12,13,14,15)
ICFJFFQQTFMIBG-UHFFFAOYSA-N
N-(2-phenylethyl)imidodicarbonimidic diamide
1-phenethylbiguanide
debeone
C10H15N5
1
Commercial source
1
98.1
3
HPLC
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/C4H8O2/c1-3-6-4(2)5/h3H2,1-2H3
XEKOWRVHYACXOJ-UHFFFAOYSA-N
ethyl acetate
ethyl ethanoate
C4H8O2
1
Commercial source
1
99.7
3
Stated by supplier
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
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/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
99.5
3
Stated by supplier
12
InChI=1S/C4H10O/c1-4(2)3-5/h4-5H,3H2,1-2H3
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N
2-methyl-1-propanol
2-methylpropan-1-ol
isobutanol
isobutyl alcohol
C4H10O
1
Commercial source
1
99.5
3
Stated by supplier
13
InChI=1S/C2H6OS/c1-4(2)3/h1-2H3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N
dimethyl sulfoxide
DMSO
dimethyl sulphoxide
methyl sulfoxide
methylsulfinylmethane
sulfinylbismethane
C2H6OS
1
Commercial source
1
99.6
3
Stated by supplier
14
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
15
InChI=1S/H2O/h1H2
XLYOFNOQVPJJNP-UHFFFAOYSA-N
water
H2O
1
Commercial source
1
99.9
3
Estimated by the compiler
1
1
1
Principal objective of the work
EP
EP
10/29/2019
1
Triple point temperature, K
DSC
Crystal
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Crystal
Liquid
Air at 1 atmosphere
1
446.85
5
1
1.22
2
1
1
Principal objective of the work
EP
EP
10/29/2019
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
11.63
4
1
0.75
3
1
1
2
1
Principal objective of the work
EP
EP
10/29/2019
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
0.002371
4
1
0.000128
1
283.15
5
1
0.002803
4
1
0.000152
1
288.15
5
1
0.003276
4
1
0.000177
1
293.15
5
1
0.003851
4
1
0.000208
1
298.15
5
1
0.004572
4
1
0.000247
1
303.15
5
1
0.005324
4
1
0.000288
1
308.15
5
1
0.006227
4
1
0.000337
1
313.15
5
1
0.007433
4
1
0.000402
1
318.15
5
1
0.008226
4
1
0.000445
1
323.15
5
1
0.01035
4
1
0.00056
4
1
1
3
1
Principal objective of the work
EP
EP
10/29/2019
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
0.001832
4
1
9.9e-05
1
283.15
5
1
0.002205
4
1
0.000119
1
288.15
5
1
0.002661
4
1
0.000144
1
293.15
5
1
0.003222
4
1
0.000174
1
298.15
5
1
0.003778
4
1
0.000204
1
303.15
5
1
0.004485
4
1
0.000242
1
308.15
5
1
0.005241
4
1
0.000283
1
313.15
5
1
0.006142
4
1
0.000332
1
318.15
5
1
0.007226
4
1
0.000391
1
323.15
5
1
0.008474
4
1
0.000458
5
1
1
4
1
Principal objective of the work
EP
EP
10/29/2019
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
0.0009751
4
1
5.27e-05
1
283.15
5
1
0.001163
4
1
6.3e-05
1
288.15
5
1
0.001372
4
1
7.4e-05
1
293.15
5
1
0.001728
4
1
9.3e-05
1
298.15
5
1
0.002084
4
1
0.000113
1
303.15
5
1
0.002495
4
1
0.000135
1
308.15
5
1
0.002896
4
1
0.000157
1
313.15
5
1
0.003411
4
1
0.000184
1
318.15
5
1
0.003956
4
1
0.000214
1
323.15
5
1
0.004523
4
1
0.000244
6
1
1
5
1
Principal objective of the work
EP
EP
10/29/2019
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
0.0008138
4
1
4.4e-05
1
283.15
5
1
0.000976
4
1
5.28e-05
1
288.15
5
1
0.001182
4
1
6.4e-05
1
293.15
5
1
0.001416
4
1
7.7e-05
1
298.15
5
1
0.001743
4
1
9.4e-05
1
303.15
5
1
0.002081
4
1
0.000112
1
308.15
5
1
0.002465
4
1
0.000133
1
313.15
5
1
0.002883
4
1
0.000156
1
318.15
5
1
0.003337
4
1
0.00018
1
323.15
5
1
0.003829
4
1
0.000207
7
1
1
6
1
Principal objective of the work
EP
EP
10/29/2019
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
0.003302
4
1
0.000178
1
283.15
5
1
0.003662
4
1
0.000198
1
288.15
5
1
0.004174
4
1
0.000226
1
293.15
5
1
0.004813
4
1
0.00026
1
298.15
5
1
0.005671
4
1
0.000307
1
303.15
5
1
0.006768
4
1
0.000366
1
308.15
5
1
0.007743
4
1
0.000419
1
313.15
5
1
0.009186
4
1
0.000497
1
318.15
5
1
0.01097
4
1
0.00059
1
323.15
5
1
0.01279
4
1
0.00069
8
1
1
7
1
Principal objective of the work
EP
EP
10/29/2019
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
0.001567
4
1
8.5e-05
1
283.15
5
1
0.001836
4
1
9.9e-05
1
288.15
5
1
0.002204
4
1
0.000119
1
293.15
5
1
0.002653
4
1
0.000143
1
298.15
5
1
0.003178
4
1
0.000172
1
303.15
5
1
0.003786
4
1
0.000205
1
308.15
5
1
0.004454
4
1
0.000241
1
313.15
5
1
0.005213
4
1
0.000282
1
318.15
5
1
0.006031
4
1
0.000326
1
323.15
5
1
0.006952
4
1
0.000376
9
1
1
8
1
Principal objective of the work
EP
EP
10/29/2019
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
0.0002115
4
1
1.14e-05
1
283.15
5
1
0.0002597
4
1
1.4e-05
1
288.15
5
1
0.0003218
4
1
1.74e-05
1
293.15
5
1
0.0003979
4
1
2.15e-05
1
298.15
5
1
0.0004941
4
1
2.67e-05
1
303.15
5
1
0.000596
4
1
3.22e-05
1
308.15
5
1
0.0007096
4
1
3.84e-05
1
313.15
5
1
0.0008401
4
1
4.54e-05
1
318.15
5
1
0.001014
4
1
5.5e-05
1
323.15
5
1
0.001193
4
1
6.4e-05
10
1
1
9
1
Principal objective of the work
EP
EP
10/29/2019
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
0.01134
4
1
0.00061
1
283.15
5
1
0.01399
4
1
0.00076
1
288.15
5
1
0.017
4
1
0.00092
1
293.15
5
1
0.02019
4
1
0.00109
1
298.15
5
1
0.02352
4
1
0.00127
1
303.15
5
1
0.02804
4
1
0.00152
1
308.15
5
1
0.03368
4
1
0.00182
1
313.15
5
1
0.04093
4
1
0.00221
1
318.15
5
1
0.04856
4
1
0.00263
1
323.15
5
1
0.05792
4
1
0.00313
11
1
1
10
1
Principal objective of the work
EP
EP
10/29/2019
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
0.0006269
4
1
3.39e-05
1
283.15
5
1
0.0007775
4
1
4.2e-05
1
288.15
5
1
0.0009233
4
1
4.99e-05
1
293.15
5
1
0.001175
4
1
6.4e-05
1
298.15
5
1
0.001423
4
1
7.7e-05
1
303.15
5
1
0.001665
4
1
9e-05
1
308.15
5
1
0.001937
4
1
0.000105
1
313.15
5
1
0.002274
4
1
0.000123
1
318.15
5
1
0.002651
4
1
0.000143
1
323.15
5
1
0.003076
4
1
0.000166
12
1
1
11
1
Principal objective of the work
EP
EP
10/29/2019
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
0.01581
4
1
0.00085
1
283.15
5
1
0.01914
4
1
0.00103
1
288.15
5
1
0.02256
4
1
0.00122
1
293.15
5
1
0.02556
4
1
0.00138
1
298.15
5
1
0.03034
4
1
0.00164
1
303.15
5
1
0.03528
4
1
0.00191
1
308.15
5
1
0.04111
4
1
0.00222
1
313.15
5
1
0.04909
4
1
0.00265
1
318.15
5
1
0.05794
4
1
0.00313
1
323.15
5
1
0.06547
4
1
0.00354
13
1
1
12
1
Principal objective of the work
EP
EP
10/29/2019
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
0.000518
4
1
2.8e-05
1
283.15
5
1
0.0006302
4
1
3.41e-05
1
288.15
5
1
0.0007919
4
1
4.28e-05
1
293.15
5
1
0.0009503
4
1
5.14e-05
1
298.15
5
1
0.001163
4
1
6.3e-05
1
303.15
5
1
0.001391
4
1
7.5e-05
1
308.15
5
1
0.001665
4
1
9e-05
1
313.15
5
1
0.001968
4
1
0.000106
1
318.15
5
1
0.002294
4
1
0.000124
1
323.15
5
1
0.002645
4
1
0.000143
14
1
1
15
1
Principal objective of the work
EP
EP
10/29/2019
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
0.0003887
4
1
2.1e-05
1
283.15
5
1
0.0004813
4
1
2.6e-05
1
288.15
5
1
0.0005855
4
1
3.17e-05
1
293.15
5
1
0.0007391
4
1
4e-05
1
298.15
5
1
0.0008879
4
1
4.8e-05
1
303.15
5
1
0.001071
4
1
5.8e-05
1
308.15
5
1
0.001263
4
1
6.8e-05
1
313.15
5
1
0.001476
4
1
8e-05
1
318.15
5
1
0.001745
4
1
9.4e-05
1
323.15
5
1
0.002062
4
1
0.000111
15
1
1
13
1
Principal objective of the work
EP
EP
10/29/2019
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
0.02175
4
1
0.00118
1
298.15
5
1
0.02497
4
1
0.00135
1
303.15
5
1
0.03051
4
1
0.00165
1
308.15
5
1
0.03592
4
1
0.00194
1
313.15
5
1
0.04308
4
1
0.00233
1
318.15
5
1
0.05085
4
1
0.00275
1
323.15
5
1
0.06028
4
1
0.00326
16
1
1
14
1
Principal objective of the work
EP
EP
10/29/2019
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
288.15
5
1
0.0001657
4
1
9e-06
1
293.15
5
1
0.0002019
4
1
1.09e-05
1
298.15
5
1
0.0002488
4
1
1.35e-05
1
303.15
5
1
0.0003117
4
1
1.69e-05
1
308.15
5
1
0.0003789
4
1
2.05e-05
1
313.15
5
1
0.0004599
4
1
2.49e-05
1
318.15
5
1
0.0005512
4
1
2.98e-05
1
323.15
5
1
0.0006499
4
1
3.51e-05