2
0
2019
yan
sha
3
journal
Original
Yang, Z.[Zehui]
Shao, D.[Danfeng]
Zhou, G.[Guoquan]
J. Chem. Eng. Data
2019
2020-09-29
Solid-Liquid Equilibrium of 5-Chloro-8-hydroxyquinoline and 5,7-Dichloro-8-hydroxyquinoline in Different Solvents and Mixing Properties of Solutions
The solubility values of 5-chloro-8-hydroxyquinoline and 5,7-dichloro-8-hydroxyquinoline in six pure solvents at temperature ranging from (283.15 to 323.15) K was determined by the isothermal saturation method. In the investigated temperature range, the values of 5-chloro-8-hydroxyquinoline are larger than that of 5,7-dichloro-8-hydroxyquinoline at all studied temperatures. They decrease according to the sequence of (N-methyl-2-pyrrolidone greater than N,N-dimethylformamide greater than 1,4-dioxane greater than ethyl acetate greater than toluene greater than acetonitrile). The determined solubility data were correlated using the modified Apelblat equation, Buchowski-Ksiazaczak h equation and NRTL model. The results of correlation indicated that the calculated and experimental values agreed very well. The maximum values of root-mean-square deviation (RMSD) and relative average deviation (RAD) were (14.8810-4 and 1.46% for 5-chloro-8-hydroxyquinoline) and (2.53 e10-4 and 2.56% for 5,7-dichloro-8-hydroxyquinoline) respectively. The calculation results of thermodynamic properties show that the process of dissolving is apparently not only spontaneous but also entropy-driving.
10.1021/acs.jced.9b00028
12
64
5057-5065
1
InChI=1S/C9H6ClNO/c10-7-3-4-8(12)9-6(7)2-1-5-11-9/h1-5,12H
CTQMJYWDVABFRZ-UHFFFAOYSA-N
5-chloro-8-hydroxyquinoline
5-chloro-8-quinolinol
quinoline, 5-chloro-8-hydroxy-
C9H6ClNO
1
Commercial source
1
99.5
3
HPLC
2
InChI=1S/C9H5Cl2NO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H
WDFKMLRRRCGAKS-UHFFFAOYSA-N
5,7-dichloro-8-hydroxyquinoline
5,7-dichloro-8-quinolinol
C9H5Cl2NO
1
Commercial source
1
99.6
3
HPLC
3
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
99.6
3
Stated by supplier
4
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
5
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
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
99.7
3
Stated by supplier
7
InChI=1S/C7H8/c1-7-5-3-2-4-6-7/h2-6H,1H3
YXFVVABEGXRONW-UHFFFAOYSA-N
toluene
methylbenzene
C7H8
1
Commercial source
1
99.5
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
99.5
3
Stated by supplier
1
1
1
Principal objective of the work
EP
EP
7/29/2019
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
395.48
5
1
1.22
2
1
1
Principal objective of the work
EP
EP
7/29/2019
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
25.3
4
1
0.95
3
2
1
Principal objective of the work
EP
EP
7/29/2019
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
452.15
5
1
1.22
4
2
1
Principal objective of the work
EP
EP
7/29/2019
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
39.77
4
1
1.11
5
1
1
6
1
Principal objective of the work
EP
EP
7/29/2019
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
283.15
5
1
0.0146
3
1
0.0004
1
288.15
5
1
0.0176
3
1
0.0004
1
293.15
5
1
0.021
3
1
0.0005
1
298.15
5
1
0.0249
3
1
0.0006
1
303.15
5
1
0.0295
3
1
0.0007
1
308.15
5
1
0.0349
3
1
0.0008
1
313.15
5
1
0.0413
3
1
0.001
1
318.15
5
1
0.0487
3
1
0.0012
1
323.15
5
1
0.0573
3
1
0.0014
6
1
1
7
1
Principal objective of the work
EP
EP
7/29/2019
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
283.15
5
1
0.0109
3
1
0.0003
1
288.15
5
1
0.0132
3
1
0.0003
1
293.15
5
1
0.0156
3
1
0.0004
1
298.15
5
1
0.0189
3
1
0.0005
1
303.15
5
1
0.0221
3
1
0.0005
1
308.15
5
1
0.0262
3
1
0.0006
1
313.15
5
1
0.0307
3
1
0.0007
1
318.15
5
1
0.0363
3
1
0.0009
1
323.15
5
1
0.0431
3
1
0.001
7
1
1
3
1
Principal objective of the work
EP
EP
7/29/2019
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
283.15
5
1
0.0284
3
1
0.0007
1
288.15
5
1
0.0332
3
1
0.0008
1
293.15
5
1
0.0393
3
1
0.0009
1
298.15
5
1
0.0462
3
1
0.0011
1
303.15
5
1
0.0535
3
1
0.0013
1
308.15
5
1
0.0617
3
1
0.0015
1
313.15
5
1
0.0715
3
1
0.0017
1
318.15
5
1
0.0813
3
1
0.002
1
323.15
5
1
0.0932
3
1
0.0022
8
1
1
4
1
Principal objective of the work
EP
EP
7/29/2019
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
283.15
5
1
0.0483
3
1
0.0012
1
288.15
5
1
0.0547
3
1
0.0013
1
293.15
5
1
0.0621
3
1
0.0015
1
298.15
5
1
0.0701
3
1
0.0017
1
303.15
5
1
0.0786
3
1
0.0019
1
308.15
5
1
0.0882
3
1
0.0021
1
313.15
5
1
0.097
3
1
0.0023
1
318.15
5
1
0.107
4
1
0.0026
1
323.15
5
1
0.117
4
1
0.0028
9
1
1
8
1
Principal objective of the work
EP
EP
7/29/2019
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
283.15
5
1
0.0021
2
1
0.0001
1
288.15
5
1
0.0026
2
1
0.0001
1
293.15
5
1
0.0032
2
1
0.0002
1
298.15
5
1
0.004
2
1
0.001
1
303.15
5
1
0.0047
2
1
0.0002
1
308.15
5
1
0.0057
2
1
0.0001
1
313.15
5
1
0.0068
2
1
0.0002
1
318.15
5
1
0.0081
2
1
0.0002
1
323.15
5
1
0.0097
2
1
0.0002
10
1
1
5
1
Principal objective of the work
EP
EP
7/29/2019
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
0.0263
3
1
0.0006
1
293.15
5
1
0.032
3
1
0.0008
1
298.15
5
1
0.0386
3
1
0.0009
1
303.15
5
1
0.0462
3
1
0.0011
1
308.15
5
1
0.0552
3
1
0.0013
1
313.15
5
1
0.0658
3
1
0.0016
1
318.15
5
1
0.0773
3
1
0.0019
1
323.15
5
1
0.0913
3
1
0.0022
11
2
1
6
1
Principal objective of the work
EP
EP
7/29/2019
1
Mole fraction
Chromatography
2
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
2
1
Pressure, kPa
Liquid
101.2
4
1
Temperature, K
Liquid
1
283.15
5
1
0.0022
2
1
0.0001
1
288.15
5
1
0.0027
2
1
0.0001
1
293.15
5
1
0.0033
2
1
0.0001
1
298.15
5
1
0.004
2
1
0.0001
1
303.15
5
1
0.0047
2
1
0.0001
1
308.15
5
1
0.0057
2
1
0.0001
1
313.15
5
1
0.0067
2
1
0.0002
1
318.15
5
1
0.0078
2
1
0.0002
1
323.15
5
1
0.0091
2
1
0.0002
12
2
1
7
1
Principal objective of the work
EP
EP
7/29/2019
1
Mole fraction
Chromatography
2
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
2
1
Pressure, kPa
Liquid
101.2
4
1
Temperature, K
Liquid
1
283.15
5
1
0.0017
2
1
0.0001
1
288.15
5
1
0.0021
2
1
0.0001
1
293.15
5
1
0.0027
2
1
0.0001
1
298.15
5
1
0.0034
2
1
0.0001
1
303.15
5
1
0.0042
2
1
0.0001
1
308.15
5
1
0.0051
2
1
0.0001
1
313.15
5
1
0.0062
2
1
0.0002
1
318.15
5
1
0.0075
2
1
0.0002
1
323.15
5
1
0.0086
2
1
0.0002
13
2
1
3
1
Principal objective of the work
EP
EP
7/29/2019
1
Mole fraction
Chromatography
2
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
2
1
Pressure, kPa
Liquid
101.2
4
1
Temperature, K
Liquid
1
283.15
5
1
0.0072
2
1
0.0002
1
288.15
5
1
0.0086
2
1
0.0002
1
293.15
5
1
0.0105
3
1
0.0003
1
298.15
5
1
0.0129
3
1
0.0003
1
303.15
5
1
0.0155
3
1
0.0004
1
308.15
5
1
0.0185
3
1
0.0004
1
313.15
5
1
0.0219
3
1
0.0005
1
318.15
5
1
0.0258
3
1
0.0006
1
323.15
5
1
0.0301
3
1
0.0007
14
2
1
4
1
Principal objective of the work
EP
EP
7/29/2019
1
Mole fraction
Chromatography
2
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
2
1
Pressure, kPa
Liquid
101.2
4
1
Temperature, K
Liquid
1
283.15
5
1
0.0107
3
1
0.0003
1
288.15
5
1
0.013
3
1
0.0003
1
293.15
5
1
0.0154
3
1
0.0004
1
298.15
5
1
0.0184
3
1
0.0004
1
303.15
5
1
0.0218
3
1
0.0005
1
308.15
5
1
0.0261
3
1
0.0006
1
313.15
5
1
0.0306
3
1
0.0007
1
318.15
5
1
0.036
3
1
0.0009
1
323.15
5
1
0.0428
3
1
0.001
15
2
1
8
1
Principal objective of the work
EP
EP
7/29/2019
1
Mole fraction
Chromatography
2
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
2
1
Pressure, kPa
Liquid
101.2
4
1
Temperature, K
Liquid
1
283.15
5
1
0.000218
3
1
5e-06
1
288.15
5
1
0.00029
3
1
7e-06
1
293.15
5
1
0.000382
3
1
9e-06
1
298.15
5
1
0.000485
3
1
1.2e-05
1
303.15
5
1
0.000609
3
1
1.5e-05
1
308.15
5
1
0.000755
3
1
1.8e-05
1
313.15
5
1
0.000908
3
1
2.2e-05
1
318.15
5
1
0.0011
3
1
3e-05
1
323.15
5
1
0.00131
3
1
3e-05
16
2
1
5
1
Principal objective of the work
EP
EP
7/29/2019
1
Mole fraction
Chromatography
2
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
2
1
Pressure, kPa
Liquid
101.2
4
1
Temperature, K
Liquid
1
288.15
5
1
0.0072
2
1
0.0002
1
293.15
5
1
0.0088
2
1
0.0002
1
298.15
5
1
0.0106
3
1
0.0003
1
303.15
5
1
0.0129
3
1
0.0003
1
308.15
5
1
0.0152
3
1
0.0004
1
313.15
5
1
0.0181
3
1
0.0004
1
318.15
5
1
0.0218
3
1
0.0005
1
323.15
5
1
0.0263
3
1
0.0006