Jouyban, A., Jalilzadeh, H., Khoubnasabjafari, M., Acree Jr., W. (2006). Solubility Prediction of Anthracene in Non-Aqueous Solvent Mixtures Using Jouyban-Acree Model. Iranian Journal of Pharmaceutical Sciences, 2(2), 73-80.
Abolghasem Jouyban; Hassan Jalilzadeh; Maryam Khoubnasabjafari; William E. Acree Jr.. "Solubility Prediction of Anthracene in Non-Aqueous Solvent Mixtures Using Jouyban-Acree Model". Iranian Journal of Pharmaceutical Sciences, 2, 2, 2006, 73-80.
Jouyban, A., Jalilzadeh, H., Khoubnasabjafari, M., Acree Jr., W. (2006). 'Solubility Prediction of Anthracene in Non-Aqueous Solvent Mixtures Using Jouyban-Acree Model', Iranian Journal of Pharmaceutical Sciences, 2(2), pp. 73-80.
Jouyban, A., Jalilzadeh, H., Khoubnasabjafari, M., Acree Jr., W. Solubility Prediction of Anthracene in Non-Aqueous Solvent Mixtures Using Jouyban-Acree Model. Iranian Journal of Pharmaceutical Sciences, 2006; 2(2): 73-80.
Solubility Prediction of Anthracene in Non-Aqueous Solvent Mixtures Using Jouyban-Acree Model
1Faculty of Pharmacy and Drug Applied Research Centre, Tabriz University of Medical Sciences, Tabriz, Iran
2Kimia Research Institute, Tabriz, Iran
3Department of Chemistry, University of North Texas, Denton, USA
Abstract
A quanitative structure property relationship was proposed to calculate the binary interaction terms of the Jouyban-Acree model using solubility parameter, boiling point, vapour pressure and density of solvents. The applicability of the proposed method for reproducing solubility data of anthracene in binary solvents has been evaluated using 116 solubility data sets collected from the literature. The mean percentage deviation (MPD) of experimental and calculated solubilities has been computed as a measure of accuracy and the MPD of the proposed method was ~ 6 %. The accuracy of the method was compared with that of a previously reported method where the MPD was ~ 12 % and the mean differences between proposed and previous methods was statistically significant.
Polycyclic aromatic hydrocarbons (PAHs) are released to the environment from incomplete combustion of organic materials. They are common constituents of complex mixtures such as automobile exhausts, petroleum refining and crude oil. Most of PAHs are considered dangerous substances because of their toxic and mutagenic or carcinogenic potentials [1]. PAHs are hydrophobic compounds, and they persist in ecosystem because of their poor aqueous solubilities and present in contaminated soil, waters and sediments and play a significant role in the environment safety and human health. Anthracene is a low molecular weight, not acutely toxic, carcinogenic or mutagenic members of PAHs. There is evidence that it is absorbed following oral and dermal exposure [2]. We used anthracene data as model system as very large database have been provided by our group, however, the proposed method could be used for modeling solubility data of a drug in mixed solvents.
Solubility data is one of the key information in chemical/pharmaceutical areas and it is usually determined in water and many organic solvents. Mixing solvents, cosolvency, is the main solubility enhancement method has been employed in practice. In addition to experimental solubility determinations, a number of equations have been proposed for mathematical representation of solubility data. Solubility of anthracene in non-aqueous mixed solvents has been extensively studied by Acree’s group. The experimentally determined data has been correlated using the Jouyban-Acree model. The general form of the model is:
where X is the mole fraction solubility of the solute, f denotes the volume fraction of the solvents 1 and 2 in the solvent mixture, subscripts m, 1 and 2 are the mixed solvent and solvents 1 and 2, respectively, and Bi is the model constants which is calculated using a no intercept least square analysis [3]. Although the model was proposed for modeling of PAHs solubilities in non-aqueous solvent mixtures, it has been shown that the model is applicable for calculating the solubility of polar and/or semi-polar compounds in aqueous solvent mixtures [4- 5].
It has also been shown that the model is applicable for modeling physicochemical properties other than solubility in solvent mixtures [6].
The main drawback of the Jouyban-Acree model is that it suffers from the presence of a number of curve-fitting parameters and needs a minimum number of experimental data points for training. In a previous work, a quantitative structure property relationship (QSPR) has been proposed to reduce the number of data points for predicting the solubility of solutes by the Jouyban-Acree model [7]. The model has been evaluated using a limited number of anthracene data sets in binary and ternary solvents and the solubility parameters of the solvents and that of anthracene have been used as independent variables. To continue our previous efforts on solubility prediction methods, the aim of this work is to propose an extended form of QSPR models using a larger number of anthracene solubility data in binary solvents. Anthracene data was choosen as model system, since a large number of its experimental data has been published so far. It is obvious that, this approach could be employed for other solutes in binary solvents.
Figure 1. Relative frequency of mean percentage deviation(MPD) values for the previous and proposed methods.
2. Computational methods
The model constants of the Jouyban-Acree model represent the extent of solvent-solvent and solvent-solute interactions in the solution and these interactions could be related to the physico-chemical properties of solvents and solutes in order to establish a quantitative structure property relationship approach. In a previous paper [7], the differences in solubility parameters of the solvents with that of solute and their square values have been used to correlate the binary interaction terms (Bi) of the Jouyban-Acree model as:
in which δ1 and δ2 are the solubility parameters of solvents 1 and 2, respectively, δs is the solute’s solubility parameter and the numerical values of the model constants calculated using experimental data of 30 data sets [7]. As a general rule, the more independent variables the more accurate the correlation and the more accurate the predictions. In this work, the experimentally obtained Bi values for 116 data sets of anthracene solubility in non-aqueous binary solvents, were regressed against (δ1-δ2)2,(BP1-BP2)2, (VP1-VP2)2 and (ρ1-ρ2)2 in which BP, VP and ρ are boiling point, vapour pressure and density of solvents, respectively and
subscripts 1 and 2 denote solvents 1 and 2. The back-calculated Bi values, have been used to predict the solubility of anthracene and mean percentage deviation (MPD) have been computed using:
Where N is the number of data points.
Table 1. List of solvents and the references of solubility data sets and their references
No.
Solvent 1
Solvent 2
Reference
1
1-Butanol
1,4-Dioxane
[8]
2
1-Butanol
1-Pentanol
[9]
3
1-Butanol
2-Butoxyethanol
[10]
4
1-Butanol
2-Ethyl-1-hexanol
[9]
5
1-Butanol
2-Methoxyethanol
[11]
6
1-Butanol
2-Pentanol
[12]
7
1-Butanol
4-Methyl-2-pentanol
[12]
8
1-Butanol
Dibutyl ether
[13]
9
1-Octanol
1,4-Dioxane
[8]
10
1-Octanol
1-Pentanol
[9]
11
1-Octanol
2-Butoxyethanol
[10]
12
1-Octanol
2-Ethyl-1-hexanol
[9]
13
1-Octanol
2-Methoxyethanol
[11]
14
1-Octanol
2-Pentanol
[12]
15
1-Octanol
4-Methyl-2-pentanol
[12]
16
1-Octanol
Dibutyl ether
[13]
17
1-Pentanol
2-Butoxyethanol
[14]
18
1-Pentanol
2-Pentanol
[12]
19
1-Pentanol
4-Methyl-2-pentanol
[12]
20
1-Propanol
1,4-Dioxane
[8]
21
1-Propanol
1-Pentanol
[9]
22
1-Propanol
2-Ethyl-1-hexanol
[9]
23
1-Propanol
2-Methoxyethanol
[11]
24
1-Propanol
2-Pentanol
[12]
25
1-Propanol
4-Methyl-2-pentanol
[12]
26
1-Propanol
Dibutyl ether
[13]
27
2,2,4-Trimethylpentane
1-Butanol
[15]
28
2,2,4-Trimethylpentane
1-Propanol
[15]
29
2,2,4-Trimethylpentane
2-Butoxyethanol
[14]
30
2,2,4-Trimethylpentane
3-Methyl-1-butanol
[16]
31
2-2-4-Trimethylpentane
1,4-Dioxane
[17]
32
2-2-4-Trimethylpentane
2-Butanol
[18]
33
2-Butanol
1,4-Dioxane
[8]
34
2-Butanol
1-Pentanol
[9]
35
2-Butanol
2-Butoxyethanol
[10]
36
2-Butanol
2-Ethyl-1-hexanol
[9]
37
2-Butanol
2-Methoxyethanol
[11]
38
2-Butanol
2-Pentanol
[12]
39
2-Butanol
4-Methyl-2-pentanol
[12]
40
2-Butanol
Dibutyl ether
[13]
41
2-Butoxyethanol
2-Ethoxyethanol
[19]
42
2-Butoxyethanol
2-Methoxyethanol
[19]
43
2-Methyl-1-propanol
1-Pentanol
[9]
44
2-Methyl-1-butanol
1-Pentanol
[9]
45
2-methyl-1-propanol
1,4-Dioxane
[8]
46
2-Methyl-1-propanol
2-Butoxyethanol
[14]
47
2-Methyl-1-Propanol
2-Ethyl-1-hexanol
[9]
48
2-Methyl-1-propanol
2-Methoxyethanol
[11]
49
2-Methyl-1-propanol
2-Pentanol
[12]
50
2-Methyl-1-propanol
4-Methyl-2-pentanol
[12]
51
2-Methyl-1-propanol
Dibutyl ether
[13]
52
2-Propanol
1,4-Dioxane
[8]
53
2-Propanol
1-Pentanol
[9]
54
2-Propanol
2-Butoxyethanol
[10]
55
2-Propanol
2-Ethyl-1-hexanol
[9]
56
2-Propanol
2-Methoxyethanol
[11]
57
2-Propanol
2-Pentanol
[12]
58
2-Propanol
4-Methyl-2-pentanol
[12]
Table 1. continued
No.
Solvent 1
Solvent 2
Reference
59
2-Propanol
Dibutyl ether
[13]
60
3-Methyl-1-butanol
1,4-Dioxane
[8]
61
3-Methyl-1-butanol
2-Butoxyethanol
[10]
62
3-Methyl-1-butanol
2-Ethyl-1-hexanol
[9]
63
3-Methyl-1-butanol
2-Methoxyethanol
[11]
64
3-Methyl-1-butanol
2-Pentanol
[12]
65
3-Methyl-1-butanol
4-Methyl-2-pentanol
[12]
66
3-Methyl-1-butanol
Dibutyl ether
[13]
67
Benzene
Methylcyclohexane
[20]
68
Benzene
Octane
[20]
69
Cyclohexane
1,4-Dioxane
[17]
70
Cyclohexane
1-Butanol
[15]
71
Cyclohexane
1-Propanol
[15]
72
CycloHexane
2-Butanol
[18]
73
Cyclohexane
2-Butoxyethanol
[14]
74
Cyclohexane
3-Methyl-1-butanol
[16]
75
Dibutyl ether
2,2,4-Trimethylpentane
[21]
76
Dibutyl ether
Cyclohexane
[21]
77
Dibutyl ether
Heptane
[21]
78
Dibutyl ether
Hexane
[21]
79
Dibutyl ether
Methylcyclohexane
[21]
80
Dibutyl ether
Octane
[21]
81
Heptane
1-Butanol
[15]
82
Heptane
1-Propanol
[15]
83
Heptane
2-Butoxyethanol
[14]
84
Heptane
3-Methyl-1-butanol
[16]
85
Hexane
1,4-Dioxane
[17]
86
Hexane
1,4-Dioxane
[17]
87
Hexane
1-Butanol
[15]
88
Hexane
1-Propanol
[15]
89
Hexane
2-Butanol
[18]
90
Hexane
2-Butanol
[18]
91
Hexane
2-Butoxyethanol
[14]
92
Hexane
3-Methyl-1-butanol
[16]
93
Methylcyclohexane
1,4-Dioxane
[17]
94
Methylcyclohexane
1-Butanol
[15]
95
Methylcyclohexane
1-Propanol
[15]
96
Methylcyclohexane
2-Butanol
[18]
97
Methylcyclohexane
2-Butoxyethanol
[14]
98
Methylcyclohexane
3-Methyl-1-butanol
[16]
99
Octane
1,4-Dioxane
[17]
100
Octane
1-Butanol
[15]
101
Octane
1-Propanol
[15]
102
Octane
2-Butanol
[18]
103
Octane
2-Butoxyethanol
[14]
104
Octane
3-Methyl-1-butanol
[16]
105
p-Xylene
2,2,4-Trimethylpentane
[20]
106
p-Xylene
Cyclohexane
[20]
107
p-Xylene
Heptane
[20]
108
p-Xylene
Hexane
[20]
109
p-Xylene
Methylcyclohexane
[20]
110
p-Xylene
Octane
[20]
111
Toluene
2,2,4-Trimethylpentane
[22]
112
Toluene
Cyclohexane
[22]
113
Toluene
Heptane
[22]
114
Toluene
Hexane
[22]
115
Toluene
Methylcyclohexane
[22]
116
Toluene
Octane
[22]
Table 2. Solubility parameter (δ), boiling points (BP), vapour pressure (VP) and density (ρ) of solvents 1 and 2, number ofexperimental data points in each set (N), and mean percentage deviations (MPD) for the previous [7] and proposed methods.
No.a
δ1
δ2
BP1
BP2
VP1
VP2
ρ1
ρ2
N
MPD
MPD
(Cal/cm3)1/2
(Cal/cm3)1/2
(°C)
(°C)
(torr)
(torr)
(g/cm3)
(g/cm3)
Previous
Proposed
method
method
1
11.39
10.02
117.7
101.3
6.180
37.100
0.806
1.028
9
14.4
9.9
2
11.39
11.10
117.7
137.8
6.180
2.350
0.806
0.812
9
9.0
0.3
3
11.39
10.17
117.7
170.2
6.180
0.852
0.806
0.894
9
4.6
4.5
4
11.39
10.17
117.7
184.3
6.180
0.143
0.806
0.829
9
5.2
5.7
5
11.39
12.12
117.7
124.6
6.180
9.700
0.806
0.960
9
4.3
5.3
6
11.39
10.76
117.7
119.0
6.180
5.830
0.806
0.805
9
9.8
0.4
7
11.39
10.31
117.7
131.7
6.180
8.200
0.806
0.804
9
10.2
2.8
8
11.39
7.77
117.7
142.2
6.180
12.500
0.806
0.764
9
28.0
11.4
9
10.32
10.02
195.2
101.3
0.075
37.100
0.822
1.028
9
11.0
7.0
10
10.32
11.10
195.2
137.8
0.075
2.350
0.822
0.812
9
0.5
1.3
11
10.32
10.17
195.2
170.2
0.075
0.852
0.822
0.894
9
1.4
1.2
12
10.32
10.17
195.2
184.3
0.075
0.143
0.822
0.829
9
1.1
0.8
13
10.32
12.12
195.2
124.6
0.075
9.700
0.822
0.960
9
13.1
4.0
14
10.32
10.76
195.2
119.0
0.075
5.830
0.822
0.805
9
4.0
1.9
15
10.32
10.31
195.2
131.7
0.075
8.200
0.822
0.804
9
4.3
1.5
16
10.32
7.77
195.2
142.2
0.075
12.500
0.822
0.764
9
22.4
1.6
17
11.10
10.17
137.8
170.2
2.350
0.852
0.812
0.894
9
3.1
3.8
18
11.10
10.76
137.8
119.0
2.350
5.830
0.812
0.805
9
8.0
0.6
19
11.10
10.31
137.8
131.7
2.350
8.200
0.812
0.804
9
7.9
1.9
20
11.98
10.02
97.2
101.3
20.850
37.100
0.800
1.028
9
16.8
14.4
21
11.98
11.10
97.2
137.8
20.850
2.350
0.800
0.812
9
12.6
0.4
22
11.98
10.17
97.2
184.3
20.850
0.143
0.800
0.829
9
7.5
9.4
23
11.98
12.12
97.2
124.6
20.850
9.700
0.800
0.960
9
2.6
5.0
24
11.98
10.76
97.2
119.0
20.850
5.830
0.800
0.805
9
15.5
1.8
25
11.98
10.31
97.2
131.7
20.850
8.200
0.800
0.804
9
14.9
4.9
26
11.98
7.77
97.2
142.2
20.850
12.500
0.800
0.764
9
29.4
12.6
27
6.84
11.39
99.2
117.7
49.000
6.180
0.688
0.806
9
12.6
14.5
28
6.84
11.98
99.2
97.2
49.000
20.850
0.688
0.800
9
5.6
14.3
29
6.84
10.17
99.2
170.2
49.000
0.852
0.688
0.894
9
6.9
14.1
30
6.84
11.10
99.2
130.5
49.000
2.370
0.688
0.807
9
11.8
11.7
31
6.84
10.02
99.2
101.3
49.000
37.100
0.688
1.028
8
3.6
16.5
32
6.84
10.80
99.2
99.6
49.000
18.290
0.688
0.803
9
5.2
2.0
33
10.80
10.02
99.6
101.3
18.290
37.100
0.803
1.028
9
23.1
16.7
34
10.80
11.10
99.6
137.8
18.290
2.350
0.803
0.812
9
4.3
0.8
35
10.80
10.17
99.6
170.2
18.290
0.852
0.803
0.894
9
12.0
7.4
36
10.80
10.17
99.6
184.3
18.290
0.143
0.803
0.829
9
2.2
4.7
37
10.80
12.12
99.6
124.6
18.290
9.700
0.803
0.960
9
11.3
7.0
38
10.80
10.76
99.6
119.0
18.290
5.830
0.803
0.805
9
5.2
0.8
39
10.80
10.31
99.6
131.7
18.290
8.200
0.803
0.804
9
3.5
0.8
40
10.80
7.77
99.6
142.2
18.290
12.500
0.803
0.764
9
34.6
18.3
41
10.17
11.49
170.2
135.6
0.852
5.300
0.894
0.925
9
1.9
1.1
42
10.17
12.12
170.2
124.6
0.852
9.700
0.894
0.960
9
6.1
1.0
43
11.20
11.10
107.7
137.8
10.220
2.350
0.798
0.812
9
4.0
2.6
44
10.77
11.10
128.7
137.8
3.120
2.350
0.815
0.812
9
4.7
0.6
45
11.20
10.02
107.7
101.3
10.220
37.100
0.798
1.028
9
21.4
16.1
46
11.20
10.17
107.7
170.2
10.220
0.852
0.798
0.894
9
11.6
9.6
47
11.20
10.17
107.7
184.3
10.220
0.143
0.798
0.829
9
3.7
0.6
48
11.20
12.12
107.7
124.6
10.220
9.700
0.798
0.960
9
8.8
7.3
49
11.20
10.76
107.7
119.0
10.220
5.830
0.798
0.805
9
14.1
6.5
50
11.20
10.31
107.7
131.7
10.220
8.200
0.798
0.804
9
6.0
0.7
51
11.20
7.77
107.7
142.2
10.220
12.500
0.798
0.764
9
33.7
18.4
52
11.49
10.02
82.3
101.3
45.160
37.100
0.781
1.028
9
24.3
18.2
53
11.49
11.10
82.3
137.8
45.160
2.350
0.781
0.812
9
3.6
2.3
54
11.49
10.17
82.3
170.2
45.160
0.852
0.781
0.894
9
14.2
8.9
Tabel 2. continued
No.a
δ1
δ2
BP1
BP2
VP1
VP2
ρ1
ρ2
N
MPD
MPD
(Cal/cm3)1/2
(Cal/cm3)1/2
(°C)
(°C)
(torr)
(torr)
(g/cm3)
(g/cm3)
Previous
Proposed
method
method
55
11.49
10.17
82.3
184.3
45.160
0.143
0.781
0.829
9
4.6
5.4
56
11.49
12.12
82.3
124.6
45.160
9.700
0.781
0.960
9
8.9
7.3
57
11.49
10.76
82.3
119.0
45.160
5.830
0.781
0.805
9
6.5
1.7
58
11.49
10.31
82.3
131.7
45.160
8.200
0.781
0.804
9
7.1
2.4
59
11.49
7.77
82.3
142.2
45.160
12.500
0.781
0.764
9
35.0
18.8
60
11.10
10.02
130.5
101.3
2.370
37.100
0.807
1.028
9
17.1
11.0
61
11.10
10.17
130.5
170.2
2.370
0.852
0.807
0.894
9
5.2
6.0
62
11.10
10.17
130.5
184.3
2.370
0.143
0.807
0.829
9
2.4
1.5
63
11.10
12.12
130.5
124.6
2.370
9.700
0.807
0.960
9
6.6
5.2
64
11.10
10.76
130.5
119.0
2.370
5.830
0.807
0.805
9
7.4
0.3
65
11.10
10.31
130.5
131.7
2.370
8.200
0.807
0.804
9
5.9
0.2
66
11.10
7.77
130.5
142.2
2.370
12.500
0.807
0.764
9
29.6
12.8
67
9.19
7.82
80.1
100.9
95.200
46.000
0.874
0.765
7
20.0
1.7
68
9.19
7.58
80.1
125.7
95.200
14.000
0.874
0.699
8
16.6
12.3
69
8.21
10.02
80.7
101.3
98.000
37.100
0.774
1.028
10
24.9
15.8
70
8.21
11.39
80.7
117.7
98.000
6.180
0.774
0.806
9
4.0
3.0
71
8.21
11.98
80.7
97.2
98.000
20.850
0.774
0.800
9
10.2
5.2
72
8.21
10.80
80.7
99.6
98.000
18.290
0.774
0.803
9
9.8
12.1
73
8.21
10.17
80.7
170.2
98.000
0.852
0.774
0.894
9
10.7
3.5
74
8.21
11.10
80.7
130.5
98.000
2.370
0.774
0.807
9
3.6
3.3
75
7.77
6.84
142.2
99.2
12.500
49.000
0.764
0.688
7
24.7
1.1
76
7.77
8.21
142.2
80.7
12.500
98.000
0.764
0.774
7
11.4
5.0
77
7.77
7.38
142.2
98.4
12.500
45.700
0.764
0.680
7
17.2
0.9
78
7.77
7.28
142.2
68.7
12.500
151.300
0.764
0.655
7
19.4
3.0
79
7.77
7.82
142.2
100.9
12.500
46.000
0.764
0.765
7
13.9
3.3
80
7.77
7.58
142.2
125.7
12.500
14.000
0.764
0.699
7
14.0
0.5
81
7.38
11.39
98.4
117.7
45.700
6.180
0.680
0.806
9
2.9
7.7
82
7.38
11.98
98.4
97.2
45.700
20.850
0.680
0.800
9
4.2
5.7
83
7.38
10.17
98.4
170.2
45.700
0.852
0.680
0.894
9
3.0
11.6
84
7.38
11.10
98.4
130.5
45.700
2.370
0.680
0.807
9
2.6
5.9
85
7.28
10.02
68.7
101.3
151.300
37.100
0.655
1.028
12
16.4
7.8
86
7.38
10.02
98.4
101.3
45.700
37.100
0.680
1.028
8
10.9
13.0
87
7.28
11.39
68.7
117.7
151.300
6.180
0.655
0.806
9
4.9
4.9
88
7.28
11.98
68.7
97.2
151.300
20.850
0.655
0.800
9
1.4
4.2
89
7.38
10.80
98.4
99.6
45.700
18.290
0.680
0.803
9
3.4
3.7
90
7.28
10.80
68.7
99.6
151.300
18.290
0.655
0.803
9
1.4
5.9
91
7.28
10.17
68.7
170.2
151.300
0.852
0.655
0.894
9
5.2
8.1
92
7.28
11.10
68.7
130.5
151.300
2.370
0.655
0.807
9
3.5
2.4
93
7.82
10.02
100.9
101.3
46.000
37.100
0.765
1.028
10
19.2
8.9
94
7.82
11.39
100.9
117.7
46.000
6.180
0.765
0.806
9
2.7
1.1
95
7.82
11.98
100.9
97.2
46.000
20.850
0.765
0.800
9
8.9
1.9
96
7.82
10.80
100.9
99.6
46.000
18.290
0.765
0.803
9
9.3
10.6
97
7.82
10.17
100.9
170.2
46.000
0.852
0.765
0.894
9
6.5
2.6
98
7.82
11.10
100.9
130.5
46.000
2.370
0.765
0.807
9
2.1
1.7
99
7.58
10.02
125.7
101.3
14.000
37.100
0.699
1.028
9
10.0
10.8
100
7.58
11.39
125.7
117.7
14.000
6.180
0.699
0.806
9
1.3
3.0
101
7.58
11.98
125.7
97.2
14.000
20.850
0.699
0.800
9
8.1
2.7
102
7.58
10.80
125.7
99.6
14.000
18.290
0.699
0.803
9
8.2
7.2
103
7.58
10.17
125.7
170.2
14.000
0.852
0.699
0.894
9
2.3
6.2
104
7.58
11.10
125.7
130.5
14.000
2.370
0.699
0.807
9
2.1
1.2
105
8.85
6.84
138.4
99.2
8.700
49.000
0.857
0.688
7
29.0
6.3
106
8.85
8.21
138.4
80.7
8.700
98.000
0.857
0.774
7
23.4
11.9
107
8.85
7.38
138.4
98.4
8.700
45.700
0.857
0.680
7
23.4
6.6
108
8.85
7.28
138.4
68.7
8.700
151.300
0.857
0.655
7
29.5
3.3
109
8.85
7.82
138.4
100.9
8.700
46.000
0.857
0.765
7
22.4
5.3
110
8.85
7.58
138.4
125.7
8.700
14.000
0.857
0.699
7
21.0
3.5
111
8.90
6.84
110.6
99.2
28.500
49.000
0.862
0.688
12
31.6
9.2
112
8.90
8.21
110.6
80.7
28.500
98.000
0.862
0.774
7
20.8
9.9
113
8.90
7.38
110.6
98.4
28.500
45.700
0.862
0.680
12
26.1
8.3
114
8.90
7.28
110.6
68.7
28.500
151.300
0.862
0.655
7
26.8
0.3
115
8.90
7.82
110.6
100.9
28.500
46.000
0.862
0.765
12
26.9
8.2
116
8.90
7.58
110.6
125.7
28.500
14.000
0.862
0.699
12
20.9
9.5
11.6±9.0
6.1±5.0
a Details of data sets are the same as in Table 1.
3. Results and discussion
The solubilities of anthracene in 116 different binary solvent mixtures (for details see Table 1) were used to compute Bi terms of each binary solvent and the Bi terms were employed to build up a quanitative structure property relationship (QSPR) model using physico-chemical properties of the solvents. Details of the physico-chemical properties were listed in Table 2. The obtained QSPR models for calculating Bi terms are:
The back-calculated Bi terms were used to calculate the solubility of anthracene in binary solvent mixtures and MPD values were also listed in Table 2. The lowest and highest MPDs were 0.2 (for solubility of anthracene in 3-methyl-1-butanol + 4-methyl-2-pentanol) and 18.8 (for solubility of anthracene in 2- propanol + dibutyl ether) and the overall MPD (± SD) was 6.1±5.0. The required information for predicting solubility of anthracene in binary solvents is the numerical values of X1 and X2, i.e. two points for each binary solvent systems. The same calculations were done using equations (2-4) taken from a previous work and MPD values were reported in Table 2. The lowest and highest MPDs were 0.5 (for solubility of anthracene in 1-octanol + 1-pentanol) and 35.0 (for solubility of anthracene in 2-propanol + dibutyl ether). The maximum MPD of previous and proposed methods belonged to the same data set. The overall MPD (±SD) was 11.6±9.0 and it was significantly different from the proposed method (paired t-test, p MPD values sorted in four subgroups, i.e. 30 %. All MPD values of the proposed method in this work lied in < 20 % category while it was 78 % for the previous method.
As general conclusion, the proposed method is able to compute solubility of anthracene in mixed solvent systems using experimental data of the solute in mono- solvent systems and the expected prediction error is ~ 6 % which is acceptable error range for prediction purposes. The corresponding prediction error of the previous method is ~12 %. Employing BP, VP and ρ of the solvents along with δ values improved the predictability of the method by a factor of 2. This is expected since employing three more physico-chemical properties provides more information from the solvent-solvent interactions and resulted in more accurate predictions.
References
[1] Nadon L, Siemiatycki J, Dewar R, Krewski D, Gerin M. Cancer risk due to occupational exposure to polycyclic aromatic hydrocarbons. Am J Ind Med 1995; 28: 303-24.
[2] Bonnet JL, Guiraud P, Dusser M, Kadri M, Laffosse J, Steiman R, Bohatier J. Assessment of anthracene toxicity toward environmental eukaryotic microorganisms: Tetrahymena pyriformis and selected micromycetes. Ecotoxicol Environ Saf 2005; 60: 87-100.
[3] Jouyban-Gharamaleki A, Hanaee J. A novel method for improvement of predictability of the CNIBS/R-K equation. Int J Pharm 1997; 154:245-7.
[4] Acree WE. Model for solubility estimation in mixed solvent systems - Comments. Int J Pharm1996; 127: 27-30.
[5] Jouyban-Gharamaleki A, Valaee L, Barzegar- Jalali M, Clark BJ, Acree WE. Comparison of various cosolvency models for calculating solute solubility in water-cosolvent mixtures. Int J Pharm 1999; 177: 93-101.
[6] Jouyban A, Khoubnasabjafari M, Acree WE.Mathematical representation of solute solubility in binary mixture of supercritical fluids by the Jouyban-Acree model. Pharmazie 2005; 60: 527-9.
[7] Jouyban A, Khoubnasabjafari M, Chan HK, Clark BJ, Acree WE. Solubility prediction of anthracene in mixed solvents using a minimum number of experimental data. Chem Pharm Bull 2002; 50:21-5.
[8] Powell JR, Miller BJ, Acree WE. Solubility of anthracene in binary alcohol plus 1,4-dioxane solvent mixtures. J Chem Eng Data 1995;40:1124-6.
[9] Powell JR, Mchale MER, Kauppila ASM, Otero P, Jayasekera M, Acree WE. Solubility of anthracene in binary alcohol plus 2-ethyl-1-hexanol solvent mixtures. J Chem Eng Data 1995; 40:1270-2.
[10] Mchale MER, Kauppila ASM, Powell JR, Acree WE. Solubility of anthracene in (binary alcohol plus 2-butoxyethanol) solvent mixtures. J Chem Thermodynamics 1996; 28: 209-14.
[11] Mchale MER, Powell JR, Kauppila ASM, Acree WE. Solubility of anthracene in binary alcohol plus 2-methoxyethanol solvent mixtures. J Chem Eng Data 1996; 41: 105-6.
[12] Powell JR, Mchale MER, Kauppila ASM, Acree WE. Solubility of anthracene in binary alcohol plus 2-pentanol and alcohol plus 4-methyl-2- pentanol solvent mixtures. J Chem Eng Data1996; 41: 728-30.
[13] Powell JR, Acree WE. Solubility of anthracene in binary alcohol plus dibutyl ether solvent mixtures. J Chem Eng Data 1995; 40: 914-6.
[14] Hernandez CE, Roy LE, Reddy GD, Martinez GL, Parker A, Jackson A, Brown G, Acree WE. Solubility of anthracene in binary alkane plus 2- butoxyethanol solvent mixtures at 298.2 K. J Chem Eng Data 1997; 42: 1249-50.
[15] Zvaigzne AI, Teng IL, Martinez E, Trejo J, Acree WE. Solubility of anthracene in binary alkane+1- propanol and alkane+1-butanol solvent mixtures. J Chem Eng Data 1993; 38: 389-92.
[16] Zvaigzne AI, Acree WE. Solubility of anthracene in binary alkane plus 3-methyl-1-butanol solvent mixtures. J Chem Eng Data 1994; 39: 708-10.
[17] Procyk AD, Bissell M, Street KW, Acree WE.Solubility in binary solvent systems. VIII. Estimation of binary alkane plus para-dioxane solvent nonideality from measured anthracene solubilities. J Pharm Sci 1987; 76: 621-5.
[18] Zvaigzne AI, Acree WE. Solubility of Anthracene in Binary Alkane Plus 2-Butanol Solvent Mixtures. J Chem Eng Data 1994; 39: 114-6.
[19] Mchale MER, Kauppila ASM, Powell JR, Acree WE. Solubility of anthracene in binary (2- alkoxyethanol plus 2-alkoxyethanol) solvent mixtures. J Chem Thermodynamics 1996; 28:589-93.
[20] Acree WE, Tucker SA. Solubility of anthracene in binary para-xylene + alkane and benzene + alkane solvent mixtures. Phys Chem Liq 1989; 20:31-8.
[21] Marthandan MV, Acree WE. Solubility of anthra- cene in binary solvent mixtures containing dibutyl ether. J Chem Eng Data 1987; 32: 301-3.
[22] Powell JR, Mchale MER, Kauppila ASM, Acree WE, Campbell SW. Solubility of anthracene in binary alcohol plus 1-pentanol solvent mixtures at25 degrees C: Comparison of expressions derived from mobile order theory and the Kretschmer - Wiebe association model. J Solution Chem 1996;25: 1001-17.
[23] Tucker SA, Murral DJ, Oswalt BM, Halmi JL, Acree WE. Solubility of anthracene in binary toluene + alkane solvent mixtures. Phys Chem Liq 1988; 18: 279-86.
Top