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534 Journal of Chemical & Engineering Data, Vol. 55, No. 1, 2010
0.44
0.40 - / --- .
0.36 /-"
0.32
. 0.28
0.24
0.20 , -.. . . --_- - - - - - !....2 ....-9 - . .
0.16 : ~~ ~ ~~ ~~
0.12
0.08
0.04
0.00
0.0 0.2 0.4 0.6
Figure 4. Experimental and predicted moles per liter
phenanthrene at various mole fractions of ethanol in ethanol
(2) mixtures: 0, experimental. The computed solubilities
method I; -, method II; - -, method III; - - - -, meth(
0.40
0.36
0.32
0.28
0.24
0.20
0.16
0.12
0.08
0.04
0.00
0.0 0.2 0.4 0.6
Figure 5. Experimental and predicted mole per liter solubi
threne at various mole fractions of 1-propanol in 1-propanol1
(2) mixtures: 0, experimental. The computed solubilities
method I; -, method II; - -, method III; - - - -, meth(
+ 1-butanol (2). The predicted solubilities in the m
using numerical methods I to IV were compai
experimental data, and the calculated MD values are
in Table 4. The minimum MDs for methods Ito IV
for the solubility data of phenanthrene in ethanol
(1.6 %), ethanol + 1-propanol (1.7 %), ethanol d
(6.1 %), and ethanol + 1-propanol (62.1 %), resp
maximum MDs of methods I to IV are obtained
+ 1-propanol (3.6 %), methanol + 1-butanol (42.9
+ 1-propanol (16.1 %), and methanol + 1-butan
and the overall MDs (I SD) were 2.6 (1 2.4) %,
%, 10.8 (1 6.1) %, and 94.5 (t 48.3) %. Metho
high prediction MD because of its higher ur
predicting solubility in neat solvents. Figures 1 to
the experimental and predicted solubility of phe
various mole fractions of the solvent 1 in the mix
basis of these figures and the MDs of methods I to IV, it is
obvious that method I provides better results which is in
agreement with previous findings.'10'"14 As an ab initio ap-
proach, method III gave acceptable results in comparison with
the other method which is in agreement with other works.'0''14
It has been shown that the predictability of the proposed model
S... - is acceptable when compared against the experimental uncer-
tainty. On the basis of previous0 and recent reports, it is possible
to suggest that method III can be used for prediction of the
solubility of phenanthrene in different nonaqueous solvent
mixtures.
0.8 1.0 Literature Cited
(1) Laha, S.; Tansel, B.; Ussawarujikulchai, A. Surfactant-Soil Interactions
r solubility of During Surfactant-Amended Remediation of Contaminated Soils by
(1) + 1-butanol Hydrophobic Organic Compounds: A Review. J. Environ. Manage.
2009, 90, 95-100.
using: - - - -, (2) Brewster, M. E.; Loftsson, T. Cyclodextrins as Pharmaceutical
)d IV. Solubilizers. Adv. Drug Delivery Rev. 2007, 59, 645-666.
(3) Li, A.; Cheung, K. A.; Reddy, K. R. Cosolvent-Enhanced Electroki-
netic Remediation of Soils Contaminated with Phenanthrene. J.
Environ. Eng. 2000, 126, 527-533.
(4) Chen, C. S.; Tseng, S. J. Effects of Cosolvent and Temperature on
the Desorption of Polynuclear Aromatic Hydrocarbons from Con-
taminated Sediments of Chien-Jen River, Taiwan. Soil Sediment
Contam. 2007, 16, 507-521.
(5) Bouchard, D. C. Cosolvent Effects of Phenanthrene Sorption-Desorp-
tion on a Fresh Water Sediment. Environ. Toxicol. Chem. 2003, 22,
- - -- -736-740.
(6) Maturi, K.; Reddy, K. R. Cosolvent-Enhanced Desorption and
Transport of Heavy Metals and Organic Contaminants in Soils during
Electrokinetic Remediation. Water, Air, Soil Pollut. 2008, 189, 199-
211.
(7) Dickhut, R. M.; Armstrong, D. E.; Andren, A. W. The Solubility of
Hydrophobic Aromatic Chemicals in Organic Solvent/Water Mixtures:
0.8 1.0 Evaluation of Four Mixed Solvent Solubility Estimation Methods.
Environ. Toxicol. Chem. 1991, 10, 881-889.
(8) Fan, C. H.; Jafvert, C. T. Margules Equations Applied to PAH
lity of phenan- Solubilities in Alcohol-Water Mixtures. Environ. Sci. Technol. 1997,
(1) + 1-butanol 31, 3516-3522.
using: - - - -, (9) Ali, S. H.; Al-Mutairi, F. S.; Fahim, M. A. Solubility of Polycyclic
Aromatics in Binary Solvent Mixtures Using Activity Coefficient
)d IV.Models. Fluid Phase Equilib. 2005, 230, 176-183.
(10) Fakhree, M. A. A.; Shayanfar, A; Acree, W. E., Jr.; Jouyban, A.
ixed solvents Solubility of Phenanthrene in Binary Mixtures of C1-C4 Alcohols +
2-Propanol and Ethanol + Methanol at 298.2 K. J. Chem. Eng. Data
red with the 2009, 54, 1405-1408.
summarized (11) Jouyban, A.; Acree, W. E., Jr. Solubility Prediction in Non-Aqueous
are observed Binary Solvents Using a Combination of Jouyban-Acree and Abraham
+ -butanol Models. Fluid Phase Equilib. 2006, 249, 24-32.
(12) Acree, W. E., Jr.; Abraham, M. H. Solubility Predictions for Crystalline
+ 1-propanol Nonelectrolyte Solutes Dissolved in Organic Solvents Based Upon
actively. The the Abraham General Solvation Model. Can. J. Chem. 2001, 79, 1466-
for methanol 1476.
(13) Loncar, E. S.; Kolarov, L. A.; Malbasa, R. V.; Skrbic, B. D. Qualitative
%), methanol TLC Determination of Some Polycyclic Aromatic Hydrocarbons in
)l (156.5 %), Sugar-Beet. J. Serb. Chem. Soc. 2005, 70, 1237-1242.
15.3 (t 23.4) (14) Shayanfar, A.; Soltani, S.; Jabbaribar, F.; Hamidi, A. A.; Acree, W. E.,
Jr.; Jouyban, A. Naphthalene Solubility in Binary Solvent Mixtures
d IV gives a of 2,2,4-Trimethylpentane + Alcohols at 298.15 K. J. Chem. Eng.
certainty in Data 2008, 53, 574-577.
5 illustrated
nanthrene at Received for review April 4, 2009. Accepted December 9, 2009.
tures. On the JE900599Q
I I I
- - - - -- - - - - - - - - -
