Evaluation of the dependence of aqueous solubility of nitro compounds on temperature and salinity: A COSMO-RS simulation

Chemosphere

Volumn 83, Issue 3, 2011, Pages 287-294

  Kholod, Yana A ^a   Gryn'ova, Ganna ^a   Gorb, Leonid ^b   Hill, Frances C ^c   Leszczynski, Jerzy ^a,c  

^a JACKSON STATE UNIVERSITY   (United States)

^b SpecPro Inc   (United States)

^c US ARMY ENGINEER RESEARCH AND DEVELOPMENT CENTER   (United States)

Author keywords

Aqueous solubility; COSMO RS; Nitro compounds; Seawater

Indexed keywords

SALINE WATER; SEAWATER;

2 ,4 ,6-TRINITROTOLUENE; 2 ,4-DINITROTOLUENE; 2 ,6-DINITROTOLUENE; AQUEOUS SOLUBILITY; CONDUCTOR-LIKE SCREENING MODEL FOR REAL SOLVENTS; COSMO-RS; NITRO COMPOUNDS; QUALITATIVE ESTIMATION;

SOLUBILITY;

2 NITROTOLUENE; 2,3 DINITROTOLUENE; 2,4 DINITROTOLUENE; 2,6 DINITROTOLUENE; 3 NITROTOLUENE; 3,4 DINITROTOLUENE; 4 NITROTOLUENE; NITRO DERIVATIVE; NITROBENZENE; TRINITROBENZENE; TRINITROTOLUENE; UNCLASSIFIED DRUG;

ACCURACY ASSESSMENT; AQUEOUS SOLUTION; AROMATIC HYDROCARBON; ESTIMATION METHOD; EXPERIMENTAL STUDY; NITROGEN COMPOUND; NUMERICAL MODEL; QUALITATIVE ANALYSIS; SALINITY; SALT; SEAWATER; SOLVENT; TEMPERATURE EFFECT;

ACCURACY; AQUEOUS SOLUTION; ARTICLE; EVALUATION; QUALITATIVE ANALYSIS; REPRODUCIBILITY; SALINITY; SIMULATION; SOLUBILITY; TEMPERATURE;

EID: 79952454209     PISSN: 00456535     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2010.12.065     Document Type: Article

References (36)

1. Al Momani F. Impact of photo-oxidation technology on the aqueous solutions of nitrobenzene: Degradation efficiency and biodegradability enhancement. J. Photochem. Photobiol. A 2006, 179:184-192.
2. Barone V., Cossi M. Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model. J. Phys. Chem. A 1998, 102:1995-2001.
3. Chickos J.S., Acree W.E., Liebman J.F. Estimating solid-liquid phase change enthalpies and entropies. J. Phys. Chem. Ref. Data 1999, 28:1535-1673.
4. Davis J.L., Brooks M.C., Larson S.L., Nestler C.C., Felt D.R. Lime treatment of explosives-contaminated soil from munitions plants and firing ranges. Soil Sediment. Contamin. 2006, 15:565-580.
5. Eckert, F., Klamt, A., 2002. COSMOtherm, Ver C1.2, Release 07.02. COSMOlogic KG, Leverkusen, Germany.
6. Nitro Compounds: Recent Advances in Synthesis and Chemistry 1990, New York, VCH Publishing. H. Feuer, A.T. Nielsen (Eds.).
7. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, Jr., J.A., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., Pople, J.A., 2004. Gaussian 03, Revision B.01, Gaussian, Inc.: Wallingford, CT.
8. 2 technique. Environ. Sci. Technol. 2002, 36:3936-3944.
9. Gorontzy T., Drzyzga O., Kahl M.W., Bruns-Nagel D., Breitung J., von Loew E., Blotevogel K.H. Microbial degradation of explosives and related compounds. Crit. Rev. Microbiol. 1994, 20(4):265-284.
10. Hawari J., Beaudet S., Halasz A., Thiboutot S., Ampleman G. Microbial degradation of explosives: Biotransformation versus mineralization. Appl. Microbiol. Biotechnol. 2000, 54(5):605-618.
11. Hawari J., Deschamps S., Beaulieu C., Paquet L., Halasz A. Photodegradation of CL-20: Insights into the mechanisms of initial reactions and environmental fate. Water Res. 2004, 38(19):4055-4064.
12. Kholod Y.A., Muratov E.N., Gorb L., Hill F.C., Artemenko A.G., Kuz'min V.E., Qasim M., Leszczynski J. Environ. Sci. Technol. 2009, 43(24):9208-9215.
13. Klamt A. Conductor-like screening model for real solvents: A new approach to the quantitative calculation of solvation phenomena. J. Phys. Chem. 1995, 99:2224-2235.
14. Klamt A., Eckert F. COSMO-RS: A novel and efficient method for the priori prediction of thermophysical data of liquids. Fluid Phase Equilibria 2000, 172:43-72.
15. Klamt A., Schüürmann G. COSMO: A new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient. J. Chem. Soc. Perkin Trans. II 1993, 799:805.
16. Klamt A., Eckert F., Hornig M., Beck M.E., Brger T. Prediction of aqueous solubility of drugs and pesticides with COSMO-RS. J. Comp. Chem. 2002, 23(2):275-281.
17. Lewandowski, G.A., DeFilippi, L.J., 1998. Biological Treatment of Hazardous Wastes. John Wiley & Sons Inc., New York.
18. Liou M.-J., Lu M.-C., Chen J.-N. Oxidation of explosives by Fenton and photo-Fenton processes. Water Res. 2003, 37(13):3172-3179.
19. Luning Prak D.J., Moran P.J. Solubility of 3,4-dinitrotoluene in pure water and seawater. J. Chem. Eng. Data 2008, 53:586-587.
20. Luning Prak D.J., O'Sullivan D.W. Solubility of 2,4-dinitrotoluene and 2,4,6-trinitrotoluene in seawater. J. Chem. Eng. Data 2006, 51:448-450.
21. Luning Prak D.J., O'Sullivan D.W. Solubility of 4-nitrotoluene, 2,6-dinitrotoluene, 2,3-dinitrotoluene, and 1,3,5-trinitrobenzene in pure water and seawater. J. Chem. Eng. Data 2007, 52:2446-2450.
22. Luning Prak D.J., O'Sullivan D.W. Assessing the salting-out behavior of nitrobenzene, 2-nitrotoluene, and 3-nitrotoluene from solubility values in pure water and seawater at temperatures between (277 and 314) K. J. Chem. Eng. Data 2009, 54:1231-1235.
23. Neilson A.H., Allard A.-S. Environmental Degradation and Transformation of Organic Chemicals 2008, CRC Press, Boca Raton, Florida.
24. Nipper M., Qian Y., Carr R.S., Miller K. Degradation of picric acid and 2, 6-DNT in marine sediments and waters: the role of microbial activity and ultraviolet exposure. Chemosphere 2004, 56:519-530.
25. Oleszek-Kudlak S., Grabda M., Shibata E., Eckert F., Nakamura T. Application of the COSMO-RS Method for prediction of the aqueous solubility of chlorobenzenes depending on temperature and salinity. Envir. Toxicol. Chem. 2005, 24(6):1368-1375.
26. Qasim M., Fredrickson H., Honea P., Furey J., Leszczynski J., Okovytyy S., Szecsody J., Kholod Y. Prediction of CL-20 chemical degradation pathways, theoretical and experimental evidence for dependence on competing modes of reaction. SAR QSAR Environ. Res. 2005, 16(5):495-515.
27. Qasim M., Kholod Y., Gorb L., Magers D., Honea P., Leszczynski J. Application of quantum-chemical approximations to environmental problems: Prediction of physical and chemical properties of TNT and related species. Chemosphere 2007, 69(7):1144-1150.
28. Rivail J.L., Rinaldi D. A quantum chemical approach to dielectric solvent effects. Chem. Phys. 1976, 18:233-240.
29. Rodgers J.D., Bunce N.J. Treatment methods for the remediation of nitroaromatic explosives. Water Res. 2001, 35:2101-2111.
30. Schafer A., Huber C., Ahlrichs R. Fully optimized contracted Gaussian basis sets of triple-ζ valence quality for atoms Li to Kr. J. Chem. Phys. 1994, 100:5829-5835.
31. Biodegradation of Nitroaromatic Compounds and Explosives 2000, Lewis Publishers, New York. J.C. Spain, J.B. Hughes, H.J. Knackmuss (Eds.).
32. Toghiani R.K., Toghiani H., Maloney S.W., Boddu V.M. Prediction of physicochemical properties of energetic materials. Fluid Phase Equilibria 2008, 264:86-92.
33. Xie W.-H., Shiu W.-Y., Mackay D. A review of the effect of salts on the solubility of organic compounds in seawater. Mar. Environ. Res. 1997, 44:429-444.
34. Yalkowsky S.H., He Y. Handbook of Aqueous Solubility Data 2003, CRC Press.
35. Yang H., Halasz A., Zhao J.-S., Monteil-Rivera F., Hawari J. Experimental evidence for in situ natural attenuation of 2,4- and 2,6-dinitrotoluene in marine sediment. Chemosphere 2008, 70:791-799.
36. Zhao J.-S., Greer C.W., Thiboutot S., Ampleman G., Hawari J. Biodegradation of the nitramine explosives hexahydro-1,3,5-trinitro-1,3,5-triazine and octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine in cold marine sediment under anaerobic and oligotrophic conditions. Can. J. Microbiol. 2004, 50:91-96.