Prediction of partitioning between complex organic mixtures and water: Application of polyparameter linear free energy relationships

Environmental Science and Technology

Volumn 40, Issue 2, 2006, Pages 536-545

  Endo, Satoshi ^a   Schmidt, Torsten C ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

FREE ENERGY; HYDROGEN BONDS; LEACHING; MIXTURES; ORGANIC COMPOUNDS; VOLUME FRACTION;

FUEL ADDITIVE; PARTITIONING COEFFICIENTS; REGRESSION EQUATION;

WATER;

ALCOHOL; COAL TAR; FUEL; OCTANOL; ORGANIC COMPOUND; PHENOL; SOLVENT; WATER;

FREE ENERGY; HYDROGEN BONDS; LEACHING; MIXTURES; ORGANIC COMPOUNDS; VOLUME FRACTION; WATER;

NONAQUEOUS PHASE LIQUID; PARTITIONING;

ARTICLE; CALCULATION; ENERGY; ERROR; HYDROGEN BOND; LEACHING; LIQUID; MATHEMATICAL ANALYSIS; MOLECULAR INTERACTION; NONAQUEOUS PHASE LIQUID; PARAMETER; PARTITION COEFFICIENT; POLYPARAMETER LINEAR FREE ENERGY; PREDICTION; SOLUTE; STATISTICAL MODEL;

ORGANIC CHEMICALS; WATER;

EID: 31144468085     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es0515811     Document Type: Article

References (45)

1. Domenico, P. A.; Schwartz, F. W. Multiphase Fluid Systems. In Physical and Chemical Hydrogeology, 2nd ed.; John Wiley & Sons: New York, 1997; Chapter 19.
2. Lane, W. F.; Loehr, R. C. Estimating the equilibrium aqueous concentrations of polynuclear aromatic hydrocarbons in complex mixtures. Environ. Sci. Technol. 1992, 26, 983-990.
3. Cline, P. V.; Delfino, J. J.; Rao, P. S. C. Partitioning of aromatic constituents into water from gasoline and other complex solvent mixtures. Environ. Sci. Technol. 1991, 25, 914-920.
4. Lee, L. S.; Hagwall, M.; Delfino, J. J.; Rao, P. S. C. Partitioning of polycyclic aromatic hydrocarbons from diesel fuel into water. Environ. Sci. Technol. 1992, 26, 2104-2110.
5. Schwarzenbach, R. P.; Gschwend, P. M.; Imboden, D. M. Environmental Organic Chemistry, 2nd ed.; John Wiley & Sons: New York, 2003.
6. Eberhardt, C.; Grathwohl, P. Time scales of organic contaminant dissolution from complex source zones: Coal tar pools vs. Blobs. J. Contam. Hydrol. 2002, 59, 45-66.
7. Reckhorn, S. B. F.; Zuquette, L. V.; Grathwohl, P. Experimental investigations of oxygenated gasoline dissolution. J. Environ. Eng. 2001, 208-216.
8. Schmidt, T. C.; Kleinen, P.; Stengel, C.; Goss, K.-U.; Haderlein, S. B. Polar fuel constituents: compound identification and equilibrium partitioning between nonaqueous phase liquids and water. Environ. Sci. Technol. 2002, 36, 4074-4080.
9. Rodgers, R. P.; White, F. M.; Hendrickson, C. L.; Marshall, A. G.; Andersen, K. V. Resolution, elemental composition, and simultaneous monitoring by Fourier transform ion cyclotron resonance mass spectrometry of organosulfur species before and after diesel fuel processing. Anal. Chem. 1998, 70, 4743-4750.
10. Motor Gasoline; Marshall, E. L., Owen, K., Eds.; RCS: London, 1995.
11. Franck, H. G. The challenge in coal-tar chemicals. J. Ind. Eng. Chem. 1963, 55, 38-44.
12. Mueller, J. G.; Chapman, P. J.; Pritchard, P. H. Creosote-contaminated sites, their potential for bioremediation. Environ. Sci. Technol. 1989, 23, 1197-1201.
13. Hale, R. C.; Aneiro, K. M. Determination of coal tar and creosote constituents in the aquatic environment. J. Chromatogr. A 1997, 774, 79-95.
14. Breivik, K.; Wania, F. Expanding the applicability of multimedia fate models to polar organic chemicals. Environ. Sci. Technol. 2003, 37, 4934-4943.
15. Goss, K.-U.; Schwarzenbach, R. P. Linear free energy relationships used to evaluate equilibrium partitioning of organic compounds. Environ. Sci. Technol. 2001, 35, 1-9.
16. Nguyen, T. H.; Goss, K.-U.; Ball, W. P. Polyparameter linear free energy relationships for estimating the equilibrium partition of organic compounds between water and the natural organic matter in soils and sediments. Environ. Sci. Technol. 2005, 39, 913-924.
17. Arey, J. S.; Gschwend, P. M. Estimating partition coefficients for fuel-water systems: Developing linear solvation energy relationships using linear solvent strength theory to handle mixtures. Environ. Sci. Technol. 2005, 39, 2702-2710.
18. Abraham, M. H.; Chadha, H. S. In Lipophilicity in drug action and toxicology, Pliska, V., Testa, B., van de Waterbeemd, H., Eds.; VCH Verlagsgesellschaft mbH: Weinheim, 1996; pp 311-337.
19. Abraham, M. H. Scales of solute hydrogen-bonding: Their construction and application to physicochemical and biochemical processes. Chem. Soc. Rev. 1993, 22, 73-83.
20. Abraham, M. H.; Ibrahim, A.; Zissimos, A. M. Determination of sets of solute descriptors from chromatographic measurements. J. Chromatogr. A 2004, 1037, 29-47.
21. Abraham, M. H.; Andonian-Haftvan, J.; Whiting, G. S.; Leo, A.; Taft, R. S. Hydrogen bonding. Part 34. The factors that influence the solubility of gases and vapors in water at 298 K, and a new method for its determination. J. Chem. Soc., Perkin Trans. 2 1994, 1777-1791.
22. Abraham, M. H.; Chadha, H. S.; Whiting, G. S.; Mitchell, R. C. Hydrogen bonding. 32. An analysis of water-octanol and water-alkane partitioning and the DLOGP parameter of seller. J. Pharm. Sci. 1994, 83, 1085-1100.
23. Abraham, M. H. Hydrogen-bonding. 31. Construction of a scale of solute effective or summation hydrogen-bond basicity. J. Phys. Org. Chem. 1993, 6, 660-684.
24. Platts, J. A.; Butina, D.; Abraham, M. H.; Hersey, A. Estimation of molecular linear free energy relation descriptors using a group contribution approach. J. Chem. Inf. Comput. Sci. 1999, 39, 835-845.
25. Arey, J. S.; Green, W. H., Jr.; Gschwend, P. M. The electrostatic origin of Abraham's solute polarity parameter. J. Phys. Chem. B 2005, 109, 7564-7573.
26. Purnell, J. H.; Vargas de Andrade, J. M. Solution and complexing studies. I. Gas-liquid chromatographic investigation of supposed complexing systems. J. Am. Chem. Soc. 1975, 97, 3585-3590.
27. Acree, W. E., Jr.; Bertrand, G. L. Thermochemical investigations of nearly ideal binary solvents. 4. Gas-liquid partition coefficients in complexing and noncomplexing systems. J. Phys. Chem. 1979, 83, 2355-2358.
28. Yang, Y.; Miller, D. J.; Hawthorne, S. B. Toluene solubility in water and organic partitioning from gasoline and diesel fuel into water at elevated temperatures and pressures. J. Chem. Eng. Data 1997, 42, 908-913.
29. Poulsen, M.; Lemon, L.; Barker, J. F. Dissolution of monoaromatic hydrocarbons into groundwater from gasoline-oxygenate mixtures. Environ. Sci. Technol. 1992, 26, 2483-2489.
30. Heermann, S. E.; Powers, S. E. Modeling the partitioning of BTEX in water-reformulated gasoline systems containing ethanol. J. Contam. Hydrol. 1998, 34, 315-341.
31. Bennett, B.; Larter, S. R. Partition behavior of alkylphenols in crude oil/brine systems under subsurface conditions. Geochim. Cosmochim. Acta 1997, 61, 4393-4402.
32. Arp, H. P. H.; Schmidt, T. C. Air-water transfer of MTBE, its degradation products, and alternative fuel oxygenates: The role of temperature. Environ. Sci. Technol. 2004, 38, 5405-5412.
33. Endo, S. Master Thesis, Eberhard-Karls-University Tübingen, 2005.
34. Abraham, M. H.; Acree, W. E., Jr. Correlation and prediction of partition coefficients between the gas phase and water, and the solvents dodecane and undecane. New J. Chem. 2004, 28, 1538-1543.
35. Acree, W. E., Jr.; Abraham, M. H. Solubility predictions for crystalline polycyclic aromatic hydrocarbons (PAHs) dissolved in organic solvents based upon the Abraham general solvation model. Fluid Phase Equilib. 2002, 201, 245-258.
36. Abraham, M. H.; Zissimos, A. M.; Acree, W. E. Partition of solutes into wet and dry ethers; an LFER analysis. New J. Chem. 2003, 27, 1041-1044.
37. Abraham, M. M.; Chadha, H. S.; Dixon, J. P.; Leo, A. J. Hydrogen bonding. 39. The partition of solutes between water and various alcohols. J. Phys. Org. Chem. 1994, 7, 712-716.
38. Abraham, M. H.; Platts, J. A.; Hersey, A.; Leo, A. J.; Taft, R. W. Correlation and estimation of gas-chloroform and water-chloroform partition coefficients by a linear free energy relationship method. J. Pharm. Sci. 1999, 88, 670-679.
39. Abraham, M. H.; Zhao, Y. H. Determination of solvation descriptors for ionic species: Hydrogen bond acidity and basicity. J. Org. Chem. 2004, 69, 4677-4685.
40. Abraham, M. H.; Le, J.; Acree, W. E., Jr. The solvation properties of the aliphatic alcohols. Collect. Czech. Chem. Commun. 1999, 64, 1748-1760.
41. Mackay, D. The chemistry and modeling of soil contamination with petroleum. In Soils Contaminated by Petroleum; Calabrese, E. J., Kostecji, P. T., Eds.; John Wiley: New York, 1988; pp 5-18.
42. Setarge, B.; Danzer, J.; Klein, R.; Grathwohl, P. Partitioning and interfacial tracers to characterize non- aqueous phase liquids (NAPLs) in natural aquifer material. Phys. Chem. Earth B 1999, 24, 501-510.
43. Peters, C. A.; Luthy, R. G. Coal tar dissolution in water-miscible solvents: experimental evaluation. Environ. Sci. Technol. 1993, 27, 2831-2843.
44. Ashworth, A. J.; Hooker, D. M. Mixed solvents in gas-liquid chromatography. Activity coefficients for benzene, cyclohexane, pentane and heptane in squalane-dinonyphthalate mixtures at 303 degK. J. Chmmatogr. 1979, 174, 307-313.
45. Medir, M.; Mackay, D. Extraction of phenol from water with mixed solvents. Can. J. Chem. Eng. 1975, 53, 274-277.