Skip to main content
Log in

Solubilities of hydrophobic compounds in aqueous-organic solvent mixtures

  • Published:
Environmental Monitoring and Assessment Aims and scope Submit manuscript

Abstract

Solubilities of several hydrophobic organic substances (paradichlorobenzene, endrin, naphthalene, and dibutyl phthalate) in aqueous solutions containing up to 0.10 mole fraction of common alcohols and ketones, were measured by gas chromatography. The solubilities are significantly increased by the alcohols and ketones. The results are interpreted in terms of the association of n molecules of alcohol or ketone with each hydrophobic organic molecule. Values of n and the equilibrium constant for this association are reported for each hydrophobic organic-alcohol and organic-ketone combination. The implications of these results for the disposal of toxic wastes by landfilling is discussed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Barone, G., Crescenzi, V., Pispisa, B., and Quadrifoglio, F.: 1966, ‘Hydrophobic Interactions in Polyelectrolyte Solutions. II. Solubility of some C3−C6 Alkanes in Poly(methacrylic acid) Solutions’, J. Macromol. Chem. 1, 761–771.

    Google Scholar 

  • Barone, G., Crescenzi, V., Liquori, A. M., and Quadrifoglio, F.: 1967, ‘Solubilization of Polycylic Aromatic Hydrocarbons in Poly(methacrylic acid) Aqueous Solutions’, J. Phys. Chem. 71, 2341–2345.

    Google Scholar 

  • Baughman, G. L. and Burns, L. A.: 1980, ‘Transport and Transformation of Chemicals: A Perspective’, in Hutzinger, O. (ed.), The Handbook of Environmental Chemistry, Springer-Verlag, Berlin.

    Google Scholar 

  • Ben-Naim, B.: 1980, Hydrophobic Interactions, Plenum, New York.

    Google Scholar 

  • Birdi, K. S.: 1976, ‘Comparative Purity of Commercially Available Sodium Dodecyl Sulfates: A Simple Criterion’, Anal. Biochem. 74, 620–622.

    Google Scholar 

  • Burns, L. A., Cline, D. M., and Lassiter, R. R.: 1981, Exposure Analyses Modeling Systems (EXAMS): User Manual and System Documentation, Draft, U.S. EPA.

  • Conway, R. A. (ed.): 1982, Environmental Risk Analysis for Chemicals, Van Nostrand Reinhold Co., New York.

    Google Scholar 

  • Franks, F.: 1968, ‘Effects of Solutes on the Hydrogen Bonding in Water’, in Covington, A. K., and Jones, P. (ed.), Hydrogen-Bonded Solvent Systems, Taylor and Francis, Ltd., London.

    Google Scholar 

  • Fuller, W. H.: 1978, Investigation of Landfill Leachate Pollutant Attenuation by Soils, EPA Report No. EPA-600/2-78-156.

  • Glew, D. N., Mak, H. D., and Rath, N. S.: 1968, ‘Aqueous Non-Electrolyte Solutions: Part VII. Water Shell Stabilization by Interstitial Nonelectrolytes’, in Covington, A. K. and Jones, P. (eds.), Hydrogen-Bonded Solvent Systems, Taylor and Francis, Ltd., London.

    Google Scholar 

  • Griffin, R. A. and Shimp, N. F.: 1978, Attenuation of Pollutants in Municipal Landfill Leachate by Clay Minerals, EPA Report No. EPA-600/2-78-157.

  • Jaffe, P., Parker, F. L., and Wilson, D. J.: 1982, ‘Distribution of Toxic Substances in Rivers’, J. Environ. Eng. ASCE 108 (EE4), 639–649.

    Google Scholar 

  • Lassiter, R. R., Baughman, G. L., and Burns, L. A.: 1974, ‘Fate of Toxic Organic Substances in the Aquatic Environment’, in Jorgensen, S. F. (ed.), State-of-the-Art in Ecological Modeling, International Society for Ecological Modeling.

  • Mukerjee, P. and Cardinal, J. R.: 1976, ‘Solubilization as a Method for Studying Self-Association: Solubility of Napthalene in the Bile Salt Sodium Cholate and the Complex Pattern of its Aggregation’, J. Pharmaceutical Sci. 65, 882–886.

    Google Scholar 

  • O'Connor, D. J., Mueller, J. A., and Farley, K. J.: 1983, ‘Distribution of Kepone in the James River Estuary’, J. Environ. Eng., ASCE 109 (2), 396–413.

    Google Scholar 

  • Office of Technology Assessment: 1983, Technologies and Management Strategies for Hazardous Waste Control-Summary, Office of Technology Assessment, Congress of the United States.

  • Park, R. A. et al.: 1980, Modeling Transport and Behavior of Pesticides in Aquatic Environments, Rennselaer Polytechnic Institute.

  • Parker, F. L., Komarov, E., and Seuss, M. J.: 1983, ‘Impact on Man and Environment, and Control of Chemical and Radioactive Wastes’, Internat. Atomic Energy Agency Intern. Conf. on Radioactive Waste Management, Seattle, Wash., May 16–20, 1983.

  • Rowlinson, J. S. and Swinton, F. L.: 1982, Liquids and Liquid Mixtures, 3rd ed., Butterworth Scientific, London, p. 174.

    Google Scholar 

  • U.S. EPA: 1977, The Prevalence of Subsurface Migration of Hazardous Chemical Substances at Selected Industrial Waste Land Disposal Sites, U.S. EPA Report No. EPA-530/SW-634.

  • U.S. EPA: 1980a, Groundwater Protection, Report No. SW-886, Water Planning Division, Office of Solid Waste, U.S. EPA.

  • U.S. EPA: 1980b, Ambient Water Quality Criteria for Dichlorobenzenes, EPA-440/5-80-040, U.S. Environmental Protection Agency.

  • U.S. EPA: 1980c, Damages and Threats Caused by Hazardous Material Sites, U.S. EPA Report No. EPA-430/9-80-004.

  • Weast, R. C.: 1964, Handbook of Chemistry and Physics, 45th ed., Chemical Rubber Company, Cleveland, Oh. (now CRC Press, Boca Raton, Fl.).

    Google Scholar 

  • Wishnia, A.: 1962, ‘The Solubility of Hydrocarbon Gases in Protein Solutions’, Proc. Nat'l, Acad. Sci. U.S.A. 48, 2200–2204.

    Google Scholar 

  • Wishnia, A. and Pinder, T. W.: 1964, ‘Hydrophobic Interactions in Proteins; Conformation Changes in Bovine Serum Albumin below pH 5’, Biochemistry 3, 1377–1384.

    Google Scholar 

  • Wishnia, A. and Pinder, T. W.: 1966, ‘Hydrophobic Interactions in Proteins. The Alkane-Binding Site of Beta-Lactoglobins A and B’, Biochemistry 5, 1534–1542.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Nyssen, G.A., Miller, E.T., Glass, T.F. et al. Solubilities of hydrophobic compounds in aqueous-organic solvent mixtures. Environ Monit Assess 9, 1–11 (1987). https://doi.org/10.1007/BF00394211

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00394211

Keywords

Navigation