Dissociation constants of chloroguaiacols in water: A comparison of measured and predicted values

Environmental Toxicology and Chemistry

Volumn 15, Issue 6, 1996, Pages 809-813

  Gundersen, Jennifer L ^a,c   Macintyre, William G ^b  

^a Department of Environmental Sciences ^*  (United States)

^b VIRGINIA INSTITUTE OF MARINE SCIENCE   (United States)

^c U S ENVIRONMENTAL PROTECTION AGENCY   (United States)

Author keywords

Chloroguaiacols; Dissociation constants; Vapor phase acidities

Indexed keywords

GUAIACOL; ORGANOCHLORINE DERIVATIVE;

ARTICLE; BIOACCUMULATION; BLEACHING; CHLORINATION; COMPARATIVE STUDY; DISSOCIATION CONSTANT; EFFLUENT; MARINE ENVIRONMENT; NONHUMAN; PAPER INDUSTRY; PARTICULATE MATTER; PRIORITY JOURNAL; PULP MILL; SEDIMENT; WATER POLLUTION;

EID: 0029884025     PISSN: 07307268     EISSN: None     Source Type: Journal    
DOI: 10.1897/1551-5028(1996)015<0809:DCOCIW>2.3.CO;2     Document Type: Article

References (37)

1. Hall, E.R., J. Fraser, S. Garden and L.-A. Cornacchio. 1989. Organo-chlorine discharges in wastewaters from kraft mill bleach plants. Pulp and Paper Canada 90:T421-T425.
2. Gergov, M., M. Priha, E. Talka, O. Välttilä, A. Kangas and K. Kukkonen. 1988. Chlorinated organic compounds in effluent treatment at kraft mills. Proceedings, TAPPI Environmental Conference, Charleston, SC, USA, April 18-20, pp. 443-456.
3. Owens, J.W. 1991. The hazard assessment of pulp and paper effluents in the aquatic environment: A review. Environ. Toxicol. Chem. 10:1511-1540.
4. Owens, J.W., S.M. Swanson and D.A. Birkholz. 1994. Environmental monitoring of bleached kraft pulp mill chlorophenolic compounds in a northern Canadian river system. Chemosphere 29:89-109.
5. McLeay, D.J., et al. 1987. Aquatic toxicology of pulp and paper mill effluent: A review. EP 4/PF/1:191. Environment Canada, Ottawa, Ontario.
6. Suntio, L., W. Shiu and D. Mackay. 1988. A review of the nature and properties of chemicals present in pulp mill effluents. Chemosphere 17:1249-1290.
7. Kringstad, K. and K. Lindstrom. 1984. Spent liquors from pulp bleaching. Environ. Sci. Technol. 18:236a-248a.
8. Oikari, A.O.J. 1986. Metabolites of xenobiotics in the bile of fish in waterways polluted by pulpmill effluents. Bull. Environ. Contam. Toxicol. 36:429-436.
9. Oikari, A.O.J., G. Baram, V. Evstafyev and M. Grachev. 1988. Determination and characterization of chloroguaiacols conjugates in fish bile by HPLC. Environ. Pollut. 55:79-87.
10. Rosemarin, A., M. Notini, M. Söderström, S. Jensen and L. Landner. 1990. Fate and effects of pulp mill chlorophenolic 4,5,6-trichloroguaiacol in a model brackish water ecosystem. Sci. Total Environ. 92:69-89.
11. Fisher, S.W. 1990. The pH dependent accumulation of PCP in aquatic microorganisms with sediment. Aquat. Toxicol. 18:199-218.
12. Carey, J., M. Fox and J. Hart. 1988. Identity and distribution of chlorophenols in the north arm of the Fraser River estuary. Water Pollut. Res. J. Can. 23:31-44.
13. Carey, J. and J. Hart. 1988. Sources of chlorophenolic compounds in the Fraser River estuary. Water Pollut. Res. J. Can. 23:55-68.
14. McKague, A.B., M.-C. Kolar and K. Kringstad. 1988. Nature and properties of some chlorinated lipophilic, organic compounds in spent liquors from pulp bleaching. 1. Liquors from conventional bleaching of softwood kraft pulp. Environ. Sci. Technol. 22:523-526.
15. Paasivirta, J., J. Knuutinen, M. Knuutila, P. Maatela, O. Pastinen, L. Virkki, R. Paukku and S. Herve. 1988. Lignin and organic chlorine compounds in lake water and the role of chlorobleaching effluents. Chemosphere 17:147-158.
16. Voss, R.H. 1983. Chlorinated neutral organics in biologically treated bleached kraft mill effluents. Environ. Sci. Technol. 17:530-537.
17. Xie, T.-M., K. Abramsson, E. Fogelqvist and B. Josefsson. 1986. Distribution of chlorophenolics in a marine environment. Environ. Sci. Technol. 20:457-463.
18. Paasivirta, J., J. Knuutinen, P. Maatela, R. Paukku, J. Soikkeli and J. Sarkka. 1988. Organic chlorine compounds in lake sediments and the role of chlorobleaching effluents. Chemosphere 17:137-146.
19. Eder, G. and K. Weber. 1980. Chlorophenols in sediments and suspended matter in the Weser Estuary. Chemosphere 9:111-118.
20. de Sousa, F., L. Strömberg and K. Kringstad. 1988. The fate of spent bleach liquor material in receiving waters: Characterization of chloroorganics in sediments. Water Sci. Technol. 20:153-160.
21. Lee, L.S., P.S.C. Rao, P. Nkedi-Kizza and J.J. Delfino. 1990. Influence of solvent and sorbent characteristics on the distribution of PCP in octanol-water and soil-water systems. Environ. Sci. Technol. 24:654-661.
22. Schellenberg, K., C. Leuenberger and R.P. Schwarzenbach. 1984. Sorption of chlorinated phenols by natural sediments and aquifer materials. Environ. Sci. Technol. 18:652-657.
23. Lagas, P. 1988. Sorption of chlorophenols in the soil. Chemosphere 17:205-216.
24. Boyd, S.A. 1982. Adsorption of substituted phenols by soil. Soil Sci. 134:337-343.
25. Boyd, S.A., M.A. Mikesell and J.-F. Lee. 1989. Chlorophenols in soils. In B.L. Sawhney and K. Brown, eds., Reactions and Movement of Organic Chemicals in Soils. Soil Science Society of America, Madison, WI, USA, pp. 209-228.
26. Isaacson, P.J. and C.R. Frink. 1984. Nonreversible sorption of phenolic compounds by sediment fractions: The role of sediment organic matter. Environ. Sci. Technol. 18:43-48.
27. Xie, T.-M. and D. Dyrssen. 1984. Simultaneous determination of partition coefficients and acidity constants of chlorinated phenols and guaiacols by gas chromatography. Anal. Chim. Acta 160:21-30.
28. Dien, K. and C. Lentner, eds. 1970. Buffer Solutions. Documenta Geigy, Scientific Tables. CIBA-Geigy, Basle, Switzerland, pp. 58-60.
29. Albert, A. and E.P. Serjeant. 1984. The Determination of Ionization Constants: A Laboratory Manual, 3rd ed. Chapman & Hall, London, UK.
30. Hirst, D.M. 1990. A Computational Approach to Chemistry. Blackwell Scientific, Oxford, UK.
31. Fujio, M., R.T. McIver and R.W. Taft. 1981. Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas-phase acidities. J. Am. Chem. Soc. 103:4017-4029.
32. Radom, L. 1974. Ab initio molecular orbital calculations on anion. Determination of gas phase acidities. J. Chem. Soc. Chem. Commun. 1974:403-404.
33. McDaniel, D.H. and H.C. Brown. 1957. An extended table of Hammett substituent constants based on the ionization of substituted benzoic acids. J. Org. Chem. 23:420-427.
34. Hammett, L.P. 1970. Physical Organic Chemistry, Reaction Rates, Equilibria and Mechanisms, 2nd ed. McGraw-Hill, New York, NY, USA.
35. a Prediction for Organic Acids and Bases. Chapman & Hall, London, UK.
36. Serjeant, E.P. and B. Dempsey. 1979. Ionisation Constants of Organic Acids in Aqueous Solutions. Pergamon, New York, NY, USA.
37. Cramer, C.J. and D.G. Truhlar. 1992. An SCF solvation model for the hydrophobic effect and absolute free energies of aqueous solvation. Science 256:213-217.