Skip to main content
Log in

Studies on the Physical Chemistry of (2,4-Dichlorophenoxy)acetic Acid in Two-phase Systems: Organic Solvent-Water

  • Original Paper
  • Published:
Journal of Solution Chemistry Aims and scope Submit manuscript

Abstract

The dissociation constants (p s K a ) of 2,4-D acid were determined in methanol-water mixtures of 10.9 to 38.9 wt.% methanol content. The Yasuda-Shedlovsky procedure was used to obtain the pK a value in zero-% methanol. The distribution of 2,4-D acid in twelve two-phase organic solvent + water systems and its dimerization in the organic phase were investigated. Values of the distribution coefficient (D HR), distribution constant (K D ), and dimerization constant (K dim) of 2,4-D were obtained. The influence of the structure and polarity of the investigated organic solvents, as well as that of pH of the aqueous phase, on the physical chemistry of 2,4-D in the two-phase systems are described.

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

  1. Wells, J.M., Yu, L.Z.: Solid-phase extraction of acidic herbicides. J. Chromatogr. A 885, 237–250 (2000).

    Google Scholar 

  2. Cserhati, T., Forgacs, E.: Phenoxyacetic acids: separation and quantitative determination. J. Chromatogr. B 717, 157–178 (1998).

    CAS  Google Scholar 

  3. Report of European Commmission, Health and Consumer Protection Directorate—General [On-Line]. Available at the web address: http://europa.eu.int/comm/food/plant/protection/evaluation/existactive/ (2001).

  4. International Programme on Chemical Safety, 2,4-D—Environmental Aspects [On-Line]. Available at the web address: http://www.inchem.org (1989).

  5. Extension Toxicology Network [On-Line]. Available at the web address: http://pmep.cce.cornell.edu/profiles/extoxnet (1993).

  6. Praczyk, T., Skrzypczak, G.: Herbicides (in Polish), PWRiL, Warsaw, pp. 10–17, 39 (2004).

  7. Biziuk, M.: Pesticides (in Polish), WNT, Warsaw, pp. 30–41, 92–113 (2001).

  8. Andreu, V., Picó, Y.: Determination of pesticides and their degradation products in soil: critical review and comparison of methods. Trends in Anal. Chem. 23, 772–789 (2004).

    Article  CAS  Google Scholar 

  9. Wyss, A., Cordente, N., von Stockar, U., Marison, W.I.: A novel approach for the extraction of herbicides and pesticides from water using liquid-core microcapsules. Biotechnol. Bioeng. 87, 734–742 (2004).

    Article  CAS  Google Scholar 

  10. Ptaszyński, B., Zwolińska, A.: Lead(II) and cadmium(II) compounds with 2,4-dichlorophenoxyacetic acid (2,4D) and 2-(2,4-dichlorophenoxy)propionic acid (2,4-DP). Synthesis and properties. J. Therm. Anal. Cal. 75, 301–315 (2004).

    Google Scholar 

  11. Zwolińska, A., Ptaszyński, B., Wrzeszcz, G.: Ability of 2,4D and 2,4DP herbicides to combine with metal ions of biological interest (part 1): copper(II) complexes. Polish J. Chem. 78, 1987–1996 (2004).

    Google Scholar 

  12. Turek, A., Kobyłecka, J., Ptaszyński, B.: Influence of synthetic auxins on the changes of the heavy metals mobility soils. Ann. Polish Chem. Soc. 3, 1186–1189 (2004).

    Google Scholar 

  13. Loconto, P.R.: Isolation and recovery from water of selected chlorophenoxy acid herbicides and similar weak acid herbicides by solid-phase extraction HPLC and photodiode array detection. J. Liq. Chromatogr. 14, 1297–1314 (1991).

    CAS  Google Scholar 

  14. Wisniak, J., Tamir, A.: Liquid-liquid Equilibrium and Extraction (Physical Science Data, No. 28), Elsevier, Amsterdam, pp. 222 (1987).

  15. Avdeef, A., Comer, J.E., Thomson, S.J.: pH-metric log P. 3. Glass electrode calibration in methanol-water, applied to pK a determination of water-insoluble substances. Anal. Chem. 65, 42–49 (1993).

    Article  CAS  Google Scholar 

  16. Gans, P., O’Sullivan, B.: GLEE, a new computer program for glass electrode calibration. Talanta 51, 33–37 (2000).

    Article  CAS  Google Scholar 

  17. Woolley, E.M., Tomkins, J., Hepler, L.G.: Ionization constants for very weak organic acids in aqueous solution and apparent ionization constants for water in aqueous organic mixtures. J. Solution Chem. 1, 341–351 (1972).

    Article  CAS  Google Scholar 

  18. Albert, A., Serjeant, E.P.: The Determination of Ionization Constant, third ed., Chapman and Hall, London, pp. 48–53 (1984).

    Google Scholar 

  19. Takács-Novák, K., Box, K.J., Avdeef, A.: Potentiometric pK a determination of water-insoluble compounds: validation study in methanol/water mixtures. Int. J. Pharm. 151, 235–248 (1997).

    Article  Google Scholar 

  20. Avdeef, A., Box, K.J., Comer, J.E.A., Gilges, M., Hadley, M., Hibbert, C., Patterson, W., Tam, K.Y.: pH-metric logP. 11. pK a determination of water-insoluble drugs in organic solvent-water mixtures. J. Pharm. Biomed. Anal. 20, 631–341 (1999).

    Article  CAS  Google Scholar 

  21. Kalembkiewicz, J., Zapała, L.: Distribution of 2-chlorobenzoic acid in aliphatic alcohol-water two-phase systems. Polish J. Chem. 70, 768–771 (1996).

    CAS  Google Scholar 

  22. Kalembkiewicz, J., Zapała, L.: Distribution of 2-chlorobenzoic acid in two-phase systems aromatic solvent-water. Polish J. Chem. 75, 1797–1800 (2001).

    CAS  Google Scholar 

  23. Kalembkiewicz, J., Szlachta, J.: Distribution of phenoxyacetic acid in aliphatic alcohol-water two-phase systems. Ann. Polish Chem. Soc. 3, 1144–1147 (2004).

    Google Scholar 

  24. Ong, K.C., Robinson, R.A., Bates, R.G.: Interpretation of potentiometric titrations of weak acids in methanol-water solvents. Anal. Chem. 36, 1971–1972 (1964).

    Article  CAS  Google Scholar 

  25. Fallavena, P.R., Schapoval, E.E.: pK a determination of nimesulide in methanol-water mixtures by potentiometric titrations. Int. J. Pharm. 158, 109–112 (1997).

    Article  CAS  Google Scholar 

  26. Atkins, P.: Physical Chemistry, sixth ed., Oxford University Press, Oxford, pp. 234–239 (1998).

    Google Scholar 

  27. Handbook of Physicochemical Data (in Polish), WNT, Warsaw (1974).

  28. Sekine, T., Hasegawa, Y.: Solvent Extraction Chemistry, Marcel Dekker, New York, pp. 25–83 (1977).

    Google Scholar 

  29. Kalembkiewicz, J., Kopacz, S.: Distribution and association of carboxylic acids in extraction systems. Wiad. Chem. 41, 437–450 (1987).

    CAS  Google Scholar 

  30. Mukerjee, P.: Dimerization of anions of long-chain fatty acids in aqueous solutions and the hydrophobic properties of the acids. J. Phys. Chem. 69, 2821–2827 (1965).

    Article  CAS  Google Scholar 

  31. Brzózka, C., Różycki, Z.: Application of monocarboxylic acids for the extraction of metal ions—literature survey. Anal. Chem. 25, 3–24 (1980).

    Google Scholar 

  32. Jeżowska-Trzebiatowska, B., Kopacz, S., Mikulski, T.: The Rare Elements Occurrence and Technology, PWN Warsaw, Elsevier. Amsterdam, pp. 113 (1990).

  33. Zapała, L., Kalembkiewicz, J.: Studies on the distribution of N-phenylantranilic acid in two-phase system: aromatic solvent-water. Talanta 69, 601–607 (2006).

    Article  Google Scholar 

  34. Papciak, B., Kopacz, S., Kalembkiewicz, J.: Investigations of 3-chlorobenzoic acid partition in two-phase systems. Proc. Int. Conf. “Analysis and utilization of oily wastes” Gdańsk (Poland) 2, 421–426 (1996).

  35. Kopacz, S., Kalembkiewicz, J., Szantula, J.: Investigation on monomer-dimer equilibrium of benzoic acid for some organic solvents. Zh. Obshch. Khim. 54, 721–728 (1984).

    CAS  Google Scholar 

  36. Kalembkiewicz, J., Kopacz, S.: Studies on distribution and association of benzoicacid in aliphatic alcohol-water systems. Zh. Obshch. Khim. 56, 441–447 (1986).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jan Kalembkiewicz.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kalembkiewicz, J., Szlachta, J. Studies on the Physical Chemistry of (2,4-Dichlorophenoxy)acetic Acid in Two-phase Systems: Organic Solvent-Water. J Solution Chem 36, 211–220 (2007). https://doi.org/10.1007/s10953-006-9104-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10953-006-9104-3

Keywords

Navigation