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.
Similar content being viewed by others
References
Wells, J.M., Yu, L.Z.: Solid-phase extraction of acidic herbicides. J. Chromatogr. A 885, 237–250 (2000).
Cserhati, T., Forgacs, E.: Phenoxyacetic acids: separation and quantitative determination. J. Chromatogr. B 717, 157–178 (1998).
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).
International Programme on Chemical Safety, 2,4-D—Environmental Aspects [On-Line]. Available at the web address: http://www.inchem.org (1989).
Extension Toxicology Network [On-Line]. Available at the web address: http://pmep.cce.cornell.edu/profiles/extoxnet (1993).
Praczyk, T., Skrzypczak, G.: Herbicides (in Polish), PWRiL, Warsaw, pp. 10–17, 39 (2004).
Biziuk, M.: Pesticides (in Polish), WNT, Warsaw, pp. 30–41, 92–113 (2001).
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).
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).
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).
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).
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).
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).
Wisniak, J., Tamir, A.: Liquid-liquid Equilibrium and Extraction (Physical Science Data, No. 28), Elsevier, Amsterdam, pp. 222 (1987).
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).
Gans, P., O’Sullivan, B.: GLEE, a new computer program for glass electrode calibration. Talanta 51, 33–37 (2000).
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).
Albert, A., Serjeant, E.P.: The Determination of Ionization Constant, third ed., Chapman and Hall, London, pp. 48–53 (1984).
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).
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).
Kalembkiewicz, J., Zapała, L.: Distribution of 2-chlorobenzoic acid in aliphatic alcohol-water two-phase systems. Polish J. Chem. 70, 768–771 (1996).
Kalembkiewicz, J., Zapała, L.: Distribution of 2-chlorobenzoic acid in two-phase systems aromatic solvent-water. Polish J. Chem. 75, 1797–1800 (2001).
Kalembkiewicz, J., Szlachta, J.: Distribution of phenoxyacetic acid in aliphatic alcohol-water two-phase systems. Ann. Polish Chem. Soc. 3, 1144–1147 (2004).
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).
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).
Atkins, P.: Physical Chemistry, sixth ed., Oxford University Press, Oxford, pp. 234–239 (1998).
Handbook of Physicochemical Data (in Polish), WNT, Warsaw (1974).
Sekine, T., Hasegawa, Y.: Solvent Extraction Chemistry, Marcel Dekker, New York, pp. 25–83 (1977).
Kalembkiewicz, J., Kopacz, S.: Distribution and association of carboxylic acids in extraction systems. Wiad. Chem. 41, 437–450 (1987).
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).
Brzózka, C., Różycki, Z.: Application of monocarboxylic acids for the extraction of metal ions—literature survey. Anal. Chem. 25, 3–24 (1980).
Jeżowska-Trzebiatowska, B., Kopacz, S., Mikulski, T.: The Rare Elements Occurrence and Technology, PWN Warsaw, Elsevier. Amsterdam, pp. 113 (1990).
Zapała, L., Kalembkiewicz, J.: Studies on the distribution of N-phenylantranilic acid in two-phase system: aromatic solvent-water. Talanta 69, 601–607 (2006).
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).
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).
Kalembkiewicz, J., Kopacz, S.: Studies on distribution and association of benzoicacid in aliphatic alcohol-water systems. Zh. Obshch. Khim. 56, 441–447 (1986).
Author information
Authors and Affiliations
Corresponding author
Rights 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
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10953-006-9104-3