Solubilization of the neutral and charged forms of 2,4,6-trichlorophenol by beta-cyclodextrin, methyl-beta-cyclodextrin and hydroxypropyl-beta-cyclodextrin in water.

The solubilities of the neutral and charged forms of 2,4,6-trichlorophenol (TCP) in beta-cyclodextrin (beta-CD) and two of its most used derivatives: methyl-beta-cyclodextrin (MCD) and hydroxypropyl-beta-cyclodextrin (HPCD) solutions were investigated. The three cyclodextrins were found to form 1:1 inclusion complexes. Binding constants estimated from an enhancement solubility method revealed that the stability of the complexes was dependent on the polarity of the compound and on the cyclodextrin used.In general, weaker binding constants were observed for TCP with beta-CD than with HPCD or MCD. The solubilization efficiencies towards TCP can be ranked in the following order: MCD > HPCD > beta-CD. For all cyclodextrins, the stability constant of neutral TCP (logK(ow)=3.85) was larger than that of charged TCP (logK(ow)=1.4).A precipitation occurred in TCP/beta-CD solution (around 10 g/l beta-CD concentration) at pH 3. However, this phenomenon is not observed for TCP/beta-CD solution at pH 8.8.