Collect. Czech. Chem. Commun. 1982, 47, 2904-2911

Study of reactions in two-phase systems hydrolysis of triphenylmethyl chloride in water-organic solvent systems

Jaroslav Šilhánek, Lenka Konrádová, Olga Šimečková and Josef Horák

Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6


The rate of hydrolysis was studied for triphenylmethyl chloride in water-organic solvent systems with an unstirred interface of a known area. The hydrolytic reaction was found to take place at the interface only. The temperature dependence of the reaction rate indicates that at lower temperatures (up to 60 °C) the rate-determining step is the chemical reaction, whereas at higher temperatures a deviation from the Arrhenius type dependence is observed, which along with the low activation energy value points to the diffusion as the governing phenomenon. The effect of salts added to the aqueous phase is consistent with the expected behaviour for the SN1 mechanism, but suprising is the inhibiting effect od some quaternary ammonium salts. In the study of the effect of the organic solvent, the reaction rate was found to correlate satisfactorily with the solubility of the organic solvent in water, but no correlation was established with the solubility of water in the solvent. From the results obtained it can be inferred that the reaction site is the laminary layer adjacent to the interface from the aqueous phase side.