Chlorinated long chain fatty acids—their properties and reactions: III. Solvent effects in the dehydrohalogenation of sodium 9,10-dichlorooctadecanoate in dilute alkaline solutions

The first stage of the alkaline dehydrohalogenation of sodium 9,10-dichlorooctadecanoate (DCO) has been studied in ethylene glycol-water mixtures and in pure water at 90 C. The rate of the reaction was found to decrease rapidly with increasing water concentration. The rate of removal of the first chlorine from sodium 9,10-dichlorooctadecanoate was determined as a function of the water concentration in various ethylene glycol-water mixtures. The rate coefficient (k_OH) in pure water solution was 1.4·10⁻⁴ kg·mole⁻¹·min⁻¹ as compared to the maximum value of 2.7·10⁻² kg·mole⁻¹·min⁻¹ in 19 wt % solution. The effects of temperature and base concentration on the reaction rate were also investigated.