Epichlorohydrin with 2-ethylhexanoic acid, reaction

Figure 2. Reaction of epichlorohydrin with 2-ethylhexanoic acid (1 1 mol ratio)...

The reaction of epichlorohydrin with 2-ethylhexanoic acid in a 1 1 molar ratio gives rise to only 50% of the desired product, the chlorohydrin ester. The mechanism depicted above indicates that the undesirable hydroxy diester is formed by reaction of 2-ethylhexanoic acid with glycidyl 2-ethylhexanoate. It appears therefore that formation of the hydroxy diester competes directly with the chlorohydrin ester formation (Fig. 9). 

The products formed during the reaction of epichlorohydrin with 2-ethylhexanoic acid are governed by the relative concentrations of the two reactants. Epichlorohydrin must be present in excess in order to achieve a high yield of chlorohydrin ester. In order to optimise the yield of chlorohydrin ester the reaction must be terminated when all the acid has been consumed otherwise the reaction is complicated by decomposition and further reactions of this material. 

---