Chlorinated long-chain fatty acids. Their properties and reactions—VI : Kinetics and mechanisms of base-catalyzed dehydrochlorination of sodium threo,threo-9,10,12,13-tetrachlorooctadecanoate

The base-catalyzed dehydrochlorination of sodium threo,threo-9,10,12,13-tetra-chlorooctadecanoate has been carried out in aqueous ethylene glycol solutions. During the first reaction step two chlorine atoms are eliminated nearly simultaneously as hydrogen chloride whereas the third and fourth chlorine atoms are released separately. The relative rates of these three reaction steps at 130°C are 497,41 and 1, respectively. The possible reaction mechanisms have been discussed in light of the kinetic results and product analyses which showed that the dehydrochlorination results mainly in conjugated diene-yne systems.