Sulfuric Acid → Hexachlorobutadiene

Participants

Reaction Conditions

Reaction Steps

In a 1 liter flask, 341 g of 39.8% strength fuming sulphuric acid (oleum) were poured onto 500 g of 97.5% pure hexachlorocyclobutene [487.5 g (1.87 moles) of hexachlorocyclobutene; remainder hexachloro-1,3-butadiene], with stirring (molar ratio of hexachlorcyclobutene:sulphuric acid:sulphur trioxide=1:1.1:0.9). The mixture was heated at 80° C. for 5 hours. After cooling, the reaction product was poured slowly into a mixture of ice and sodium chloride, with vigorous stirring, and the organic phase was then separated immediately from the aqueous phase. A mixture of 326 g of tetrachlorocyclobutenone, 25 g of hexachlorocyclobutene and 23 g of hexachloro-1,3-butadiene was obtained. The selectivity of the reaction was thus 90.5% of theory with a conversion of 92% of theory.

Provenance & Evidence