Sulfuric Acid → Hexachlorobutadiene

Participants

Reaction Conditions

Reaction Steps

In a 500 cc flask, 105.7 g of 29% strength fuming sulphuric acid were poured onto 102.5 g of 97.6% pure hexachlorocyclobutene [100 g (0.383 mole) of hexachlorocyclobutene; remainder hexachloro-1,3-butadiene], with stirring (molar ratio of hexachlorocyclobutene:sulphuric acid:sulphur trioxide=1:2:1). The mixture was heated at 80° C. for 1 hour. 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 41.1 g of tetrachlorocyclobutenone, 9.5 g of hexachlorocyclobutene and 2.4 g of hexachloro-1,3-butadiene was obtained. The selectivity of the reaction was thus 72% of theory with a conversion of 91% of theory.

Provenance & Evidence