Sulfuric Acid → Hexachlorobutadiene

Participants

Reaction Conditions

Reaction Steps

In a 500 cc flask, 143.4 g of 21.4% strength fuming sulphuric acid (oleum) were poured onto 209.8 of 95.3% pure hexachlorocyclobutene [199.9 g (0.766 mole) of hexachlorocyclobutene; remainder hexachloro-1,3-butadiene], with stirring (molar ratio of hexachlorocyclobutene:sulphuric acid:sulphur trioxide=1:1.5:0.5). 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 83.2 g of tetrachlorocyclobutenone, 58.9 g of hexachlorocyclobutene and 8.6 g of hexachloro-1,3-butadiene was obtained. The selectivity of the reaction was thus 75% of theory with a conversion of 71% of theory.

Provenance & Evidence