Sulfuric Acid → Hexachlorobutadiene

HRID 1680313

Reaction equation

HRID 1680313 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1([Cl:15])[C:10]([Cl:11])=[C:9]([Cl:12])[C:8]1([Cl:14])[Cl:13].S(=O)(=O)=O.[Cl-].[Na+]>>[Cl:6][C:7]([Cl:15])=[C:10]([Cl:11])[C:9]([Cl:12])=[C:8]([Cl:14])[Cl:13]

Participants

5

Reactant 4

HCID 1118Sulfuric Acid2×HCID 5234Sodium ChlorideHCID 22504Hexachlorocyclobutene3×HCID 24682Sulfur trioxide

Product 1

HCID 6901HexachlorobutadieneYield 2.4%

Conditions

Temperature
80 °C

Procedure

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.

Workup

  1. temperatureAfter cooling
  2. customthe organic phase was then separated immediately from the aqueous phase
  3. additionA mixture of 41.1 g of tetrachlorocyclobutenone, 9.5 g of hexachlorocyclobutene

Sources & evidence

ORD record
ord-43836f5b62d84c35a3fcfc40caba70b9
Source dataset
uspto-grants-1981_06
Patent number
US04272633

Linked notes

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