Sulfuric Acid → Hexachlorobutadiene

HRID 1680312

Reaction equation

HRID 1680312 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 2.5%

Conditions

Temperature
80 °C

Procedure

In a 1 liter flask, 200.6 g of 50% strength fuming sulphuric acid (oleum) were poured onto 300 g of 97.5% pure hexachlorocyclobutene [292.5 g (1.12 moles) of hexachlorocyclobutene; remainder hexachloro-1,3-butadiene], with stirring (molar ratio of hexachlorocyclobutene:sulphuric acid:sulphur trioxide=1:0.9:1.1). 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. The organic phase was then separated immediately from the aqueous phase. A mixture of 185 g of tetrachlorocyclobutenone, 14.4 g of hexachlorocyclobutene and 7.2 g of hexachloro-1,3-butadiene was obtained. The selectivity of the reaction was thus 88% of theory with a conversion of 95% of theory.

Workup

  1. temperatureAfter cooling
  2. customThe organic phase was then separated immediately from the aqueous phase
  3. additionA mixture of 185 g of tetrachlorocyclobutenone, 14.4 g of hexachlorocyclobutene

Sources & evidence

ORD record
ord-50f300191b57434ab8ffac1c7301ac6a
Source dataset
uspto-grants-1981_06
Patent number
US04272633

Linked notes

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