Sulfuric Acid → Hexachlorobutadiene

HRID 1680311

Reaction equation

HRID 1680311 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 4.7%

Conditions

Temperature
80 °C

Procedure

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.

Workup

  1. temperatureAfter cooling
  2. customthe organic phase was then separated immediately from the aqueous phase
  3. additionA mixture of 326 g of tetrachlorocyclobutenone, 25 g of hexachlorocyclobutene

Sources & evidence

ORD record
ord-b6ddc309b7714971a1690196b1ba5a28
Source dataset
uspto-grants-1981_06
Patent number
US04272633

Linked notes

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