Sulfuric Acid → Hexachlorobutadiene

HRID 1680314

Reaktionsgleichung

Reaktionsgleichung von HRID 1680314
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]

Komponenten

5

Edukt 4

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

Produkt 1

HCID 6901HexachlorobutadieneAusbeute 4,3 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe organic phase was then separated immediately from the aqueous phase
  3. additionA mixture of 83.2 g of tetrachlorocyclobutenone, 58.9 g of hexachlorocyclobutene

Quellen und Nachweise

ORD-Eintrag
ord-2aefc9fd1d2b4cc19004975c6dc8b60a
Quelldatensatz
uspto-grants-1981_06
Patentnummer
US04272633

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