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Sulfuric Acid → Hexachlorobutadiene

HRID 46751
Notes
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Reaction equation

HRID 46751 reaction equation
ClC1(Cl)C(=O)C(Cl)=C1Cl.[Cl:10][C:11]1([Cl:19])[C:14]([Cl:15])=[C:13]([Cl:16])[C:12]1([Cl:18])[Cl:17].S(=O)(=O)(O)O.S(=O)(=O)=O>>[Cl:10][C:11]1([Cl:19])[C:14]([Cl:15])=[C:13]([Cl:16])[C:12]1([Cl:18])[Cl:17].[Cl:10][C:11]([Cl:19])=[C:14]([Cl:15])[C:13]([Cl:16])=[C:12]([Cl:18])[Cl:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1118Sulfuric Acid2×HCID 185452,3,4,4-Tetrachloro-2-cyclobuten-1-oneHCID 22504Hexachlorocyclobutene2×HCID 24682Sulfur trioxide2×

Product 2

HCID 6901HexachlorobutadieneHCID 22504Hexachlorocyclobutene

Procedure

Tetrachlorocyclobutenone, required as a starting material, is obtained with high yields and conversions by a not yet published process from hexachlorocyclobutene and a mixture of sulphuric acid and sulphur trioxide at elevated temperatures, e.g., by reaction of 1 mol hexachlorocyclobutene with approximately 1 mol each of sulphuric acid and sulphur trioxide at a temperature of 80° C. within 5 hours. Hexachlorocyclobutene can be obtained from hexachloro-1,3-butadiene in yields of near 100% of theory (DE-OS No. 26 18 557), corresponding to U.S. Pat. No. 4,115,460), for example by rectifying commercial hexachlorobutadiene at a pressure of from 2 to 100 mm Hg with a reflux ratio of from 300:1 to 600:1, subjecting hexachlorobutadiene remaining in the bottoms to a heat treatment at from 150° to 200° C. and then returning it to the rectifying column together with fresh commercial hexachlorobutadiene while withdrawing the product rich in hexachlorocyclobutene over the top. A suitable starting material is not only pure tetrachlorocyclobutenone but also crude tetrachlorocyclobutenone which may, for example, contain hexachlorobutadiene and hexachlorocyclobutene originating from its process of manufacture.

Workup

  1. customis obtained
  2. customwith high yields

Sources & evidence

ORD record
ord-836302dff01f4cb2b1919c94896ee549
Source dataset
uspto-grants-1979_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04175095

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes