Hexachlorocyclopentadiene → HCID 54503278, compound
Reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]#[C:4][C:5]([F:11])([F:10])[C:6]([F:9])([F:8])[F:7].ClC1(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl.[F-].[F-].[F-].[Cl-:28].[Cl-:29].[Sb+5].ClC1C(F)(F)C(F)(F)C(F)(F)C=1Cl>>[Cl:28][C:3](=[C:4]([Cl:29])[C:5]([F:10])([F:11])[C:6]([F:8])([F:7])[F:9])[C:2]([F:12])([F:13])[F:1]Participants
5
Procedure
For example, a process for synthesizing perfluoro-2-pentyne is described in J. Am. Chem. Soc., vol. 76, p 611 (1954) wherein hexachlorocyclopentadiene is treated with antimony trifluorodichloride to synthesize 1,2-dichloro-3,3,4,4,5,5-hexafluorocyclopentene; and, 2,3-dichloro-1,1,1,4,4,5,5,5-octafluoro-2-pentene as produced as a by-product in this synthetic process is dechlorinated with zinc to give perfluoro-2-pentyne. This process has a problem such that an antimony pentahalide, which is troublesome to handle, must be used for obtaining the raw material (i.e., 2,3-dichloro-1,1,1,4,4,5,5,5-octafluoro-2-pentene), and the yield of perfluoro-2-pentyne is low.
Sources & evidence
- ORD record
- ord-0a3666e2c4ba4c429f74b4182e1b7353
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07652179B2
Reaction notes
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