1,1,1-Trichloroethane → 1,1,1,3,3-Pentachlorobutane

HRID 1088526

Reaction equation

[Cl:1][C:2]([Cl:5])([Cl:4])[CH3:3].[C:6]([Cl:9])([Cl:8])=[CH2:7]>>[Cl:1][C:2]([Cl:5])([Cl:4])[CH2:3][C:6]([Cl:9])([Cl:8])[CH3:7]

Participants

Reactant 2

HCID 62781,1,1-Trichloroethane

HCID 6366Vinylidene chloride

Product 1

HCID 891231,1,1,3,3-Pentachlorobutane

Procedure

2,2,4,4,4-Pentafluorobutane is another undesirable by-product of the fluorination of 1,1,1-trichloroethane. I believe that it is formed by the reaction between 1,1,1-trichloroethane and vinylidene chloride, followed by the reaction of additional 1,1,1-trichloroethane with vinylidene chloride to give 1,1,1,3,3-pentachlorobutane. Grigor'ev et al., Izv. Akad. Nauk. SSSR. Ser. Khim., 6, 1333-6 (1980). Hydrofluorination of the latter produces 2,2,4,4,4-pentafluorobutane.

Sources & evidence

ORD record: ord-14c839df0dcf454db996b3047090e19a
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04962244

Linked notes

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