2-Chloro-1,1,1,4,4,4-hexafluoro-2-butene → 1,1,1,4,4,4-Hexafluorobutane

HRID 2106829Notes

Reaction equation

HRID 2106829 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3](Cl)=[CH:4][C:5]([F:8])([F:7])[F:6].[OH-].[Na+]>COCCOCCOC.[Ni]>[F:1][C:2]([F:11])([F:10])[CH2:3][CH2:4][C:5]([F:8])([F:7])[F:6]

Participants

5

Reactant 2

HCID 98152-Chloro-1,1,1,4,4,4-hexafluoro-2-buteneHCID 14798Sodium Hydroxide

Product 1

HCID 678901,1,1,4,4,4-HexafluorobutaneYield 75.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8150DiglymeSolvent

Procedure

1,1,1,4,4,4-Hexafluoro-2-chloro-2-butene (199 g, 1 mole) in 800 ml diglyme was hydrogenated in the presence of sodium hydroxide (45 g) and Raney nickel (30 g) at a temperature of 20° to 40° C. and under a pressure of 20 to 40 bar. The solid constituents were filtered off and the filtrate was extracted with water. The organic phase was separated and purified by fractional distillation, giving 125 g (75% of theory) of 1,1,1,4,4,4-hexafluorobutane, boiling point 24°-27° C. at 1013 mbar. The 19F-nmr spectrum showed a resonance at -10.7 ppm (standard: CF3CO2H).

Workup

  1. filtrationThe solid constituents were filtered off
  2. extractionthe filtrate was extracted with water
  3. customThe organic phase was separated
  4. distillationpurified by fractional distillation

Sources & evidence

ORD record
ord-7cf76e483096422bb19b93593018cee4
Source dataset
uspto-grants-1990_06
Patent number
US04931482

Reaction notes

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