Carbon Dioxide → 1,1,1,2,4,4,5,5,6,6,6-Undecafluoro-2-(trifluoromethyl)-3-hexanone

HRID 1937265Notes

Reaction equation

HRID 1937265 reaction equation
[F-:1].[K+].C(=O)=O.[C:6]([C:16](F)=[O:17])([C:9]([C:12]([F:15])([F:14])[F:13])([F:11])[F:10])([F:8])[F:7].[F:19][C:20]([F:27])([F:26])[C:21]([F:25])=[C:22]([F:24])[F:23]>COCCOCCOC>[F:19][C:20]([F:27])([F:26])[C:21]([F:25])([C:22]([F:1])([F:24])[F:23])[C:16](=[O:17])[C:6]([F:7])([F:8])[C:9]([F:10])([F:11])[C:12]([F:13])([F:14])[F:15]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 8302Hexafluoropropylene3×HCID 67632Heptafluorobutyroyl fluorideHCID 522689Potassium Fluoride

Product 1

HCID 111430681,1,1,2,4,4,5,5,6,6,6-Undecafluoro-2-(trifluoromethyl)-3-hexanoneYield 665.2%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
85 °C

Procedure

Into a clean dry 600 mL Parr reactor equipped with stirrer, heater and thermocouple were added 5.8 g (0.10 mol) of anhydrous potassium fluoride and 108 g of anhydrous diglyme. The contents of the reactor were stirred and cooled with dry ice while 232.5 g (1.02 mol) of n-C3F7COF (available from 3M Co., approximately 95.0 percent purity) was added to the sealed reactor. The reactor and its contents were then heated, and when a temperature of 72° C. had been reached, 141 g (0.94 mol) of hexafluoropropylene was added at a pressure of 85 psig (5150 torr) over a 3.25 hour time period. During the addition of hexafluoropropylene the temperature of the reactor was increased slowly to 85° C. while maintaining the pressure at less than 90 psig (5400 torr). The pressure at the end of the hexafluoropropylene addition was 40 psig (2800 torr) and did not change over an additional 4-hour hold period. The lower phase was fractionally distilled to give 243.5 grams of 1,1,1,2,4,4,5,5,6,6,6-undecafluoro-2-trifluoromethylhexan-3-one, having a boiling point of 72.5° C. and a purity of 99.9% as determined by gas chromatography. The structure was confirmed by gas chromatography and mass spectrometry (GCMS).

Workup

  1. customInto a clean dry 600 mL Parr reactor
  2. customequipped with stirrer
  3. additionwas added to the sealed reactor
  4. temperatureThe reactor and its contents were then heated
  5. customa temperature of 72° C.
  6. temperaturewhile maintaining the pressure at less than 90 psig (5400 torr)
  7. waitdid not change over an additional 4-hour
  8. waithold period
  9. distillationThe lower phase was fractionally distilled

Sources & evidence

ORD record
ord-d95c15d6057d4448a1ab80520d9c9906
Source dataset
uspto-grants-2002_05
Patent number
US06394107B1

Reaction notes

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