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

HRID 2230008Notes

Reaction equation

HRID 2230008 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].[C:19](=[C:22]([C:24]([F:27])([F:26])[F:25])[F:23])([F:21])[F:20]>COCCOCCOC>[F:20][C:19]([F:1])([F:21])[C:22]([F:23])([C:24]([F:27])([F:26])[F:25])[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 (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 CF2═CFCF3 (hexafluoropropylene) was added at a pressure of 85 psig (5150 torr absolute) 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 absolute). The pressure at the end of the hexafluoropropylene addition was 40 psig (2800 torr absolute) 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 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 absolute)
  7. waitdid not change over an additional 4-hour
  8. waithold period
  9. distillationThe lower phase was fractionally distilled

Sources & evidence

ORD record
ord-17a7c39ca95b4366af113cf35764365f
Source dataset
uspto-grants-2002_07
Patent number
US06423673B1

Reaction notes

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