Heptyl acetate → HCID 12654515, compound

HRID 2185605Notes

Reaction equation

HRID 2185605 reaction equation
[F:1][C:2]([F:29])([C:25]([F:28])([F:27])[F:26])[C:3]([F:24])([F:23])[C:4]([F:22])([F:21])[C:5]([F:20])([F:19])[C:6]([F:18])([F:17])[C:7]([O:10]C(=O)C(F)(F)F)(F)F.C(OCCCCCCC)(=O)C.[F:41]F.[F-].[K+].[F:45][C:46]([F:53])([F:52])[C:47]([F:51])=[C:48]([F:50])[F:49]>COCCOCCOC>[F:45][C:46]([F:53])([F:52])[C:47]([F:51])([C:48]([F:41])([F:50])[F:49])[C:7](=[O:10])[C:6]([F:17])([F:18])[C:5]([F:19])([F:20])[C:4]([F:21])([F:22])[C:3]([F:23])([F:24])[C:2]([F:29])([F:1])[C:25]([F:28])([F:27])[F:26]

Participants

7

Reactant 5

HCID 8159Heptyl acetateHCID 8302Hexafluoropropylene2×HCID 24524FluorineHCID 522689Potassium FluorideHCID 86758092HCID 86758092, compound

Product 1

HCID 12654515HCID 12654515, compound

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
50 °C

Procedure

A mixture consisting of 2027 g of trifluoroacetic acid pentadecafluoroheptyl ester (made by reacting heptyl acetate with fluorine gas as described in U.S. Pat. No. 5,399,718 (Costello et al.)), 777 g of 3M™ PF-5052 Performance Liquid (a mixture of perfluorinated solvents, available from 3M Company), 3171 g of anhydrous diglyme and 79 g of anhydrous potassium fluoride were added to a 2-gallon (7.6 L) stainless steel stirred pressure vessel. The vessel was heated and 1816 g of hexafluoropropylene was added over a 2-hour period while maintaining a reaction temperature of about 50° C. The vessel was held at 50° C. for an additional 1½ hours after the hexafluoropropylene addition was complete. The reactor was cooled and drained. The resulting liquid was phase split and the lower phase fractionally distilled to give 565 g of 1,1,1,2,4,4,4-heptafluoro-3-trifluoromethyl-butan-2-one having a boiling point of 25° C. and purity of 95% and 1427 g of 1,1,1,2,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluoro-2-trifluoromethyl-nonan-3-one, having a boiling point of 134° C. and a 98.5% purity as determined by gas chromatography and mass spectroscopy.

Workup

  1. temperatureThe vessel was heated
  2. waitThe vessel was held at 50° C. for an additional 1½ hours
  3. temperatureThe reactor was cooled
  4. customsplit
  5. distillationthe lower phase fractionally distilled

Sources & evidence

ORD record
ord-00460807e8614b7b92b607a0e21cf453
Source dataset
uspto-grants-2002_06
Patent number
US06403149B1

Reaction notes

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