Ammonia → Perfluoroheptanamide

HRID 1810721Notes

Reaction equation

HRID 1810721 reaction equation
[F:1][C:2]([F:23])([C:7]([F:22])([F:21])[C:8]([F:20])([F:19])[C:9]([F:18])([F:17])[C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])[C:3](OC)=[O:4].[NH3:24].[NH4+]>O1CCCC1>[F:1][C:2]([F:23])([C:7]([F:22])([F:21])[C:8]([F:20])([F:19])[C:9]([F:18])([F:17])[C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])[C:3]([NH2:24])=[O:4]

Participants

5

Reactant 3

HCID 222Ammonia3×HCID 223AmmoniumHCID 526471Methyl perfluoroheptanoate

Product 1

HCID 2769670PerfluoroheptanamideYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

A 3-1, four-necked, round-bottomed flask equipped with stirrer, thermometer, reflux condenser with bubble counter and inlet gas-tube, is charged with 658 g (1.74 mol) of methyl perfluoroheptanoate and 1.5 l tetrahydrofurane. A stream of ammonia is passed from a pressure tank into the stirring solution. The ammonia feed rate is such that a negligible amount of gas is observed exiting the reactor as observed in the bubble counter. Temperature of the mixture increases to 40-50° C. Ammonium supply is continued until the temperature begins to decrease and an increasing volume of gas is observed exiting the reactor in the bubble counter. After ending the ammonia supply, the mixture is left to stand for 12 hr. Solvent is removed under reduced pressure, yielding 626 g p perfluoroheptanoic acid amide (99%), mp 127-128° C.

Workup

  1. customA 3-1, four-necked, round-bottomed flask equipped with stirrer
  2. temperaturethermometer, reflux condenser
  3. customwith bubble counter and inlet gas-tube
  4. waitthe mixture is left
  5. customSolvent is removed under reduced pressure

Sources & evidence

ORD record
ord-5e9656729ad34425b10541552caa1886
Source dataset
uspto-grants-2013_01
Patent number
US08362167B2

Reaction notes

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