Ammonia → Perfluoroheptanamide

HRID 1296825Notes

Reaction equation

HRID 1296825 reaction equation
N.[OH-:2].[K+].[C:4]([C:23]#[N:24])([C:7]([C:10]([C:13]([C:16]([C:19]([F:22])([F:21])[F:20])([F:18])[F:17])([F:15])[F:14])([F:12])[F:11])([F:9])[F:8])([F:6])[F:5]>>[F:5][C:4]([F:6])([C:7]([F:9])([F:8])[C:10]([F:12])([F:11])[C:13]([F:15])([F:14])[C:16]([F:17])([F:18])[C:19]([F:20])([F:21])[F:22])[C:23]([NH2:24])=[O:2]

Participants

4

Reactant 3

HCID 222Ammonia3×HCID 14797Potassium HydroxideHCID 2782568Perfluoroheptanenitrile

Product 1

HCID 2769670PerfluoroheptanamideYield 98.5%

Procedure

A ten-fold excess, fifty (50) ml, of anhydrous ammonia gas were condensed into a four-neck flask fitted with an agitator, reflux condenser, dropping funnel, thermometer, and a drying tube (filled with solid KOH) which had been cooled in a dry ice/ethanol bath. The ammonia was condensed into the flask via the drying tube. With good agitation and cooling, 60 g of a reaction product (perfluoroheptanonitrile), made in accordance with the technique described in Example 4 for conversion of a perfluoroacid to a nitrile, having the structure C6F13CN was added slowly. After addition was completed, the temperature was allowed to slowly rise to ambient allowing the excess ammonia to evaporate. The resulting white solid product was air dried to yield 62.0 g of perfluoroheptanamide having the following formula (a yield of 98.5% with a m.p. at 75-76° C.).

Workup

  1. customcondensed into a four-neck flask
  2. customfitted with an agitator
  3. temperaturereflux condenser
  4. temperaturehad been cooled in a dry ice/ethanol bath
  5. customcondensed into the flask via the drying tube
  6. temperatureWith good agitation and cooling
  7. additionwas added slowly
  8. additionAfter addition
  9. customto evaporate
  10. customdried

Sources & evidence

ORD record
ord-c251cda011154bd3a681d1f756cf09c0
Source dataset
uspto-grants-2007_07
Patent number
US07247749B2

Reaction notes

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