Hydrochloric Acid → Nonadecafluorodecanoyl chloride

HRID 570046Notes

Reaction equation

HRID 570046 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[F:7][C:8]([F:37])([C:12]([F:36])([F:35])[C:13]([F:34])([F:33])[C:14]([F:32])([F:31])[C:15]([F:30])([F:29])[C:16]([F:28])([F:27])[C:17]([F:26])([F:25])[C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20])[C:9](O)=[O:10].[ClH:38]>>[F:7][C:8]([F:37])([C:12]([F:36])([F:35])[C:13]([F:34])([F:33])[C:14]([F:32])([F:31])[C:15]([F:30])([F:29])[C:16]([F:28])([F:27])[C:17]([F:26])([F:25])[C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20])[C:9]([Cl:38])=[O:10]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 9555Perfluorodecanoic acidHCID 24819Phosphorus pentachloride2×

Product 1

HCID 13196894Nonadecafluorodecanoyl chlorideYield 70%

Procedure

Phosphorus pentachloride (PCl5), (10.53 g, 50 mmol) was added in small portions to perfluorodecanoic acid (25 g, 49 mmol). Although the ensuing reaction was not too exothermic, HCl gas evolution was vigorous. The resulting solution was refluxed for three hours then a second portion of PCl5 (10.53 g, 50 mmol) was added and the mixture refluxed an additional two hours. Distillation afforded 18.25 g (70%) of perfluorodecanoyl chloride as a colorless liquid.

Workup

  1. customAlthough the ensuing reaction
  2. temperatureThe resulting solution was refluxed for three hours
  3. temperaturethe mixture refluxed an additional two hours
  4. distillationDistillation

Sources & evidence

ORD record
ord-a6cceb1ba888407b8789320043c7c88d
Source dataset
uspto-grants-1988_03
Patent number
US04734517

Reaction notes

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