Sulfuric Acid → 4-(Trifluoroethenyloxy)hexafluorobutyric acid

HRID 52821Notes

Reaction equation

HRID 52821 reaction equation
[OH-].[Na+].[F:3][C:4]([F:21])([C:9]([F:20])([F:19])[C:10]([F:18])([F:17])[O:11][C:12]([F:16])=[C:13]([F:15])[F:14])[C:5]([O:7]C)=[O:6].[Na].S(=O)(=O)(O)O>O>[F:3][C:4]([F:21])([C:9]([F:19])([F:20])[C:10]([F:18])([F:17])[O:11][C:12]([F:16])=[C:13]([F:14])[F:15])[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 11403991Methyl 4-trifluoroethenoxy-2,2,3,3,4,4-hexafluorobutanoate

Product 1

HCID 141743144-(Trifluoroethenyloxy)hexafluorobutyric acidYield 313.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(1') An aqueous solution containing 40 g (0.1 mole) of sodium hydroxide dissolved in 160 ml of water was added to 306 g (0.1 mole)of methyl perfluoro(4-vinyloxybutyrate) at 0°-5° C. over 5 hours, and the mixture was returned to room temperature with stirring over 1.5 hours and then left standing for 12 hours. By distilling off water and heating the residue to dryness under reduced pressure, sodium perfluoro(4-vinyloxybutyrate) was quantitatively obtained. 100 g of the sodium salt was suspended in excess amount of concentrated sulfuric acid and the suspension was distilled under reduced pressure, whereby 91.5 g of perfluoro(4-vinyloxybutyric acid) was obtained as a fraction having a boiling point of 80°-81.5° C./20 mmHg (yield:93%). ##STR16##

Workup

  1. customwas returned to room temperature
  2. waitleft
  3. waitstanding for 12 hours
  4. distillationBy distilling off water
  5. temperatureheating the residue to dryness under reduced pressure, sodium perfluoro(4-vinyloxybutyrate)
  6. customwas quantitatively obtained
  7. distillationthe suspension was distilled under reduced pressure

Sources & evidence

ORD record
ord-9c393c07e2cf42fb89aba0a3c4667199
Source dataset
uspto-grants-1997_04
Patent number
US05616813

Reaction notes

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