Acryloyl chloride → Hexafluoroisopropyl acrylate

HRID 1879612Notes

Reaction equation

HRID 1879612 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[F:6][C:7]([F:15])([F:14])[CH:8]([OH:13])[C:9]([F:12])([F:11])[F:10].C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C.OS(O)(=O)=O.O=S(=O)=O>>[C:1]([O:13][CH:8]([C:9]([F:12])([F:11])[F:10])[C:7]([F:15])([F:14])[F:6])(=[O:4])[CH:2]=[CH2:3]

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 135291,1,1,3,3,3-Hexafluoro-2-propanolHCID 24681Fuming sulfuric acidHCID 314042,6-Di-tert-butyl-4-methylphenol

Product 1

HCID 75096Hexafluoroisopropyl acrylateYield 95.7%

Procedure

With reference to scheme (13) above, a 1000 mL three-neck flask can be equipped with a thermometer, agitator, and dropping funnel with a dip tube. Into the flask can be added about 130.6 grams of acryloyl chloride, 168.8 grams 1,1,1,3,3,3-hexafluoropropan-2-ol, and 1 grain of 2,6-di-tert-butyl-4-methylphenol to form a mixture. About 30% (wt/wt) oleum can then be added to the mixture through the dip tube while maintaining the mixture at 60° C.-75° C. After addition, the mixture can be maintained at 60° C.-70° C. for about 4 hours. Single stage vacuum distillation of the mixture can yield about 183 grains of crude product 1,1,1,3,3,3-hexafluoropropan-2-yl acrylate being about 95.7% (area percent by as chromatography). The crude 1,1,1,3,3,3-hexafluoropropan-2-yl can be distilled further to increase purity to 99.7% (area percent by gas chromatography).

Workup

  1. customWith reference to scheme (13) above, a 1000 mL three-neck flask can be equipped with a thermometer, agitator
  2. customto form a mixture
  3. temperaturewhile maintaining the mixture at 60° C.-75° C
  4. additionAfter addition
  5. temperaturethe mixture can be maintained at 60° C.-70° C. for about 4 hours
  6. distillationSingle stage vacuum distillation of the mixture

Sources & evidence

ORD record
ord-6832a404f5f44c3bbfdd9241e5606f73
Source dataset
uspto-grants-2012_11
Patent number
US08318656B2

Reaction notes

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