Ethanol → 1-(2H-Perfluoropropyl)ethanol

HRID 1479142Notes

Reaction equation

HRID 1479142 reaction equation
[CH3:1][CH2:2][OH:3].[F:4][C:5]([F:12])([F:11])[C:6]([F:10])=[C:7]([F:9])[F:8]>>[F:8][C:7]([F:9])([CH:6]([F:10])[C:5]([F:12])([F:11])[F:4])[CH:2]([OH:3])[CH3:1]

Participants

3

Reactant 2

HCID 702EthanolHCID 8302Hexafluoropropylene

Product 1

HCID 27750191-(2H-Perfluoropropyl)ethanolYield 95.6%

Procedure

A quantity of 3,3,4,5,5,5-hexafluoropentan-2-ol was prepared by combining absolute ethanol 200 proof (100 g, 2.17 moles, AAPER Alcohol and Chemical Co.) with t-amyl peroxy-2-ethylhexanoate (5 g, 0.021 moles) (available as Luperox 575 from Arkema, Oakville, Ontario, Canada) in a 600 mL Parr pressure reactor. The reactor was heated to 75 C and hexafluoropropene (120 g, 0.8 moles) (MDA Manufacturing Inc., Decatur, Ala.) was added at a constant rate. The reactor was allowed to stir at this temperature for 16 h. The crude reaction material was distilled using a ten plate Oldershaw column to afford 150 g of 3,3,4,5,5,5-hexafluoropentan-2-ol (b.p.=121° C.).

Workup

  1. customA quantity of 3,3,4,5,5,5-hexafluoropentan-2-ol was prepared
  2. additionwas added at a constant rate
  3. customThe crude reaction material
  4. distillationwas distilled

Sources & evidence

ORD record
ord-e158ec4aaee4423d8fe873a526cb6e58
Source dataset
uspto-grants-2016_08
Patent number
US09406977B2

Reaction notes

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