Sulfuric Acid → 2,2-Difluoro-3-(nonafluorobutoxy)propanoic acid

HRID 733495Notes

Reaction equation

HRID 733495 reaction equation
[C:1]([C:5]([C:8]([C:11]([O:14][CH2:15][C:16]([C:19](F)=[O:20])([F:18])[F:17])([F:13])[F:12])([F:10])[F:9])([F:7])[F:6])([F:4])([F:3])[F:2].S(=O)(=O)(O)[OH:23]>>[C:1]([C:5]([C:8]([C:11]([O:14][CH2:15][C:16]([C:19]([OH:23])=[O:20])([F:17])[F:18])([F:13])[F:12])([F:9])[F:10])([F:6])[F:7])([F:3])([F:2])[F:4]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 714186552,2-Difluoro-3-(nonafluorobutoxy)propanoyl fluoride

Product 1

HCID 714186542,2-Difluoro-3-(nonafluorobutoxy)propanoic acid

Procedure

A 28-g portion of the CF3CF2CF2CF2OCH2CF2COF obtained was hydrolyzed by gradually pouring the same into dilute sulfuric acid with stirring. The product was washed several times with dilute sulfuric acid and distilled under reduced pressure to give 25.7 g of pure CF3CF2CF2CF2OCH2CF2COOH. The CF3CF2CF2CF2OCH2CF2COOH obtained had a boiling point of 75.5° C. at a pressure of 1.3×103 Pa. A 3.0-g portion of the CF3CF2CF2CF2OCH2CF2COOH obtained was neutralized with an aqueous solution of sodium hydroxide, and the product was dried to give the desired compound. A 0.2% (by mass) aqueous solution of this CF3CF2CF2CF2OCH2CF2COONa had a surface tension of 63.4 mN/m. A 2.0% (by mass) aqueous solution thereof had a surface tension of 37.5 mN/m.

Workup

  1. washThe product was washed several times with dilute sulfuric acid
  2. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-c9fad991cad04bd7ada1aff15eb0a907
Source dataset
uspto-grants-2009_09
Patent number
US07589234B2

Reaction notes

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