2,2,3,3-Tetrafluoro-1-propanol → 2,2,3,3-Tetrafluoropropyl nonafluorobutane-1-sulfonate

HRID 2357139Notes

Reaction equation

HRID 2357139 reaction equation
[F:1][C:2]([F:8])([CH:5]([F:7])[F:6])[CH2:3][OH:4].[F:9][C:10]([F:25])([S:21](F)(=[O:23])=[O:22])[C:11]([F:20])([F:19])[C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14].[OH-].[K+]>O>[F:1][C:2]([F:8])([CH:5]([F:7])[F:6])[CH2:3][O:4][S:21]([C:10]([F:9])([F:25])[C:11]([F:19])([F:20])[C:12]([F:17])([F:18])[C:13]([F:16])([F:15])[F:14])(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 64412,2,3,3-Tetrafluoro-1-propanolHCID 14797Potassium Hydroxide2×HCID 67814Perfluoro-1-butanesulfonyl fluoride

Product 1

HCID 235052222,2,3,3-Tetrafluoropropyl nonafluorobutane-1-sulfonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,2,3,3-tetrafluoropropan-1-ol (202 grams, 1.52 moles, Sinochem Corp., Beijing, China), 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride (3M Company, Saint Paul, Minn., 465 grams, 1.52 moles) and water (500 g) were combined in a 3-liter, 3-necked round bottom flask. The flask was equipped with a magnetic stirrer, cold water condenser, thermocouple and an addition funnel. Aqueous potassium hydroxide (45 percent by weight, 211.5 g, 1.7 moles, Aldrich Chemical Co., Milwaukee, Wis.) was added dropwise via the addition funnel at such a rate that the temperature did not exceed 35° C. Once the addition of the potassium hydroxide was complete, the mixture was stirred for 16 hours at room temperature. Precipitated salts were then filtered from the mixture and the lower liquid fluorochemical product phase was separated from the upper aqueous phase. Unreacted 2,2,3,3-tetrafluoropropan-1-ol and 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride were removed from the liquid fluorochemical product phase by atmospheric distillation. Approximately 500 g of 2,2,3,3-tetrafluoropropyl-1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate was recovered at a purity of 98.9 percent as determined by gas chromatography analysis.

Workup

  1. customThe flask was equipped with a magnetic stirrer, cold water condenser
  2. customdid not exceed 35° C
  3. filtrationPrecipitated salts were then filtered from the mixture
  4. customthe lower liquid fluorochemical product phase was separated from the upper aqueous phase
  5. customwere removed from the liquid fluorochemical product phase by atmospheric distillation
  6. customApproximately 500 g of 2,2,3,3-tetrafluoropropyl-1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate was recovered at a purity of 98.9 percent

Sources & evidence

ORD record
ord-69526098de7d461fb2d69b420de7382b
Source dataset
uspto-grants-2010_07
Patent number
US07759512B2

Reaction notes

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