Potassium Hydroxide → 2,2,3,4,4,4-Hexafluorobutyl nonafluorobutane-1-sulfonate

HRID 2357140Notes

Reaction equation

HRID 2357140 reaction equation
[F:1][C:2]([F:11])([CH:5]([F:10])[C:6]([F:9])([F:8])[F:7])[CH2:3][OH:4].[F:12][C:13]([F:28])([S:24](F)(=[O:26])=[O:25])[C:14]([F:23])([F:22])[C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17].[OH-].[K+]>O>[F:28][C:13]([F:12])([S:24]([O:4][CH2:3][C:2]([F:11])([F:1])[CH:5]([F:10])[C:6]([F:9])([F:7])[F:8])(=[O:26])=[O:25])[C:14]([F:22])([F:23])[C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 5339902,2,3,4,4,4-Hexafluorobutan-1-ol

Product 1

HCID 866383052,2,3,4,4,4-Hexafluorobutyl nonafluorobutane-1-sulfonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,2,3,4,4,4-hexafluorobutan-1-ol (202 grams, 1.1 moles, Sinochem Corp.), 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride (332 grams, 1.1 moles, 3M Company) and water (300 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 addition funnel. Aqueous potassium hydroxide, 45 percent (149.3 grams, 1.22 moles, Aldrich Chemical Co.) was added dropwise via an addition funnel at such a rate that the temperature did not exceed 35° C. Once the addition of the base 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 2,2,3,4,4,4-hexafluorobutan-1-ol and 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride were removed by atmospheric distillation. Approximately 400 grams of 2,2,3,4,4,4-hexafluorobutyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate were recovered at a purity of 98.9 percent as measured by gas chromatographic analysis.

Workup

  1. customThe flask was equipped with a magnetic stirrer, cold water condenser
  2. additionthermocouple, and addition funnel
  3. customdid not exceed 35° C
  4. additionOnce the addition of the base
  5. filtrationPrecipitated salts were then filtered from the mixture
  6. customthe lower liquid fluorochemical product phase was separated from the upper aqueous phase
  7. customwere removed by atmospheric distillation
  8. customApproximately 400 grams of 2,2,3,4,4,4-hexafluorobutyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate were recovered at a purity of 98.9 percent

Sources & evidence

ORD record
ord-b66a4250429849ee9319d0e57c5fa157
Source dataset
uspto-grants-2010_07
Patent number
US07759512B2

Reaction notes

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