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

HRID 2382495Notes

Reaction equation

HRID 2382495 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 g, 1.1 mol, obtained from Sinochem Corp., Beijing, China), 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride (332 g, 1.1 mol, obtained from 3M Company of Saint Paul, Minn.) and water (300 g) were combined in a 3-L, 3-necked round bottom flask. The flask was equipped with a magnetic stirrer, cold water condenser, thermocouple and a 250-mL addition funnel. Aqueous potassium hydroxide (149.3 g, 45 weight percent, 1.22 equivalents) 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. The 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.

Workup

  1. customThe flask was equipped with a magnetic stirrer, cold water condenser
  2. additionthermocouple and a 250-mL addition funnel
  3. customdid not exceed 35° C
  4. additionOnce the addition of the base
  5. filtrationThe precipitated 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

Sources & evidence

ORD record
ord-42f9040d960649a38fb968bcab3c1ca4
Source dataset
uspto-grants-2012_09
Patent number
US08261560B2

Reaction notes

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