Reaction #1755447

Reaction equation

potassium hydroxide

2,2,3,4,4,4-hexafluorobutan-1-ol

1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride

→

2,2,3,4,4,4-hexafluorobutyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate

Solvents

water

Conditions

Workup

1. 1
   OtherThe flask was equipped with a magnetic stirrer, cold water condenser
2. 2
   workup.ADDITIONthermocouple and a 250-mL addition funnel
3. 3
   Otherdid not exceed 35° C
4. 4
   workup.ADDITIONOnce the addition of the base
5. 5
   FiltrationThe precipitated salts were then filtered from the mixture
6. 6
   Otherthe lower liquid fluorochemical product phase was separated from the upper aqueous phase
7. 7
   Otherwere removed by atmospheric distillation

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.

Source