Acetic Acid → 1,4-Butanedisulfonic acid, 1,1,2,2,3,3,4,4-octafluoro-
Reaction equation
[F:1][C:2]([F:18])([S:15]([O-:17])=[O:16])[C:3]([F:14])([F:13])[C:4]([F:12])([F:11])[C:5]([F:10])([F:9])[S:6]([O-:8])=[O:7].[Na+].[Na+].OO.[OH-:23].[Na+].C(O)(=[O:27])C>>[F:9][C:5]([F:10])([S:6]([OH:27])(=[O:8])=[O:7])[C:4]([F:11])([F:12])[C:3]([F:13])([F:14])[C:2]([F:1])([F:18])[S:15]([OH:17])(=[O:16])=[O:23]Participants
Procedure
To a mixture of 25 mL of acetonitrile and 15 mL of water were added 8.44 g (18.6 mmol) of diiodoperfluorobutane, 8.50 g (48.8 mmol) of sodium hydrosulfite, and 4.60 g (55 mmol) of sodium hydrogen carbonate. The resultant mixture was stirred at room temperature for 1 hour. This reaction mixture solution was filtered and the filtrate was cooled with ice. As a result, a white solid precipitated. This precipitate was taken out by filtration and dried to obtain sodium perfluorobutane-1,4-disulfinate in an amount of 6.8 g (98%). Subsequently, 7.2 g (19.2 mmol) of the sodium perfluorobutane-1,4-disulfinate was added to a mixture of 80 mL of aqueous hydrogen peroxide solution (30%) and 8 mL of acetic acid, and the resultant mixture was stirred at 60° C. for 4 hours. A reaction proceeded stoichiometrically. After completion of the reaction was ascertained by 19F-NMR spectroscopy, the reaction mixture was neutralized by adding 30 mL of 1-N NaOH solution thereto. Thus, an aqueous solution of perfluorobutane-1,4-disulfonic acid ((I)-44) was obtained.
Sources & evidence
- ORD record
- ord-50ff88c097a645b6b1440db635707572
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07914965B2
Reaction notes
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