2-Chloroethanol → HCID 20272208, compound

HRID 484775Notes

Reaction equation

HRID 484775 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH2:33][CH2:34][OH:35])[S:5]([C:8]([F:32])([F:31])[C:9]([F:30])([F:29])[C:10]([F:28])([F:27])[C:11]([F:26])([F:25])[C:12]([F:24])([F:23])[C:13]([F:22])([F:21])[C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])(=[O:7])=[O:6].FC(F)(S(N)(=O)=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)[C:42](F)(F)[C:43](F)(F)[C:44](F)(F)F.C(Cl)C[OH:67].[CH2:69]([CH:71]1[O:73][CH2:72]1)Cl.[OH-].[Na+]>>[CH2:69]([O:1][CH2:2][CH2:3][N:4]([CH2:33][CH2:34][O:35][CH2:44][CH:43]1[O:67][CH2:42]1)[S:5]([C:8]([F:32])([F:31])[C:9]([F:29])([F:30])[C:10]([F:27])([F:28])[C:11]([F:25])([F:26])[C:12]([F:23])([F:24])[C:13]([F:22])([F:21])[C:14]([F:19])([F:20])[C:15]([F:18])([F:17])[F:16])(=[O:7])=[O:6])[CH:71]1[O:73][CH2:72]1

Participants

6

Reactant 5

HCID 342-ChloroethanolHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 69785PerfluorooctanesulfonamideHCID 3016206Heptadecafluoro-N,N-bis(2-hydroxyethyl)octanesulphonamide

Product 1

HCID 20272208HCID 20272208, compound

Conditions

Temperature
65 °C

Procedure

Into a 1 L 3-neck flask equipped with an agitator, thermometer, and a reflux condenser was placed 171 g (0.3 mole) of N,N-bis(2-hydroxyethyl)perfluorooctanesulfonamide (prepared from perfluorooctanesulfonamide and ethylenechlorohydrin as described in Example 2 of U.S. Pat. No. 4,289,892) and 277.5 g (3.0 moles) of epichlorohydrin. The reaction mixture was stirred and heated to 65° C. Then 12.2 g (of a total of 53 g, 1.3 moles) of sodium hydroxide was added. The reaction mixture was heated to 90° C. and stirred at that temperature for 4 hours, cooled to about 40° C., and filtered from sodium chloride. The filter cake was then washed with about 50 mL epichlorohydrin. The combined filtrates along with the remaining sodium hydroxide were heated to 90° C. and stirred at that temperature for 4 hours. The reaction mixture was cooled, filtered, and the filtrate concentrated under vacuum at a temperature of 50° to 90° C. to remove excess epichlorohydrin. GC and infrared spectroscopic (IR) analysis of the product indicated the presence of N,N-bis(2-glycidoxyethyl)perfluorooctanesulfonamide in about 90% purity. The impurity was mainly N-(2-hydroxyethyl), N(2-glycidoxyethyl)perfluorooctanesulfonamide.

Workup

  1. customInto a 1 L 3-neck flask equipped with an agitator
  2. customthermometer, and a reflux condenser was placed
  3. temperatureThe reaction mixture was heated to 90° C.
  4. stirringstirred at that temperature for 4 hours
  5. temperaturecooled to about 40° C.
  6. filtrationfiltered from sodium chloride
  7. washThe filter cake was then washed with about 50 mL epichlorohydrin
  8. temperatureThe combined filtrates along with the remaining sodium hydroxide were heated to 90° C.
  9. stirringstirred at that temperature for 4 hours
  10. temperatureThe reaction mixture was cooled
  11. filtrationfiltered
  12. concentrationthe filtrate concentrated under vacuum at a temperature of 50° to 90° C.
  13. customto remove excess epichlorohydrin

Sources & evidence

ORD record
ord-0fc99e40daf24fe1967fe25cb62bea07
Source dataset
uspto-grants-1985_08
Patent number
US04533713

Reaction notes

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