Potassium 1,1,2,2-tetrafluoroethanesulfonate → (3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluorooctyl)-trioctylphosphonium 1,1,2,2-tetrafluoroethanesulfonate

HRID 1175548Notes

Reaction equation

HRID 1175548 reaction equation
[F:1][C:2]([F:10])([S:6]([O-:9])(=[O:8])=[O:7])[CH:3]([F:5])[F:4].[K+].[I-].[F:13][C:14]([F:58])([C:42]([F:57])([F:56])[C:43]([F:55])([F:54])[C:44]([F:53])([F:52])[C:45]([F:51])([F:50])[C:46]([F:49])([F:48])[F:47])[CH2:15][CH2:16][P+:17]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>CC(C)=O>[F:1][C:2]([F:10])([S:6]([O-:9])(=[O:8])=[O:7])[CH:3]([F:5])[F:4].[F:58][C:14]([F:13])([C:42]([F:56])([F:57])[C:43]([F:54])([F:55])[C:44]([F:52])([F:53])[C:45]([F:50])([F:51])[C:46]([F:47])([F:48])[F:49])[CH2:15][CH2:16][P+:17]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]

Participants

4

Reactant 2

HCID 58905542Potassium 1,1,2,2-tetrafluoroethanesulfonateHCID 86611566(3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluorooctyl)trioctylphosphonium iodide

Product 1

HCID 86611564(3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluorooctyl)-trioctylphosphonium 1,1,2,2-tetrafluoroethanesulfonateYield 109.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

Trioctyl phosphine (31 g) was partially dissolved in reagent-grade acetonitrile (250 ml) in a large round-bottomed flask and stirred vigorously. 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane (44.2 g) was added, and the mixture was heated under reflux at 110 degrees C. for 24 hours. The solvent was removed under vacuum giving (3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-trioctylphosphonium iodide as a waxy solid (30.5 g). Potassium 1,1,2,2-tetrafluoroethanesulfonate (TFES-K, 13.9 g) was dissolved in reagent grade acetone (100 ml) in a separate round-bottomed flask, and to this was added (3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-trioctylphosphonium iodide (60 g). The reaction mixture was heated at 60 degrees C. under reflux for approximately 16 hours. The reaction mixture was then filtered using a large frit glass funnel to remove the white KI precipitate formed, and the filtrate was placed on a rotary evaporator for 4 hours to remove the acetone. The liquid was left for 24 hours at room temperature and then filtered a second time (to remove KI) to yield the product (62 g) as shown by proton NMR.

Workup

  1. temperatureunder reflux for approximately 16 hours
  2. filtrationThe reaction mixture was then filtered
  3. customto remove the white KI precipitate
  4. customformed
  5. customthe filtrate was placed on a rotary evaporator for 4 hours
  6. customto remove the acetone
  7. filtrationfiltered
  8. customa second time (to remove KI)

Sources & evidence

ORD record
ord-0f95645af2e043e988a9c25aac3ac627
Source dataset
uspto-grants-2010_11
Patent number
US07838679B2

Reaction notes

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