Water → HCID 12095352, compound

HRID 529192Notes

Reaction equation

HRID 529192 reaction equation
O.[F:2][C:3]([F:43])([C:39]([F:42])([F:41])[F:40])[C:4]([F:38])([F:37])[C:5]([P:8]([C:24]([F:36])([F:35])[C:25]([F:34])([F:33])[C:26]([F:32])([F:31])[C:27]([F:30])([F:29])[F:28])([C:11]([F:23])([F:22])[C:12]([F:21])([F:20])[C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])(F)F)([F:7])[F:6]>>[P:8]([C:5]([C:4]([C:3]([C:39]([F:40])([F:41])[F:42])([F:2])[F:43])([F:37])[F:38])([F:6])[F:7])([C:24]([C:25]([C:26]([C:27]([F:30])([F:29])[F:28])([F:32])[F:31])([F:34])[F:33])([F:36])[F:35])[C:11]([C:12]([C:13]([C:14]([F:17])([F:16])[F:15])([F:19])[F:18])([F:21])[F:20])([F:23])[F:22]

Participants

3

Reactant 2

HCID 962WaterHCID 9940143Phosphorane, difluorotris(nonafluorobutyl)-

Product 1

HCID 12095352HCID 12095352, compound

Conditions

Temperature
120 °C

Procedure

0.28 g (15.5 mmol) of water is added to 14.04 g (19.3 mmol) of tris(nonafluorobutyl)difluorophosphorane, (C4F9)3PF2, in a 100 ml glass round-bottomed flask and warmed (120° C. oil-bath temperature). A cooled (−30° C. to −35° C.) intensive reflux condenser is connected downstream of the flask. Liquid SO2 (about 5 ml), which is slowly released into the system, is via a T-piece connected in between with connected Young trap. The emulsion is stirred at 120° C. for 7.5 h before the intensive condenser is warmed to −5° C. in order to discharge excess SO2 in gaseous form. Virtually complete consumption (98.4%) of (C4F9)3PF2 and formation of (C4F9)3P═O (78.0%), (C4F9)2P(O)OH (14.0%) can be detected. The entire suspension is condensed at 75° C. in vacuo (10−3 mbar). Clear and colourless (C4F9)3P═O (8.81 g; 12.5 mmol; 79%) can be isolated in 92% purity. Pure, crystalline, clear and colourless (C4F9)2P(O)OH can be isolated from the solid residue by sublimation at 75° C. in vacuo (10−3 mbar).

Workup

  1. temperatureA cooled (−30° C. to −35° C.) intensive reflux condenser
  2. temperatureis warmed to −5° C. in order
  3. customVirtually complete consumption (98.4%) of (C4F9)3PF2 and formation of (C4F9)3P═O (78.0%), (C4F9)2P(O)OH (14.0%)
  4. customcondensed at 75° C. in vacuo (10−3 mbar)

Sources & evidence

ORD record
ord-5144047838284bc7a1e6933515f8cb1e
Source dataset
uspto-grants-2016_05
Patent number
US09346838B2

Reaction notes

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