Ammonia → HCID 131727633, compound

HRID 218975Notes

Reaction equation

HRID 218975 reaction equation
[C:1]([C:5]([C:8]([O:11][C:12]([C:15]([C:18]([OH:20])=[O:19])([F:17])[F:16])([F:14])[F:13])([F:10])[F:9])([F:7])[F:6])([F:4])([F:3])[F:2].[C:21]([C:25]([C:28]([O:31][CH:32]([C:34]([C:37]([OH:39])=[O:38])([F:36])[F:35])[F:33])([F:30])[F:29])([F:27])[F:26])([F:24])([F:23])[F:22].[NH3:40]>O>[C:1]([C:5]([C:8]([O:11][C:12]([C:15]([C:18]([O-:20])=[O:19])([F:17])[F:16])([F:14])[F:13])([F:10])[F:9])([F:7])[F:6])([F:4])([F:3])[F:2].[NH4+:40].[C:21]([C:25]([C:28]([O:31][CH:32]([C:34]([C:37]([O-:39])=[O:38])([F:36])[F:35])[F:33])([F:29])[F:30])([F:27])[F:26])([F:24])([F:23])[F:22].[NH4+:40]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 30138662,2,3,3-Tetrafluoro-3-(heptafluoropropoxy)propionic acidHCID 714186532,2,3-Trifluoro-3-(heptafluoropropoxy)propanoic acid

Product 2

HCID 131727633HCID 131727633, compoundHCID 131727634HCID 131727634, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100-ml PFA-made vessel equipped with a gas inlet pipe was charged with 39.6 g of the CF3CF2CF2OCH2CF2COOH prepared in Synthesis Example 1, and nitrogen was passed through the vessel at a flow rate of 20 ml/minute for 10 minutes to deprive the system of oxygen and moisture. Fluorine gas diluted to 24% with nitrogen was passed through the vessel warmed on a water bath at 60° C. at a flow rate of 40 ml/minute for 15.3 hours. After substitution of the vessel inside atmosphere with nitrogen, 37.5 g of the reaction product was recovered. This reaction product was rectified at ordinary pressure to give 25.1 g of fraction 1 (boiling point 58° C.) and 11.9 g of fraction 2 (boiling point 80.5° C.). Gas chromatography revealed that the fraction 1 had a purity of 95% and the fraction 2 had a purity of 99.5%. Based on the results of F-NMR, the fraction 1 was identified as CF3CF2CF2OCF2CF2COOH in view of the appearance of a spectral peak at −123.3 ppm and the fraction 2 as CF3CF2CF2OCHFCF2COOH in view of the appearance of a spectral peak at −148.4 ppm. A 1-g portion of each fraction was dissolved in 10 g of water, the solution was adjusted to pH 8 by addition of aqueous ammonia, followed by drying at 80° C. under vacuum. Thus were obtained CF3CF2CF2OCF2CF2COONH4 and CF3CF2CF2OCHFCF2COONH4, respectively.

Workup

  1. customresults of F-NMR
  2. customby drying at 80° C. under vacuum

Sources & evidence

ORD record
ord-291a6c335f6d466681521350d78d7f52
Source dataset
uspto-grants-2012_06
Patent number
US08198480B2

Reaction notes

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