1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-6-iodohexane → 1H-Perfluorohexane

HRID 1061120Notes

Reaction equation

HRID 1061120 reaction equation
[F:1][C:2](I)([F:19])[C:3]([F:18])([F:17])[C:4]([F:16])([F:15])[C:5]([F:14])([F:13])[C:6]([F:12])([F:11])[C:7]([F:10])([F:9])[F:8].[H][H]>[Ni]>[CH:2]([F:19])([F:1])[C:3]([F:17])([F:18])[C:4]([F:15])([F:16])[C:5]([F:13])([F:14])[C:6]([F:12])([F:11])[C:7]([F:10])([F:9])[F:8]

Participants

4

Reactant 2

HCID 677331,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-6-iodohexaneHCID 178418361HCID 178418361, compound

Product 1

HCID 677301H-PerfluorohexaneYield 81.1%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Conditions

Temperature
-80 °C

Procedure

A 225-mL Hastelloy™ nickel alloy tube was charged with 134.0 g (0.30 mol) of perfluorohexyl iodide, cooled to −80° C. and evacuated, then warmed to 22° C. and pressured to 380 psi (2.72 mPa) with hydrogen (0.17 mol). Heating to 300° C. was accompanied by at least three temperature spikes, the first beginning at 240° C. The pressure at 300° C. began at 990 psi (6.93 mPa) and dropped to 860 psi (6.03 mPa) within 2 hours. When cooled to 25° C., the reactor showed zero pressure on the gauge. Distillation of the liquid product afforded 77.9 g (81%) of pure 1H-perfluorohexane (Boiling Point 70.6-71.2° C.), confirmed by GC and NMR.

Workup

  1. customevacuated
  2. temperaturewarmed to 22° C.
  3. temperatureHeating to 300° C.
  4. customat 240° C
  5. customat 300° C.
  6. additiondropped to 860 psi (6.03 mPa) within 2 hours
  7. temperatureWhen cooled to 25° C.
  8. distillationDistillation of the liquid product

Sources & evidence

ORD record
ord-515fbe86920d428280fd1802e8ce4050
Source dataset
uspto-grants-2003_02
Patent number
US06525231B1

Reaction notes

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