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Methanol → 1H-Perfluorohexane

HRID 53413
Notes
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Reaction equation

HRID 53413 reaction equation
CO.C(O)(C)C.[OH-].[K+].[C:9](I)([C:12]([C:15]([C:18]([C:21]([C:24]([F:27])([F:26])[F:25])([F:23])[F:22])([F:20])[F:19])([F:17])[F:16])([F:14])[F:13])([F:11])[F:10]>[Cr].[Co].O>[CH:9]([C:12]([C:15]([C:18]([C:21]([C:24]([F:25])([F:26])[F:27])([F:22])[F:23])([F:19])[F:20])([F:17])[F:16])([F:14])[F:13])([F:11])[F:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 887MethanolHCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 677331,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-6-iodohexane

Product 1

HCID 677301H-PerfluorohexaneYield 93%

Reagents, catalysts & solvents 2

HCID 11332432
Hastelloy C
Catalyst
HCID 962WaterSolvent

Procedure

Into a 20 l Hastelloy C autoclave equipped with a stirrer, a reflux condenser and a thermometer, 5130 g of methanol and 60 g of isopropyl alcohol and 1485 g (22.5 mols) of 85% potassium hydroxide were charged. The reactor was heated to bring the internal temperature to 50° C. Then, 4460 g (10 mols) of C6F13I was fed thereto over a period of two hours. While maintaining the internal temperature of the reactor at a level of from 50° to 55° C. stirring was continued for 10 hours. The conversion was more than 99.9%. The reactor was cooled to room temperature, and then, 3200 g of water was added to dissolve precipitated potassium iodide. The crude reaction solution was separated into two layers, and the fluorocarbon layer (lower layer) was further washed twice with 3200 g of water to obtain 2975 g (purity: 99.9%) of C6F13H. In the reactor, no formation of tar was observed.

Workup

  1. temperatureThe reactor was heated
  2. customto 50° C
  3. temperatureWhile maintaining the internal temperature of the reactor at a level of from 50° to 55° C.
  4. waitwas continued for 10 hours
  5. dissolutionto dissolve
  6. customprecipitated potassium iodide
  7. customThe crude reaction solution
  8. customwas separated into two layers
  9. washthe fluorocarbon layer (lower layer) was further washed twice with 3200 g of water

Sources & evidence

ORD record
ord-a39525dfa9c34ad0ae8e59b487ad02c5
Source dataset
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05618986

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes