Toluene → 1,1,1,3,3,3-Hexafluoropropane

HRID 440181

Reaction equation

HRID 440181 reaction equation
[CH:1](C(OC)(F)F)([C:6]([F:9])([F:8])[F:7])[C:2]([F:5])([F:4])[F:3].CCOCC.C1(C)C=CC=CC=1>[Ni].O>[CH2:1]([C:6]([F:9])([F:8])[F:7])[C:2]([F:5])([F:4])[F:3]

Participants

6

Reactant 3

HCID 1140TolueneHCID 3283Diethyl EtherHCID 454591,1,1,3,3-Pentafluoro-3-methoxy-2-(trifluoromethyl)propane

Product 1

HCID 127221,1,1,3,3,3-Hexafluoropropane

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

A 100 g mixture containing 59.0% (CF3)2CHCF2OCH3 (ether A), 20% (CF3)2C=CFOCH3 (ether B), 15.9% toluene and 150 mL water was heated in a Hastelloy™ nickel alloy tube for 3 hours at 135° C. and 6 hours at 200° C. The volatiles were bubbled through a solution of aqueous NaOH and a CaSO4 drying column, and condensed in a dry ice cooled trap to give 12.9 g HFC-236fa identified by its infrared spectrum. The liquid contents of the tube contained two layers. The upper layer, 14.9 g, was shown by 1H and 19F NMR spectroscopy to contain 16.5 wt. percent HFC-236fa and toluene. The combined HFC-236fa from the volatiles and the toluene corresponded to a yield of 15.4 g, 29.0% based on the starting ethers.

Workup

  1. customThe volatiles were bubbled through a solution of aqueous NaOH
  2. customa CaSO4 drying column, and condensed in a dry ice cooled trap

Sources & evidence

ORD record
ord-f137768d8b5240dea90972830d455474
Source dataset
uspto-grants-1996_05
Patent number
US05516946

Linked notes

Loading…