2,4,6-Tribromophenol → Carbon Dioxide

HRID 1739364Notes

Reaction equation

HRID 1739364 reaction equation
N1C(Cl)=NC(Cl)=NC=1Cl.BrC1C=C(Br)C=C(Br)C=1O.[C:20](=[O:23])([O-:22])[O-:21].[Na+:24].[Na+].[OH-].[Na+]>CC(C)=O.C(C(C)=O)C>[C:20](=[O:21])([OH:23])[O-:22].[Na+:24].[C:20](=[O:22])=[O:21].[C:20](=[O:21])([O-:23])[O-:22].[Na+:24].[Na+:24]

Participants

9

Reactant 4

HCID 14832,4,6-TribromophenolHCID 7954Cyanuric chlorideHCID 10340Sodium CarbonateHCID 14798Sodium Hydroxide

Product 3

HCID 280Carbon DioxideHCID 10340Sodium CarbonateHCID 516892Sodium Bicarbonate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

The compound, tris(2,4,6-tribromophenoxy)-s-1,3,5-triazine, was reported in French Patent 1,566,675, in 1969. The compound is useful as a flame retardant. In U.S. Pat. Nos. 3,843,650 and 3,950,306 a process for the production of tris(2,4,6-tribromophenoxy)-s-1,3,5-triazine is described. In addition, two recommended processes utilize the reaction of cyanuric chloride and 2,4,6-tribromophenol in the presence of either sodium carbonate and methyl ethyl ketone or aqueous sodium hydroxide and acetone. The product has poor solubility in ketone solvents and is readily removed by filtration. When sodium hydroxide is used as the base, water is formed as a by-product; sodium bicarbonate or carbon dioxide is formed when sodium carbonate is used. While workable, the foregoing processes are not as efficient as desired.

Workup

  1. customis readily removed by filtration
  2. customwater is formed as a by-product

Sources & evidence

ORD record
ord-c447a1779a7e43a9ba1f067aee2fdf48
Source dataset
uspto-grants-1999_10
Patent number
US05965731

Reaction notes

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