1,2,4,5-Tetrachlorobenzene → 2,4,5-Trichlorophenol

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[CH:4][C:3]=1Cl.[OH-:11].[Na+]>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[CH:4][C:3]=1[OH:11]

Participants

Reactant 2

HCID 72701,2,4,5-Tetrachlorobenzene

HCID 14798Sodium Hydroxide2×

Product 1

HCID 72712,4,5-Trichlorophenol

Procedure

The presently employed technology to produce 2,4,5-trichlorophenoxyacetic acid (2,4,5-T) and 2,4,5-trichlorophenol (2,4,5-TCP) commercially involves the declorination of 1,2,4,5-tetrachlorobenzene with aqueous sodium hydroxide or anhydrous sodium hydroxide in the presence of alcohols under elevated temperatures and pressures to form 2,4,5-TCP according to the flow diagram: ##STR1## Under the conditions of alkalinity, temperature and pressure this process produces between 1 to 100 parts per million of the highly toxic teratogen 2,3,7,8-tetrachloro-dibenzo-p-dioxin (TCDD) according to the reaction: ##STR2##

Sources & evidence

ORD record: ord-fae4a4ad09ea4bdbb8114fea4089e1f4
Source dataset: uspto-grants-1982_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04346248

Reaction notes

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