1-Chloro-2,4-Dinitrobenzene → 2-Chloro-4,6-dinitrophenol

Participants

Reaction Steps

203 parts of 2,4-dinitrochlorobenzene (setting point 49° C.) are saponified to 2,4-dinitrophenol in a mixture of 303 parts of 33% strength sodium hydroxide solution and 200 parts of water at 95° C. under a nitrogen atmosphere. The resulting suspension is adjusted to a pH value of 3.5 by adding 185 parts of 31% strength hydrochloric acid. After 10 parts of the sodium salt of a naphthalenesulfonic acid/formaldehyde condensation product (dispersing agent), 1 part of iron(III) chloride and 1 part of iodine trichloride have been added, 650 parts of 13 percent strength by weight chlorine bleach liquor (containing 150 parts of active chlorine per liter) are added dropwise at 10° C. in the course of 8 hours, the pH increasing meanwhile. Towards the end of the addition, the pH reaches a value of 6. After it has reached this value, the pH is kept at this value (pH 6) by the simultaneous dropwise addition of 5-20 parts of 31% strength hydrochloric acid and the remainder of the chlorine bleach liquor. The pH of the suspension is then adjusted to a value of 1.0 by adding 170 parts of 31% strength hydrochloric acid, and small amounts of sodium hypochlorite still present are destroyed by means of 15 parts of 40% strength sodium bisulfite solution. The resulting product is then isolated by being filtered off at about 10° C. This gives only 130 parts of 6-chloro-2,4-dinitrophenol with a black-brown appearance and a content of unsaponified 2,4-dinitrochlorobenzene which is clearly detectable in a thin layer chromatogram.

Provenance & Evidence