Sulfite → 1,4,5,8-Naphthalenetetracarboxylic acid

Participants

Reaction Steps

In the aqueous-alkaline hypohalite oxidation of organic compounds, in particular in the alkaline hypochlorite oxidation of 2,7-dibromodiindanedione (3) to give the tetraalkali metal salt of naphthalene-1,4,5,8-tetracarboxylic acid, the ecological pollution by halogen-containing compounds of the classes CHX3 and CX4, in which X is chlorine, bromine or a combination thereof, is eliminated by carrying out the aqueous-alkaline hypohalite oxidation at a temperature of between 20° and 60° C., preferably 40° to 55° C., in a closed vessel under the autogenous pressure which is established at the corresponding temperature, subjecting the reaction mixture, after the oxidation has ended, to a heat treatment at a temperature of between 90° and 120° C., preferably 90° to 100° C., under the autogenous pressure of 1 to 10 bar, preferably 1 to 5 bar, which is established, in the presence of sulfite, cooling the resulting suspension of the tetrasodium salt of naphthalene-1,4,5,8-tetracarboxylic acid, after the reaction vessel has been let down, to a temperature of below 40° C., preferably to 20° to 30° C., subsequently adjusting the pH to 4.5 to 5 by acidification, isolating the resulting disodium salt of naphthalene-1,4,5,8-tetracarboxylic acid, converting this salt into the tetrasodium salt of naphthalene-1,4,5,8-tetracarboxylic acid in an aqueous alkali metal hydroxide solution and, if appropriate after removal of insoluble impurities, precipitating naphthalene-1,4,5,8-tetracarboxylic acid 1,8-monoanhydride by acidification to a pH of less than 2, preferably less than 1, at a temperature of 80° to 100° C.

Provenance & Evidence