1,3-Butadiene → 1-Nitroanthraquinone

Participants

Reaction Conditions

Reaction Steps

A 1 liter glass pressure reactor is charged with 600 parts of toluene and 122 parts of technical 5-nitro-1,4-naphthoquinone (100%) as ca. 93% product. The reactor is blanketed with nitrogen and 57.6 parts of butadiene are introduced under pressure. The mixture is then heated in the closed system to 80° C. and stirred for 4 hours at this temperature. The pressure falls from a maximum of 3.5 to 4 bar to ca. 3 bar at the conclusion of the reaction. The mixture is cooled, the pressure in the reactor removed over a cooling trap, and excess butadiene is distilled at 400 mbar from the autoclave into the cooling trap. At a distillation temperature of 80° C., a total amount of 336 parts of butadiene/toluene is present in the cooling trap, with a butadiene content of ca. 6%. Then the residual toluene is removed with steam, such that at the conclusion of the steam distillation the suspension of 1-nitro-5,8,11,12-tetrahydroanthraquinone in 750 parts of water is free from toluene. The suspension is then run at 10° C. into a mixture of 160 parts of 50% aqueous sodium hydroxide and 50% aqueous potassium hydroxide. Further processing as described in Example 11 gives 138 parts of pure (99%) 1-nitroanthraquinone, i.e. 90% of theory, based on 5-nitro-1,4-naphthoquinone.

Provenance & Evidence