1,5-Dinitronaphthalene

Chemical properties

Yellow to yellow-green needles or fluffy powder

The Uses of 1,5-Dinitronaphthalene

1,5-Dinitronaphthalene is an intermediate in the production of naphthazarin (5,8- dihydroxy-1,4-naphthoquinone) and 1,5- naphthalenediamine, which is mainly converted to naphthalene 1,5-diisocyanate. As a sensitizing agent for ammonium nitrate explosives the use of mixed isomers is adequate.

Definition

ChEBI: 1,5-dinitronaphthalene is a dinitronaphthalene carrying nitro groups at positions 1 and 5. It has a role as a genotoxin.

Production Methods

Naphthalene is added slowly to mixed acid (22/58/20) at 40 ℃, and the temperature is raised to 80 ℃ over 4 h to give a mixture of 1,5- and 1,8-dinitronaphthalenes. The isomers are separated by fractional crystallization (e.g., from ethylene dichloride) or, preferably, by solvent extraction. The 1,5-isomer can be extracted with toluene, leaving 99 % pure 1,8- dinitronaphthalene. After evaporation of the toluene, the residue is extracted with a strongly polar solvent (e.g., sulfolane) to leave 99 % pure 1,5-isomer.

General Description

Yellowish white needles or light yellow fluffy solid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

1,5-Dinitronaphthalene is incompatible with strong oxidizers and strong bases. Mixtures with sulfur or sulfuric acid may explode if heated to 248° F .

Fire Hazard

Flash point data for 1,5-Dinitronaphthalene are not available; however, 1,5-Dinitronaphthalene is probably combustible.

Safety Profile

A suspected carcinogen. Mutation data reported. Mxtures with sulfur or sulfuric acid (used in commercial reactions) may explode if heated to 120℃. Initiation temperature depends on the quality of the dinitronaphthalene. When heated to decomposition it emits toxic fumes of NOx. See also NITRO COMPOUNDS of AROMATICHYDROCARBONS