1,3,5-TRINITROBENZENE

Chemical properties

Trinitrobenzene is a yellow crystalline solid.

The Uses of 1,3,5-TRINITROBENZENE

Explosive. 1,3,5-Trinitrobenzene is a vulcanizing agent for natural rubber. Indicator for pH 12.0-14.0.

The Uses of 1,3,5-TRINITROBENZENE

Trinitrobenzene is used as an explosive. It is obtained by oxidation of trinitrotoluene.

The Uses of 1,3,5-TRINITROBENZENE

1,3,5-Trinitrobenzene can be used for direct analysis in real time mass spectrometry for fast screening of explosives.

Definition

ChEBI: A trinitrobenzene in which each of the nitro groups is meta- to the other two.

Synthesis Reference(s)

The Journal of Organic Chemistry, 22, p. 1046, 1957 DOI: 10.1021/jo01360a012

General Description

A light yellow crystalline sludge or slurry. Burns but may require some effort to ignite. A high explosive when dry. Easily ignited and burns very vigorously when dry. Soluble in alcohol and ether; insoluble in water. Produces toxic oxides of nitrogen during combustion.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Aromatic nitro compounds, such as TRINITROBENZENE, range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. The aromatic nitro compounds may explode in the presence of a base such as sodium hydroxide or potassium hydroxide even in the presence of water or organic solvents. The explosive tendencies of aromatic nitro compounds are increased by the presence of multiple nitro groups.

Health Hazard

Some are toxic and may be fatal if inhaled, swallowed or absorbed through skin. Contact may cause burns to skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may cause pollution.

Health Hazard

The toxic effects from ingestion of the solid or inhalation of its dusts include irritation of respiratory tract, headache, dyspnea, and cyanosis. Other effects noted in animals were degenerative changes in the brain. The oral LD50 values in rats and mice are 450 and 570 mg/kg, respectively.

Fire Hazard

Trinitrobenzene is a high explosive, similar to trinitrotoluene. However, it is less sensitive to impact than the latter. Its brisance and power are higher than those of TNT. It detonates when heated rapidly. The dry material is highly sensitive to shock and heat.Slow and careful heating of a small amount of material does not cause detonation. Trinitrobenzene is a flammable solid. It reacts vigorously with reducing substances. It emits highly toxic oxides of nitrogen on decomposition. .

Safety Profile

Poison by ingestion and intravenous routes. Mutation data reported. A severe explosion hazard when shocked or exposed to heat. Trinitrobenzene is considered a powerful high explosive and has more shattering power than TNT. Although it is less sensitive to impact than TNT, it is not used much because it is difficult to produce. The complex with potassium trimethyl stannate explodes at room temperature. Forms heat-sensitive explosive complexes with alkyl or aryl metallates (e.g., lithium or potassium salts of trimethyl-, triethyl-, or triphenyl-germanate, -silanate, or -stamate). Can react vigorously with reducing materials. When heated to decomposition it emits highly toxic fumes of NOx and explodes. See also NITRO COMPOUNDS of AROMATIC HYDROCARBONS.

Synthesis

One synthesis route of 1,3,5-Trinitrobenzene is through the decarboxylation of 2,4,6-trinitrobenzoic acid (obtained from TNT by oxidation with chromic acid) by heating in aqueous medium.

Potential Exposure

Trinitrobenzene is explosive when dry. Used as an explosive; as a vulcanizing agent for natural rubber. Trinitrobenzene may be more powerful than TNT; and is reported to be less sensitive to impact than TNT. However it is difficult to produce, and is not used as widely as TNT.

storage

Storage and shipping are similar to those used for TNT and other high explosives. Trinitrobenzene is stored in a permanent magazine well separatedfrom initiator explosive, combustible and oxidizing materials, and heat sources. It is shipped in metal containers enclosed in wooden boxes or strong siftproof cloth or paper bags in amounts not exceeding 60 lb net weight (NFPA 1997).

Shipping

UN0214 Trinitrobenzene, dry or wetted with <30% water, by mass, Hazard Class: 1.1D; Labels:1.1DExplosives (with a mass explosion hazard); D-Substances or articles which may mass detonate (with blast and/or fragment hazard) when exposed to fire. UN1354 Trinitrobenzene, wetted with not <30% water, by mass, Hazard Class: 4.1; Labels: 4.1-Flammable solid.

Purification Methods

Crystallise it from glacial acetic acid, CHCl3, CCl4, EtOH aqueous EtOH or EtOH/*benzene, after (optionally) heating with dilute HNO3. Dry it in air. Fuse it and crystallise it under vacuum. [Beilstein 5 H 271, 5 I 140, 5 II 203, 5 III 643, 5 IV 754.]

Incompatibilities

Sensitive to shock and heat. Incompatible with initiating explosives, combustible materials. Aromatic nitro compounds, such as trinitrobenzene, range from slight to strong oxidizing agents. Keep away from strong reducing agents, including hydrides, alkali metals; aluminium and other metal powder; phosphorus; sulfides and nitrides, alkaline material, strong bases; contact may initiate vigorous reactions that culminates in a detonation. The aromatic nitro compounds may explode in the presence of a base such as sodium hydroxide or potassium hydroxide even in the presence of water or organic solvents. The aromatic nitro compounds may explode in the presence of a base such as sodium hydroxide or potassium hydroxide even in the presence of water or organic solvents. Incompatible with strong oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions.

Waste Disposal

Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. Dissolve in a combustible solvent and spray into an incinerator equipped with afterburner and scrubber.