TNT (Molecule of the Month for January 2006)
2,4,6-Trinitrotoluene is a yellow odorless solid, commonly known as TNT. It is not naturally occuring, but can be produced by the nitration of toluene by HNO3. TNT is insoluble in water but dissolves in benzene and acetone. It reacts with nucleophiles which attack the positively charged nitrogen atoms. TNT will undergo violent decomposition in the presence of a detonator, such as Mercury fulminate (Hg(ONC)2). It is therefore a useful explosive agent, used by the military in shells, bombs, and grenades. It was one of the principle explosives used in World War One, but had been replaced by more powerful explosives by 1939.
TNT molecules collapse when jolted. The oxygen atoms then combine with carbon and hydrogen atoms, making carbon monoxide and water. The nitrogen atoms are freed and nitrogen gas is released. This transformation from a compact solid to a volumous cloud of gas produces a powerful explosion.TNT has a melting point of 82 degree C but it does not decompose below 240 degree C. This means that it can be melted and then poured into casts without danger of explosion.
There are number of ways for TNT to be entered into the food chain, including bad disposal of waste water and solids by TNT manufactures. Some TNT released into the environment is broken down rapidly to other chemicals by sunlight and more is broken down by microorganisms. Despite this small amounts can still build up in fish and plants. Human exposure to this TNT can lead to abnormal liver function, anemia, and, in the long term, cataracts. TNT can also be absorbed through the skin, again causing the above effects. There is a possibility that TNT may be a human carcinogen.
Formal Chemical Name (IUPAC)
Update by Karl Harrison
(Molecule of the Month for January 2006 )