In organic chemistry, a nitrate ester is an organic functional group with the formula R−ONO2, where R stands for any organyl group. They are the esters of nitric acid and alcohols. A well-known example is nitroglycerin, which is not a nitro compound, despite its name.
Pentaerythritol tetranitrate (PETN), also known as PENT, pentyl, PENTA (ПЕНТА, primarily in Russian), TEN (tetraeritrit nitrate), corpent, or penthrite (or, rarely and primarily in German, as nitropenta), is an explosive material. It is the nitrate ester of pentaerythritol, and is structurally very similar to nitroglycerin. Penta refers to the five carbon atoms of the neopentane skeleton. PETN is a very powerful explosive material with a relative effectiveness factor of 1.66. When mixed with a plasticizer, PETN forms a plastic explosive. Along with RDX it is the main ingredient of Semtex.
In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group (−NO2) into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters (−ONO2) between alcohols and nitric acid (as occurs in the synthesis of nitroglycerin). The difference between the resulting molecular structures of nitro compounds and nitrates (NO−3) is that the nitrogen atom in nitro compounds is directly bonded to a non-oxygen atom (typically carbon or another nitrogen atom), whereas in nitrate esters (also called organic nitrates), the nitrogen is bonded to an oxygen atom that in turn usually is bonded to a carbon atom (nitrito group).
There are many major industrial applications of nitration in the strict sense; the most important by volume are for the production of nitroaromatic compounds such as nitrobenzene. The technology is long-standing and mature.
Nitroglycerin (NG) (alternative spelling nitroglycerine), also known as trinitroglycerol (TNG), nitro, glyceryl trinitrate (GTN), or 1,2,3-trinitroxypropane, is a dense, colorless or pale yellow, oily, explosive liquid most commonly produced by nitrating glycerol with white fuming nitric acid under conditions appropriate to the formation of the nitric acid ester. Chemically, the substance is a nitrate ester rather than a nitro compound, but the traditional name is retained. Discovered in 1846 by Ascanio Sobrero, nitroglycerin has been used as an active ingredient in the manufacture of explosives, namely dynamite, and as such it is employed in the construction, demolition, and mining industries. It is combined with nitrocellulose to form double-based smokeless powder, used as a propellant in artillery and firearms since the 1880s.
As is the case for many other explosives, nitroglycerin becomes more and more prone to exploding (i.e., spontaneous decomposition) as the temperature is increased. Upon exposure to heat above 218 °C at sea-level atmospheric pressure, nitroglycerin becomes extremely unstable and tends to explode. When placed in vacuum, it has an autoignition temperature of 270 °C instead. With a melting point of 12.8 °C, the chemical is almost always encountered as a thick and viscous fluid, changing to a crystalline solid when frozen. Although the pure compound itself is colorless, in practice the presence of nitric oxide impurities left over during production tends to give it a slight yellowish tint.