esters of nitric acid with alcohols that contain one or more nitrate groups, —ONO2, bound to a carbon atom (for example, alkyl nitrates, glycol nitrates, glycerol nitrates, and cellulose nitrates). In industry, chemically incorrect names containing the prefix “nitro-” are common—for example, nitroglycol, nitroglycerin, and nitromannitol. A distinction is made among mono-, di-, and poly-nitroesters according to the number of nitrate groups in the molecule.
In industry, nitroesters are produced by treatment of the corresponding alcohols with concentrated nitric acid or a nitrating mixture, for example,
Alkyl nitrates are liquids with a pleasant odor that are insoluble in water but readily soluble in alcohol and ether. They are easily hydrolyzed. In comparison with polynitro compounds, polynitroesters are usually more sensitive to impact and friction. The production of nitroesters involves extreme danger of explosion. A number of polynitroesters are powerful explosives. The nitroester of pentaerythritol, C(CH2ONO2)4 (PETN), and diethanol-N-nitraminedinitrate, O2N—N(CH2CH2ONO2)2 (DINA), are explosives used mainly for military purposes. For example, the velocity of detonation of PETN is 7,900 m/sec at a density of 1.6 g/cm3. Pure PETN is used as a secondary charge for loading blasting caps, and the stabilized compound (containing inert additives) is used in proportions up to 5 percent to load blasting fuses, detonators, and shaped-charge shells. As opposed to other nitroesters, PETN is chemically stable. Cellulose nitrates are used in the production of powders and dynamites.
Nitroesters are physiologically active.