nitroparaffin

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American Heritage Dictionary:

ni·tro·par·af·fin

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('trō-păr'ə-fĭn) pronunciation
n.
Any of a group of organic compounds formed by replacing one or more of the hydrogen atoms of a paraffin hydrocarbon with the univalent group, NO2, as in nitromethane, CH3NO2.


Any derivative of an aliphatic hydrocarbon that contains one or more NO2 groups bonded via nitrogen to the carbon framework. Nitroparaffins are also known as nitroalkanes.

Low-molecular-weight nitroparaffins are prepared via the vapor-phase nitration of alkanes at >400°C (750°F). However, the process is not generally satisfactory for higher-molecular-weight nitroparaffins because of polynitration and chain cleavage. The direct nitration of propane is used commercially to prepare nitromethane (boiling point 101°C or 214°F), nitroethane (bp 114°C or 237°F), 1-nitropropane (bp 131°C or 268°F), and 2-nitropropane (bp 120°C or 248°F). Nitroparaffins are prepared in the laboratory by the reaction of nitrite salts with alkyl bromides or iodides, from the oxidation of amines or oximes by using peroxycarboxylic acids, and by the chain homologation of simple nitroparaffins. See also Nitration.

Nitromethane, nitroethane, and the nitropropanes are useful solvents with high dielectric constants that readily dissolve many polymers. In addition, these simple nitroparaffins are versatile intermediates for the synthesis of specialty chemicals.


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