The oxygen content of nitromethane enables it to burn with much less atmospheric oxygen than conventional fuels. In this context, nitromethane is commonly referred to as "nitro fuel" or simply "nitro", and is the principal ingredient for fuel used in the " Top Fuel" category of drag racing. Nitromethane is used as a fuel in motor racing, particularly drag racing, as well as for radio-controlled model power boats, cars, planes and helicopters. In more specialized organic synthesis, nitromethane serves as a Michael donor, adding to α,β-unsaturated carbonyl compounds via 1,4-addition in the Michael reaction. Reduction of the latter gives tris(hydroxymethyl)aminomethane, (HOCH 2) 3CNH 2, better known as tris, a widely used buffer. Some important derivatives include the pesticides chloropicrin (Cl 3CNO 2), beta-nitrostyrene, and tris(hydroxymethyl)nitromethane, ((HOCH 2) 3CNO 2).
Thus, under base catalysis, nitromethane adds to aldehydes in 1,2-addition in the nitroaldol reaction. Its acidity allows it to undergo deprotonation, enabling condensation reactions analogous to those of carbonyl compounds. In organic synthesis nitromethane is employed as a one carbon building block. Protonation of the conjugate base O 2NCH 2 −, which is nearly isosteric with nitrate, occurs initially at oxygen. The reason of that being so acidic is due to the resonance structure below: This value indicates an aqueous pK a of about 11. Nitromethane is a relatively acidic carbon acid. However, its relatively high acidity and explosive properties (see below) limit its applications. This makes it useful for dissolving positively charged, strongly electrophilic species. Thus, it is a rare example of a polar solvent that is also weakly coordinating. Other mixtures include ANNM and ANNMAl – explosive mixtures of ammonium nitrate, nitromethane and aluminium powder.Īs an organic solvent, it is considered to be highly polar (ε r = 36 at 20 ☌ and μ = 3.5 Debye) but is aprotic and possesses very low Lewis basicity. It can be used as an explosive, when gelled with several percent of gelling agent. It is also used as a fuel in some forms of racing. It is also used most effectively as a solvent or dissolving agent for acrylate monomers, such as cyanoacrylates (more commonly known as "super-glues"). The principal use of nitromethane is as a stabilizer for chlorinated solvents, which are used in dry cleaning, semiconductor processing, and degreasing.
The reaction of sodium chloroacetate with sodium nitrite in aqueous solution produces this compound: ClCH 2COONa + NaNO 2 + H 2O → CH 3NO 2 + NaCl + NaHCO 3 Uses It can be prepared in other methods that are of instructional value. These alkoxy radicals are susceptible to C-C fragmentation reactions, which explains the formation of a mixture of products.
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The reaction involves free radicals, including the alkoxyl radicals of the type CH 3CH 2CH 2O, which arise via homolysis of the corresponding nitrite ester.
This exothermic reaction produces the four industrially significant nitroalkanes: nitromethane, nitroethane, 1-nitropropane, and 2-nitropropane. Nitromethane is produced industrially by combining propane and nitric acid in the gas phase at 350–450 ☌ (662–842 ☏).
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