Transnitration

Nitrations can be performed in homogeneous media, using tetramethylene sulfone or nitromethane (nitroethane) as solvent. A large variety of aromatic compounds have been nitrated with nitronium salts in excellent yields in nonaqueous media. Sensitive compounds, otherwise easily hydroly2ed or oxidized by nitric acid, can be nitrated without secondary effects. Nitration of aromatic compounds is considered an irreversible reaction. However, the reversibihty of the reaction has been demonstrated in some cases, eg, 9-nitroanthracene, as well as pentamethylnitrobenzene transnitrate benzene, toluene, and mesitylene in the presence of superacids (158) (see Nitration). 

Another, lengthier, method involving transnitration of salicylic acid by the NGu is described in Ref 4. It may not retain otherwise gpod accuracy on very finely divided NGu. 

M.I. Fauth H. Stalcup, AnalChem 30,1670— 72(1958) Be CA 53, 2929(1959) [Evaluation of six methods for detn of nitrogen in NGu. (Nitro N methods tested are modified nitrometer — greatest precision of the six acetate-buffered titanous chloride transnitration with sulfuric acid and Bowman-Scott). Total N methods are modified Kjeldahl and micro-Dumas — better of these two. The titanous chloride and trans-nitration methods are satisfactory]... 

Chimlnd, Bruxelles, Belgium 3(1954) CA 50, 7479(1956)(Detn of N content in NC) 26)J. Tranchant, Ibid 3(1954) CA 51, 1607(1957) (Titanometric detn of N content in NC) 27)P. Miaud, MP 37, 465-97( 1955)(Detn of water in NC cakes by means of high-frequency current) 27)H.Stalcup R.Williams, AnalChem 27, 543-6 (1955)(Volumetric detn of NC NGu by transnitration of salicylic acid) 28)Ott vol 5, part 3(1955), 1394(Detn of viscosity of NC) 1407(Detn of N content) 1411-13(Stability tests) 1414-15(Detn of impurities, such as ash, acidity, alkalinity, sulfur chlorides in NC) 14l6(Detn of density) 29)T.C.Castorina, PATR 2107(1955XRadiometric method for detn of sulfate in crude NC) 30)E.Thonert F.Lobato, Explosivst 1955, 109-13 CA 51, 9160(1957)... 

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