By Tadeusz Urbanski
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Extra resources for Chemistry and Technology of Explosives: 3-Volume Set
Moreover in esterification with nitric acid, the acetic acid present in the mixture or formed in the reaction does not hydrolyse the nitric acid ester formed. Nitric and acetic acids. According to A. 52) to give a kind of mixed orthonitric and acetic anhydride, the so-called diacetylorthonitric acid (b. p. 4) are mixed. However, no research work on the structure of the compound has been carried out yet. In particular there is no evidence to decide whether diacetylorthonitric acid is a true chemical compound or only an azeotrope.
Menke  inferred from the results of his studies on nitration of aromatic hydrocarbons with mixtures of nitric acid and acetic anhydride that the latter acted not only as a dehydrating substance but also as a catalyst. Recently Paul  examined kinetics of the nitration of benzene using solutions of nitric acid in acetic anhydride and acetic acid at 25°C. In a number of his experiments he also added sulphuric acid in a small quantity (ca. 01 M). The results favour nitronium ion attack on benzene as the rate-determining step: HNO 3 + H + <-> H 2 NO 3 + (a) NITRATION AND NITRATING AGENTS H 2NO 3+ + (CH3CO)2O <-> NO2+ + 2CH 3COOH 45 (b) (c) Such a mechanism accounts for the first-order dependence of the rate on reaction the nitric acid concentration in presence of sulphuric acid.
Thus, the results obtained by W. M. Lauer and Noland and by Banner and his co-workers supported Melander’s earlier observation, that the rupture of the C-H bond was not a determining factor for the rate of nitration of aromatic compounds. All these investigations confirm that the nitration process is a two-stage substitution reaction, where the first slope consists in attaching the nitronium ion, according to eqns. (22) and (23), p. 60, or according to Melander (as above). Bunton, Halevi and Llewellyn  studied the oxygen atom exchange between nitric acid and water, using heavy oxygen 18O as the labelled element.