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Ebook Organic chemistry of explosives: Part 2

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(BQ) Part 2 book "Organic chemistry of explosives" has contents: Energetic compounds 2 - Nitramines and their derivatives, miscellaneous explosive compounds, dinitrogen pentoxide – an eco friendly nitrating agent. | 6 Energetic Compounds 2: Nitramines and Their Derivatives In Chapter 5 we discussed the methods used to incorporate N -nitro functionality into compounds in addition to the synthesis of the heterocyclic nitramine explosives RDX and HMX. The high performance of such heterocyclic nitramines has directed considerable resources towards the synthesis of compounds containing strained or caged skeletons in conjunction with N -nitro functionality. These compounds derive their energy release on detonation from both the release of molecular strain and the combustion of the carbon skeleton. Some nitramine compounds contain heterocyclic structures with little to no molecular strain. Even so, such skeletons often lead to an increase in crystal density relative to the open chain compounds and this usually results in higher explosive performance. A common feature of explosives containing N -nitro functionality is their higher performance compared to standard C-nitro explosives like TNT. Compounds containing strained or caged skeletons in conjunction with N -nitro functionality are some of the most powerful explosives available. 6.1 CYCLOPROPANES NHAc AcHN NHAc 1 NHNO2 1. Ac2O, HNO3 or TFAA, HNO3 2. NH4OH 3. H+ O2NHN NHNO2 2 Figure 6.1 1,2,3-Tris(nitramino)cyclopropane (2) has been synthesized via the nitration of 1,2,3tris(acetamido)cyclopropane (1) with acetic anhydride–nitric acid, followed by ammonolysis of the resulting secondary nitramide and subsequent acidification of the ammonium salt.1 This strategy is a common route to primary nitramines (see Section 5.10). 1,2,3Tris(nitramino)cyclopropane has a favourable oxygen balance and is predicted to exhibit high performance.1 Organic Chemistry of Explosives J. P. Agrawal and R. D. Hodgson C 2007 John Wiley & Sons, Ltd. 264 Nitramines and Their Derivatives 6.2 CYCLOBUTANES H2N 81 % OEt 3 O O OEt KOCN, HCl (aq) H2N O HN NH OEt N H 4 H2SO4 (aq) 44 % HN OEt NH 5 Ac2O, reflux 68 % O K2CO3, EtOH (aq) AcN .