Preparation ethylenedinitramine

Franchimont and Klobbie [17] prepared ethylenedinitramine (EDNA, Haleite) by the nitration of ethylene urea (2-imidazolidone) with a mixture of nitric and sulphuric acids. (According to Schweitzer [18], ethylene urea is obtainable either by the action of urea on ethylenediamine at 110°C (initially) to 240-250°C (finally) in quantitative yield or by the action of urea on ethylene glycol at 160-240°C in 55% yield. W. E. Bachmann et al. [19] prepared ethylene urea by the action of ethyl carbonate on ethylenediamine in approximately 60% yield.) Hydrolysis of the dinitroethy-lene urea so formed gives ethylenedinitramine. Bachmann recommends nitration with mixed nitric acid and acetic anhydride ... 

Another method of preparing ethylenedinitramine (also by Franchimont and Klobbie [17]), involves the action of chloroformate on ethylenediamine and nitration with nitric acid alone (98%). Bis-urethan after nitration is hydrolysed with ammonia solution (approximately 14%) at about 90°C ... 

The facile hydrolysis of A, A -dinitro-2-imidazolidone to ethylenedinitramine (EDNA) shows that A, A -dinitroureas can be useful precursors to linear dinitramines. Cyclic N,N -dinitroureas can be prepared indirectly from nitroguanidine. Nitroguanidine is found to... 

McKay and co-workers " " prepared a number of cyclic iV, M-dinitroureas via the ni-troguanidine route hydrolysis to the parent linear dinitramines was effected with boiling water or aqueous sodium hydroxide. This route was used to synthesize ethylenedinitramine (2), l,2-dinitraminopropane(176), l,3-dinitraminopropane(174), l,3-dinitraminobutane(177) and 1,4-dinitraminobutane (175). 

Ethylenedinitramine is prepared by nitration of ethylene urea with mixed acid, to yield dinitroethylene-urea the latter compound liberates carbon dioxide with form ethylenedinitramine. 

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