COMPARISON OF THE NITROLYSIS OF 1, 3-DICYCLOHEXYLIMIDAZOLIDINE WITH THAT OF HEXAMETHYLENETETRAMINE

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Abstract
The nitrolysis of N,N′-dicyclohexylimidazolidine has been effected with formation of the nitrate salt, the nitroso derivative, and the aceto derivative of N,N′-dicyclohexyl-N-nitro-1,2-diaminoethane. The absence of the dinitro derivative suggests that demethylolation is not related to nitramine formation. When formaldehyde splits off to leave a weakly basic amine, as in hexamethylenetetramine nitrolysis, then subsequent nitration will occur; but it will not take place if the resulting amine is strongly basic. Nitrolysis will depend also on reactivity of nitric acid, which can be decreased by addition of ammonium nitrate. This decrease will prevent esterification of intermediate N-methylolamines but not nitrolysis of hexamethylenetetramine types. However both nitrolysis and esterification are thus prevented with dicyclohexylimidazolidine. On the other hand the two nitrolyses are related by the fact that both are accelerated by electropositive chlorine.

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