THE NITROLYSIS OF HEXAMETHYLENETETRAMINE: I. THE SIGNIFICANCE OF 1,5-ENDOMETHYLENE-3,7-DINITRO-1,3,5,7-TETRAZACYCLOÖCTANE (DPT)

Abstract

The nitrolysis of hexamethylenetetramine by the method of Hale yields, in addition to Cyclonite, an aqueous diluate which contains either dimethylolnitramide, its dinitrate ester, or both. The presence of dimethylolnitramide can be demonstrated by its condensation with methylenediamine to give 1,5-dinitro-3,7-endomethy¡ene-1,3,5,7-tetrazacycloöctane (DPT). The latter compound was identified by nitrolysis to 1,3,5,7-tetranitro-1,3,5,7-tetrazacycloöctane. The validity of the Mannich-type condensation of dimethylolnitramide from the Hale diluate (or from formaldehyde and nitramide) to form DPT has been attested by similar condensations with methylamine, ethylenediamine, cyclohexylamine, and benzylamine. In one of these condensations acetaldehyde has replaced part of the formaldehyde. Dimethylolnitramide has further been characterized by its conversion to 3,7-dinitro-3,7-diaza-1,5-dioxacycloöctane. Nitrolysis of the latter forms sym. dinitroxydimethylnitramide, which can be acetolyzed to sym. diacetoxydimethylnitramide.