Synthesis of Energetic Materials
Abstract
Salts of ethylenedinitramine (EDNA) and methylenedinitramine (MEDINA) reacted successfully with 4, 5-dichloro-1, 3-dioxalan-2-one to yield bicyclic carbonate esters, which underwent ester cleavage with boron tribromide to give 2, 3-dibromo-1, 4-dinitropyrazine and 4, 5-dibromo-1, 3-dinitroimidazolidine respectively. Attempts to convert the latter dibromide into bicyclo-HMX by reaction with salts of MEDINA were unsuccessful, probably as a result of debromination leading to an unstable olefinic cyclic dinitramine. (U) The cyclic dinitramine derivative, 2, 3-diacetoxy-1, 4-dinitropyrazine reacted with excess ethyl urethane, under boron trifluoride catalysis in trifluoroacetic acid, to give the 2, 3-bisurethane derivative. This conversion represents the first successful attempt to introduce nitrogen functionality adjacent to a nitramino group to form an animal-type linkage. Similarly, the diacetoxy pyrazine reacted with urea to give a bicyclic urea derivative, which was nitrated with nitric acid-acetic anhydride to yield the tetranitro-tetraazabicyclononanone. Nitramines; Esters; Chlorine compounds; Cyclic compounds; Energetic materials.
Document Details
- Document Type
- Technical Report
- Publication Date
- Mar 01, 1988
- Accession Number
- ADA199472
Entities
People
- M. Chaykovsky
- W. M. Koppes
Organizations
- Naval Surface Warfare Center