Synthesis and characteristics of FOX-7 and its monohydrazino analogue

Authors:

  • Sandberg Camilla
  • Goede Patrick
  • Tryman Rolf
  • Latypov Nikolaj

Publish date: 2003-01-01

Report number: FOI-R--0818--SE

Pages: 22

Written in: Swedish

Abstract

Nitration of 2-methylimidazole and 2-methoxy-2-methyl-4,5-imizasolidinedione to 2-(dinitromethylen)-4,5-imidazolidinedione has been studied. The yields were 10% and 70-75% respectively. The nitration of 2-methoxy-2-methyl-4,5-imidazolidinedione was also easier to perform and a pure product was easily obtained. The hydrolysis of 2-(dinitromethylen)-4,5-imidazolidinedione to FOX-7 at pH 9,11 and 13 was also analysed using HPLC. An intermediate product was formed at pH 9 and 11, which disappeared after approximately 20 hours. Oxalic acid was also produced as a product of the hydrolysis reaction. No other by products were detected. FOX-7 was further reacted with hydrazine in an attempt to produce a more energetic material. The monosubstituted product 1-amino-1-hydrazino-2,2-dinitroethen (HDF) was formed. Further attempts to produce the analogous di-substituted derivative failed. The acid -basic properties of FOX-7 and HDF were analysed using UV spectroscopy. Both FOX-7 and HDF showed zwitterionic character and two different structures of FOX-7 and three different structures of HDF were determined. Both substances were shown to undergo proton exchange with the surrounding solution. Quantum mechanical calculations of the charge distributions indicated that both FOX-7 and HDF should undergo substitution reactions with nucleophiles at the amide carbon due to the charge distribution. However, that didn´t prove to be the case with reaction of HDF with hydrazine.