Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (03): 414-418. Previous Articles     Next Articles

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  1. (a北京理工大学化工与环境学院 北京 100081) (b西安近代化学研究所 西安 710061)
  • 收稿日期:2009-05-22 修回日期:2009-06-29 发布日期:2010-03-28
  • 通讯作者: 孟子晖

Reaction Mechanism of One-Pot Synthesis of Dinitro
Pentamethylene Tetramine

Song Hongyana,Wang Penga,Qin Guangmingb,Ge Zhongxueb,Wang Bozhoub
Meng Zihui*,a,Li Qingxiaa   

  1. (a School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081)
    (b Xi'an Morden Chemistry Research Insitute, Xi'an 710061)
  • Received:2009-05-22 Revised:2009-06-29 Published:2010-03-28

Dinitro pentamethylene tetramine (DPT) is an important precursor of octogen (cyclotetramethylene-tetranitramine. Starting from urea without isolation of intermediates, DPT was obtained by nitration, hydrolysis and Mannich condensation, in total yield of 63.2%. The reaction mechanism of one-pot synthesis of DPT was studied by isolating and capturing intermediates, and isotope tracing experiments. The stable intermediates dinitrourea, nitramide and bis(hydroxymethyl)nitroamine were isolated, and the active intermediate 1-nitro-hexahydrotriazine was captured by benzenesulfonyl chloride. The H2 labeled DPT (DPT-D) was synthesized by the reaction of CD2O with NH3 and bis(hydroxymethyl)nitroamine. The analysis results from 1H NMR and MS of DPT-D indicate that in the course of the reaction bis(hydroxymethyl)nitroamine is decomposed into CH2O and nitramide, and the small molecule species make up randomly to form triazine, then DPT.

Key words: octogen, dinitro pentamethylene tetramine, reaction mechanism, isotope tracing