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Citation: Xiao-Feng Cao, Bin-Dong Li, Min Wang. An efficient method to synthesize TNAD by the nitration of 1,4,5,8-tetraazabicyclo-[4,4,0]-decane with N2O5 and acidic ionic liquids[J]. Chinese Chemical Letters, ;2014, 25(3): 423-426. doi: 10.1016/j.cclet.2013.12.015 shu

An efficient method to synthesize TNAD by the nitration of 1,4,5,8-tetraazabicyclo-[4,4,0]-decane with N2O5 and acidic ionic liquids

  • 1.

    Chemical Engineering College, Nanjing University of Science and Technology, Nanjing 210094, China

  • Corresponding author: Bin-Dong Li, 
  • Received Date: 12 August 2013
    Available Online: 10 December 2013

    Fund Project: We are grateful for the financial support from the Nature Science Foundation of Jiangsu Province (No. BK2011697). (No. BK2011697)

  • An experimental study was carried out on the direct nitration of 1,4,5,8-tetraaza-bicyclo-[4,4,0]-decane to synthesize 1,4,5,8-tetranitro-1,4,5,8-tetraazabicyclo-[4,4,0]-decane (TNAD) with N2O5 catalyzed by acidic ionic liquids. Various ionic liquids, such as [HMim]X, [(CH2)4SO3HMim]X and [Capl]X (X- = pTSO-, NO3-, HSO4-), and various parameters such as equivalents of ionic liquid, molar ratio of N2O5 to the starting material, reaction time and temperature, and solvent were investigated. Ionic liquid [(CH2)4SO3HMim]HSO4 showed better catalytic activity. In the presence of 3% molar ratio of [(CH2)4SO3HMim]HSO4 ionic liquid to the staring material, the yield of 1,4,5,8-tetranitro-1,4,5,8-tetraazabicyclo-[4,4,0]-decane was improved by 6.2% compared to the system without ionic liquid.
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