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
作者： Xiao-Feng Cao , Bin-Dong Li , Min Wang
DOI: 10.1016/J.CCLET.2013.12.015
关键词: Yield (chemistry) 、 Inorganic chemistry 、 Chemistry 、 Solvent 、 Decane 、 Molar ratio 、 Nitration 、 Ionic liquid 、 Catalysis
摘要: Abstract 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 liquids, such as [HMim]X, [(CH2)4SO3HMim]X and [Capl]X (X− = pTSO−, NO3−, HSO4−), various parameters equivalents liquid, molar ratio starting material, reaction time temperature, solvent were investigated. Ionic liquid [(CH2)4SO3HMim]HSO4 showed better catalytic activity. In presence 3% staring yield improved 6.2% compared system without liquid.
imm.ac.cn参考文章(19)
Hui Zhen Zhi, Jun Luo, Guang An Feng, Chun Xu Lv, An efficient method to synthesize HMX by nitrolysis of DPT with N2O5 and a novel ionic liquid Chinese Chemical Letters. ,vol. 20, pp. 379- 382 ,(2009) , 10.1016/J.CCLET.2008.12.040
Barbara Barletta, Ezio Bolzacchini, Simone Meinardi, Marco Orlandi, Bruno Rindone, The NO3 Radical-Mediated Liquid Phase Nitration of Phenols with Nitrogen Dioxide Environmental Science & Technology. ,vol. 34, pp. 2224- 2230 ,(2000) , 10.1021/ES990844M
Kenneth K. Laali, Volker J. Gettwert, Electrophilic nitration of aromatics in ionic liquid solvents. Journal of Organic Chemistry. ,vol. 66, pp. 35- 40 ,(2001) , 10.1021/JO000523P
Kun Qiao, Chiaki Yokoyama, Nitration of Aromatic Compounds with Nitric Acid Catalyzed by Ionic Liquids Chemistry Letters. ,vol. 33, pp. 808- 809 ,(2004) , 10.1246/CL.2004.808
M.G. Kuba, R. Prins, G.D. Pirngruber, Gas-phase nitration of toluene with zeolite beta Applied Catalysis A-general. ,vol. 333, pp. 78- 89 ,(2007) , 10.1016/J.APCATA.2007.09.007
Martyn J. Earle, Suhas P. Katdare, Kenneth R. Seddon, Paradigm confirmed: the first use of ionic liquids to dramatically influence the outcome of chemical reactions. Organic Letters. ,vol. 6, pp. 707- 710 ,(2004) , 10.1021/OL036310E
Qi-Long Yan, Xiao-Jiang Li, Ying Wang, Wei-Hua Zhang, Feng-Qi Zhao, Combustion mechanism of double-base propellant containing nitrogen heterocyclic nitroamines (I): The effect of heat and mass transfer to the burning characteristics Combustion and Flame. ,vol. 156, pp. 633- 641 ,(2009) , 10.1016/J.COMBUSTFLAME.2008.12.004
Ross W. Millar, Simon P. Philbin, Clean nitrations: Novel syntheses of nitramines and nitrate esters by nitrodesilylation reactions using dinitrogen pentoxide (N2O5) Tetrahedron. ,vol. 53, pp. 4371- 4386 ,(1997) , 10.1016/S0040-4020(97)00093-8
G. Cheng, X. Li, X. Qi, C. Lu, Synthesis of RDX Catalyzed by Br⊘nsted Acidic Ionic Liquids Journal of Energetic Materials. ,vol. 28, pp. 35- 44 ,(2010) , 10.1080/07370650903124526
R. L. Wilier, Synthesis and characterization of high energy compounds. I. Trans-1,4,5,8-tetranitro-1,4,5,8-tetraazadecalin (TNAD) Propellants, Explosives, Pyrotechnics. ,vol. 8, pp. 65- 69 ,(1983) , 10.1002/PREP.830080302