Investigate some factors affecting the synthesis yield of 2,6,8,12-tetraacetyl-4,10-dibenzyl -2,4,6,8,10,12-hexaazaisowurtzitane (TADBIW) used to make CL-20 explosive
248 viewsDOI:
https://doi.org/10.54939/1859-1043.j.mst.86.2023.63-70Keywords:
CL-20; TADBIW; Hexaazaisowurtzitane.Abstract
TADBIW is the raw material used to synthesize CL-20 explosive (an important energy additive in the production of mixed solid missile fuel. This paper presents the synthesis of TADBIW in two steps: Step 1- Synthesis of hexabenzyl-hexaazaisowurtzitan (HBIW) from glyoxal and benzylamine; Step 2- Synthesize TADBIW from HBIW by acetylation reaction using catalyst Pd(OH)2/C, H2. The structure of TADBIW has been studied by spectroscopic techniques FT-IR, 1HNMR, EDX. Several factors affecting the yield of the synthesis have been evaluated. Experimental results show that with catalyst used Pd(OH)2/C (10% Pd), H2 at atmospheric pressure, ethyl acetate as solvent, reaction time 20 hours, reaction efficiency reached 31.8%.
References
[1]. TCVN 4336:1986, "Hợp chất hữu cơ phương pháp xác định nhiệt độ nóng chảy", (1986).
[2]. Phan Đức Nhân, Cơ sở công nghệ nhiên liệu tên lửa rắn hỗn hợp, Nhà xuất bản Quân đội nhân dân, (2011).
[3]. AK Sider, Nirmala Sikder, BR Gandhe, JP Agrawal, Haridwar Singh, "Hexanitrohexaazaisowurtzitane or CL-20 in India: synthesis and characterisation", Defence Science Journal. 52 (2), pp. 135, (2002). DOI: https://doi.org/10.14429/dsj.52.2158
[4]. Anthony J Bellamy, "Reductive debenzylation of hexabenzylhexaazaisowurtzitane", Tetrahedron. 51 (16), pp. 4711-4722, (1995). DOI: https://doi.org/10.1016/0040-4020(95)00155-2
[5]. Arnold T Nielsen, Robin A Nissan, David J Vanderah, Clifford L Coon, Richard D Gilardi, Clifford F George, Judith Flippen-Anderson, "Polyazapolycyclics by condensation of aldehydes with amines. 2. Formation of 2, 4, 6, 8, 10, 12-hexabenzyl-2, 4, 6, 8, 10, 12-hexaazatetracyclo [5.5. 0.05. 9.03, 11] dodecanes from glyoxal and benzylamines", The Journal of Organic Chemistry. 55 (5), pp. 1459-1466, (1990). DOI: https://doi.org/10.1021/jo00292a015
[6]. Dabir S Viswanath, Tushar K Ghosh, Veera M Boddu, "Emerging energetic materials: synthesis, physicochemical, and detonation properties", Springer, (2018). DOI: https://doi.org/10.1007/978-94-024-1201-7
[7]. J Venkata, KJ Venugopal, NV Srinivasa, A Venkataraman, "An overview on importance, synthetic strategies and studies of 2, 4, 6, 8, 10, 12-hexanitro-2, 4, 6, 8, 10, 12-hexaazaisowurtzitane (HNIW)", Defence Technology. 12 (5), pp. 401-418, (2016). DOI: https://doi.org/10.1016/j.dt.2016.05.002
[8]. Sahar Shokrollahi, Ali Ramazani, Seyed Jamal, Seyed Jamal Tabatabaei Rezaei, Asemeh Malekzadeh, Azimzadeh Asiabi, Sang Joo, "Citric acid as an efficient and green catalyst for the synthesis of hexabenzyl hexaazaisowurtzitane (HBIW)", Iranian journal of catalysis. 6, pp. 65-68, (2015).
[9]. T.Nielsen Arnold, Santa Barbara, Calif, Caged Polyntramine Compound, United States Patent No. 5693794, (1997).
[10]. Yuxiang Ou, Huiping Jia, Yongjiang Xu, Boren Chen, Guangyu Fan, Lihua Liu, Fuping Zheng, Zelin Pan, Cai Wang, "Synthesis and crystal structure of β-hexanitrohexaazaisowurtzitane", Science in China Series B: Chemistry. 42 (2), pp. 217-224, (1999). DOI: https://doi.org/10.1007/BF02875520
