Tetraacetyl‐dibenzyl‐hexaazaisowurtzitane Nitrosation – Studies on Scale‐up Synthesis of HNIW

Abstract

A study made on 2,4,6,4,6,8,10, nitrosation in acetic acid to 2,4,6,8-tetraacetyl-10,12-dinitroso-2,4,6,8,10,12-hexaazaisowurtzitane (TADNOIW) allows the reaction time to be considerably shortened. During the study, the reaction yield was found to be affected by variables such as temperature, time and UV radiation. The major factor controlling the reaction rate was found to be the concentration of NO 2 molecules in the reaction mixture. Under optimal conditions the product is obtained in a 90 -93% yield after 6 h of the reaction conducted at 70 8C. UV radiation increases the reaction rate, yet the product obtained is of inferior purity on account of the by-product formed.

An Efficient and Facile Synthesis of CL‐20 from TADNO Using HNO3/N2O5 and Optimization of Reaction Parameters by Taguchi Method

“…TADNO as the one of the CL‐20 precursors has been traditionally prepared through nitroso‐debenzylation reaction of TADB using NOBF 4 salt or N 2 O 4 . Nitrolysis and the oxidative reaction of TADNO for the synthesis of CL‐20 in the final step require using a mixture of H 2 SO 4 /HNO 3 (“mixed acids”) . According to the literature, the preparation of CL‐20 from TADNO is a slow reaction even by using 99 % nitric acid at a temperature range from 60 to 75 °C.…”

“…However,i thasl ately been investigated as the one of the components of composite and gun propellants [1][2][3].There are several substituted cages tructuresa si ntermediateso rp recursors in the multi-step synthesis of 5].H exabenzylhexaazaisowurtzitane (HBIW)i st he first precursori nt he synthesis of CL-20.T he benzyl elimination step is required due to the failure of the direct synthesiso f CL-20 using HBIW.H owever,t he structure of hexaazaisowurtzitane is unstablea nd removingt he benzylg roups through catalytic hydrogenationw ithoutt he acetylation causes destruction of the cage structure. Te traacetyldibenzylhexaazaisowurtzitane (TADB) is the second and key precursor in the synthesis of CL-20 [6][7][8].T ADNO as the one of the CL-20 precursors has been traditionally prepared through nitroso-debenzylation reaction of TADB using NOBF 4 salt or N 2 O 4 [8].N itrolysis and the oxidative reaction of TADNO for the synthesis of CL-20 in the final step require using am ixtureo fH 2 SO 4 /HNO 3 ("mixed acids") [9]. According to thel iterature, the preparation of CL-20 from TADNO is as low reactione ven by using 99 %n itric acid at at emperaturer ange from 60 to 75 8C.…”

[Hmim][HSO4], a Green and Recyclable Acidic Ionic Liqiud Medium for the One‐Pot Nitration of TADB to HNIW

“…In the synthesis of HNIW, HBIW is first reductively acylated to form TADB. The remaining benzyl groups can be removed to give HNIW by nitration with different nitrating systems [1,2,[8][9][10][11][12] (Figure 1).…”

Theoretical investigation on the structures, densities, and detonation properties of polynitrotetraazaoctahydroanthracenes

“…The two most prominent members of this class are RDX14–17 and HMX 18–21. CL‐20 (2,4,6,8,10,12‐hexanitrohexaazaisowurtzitane) is another new nitramine explosive, which has six NNO 2 groups in its polycyclic structure, resulting in an increased density and heat of formation 22–24. CL‐20 is reported as an attractive high thermally stable explosive with decomposition temperature 228°C.…”