Methods of synthesis and properties of hexanitrohexaazaisowurtzitane

Sysolyatin, S. V.; Lobanova, A. A.; Chernikova, Yuliya T; Сакович, Г. В.

doi:10.1070/rc2005v074n08abeh001179

Cited by 100 publications

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“…[1][2][3][4][5][6][7][8] While N nitration of secondary amines leads to the neutral species, nitramines derived from primary amines are strong acids. 9 An acidic proton present in their structure (as well as the anionic center formed upon this proton abstraction) is capable to migrate between the nitrogen and oxygen atoms.…”

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confidence: 99%

4,4′-Bis(nitramino)azofurazan and its salts. Study of molecular and crystal structure based on X-ray and quantum chemical data

et al. 2009

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4,4´ Bis(nitramino)azofurazan 2 was obtained by nitration of 4,4 diaminoazofurazan 1. Molecular and crystal structure of nitramine 2 and its ammonium salt 3 were studied by X ray method and quantum chemical calculations at M052X/aug cc pvdz level of theory. Both com pounds adopt ap ap ap conformation. It was shown that the structure of furazan cycle signifi cantly depends on the nature of the substituents at carbon atoms. Crystal structures of 2 and 3 are characterized by sufficiently high density (1.996 and 1.832 g cm -3 at 110K and 1.919 and 1.766 g cm -3 at 295 K, respectively), which is provided, in particular, by strong intermolecular hydrogen bonding and π-π stacking interactions. Among substituted azofurazans and primary nitramines examined by X ray diffraction analysis, 4,4´ bis(nitramino)azofurazan 2 is charac terized by the highest density.

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4,4′-Bis(nitramino)azofurazan and its salts. Study of molecular and crystal structure based on X-ray and quantum chemical data

et al. 2009

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“…3, 4 However, due to the absence of an economical industrial method of the synthesis of CL 20 its wide use is limited. 1 The best known method for the synthesis of CL 20 is presented in Scheme 1. Based on this protocol, in 1990 the Thiokol corporation (USA) made a pilot unit for the synthesis of CL 20.…”

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Reductive debenzylation of hexabenzylhexaazaisowurtzitane — the key step of the synthesis of polycyclic nitramine hexanitrohexaazaisowurtzitane

2007

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“…TADB was chosen since its preparation takes fewer steps than the other methods. 25 The structure of TADB is presented in Figure 1. As observed, there are two kinds of positions for nitrolysis in TADB molecule: benzylamine and acetamide groups.…”

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Synthesis of CL-20 from TADB in a One-Pot Method by Zeolite/HNO₃as a New Nitrolysis System

Bayat¹,

Hajighasemali²,

Mohajeri³

2016

Journal of the Brazilian Chemical Society

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Hexanitrohexaazaisowurtzitane is the most powerful non-nuclear explosive in the world. Herein, a greener and safer new one-pot method for the synthesis of CL-20 from tetraacetyldibenzylhexaazaisowurtzitane (TADB) has been developed through zeolite/98% HNO 3 . The H-ZSM-5 catalyst, with both Brønsted and Lewis acid sites, indicated higher catalytic activity. The reaction using H-ZSM-5 has been optimized with respect to reaction temperature, reaction time, amount of acid and amount of catalyst to substrate ratio. Keywords: debenzylation, nitrolysis, zeolite, tetraacetyldibenzylhexaazaisowurtzitane, CL-20Introduction 2 , 4 , 6 , 8 , 1 0 , 1 2 -H e x a n i t r o -2 , 4 , 6 , 8 , 1 0 , 1 2 -hexaazaisowurtzitane , first proposed by Willer 1 and synthesized by Nielsen et al., 2 has been subjected to extensive studies.3 It is a well-known caged nitramine with significantly higher density (e-form), 4 higher performance and minimum signature than the other nitramines (HMX, RDX); therefore, CL-20 has found numerous military applications. 5 All the processes for CL-20 synthesis are based on the same starting materials. 6 In the first step, the hexa substituted hexaazaisowurtzitane derivatives are formed in the condensation reactions (glyoxal and primary amines). Subsequently, CL-20 is prepared by debenzylation and nitration of hexaazaisowurtzitane derivatives. 9 have been introduced for the synthesis of CL-20 from TADB. The preparation of CL-20 in the final step requires the use of HNO 3 /H 2 SO 4 which has many disadvantages including formation of environmentally unfriendly wastes that are expensive to dispose of, strong acidic media, over nitration and safety problems. Presently, the environmental concerns would not allow such means of disposal; thus, there still remains a need to develop commercially valuable process and environment-friendly methods for preparation of CL-20. 10The synthesis of CL-20 from TADB by applying melamine hydrogen sulfate/HNO 3 11 and acidic ionic liquids/HNO 3 12 in the one-pot reactions is reported in the recent studies of these authors. Nevertheless, these methods (Table 1) are affected by the use of stoichiometric quantities of expensive reagents and the high temperature of reaction which is a drawback of industrial scales.Zeolites, with their unique advantages of high thermal and acid stability and high selectivity (through homogeneous pore shape and size with their defined cages and channels) have been considered at industrial scale. [13][14][15] Zeolite is applied in catalytic cracking, isomerization and alkylation, as well as in the nitration reactions, including nitration of xylene, 16 To the best knowledge of the authors of this article, no report is available in the literature where a zeolite was Synthesis of CL-20 from TADB in a One-Pot Method by Zeolite/HNO 3 as a New Nitrolysis System J. Braz. Chem. Soc. 1104 applied in nitrolysis of the substrate. In this study, the zeolite/HNO 3 as a nitrolysis system (nitro-debenzylation, nitro-deacetylation) was applied in order to prepar...

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Methods of synthesis and properties of hexanitrohexaazaisowurtzitane

Cited by 100 publications

References 1 publication

4,4′-Bis(nitramino)azofurazan and its salts. Study of molecular and crystal structure based on X-ray and quantum chemical data

4,4′-Bis(nitramino)azofurazan and its salts. Study of molecular and crystal structure based on X-ray and quantum chemical data

Reductive debenzylation of hexabenzylhexaazaisowurtzitane — the key step of the synthesis of polycyclic nitramine hexanitrohexaazaisowurtzitane

Synthesis of CL-20 from TADB in a One-Pot Method by Zeolite/HNO₃as a New Nitrolysis System

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Methods of synthesis and properties of hexanitrohexaazaisowurtzitane

Cited by 100 publications

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4,4′-Bis(nitramino)azofurazan and its salts. Study of molecular and crystal structure based on X-ray and quantum chemical data

4,4′-Bis(nitramino)azofurazan and its salts. Study of molecular and crystal structure based on X-ray and quantum chemical data

Reductive debenzylation of hexabenzylhexaazaisowurtzitane — the key step of the synthesis of polycyclic nitramine hexanitrohexaazaisowurtzitane

Synthesis of CL-20 from TADB in a One-Pot Method by Zeolite/HNO3as a New Nitrolysis System

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Synthesis of CL-20 from TADB in a One-Pot Method by Zeolite/HNO₃as a New Nitrolysis System