Synthesis of RDX by nitrolysis of hexamethylenetetramine in fluorous media

Yi, Wen‐Bin; Cai, Chun

doi:10.1016/j.jhazmat.2007.10.040

Cited by 17 publications

(13 citation statements)

References 24 publications

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“…For related literature, see: Akhavan (2004); Bachmann & Sheehan (1949); Brockman et al (1949); Choi & Prince (1972); Ciezak et al (2007); Davidson et al (2008); Harris et al (1959); Henning (1899); von Herz et al (1920); Hultgren (1936); McCrone (1950); Yi & Cai (2008).…”

Section: Related Literaturementioning

confidence: 99%

Redetermination ofcyclo-trimethylenetrinitramine

Hakey

Ouellette

Zubieta

et al. 2008

Acta Crystallogr E Struct Rep Online

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The redetermined structure of 1,3,5-trinitro-1,3,5-triazacyclohexane, C3H6N6O6, at 90 (2) K has orthorhombic (Pbca) symmetry. It is of interest with respect to energetic compounds. The structure was originally investigated through X-ray diffraction by Hultgren [(1936). J. Chem. Phys. 4, 84]. Later X-ray investigations were completed by McCrone [(1950). Anal. Chem. 22, 954–955] and Harris, Reed & Gluyas [(1959). AFOSR-TR-59-165 Ohio State University Research Foundation, Columbus, Ohio, USA]. A single-crystal neutron diffraction study was performed by Choi & Prince [(1972). Acta Cryst. B28, 2857–2862] to ascertain the H-atom positions, which had not been defined by the earlier X-ray diffraction studies. All previous studies were performed at or near room temperature. The structure provided is the α polymorph of the title compound. The ring atoms are arranged in the chair conformation with two nitro groups occupying pseudo-equatorial positions and the remaining nitro group is axial. The crystal packing is stabilized by close intramolecular interactions from one H atom in each methylene group to O atoms of adjacent nitro groups, ranging from 2.251 to 2.593 Å.

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Section: Related Literaturementioning

confidence: 99%

Redetermination ofcyclo-trimethylenetrinitramine

Hakey

Ouellette

Zubieta

et al. 2008

Acta Crystallogr E Struct Rep Online

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“…If NO 3 can react with RDX, NO 3 will attack N atom of N À NO 2 first. Therefore, we placed the NO 3 radical near the N atom of N À NO 2 when we designed the initial interaction structure of RDX and NO 3 . In our present calculation, the O 22 atom of NO 3 radical was placed near the N 11 atom of RDX.…”

Section: Interactions Of No 3 With Rdx and Four Intermediatesmentioning

confidence: 99%

“…It is found that the charges of NO 3 change greatly during interactions. Particularly, the total charges of NO 3 becomes a negative value which demonstrates that electrons transfer from RDX or decomposition intermediates to NO 3 . This indicates that new bonds were produced after interactions.…”

Section: Binding Energy Charge Transfermentioning

confidence: 99%

Quantum Chemical Study on the Interactions of NO₃ with RDX and Four Decomposition Intermediates

Zhang

Cheng

Zhao³

2010

Propellants Explo Pyrotec

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Recently, NO 3 (nitrate radical) was predicted to be formed during the decomposition of RDX. However, experimental studies of the gaseous products have never detected it. In order to verify the prediction, we studied the interactions of NO 3 with RDX and four RDX decomposition intermediates (RDR, C 3 H 5 N 5 O 4 , OST, and TAZ) by using density functional theory (DFT). It is found that NO 3 radical can be converted into NO 2 during the process of interactions with the above-mentioned five molecules. In other words, NO 3 radical can be consumed in these processes, which gives an explanation for the disappearance of NO 3 . Transition state theory (TST) calculations lead to the same results. The binding energies are calculated to estimate the strength of interactions. The energy of NO 3 with RDR is the largest, which indicates this process is most likely to occur. Our calculation provides a support to the prediction of the formation of NO 3 .

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“…This 4,10-dinitro-2,6,8,12-tetraoxa-4,10-diazaisowurtzitane (TEX), an illustrious caged nitramine, gaining interest in the field of high energy materials (HEMs). 1,2,14 Owing to have combined properties of high energy, density, detonation pressure and low sensitivity, the cage crystal molecules containing the nitro groups are important and widely used as energetic materials. 15 In general, TEX is synthesized in a reaction by nitrolysis of hexa-substituted piperazine derivatives.…”

Section: Introductionmentioning

confidence: 99%

An Improved and Scalable Synthesis of Insensitive High Explosive 4,10-Dinitro-2,6,8,12-tetraoxa-4,10-diazaisowurtzitane (TEX)

Deshmukh

Borse

Mahulikar

et al. 2016

Org. Process Res. Dev.

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4,10-dinitro-2,6,8,12-tetraoxa-4,10-diazaisowurtzitane (TEX), a well-known nitramine category explosive, is much less sensitive to impact and friction stimuli as compared to the familiar explosives, RDX and HMX. TEX is currently produced on pilot plant scale and is being pursued as an insensitive explosive. Herein a newer, improved, efficient and high yielding protocol is developed for the synthesis of TEX by using solid acidic silica sulfuric acid as an efficient and recyclable catalyst. Sequentially for process parameters optimization, a study was carried out with variation of catalyst loading, nitric acid and mole ratio of reactants. The process scale-up is also achieved successfully.

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Synthesis of RDX by nitrolysis of hexamethylenetetramine in fluorous media

Cited by 17 publications

References 24 publications

Redetermination ofcyclo-trimethylenetrinitramine

Redetermination ofcyclo-trimethylenetrinitramine

Quantum Chemical Study on the Interactions of NO₃ with RDX and Four Decomposition Intermediates

An Improved and Scalable Synthesis of Insensitive High Explosive 4,10-Dinitro-2,6,8,12-tetraoxa-4,10-diazaisowurtzitane (TEX)

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Synthesis of RDX by nitrolysis of hexamethylenetetramine in fluorous media

Cited by 17 publications

References 24 publications

Redetermination ofcyclo-trimethylenetrinitramine

Redetermination ofcyclo-trimethylenetrinitramine

Quantum Chemical Study on the Interactions of NO3 with RDX and Four Decomposition Intermediates

An Improved and Scalable Synthesis of Insensitive High Explosive 4,10-Dinitro-2,6,8,12-tetraoxa-4,10-diazaisowurtzitane (TEX)

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Quantum Chemical Study on the Interactions of NO₃ with RDX and Four Decomposition Intermediates