Hexanitrobenzene
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Image:Hexanitrobenzene-alt.png | |
| 1,2,3,4,5,6-hexanitrobenzene IUPAC name | |
| Chemical formula | C6N6O12 |
| Molar mass | 348.0996 g/mol |
| Shock sensitivity | None |
| Friction sensitivity | None |
| Density | 1.985 g/cm3 |
| Explosive velocity | 9,340 m/s |
| RE factor | ? |
| Melting point | 256-264 °C |
| Autoignition temperature | N/A |
| Appearance | Yellow or brown powdered crystals |
| CAS number | |
| PubChem | [1] |
| SMILES | |
Hexanitrobenzene, also known as HNB, is a high-density explosive compound with chemical formula C6N6O12, obtained by oxidizing the amine group of pentanitroaniline with hydrogen peroxide in sulfuric acid. Its molecular mass is 348.0996 g/mol, its density 1.985 g/cm³, and its heat of formation is 17.48 kJ/mol.
HNB has the undesirable property of being moderately sensitive to light and therefore hard to utilize safely. It is not currently used in any production explosives applications, though it is used as a precursor chemical in one method of production of TATB, another explosive.
HNB was experimentally used as a gas source for explosively pumped gas dynamic laser [2]. In this application HNB and tetranitromethane is preferred to more conventional explosives because the explosion products CO2 + N2 are enough simple mixture to simulate gas dynamic processes, and it's quite similar to conventional gas dynamic laser medium. Water and hydrogen as product of many explosive could interfere with vibrational states of CO2 in this type of laser.
Preparation
During World War II a method of synthesis of hexanitrobenzene was suggested
in Germany, and the product was supposed to be manufactured on a semi-industrial
scale according to the following scheme:
C6H3(N02)3 -> partial reduction -> C6H3(NH0H)3 -> Nitration -> C6(NO2)3(NH0H)3 -> oxidation -> C6(NO2)6
straightway nitration of benzene is practically impossible, because
-NO2 are deactivating groups for further nitration.
Properties
- Velocity of detonation:
- 9,340 m/s measured at density 1.965 [3]
- Chapman-Jouget detonation pressure: 43 GPa
- Crystal Density: 2.01
See also
References
Heats of Formation and Chemical Compositions
R. L. Atkins, R. A. Hollins, W. S. Wilson (1986). "Synthesis of polynitro compounds. Hexasubstituted benzenes". J. Org. Chem. 51: 3261-3266. doi:10.1021/jo00367a003.
A. T. Nielsen, R. L. Atkins, W. P. Norris (1979). "Oxidation of poly(nitro)anilines to poly(nitro)benzenes. Synthesis of hexanitrobenzene and pentanitrobenzene". J. Org. Chem. 44: 1181-1182. doi:10.1021/jo01321a041.
Z. A. Akopyan, Yu. T. Struchkov, V. G. Dashevskii (1966). "Crystal and molecular structure of hexanitrobenzene". Journal of Structural Chemistry 7: 385-392. doi:10.1007/BF00744430.ar:بنزين سداسي النيترو ja:ヘキサニトロベンゼン
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
