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Benzotrifuroxan

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Benzotrifuroxan is a heterocyclic organic compound that is related to 1,2,5-oxadioles. The high-energy compound is explosive.

History

The compound was first synthesized in 1924 by O. Turek as hexanitrosobenzene. In addition to the hexanitroso structure, symmetric polycyclic structures could also be formulated.

1. Hexa(1-aza-2-oxaethenyl)benzene, 2. 5,7,9,11,13,15-hexaza-6,8,10,12,14,16-hexoxa--hexacycloctadec-1,3,17-triene, 3. 2,5,8,11,14,17-hexaza-3,4,9,10,15,16-hexoxa--tricyclooctadex-6,12,18-triene
Historical, non-real structures of benzotrifuroxan

Characteristics

Physical Properties

Benzotrifuroxan is a crystalline solid that melts at 195 °C.  The compound crystallizes in an orthorhombic crystal lattice with the space group Pna2 1 .  The molar enthalpy of formation is 606 kJ·mol , the enthalpy of combustion is −2967 kJ·mol .

Chemical Properties

Benzotrifuroxan can decompose explosively. The heat of explosion is 5903 kJ·kg  , the detonation speed is 8.61 km·s .  The compound is sensitive to impact .

Benzotrifuroxan forms stable complexes with aromatic hydrocarbons such as naphthalene, 1-phenylnaphthalene, 2-phenylnaphthalene and tetrahydronaphthalene . Recrystallization in benzene yields a 1:1 complex, whereby the benzene can only be removed at 100 °C in vacuum .

Synthesis

Benzotrifuroxan can be obtained by thermal degradation of 1,3,5-triazido-2,4,6-trinitrobenzene .

1,3,5-Triazido-2,4,6-trinitrobenzene decomposition





A further synthesis can be carried out by reacting 5,7-dichloro-4,6-dinitronbenzofuroxan with sodium azide.

Uses

In combination with TNT, the compound can be used to produce nanodiamonds using detonation shock waves.

References

  1. A. S. Bailey, JR Case: . In: . band 3 , No. 2 , 1958, p. 113–131 , doi:10.1016/0040-4020(58)80003-4 .
  2. ↑ H. H. Cady, AC Larson, DT Cromer: . In: . band 20 , No. 3 , 1 March 1966, p. 336–341 , doi : 10.1107/S0365110X6600080X .
  3. ↑ J. CA Boeyens, FH Herbstein: . In: . band 69 , No. 7 , 1 July 1965, p. 2153–2159 , doi : 10.1021/j100891a003 .
  4. ↑ This substance has either not yet been classified in terms of its hazard or a reliable and citable source has not yet been found.
  5. ↑ O. Turek: . In: . band 26 , 1931, p. 781–794 .
  6. ↑ O. Turek: . In: . No. 7 , 1932, p. 76–79; 97–104 .
  7. ↑ Neville Bacon, AJ Boulton, AR Katritzky:  . In:  . band 63 , No. 0 , 1 January 1967, p. 833–835 , doi : 10.1039/TF9676300833 .
  8. ↑ EA Chugunova, RE Timasheva, EM Gibadullina, AR Burilov, R. Goumont:  . In:  . band 37 , No. 4 , 20 July 2012, p. 390–392 , doi : 10.1002/prep.201200080 .
  9. ↑ EN Maslen:  . In:  . band 24 , No. 9 , 1 September 1968, p. 1170–1172 , doi : 10.1107/S0567740868003912 .
  10. ↑ Prince E. Rouse:  . In:  . band 21 , No. 1 , 1 January 1976, p. 16–20 , doi : 10.1021/je60068a026 .
  11. ↑ Betsy M. Rice, Jennifer Hare:  . In:  . band 384 , No. 1–2 , 25 February 2002, p. 377–391 , doi : 10.1016/S0040-6031(01)00796-1 .
  12. ↑ H. Muthurajan, R. Sivabalan, MB Talawar, SN Asthana:  . In:  . band 112 , No. 1–2 , 9 August 2004, p. 17–33 , doi : 10.1016/j.jhazmat.2004.04.012 .
  13. ↑ VI Pepekin, BL Korsunskii, AA Denisaev:  . In:  . band 44 , No. 5 , 1 September 2008, p. 586–590 , doi : 10.1007/s10573-008-0089-7 .
  14. ↑ NV Kozyrev:  . In:  . band 44 , No. 6 , 1 November 2008, p. 698–703 , doi : 10.1007/s10573-008-0105-y .
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