Difference between revisions of "Tetranitroglycoluril"

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| OtherNames = Sorguyl<br>TNGU
 
| OtherNames = Sorguyl<br>TNGU
 
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==Preparation==
 
==Preparation==
The original preparation of TNGU involves nitrating [[glycoluril]] using a mixture of 100% [[nitric acid]] and [[phosphorus pentoxide]] at 50 °C.<ref>J.Boileau, J. M. L. Emeury, and J. P.  A. Kehren, Get, Offen., 2,435,651, Feb. 6, 1975. “Encyclopedia of Explosives and Related Items, B. T. Federoff et  al., Vol. 1, p. A65, 1960, Picatinny Arsenal, Dover, NJ.</ref>
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The original preparation of TNGU involves nitrating [[glycoluril]] using a mixture of 100% [[nitric acid]] and [[phosphorus pentoxide]] at 50 °C for 1-2 hours.<ref>J.Boileau, J. M. L. Emeury, and J. P.  A. Kehren, Get, Offen., 2,435,651, Feb. 6, 1975. “Encyclopedia of Explosives and Related Items, B. T. Federoff et  al., Vol. 1, p. A65, 1960, Picatinny Arsenal, Dover, NJ.</ref>
  
 
TNGU can be prepared by nitrating [[glycoluril]] with a mixture of conc. [[nitric acid|nitric]] and [[sulfuric acid]]s in the presence of [[acetic anhydride]] at 20 °C, for 30-120 min. The yield of this reaction is 72%.<ref>Kovalenko, A. L.; Serov, Yu. V.; Tselinskii, I. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 61; nb. 12; (1991); p. 2778 - 2780,2581 - 2582</ref><ref>https://patents.google.com/patent/US4487938A/en</ref>
 
TNGU can be prepared by nitrating [[glycoluril]] with a mixture of conc. [[nitric acid|nitric]] and [[sulfuric acid]]s in the presence of [[acetic anhydride]] at 20 °C, for 30-120 min. The yield of this reaction is 72%.<ref>Kovalenko, A. L.; Serov, Yu. V.; Tselinskii, I. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 61; nb. 12; (1991); p. 2778 - 2780,2581 - 2582</ref><ref>https://patents.google.com/patent/US4487938A/en</ref>

Latest revision as of 21:39, 26 October 2020

Tetranitroglycoluril
Tetranitroglycoluril structure.png
Structure of TNGU
Names
IUPAC name
2,4,6,8-Tetranitro-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione
Other names
Sorguyl
TNGU
Properties
C4H2N8O10
Molar mass 322.107 g/mol
Appearance White powdered solid[1]
Odor Odorless
Density 1.95-2.04 g/cm3
Melting point 226–232 °C (439–450 °F; 499–505 K) [3]
Boiling point Decomposes
Insoluble
Solubility Soluble in glacial acetic acid, acetone, acetonitrile, dioxane, ethyl acetate
Poorly soluble in methanol
Insoluble in heptane, hexane
Solubility in acetic acid 15.7 g/100 ml (25 °C)[2]
Solubility in dioxane 17 g/100 ml (27 °C)
Vapor pressure ~0 mmHg
Hazards
Safety data sheet None
Related compounds
Related compounds
HMX
HNIW
RDX
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Tetranitroglycoluril, also known as sorguyl or TNGU, is a very powerful high explosive compound, a nitroamine.

Although it is more powerful than conventional high explosives, sorguryl is more susceptible to hydrolysis, which limits its use.

Properties

Chemical

TNGU will decompose if heated and may explode if initiated by a blasting cap.

Physical

TNGU is a white solid. It is insoluble in water and slightly soluble in methanol, but more soluble in acetone, acetonitrile and ethyl acetate.[4] Sorguryl has an average density between 1.93-2.04 g/cm3 at room temperature, density depending on its purity and recrystallization solvent used.

Explosive

TNGU is slightly more powerful than TNT or RDX, having similar performance to HMX or HNIW, though it's much more sensitive than the latter compounds.[5] It has a detonation velocity of 9,150 m/s at a density of 1.95 g/cm3.

Availability

TNGU is not available to the general public.

Preparation

The original preparation of TNGU involves nitrating glycoluril using a mixture of 100% nitric acid and phosphorus pentoxide at 50 °C for 1-2 hours.[6]

TNGU can be prepared by nitrating glycoluril with a mixture of conc. nitric and sulfuric acids in the presence of acetic anhydride at 20 °C, for 30-120 min. The yield of this reaction is 72%.[7][8]

A slightly different route involves nitrating mononitroglycouril with fuming nitric acid and dinitrogen pentoxide, by stirring at 15 °C, for 2 hours.[9]

Projects

  • Make blasting charges
  • Make shaped charges

Handling

Safety

TNGU is a powerful explosive and should be handled with care.

Storage

In closed bottles, in a safe area.

Disposal

Can be burned outside.

References

  1. https://www.researchgate.net/publication/318446607_Solubility_and_dissolution_thermodynamics_of_tetranitroglycoluril_in_organic_solvents_at_295-318_K
  2. https://patents.google.com/patent/US4487938A/en
  3. Kovalenko, A. L.; Serov, Yu. V.; Tselinskii, I. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 61; nb. 12; (1991); p. 2778 - 2780,2581 - 2582
  4. https://pubs.acs.org/doi/10.1021/je500392g
  5. https://onlinelibrary.wiley.com/doi/abs/10.1002/prep.201400041
  6. J.Boileau, J. M. L. Emeury, and J. P. A. Kehren, Get, Offen., 2,435,651, Feb. 6, 1975. “Encyclopedia of Explosives and Related Items, B. T. Federoff et al., Vol. 1, p. A65, 1960, Picatinny Arsenal, Dover, NJ.
  7. Kovalenko, A. L.; Serov, Yu. V.; Tselinskii, I. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 61; nb. 12; (1991); p. 2778 - 2780,2581 - 2582
  8. https://patents.google.com/patent/US4487938A/en
  9. Boileau, J.; Wimmer, E.; Carail, M.; Gallo, R.; Bulletin de la Societe Chimique de France; nb. 3; (1986); p. 465 - 469

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