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. | + | 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
 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.
Contents
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
- ↑ https://www.researchgate.net/publication/318446607_Solubility_and_dissolution_thermodynamics_of_tetranitroglycoluril_in_organic_solvents_at_295-318_K
- ↑ https://patents.google.com/patent/US4487938A/en
- ↑ 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
- ↑ https://pubs.acs.org/doi/10.1021/je500392g
- ↑ https://onlinelibrary.wiley.com/doi/abs/10.1002/prep.201400041
- ↑ 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.
- ↑ 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
- ↑ https://patents.google.com/patent/US4487938A/en
- ↑ Boileau, J.; Wimmer, E.; Carail, M.; Gallo, R.; Bulletin de la Societe Chimique de France; nb. 3; (1986); p. 465 - 469
