Urea nitrate

Urea nitrate
Identifiers
CAS Number	124-47-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	29035 ;
ECHA InfoCard	100.004.276
PubChem CID	31295;
UNII	DHJ35702MG ;
CompTox Dashboard (EPA)	DTXSID60924672 ;
	InChI InChI=1S/CH4N2O.HNO3/c22-1(3)4/h(H4,2,3,4);(H,2,3,4) Key: AYTGUZPQPXGYFS-UHFFFAOYSA-N ; InChI=1/CH4N2O.HNO3/c22-1(3)4/h(H4,2,3,4);(H,2,3,4) Key: AYTGUZPQPXGYFS-UHFFFAOYAL;
	SMILES C(=O)(N)N.[N+](=O)(O)[O-];
Properties
Chemical formula	CH5N3O4
Molar mass	123.068 g·mol−1
Density	1.67±0.011 g/cm3
Melting point	157–159 °C (315–318 °F; 430–432 K)
Solubility in water	167.2±0.5 mg/mL
Solubility in Ethanol	14.2±0.1 mg/mL
Solubility in Acetone	10.4±0.2 mg/mL
Solubility in Methanol	54.8±0.9 mg/mL
Explosive data
Shock sensitivity	Low
Friction sensitivity	Low
Detonation velocity	4700 m/s
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H201, H271, H301, H304, H314, H332
Precautionary statements	P220, P233, P250, P260, P305+P351+P338
NFPA 704 (fire diamond)	2 1 3
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Urea nitrate is a fertilizer-based high explosive that has been used in improvised explosive devices in Afghanistan, Pakistan, Iraq, and various terrorist acts elsewhere in the world such as in the 1993 World Trade Center bombings.^[2] It has a destructive power similar to better-known ammonium nitrate explosives, with a velocity of detonation between 3,400 m/s (11,155 ft/s) and 4,700 m/s (15,420 ft/s).^[3] It has chemical formula of CH₅N₃O₄ or (NH₂)₂COHNO₃.

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Urea nitrate is produced in one step by reaction of urea with nitric acid. This is an exothermic reaction, so steps must be taken to control the temperature.

It was discovered in 1797 by William Cruickshank,^[4] inventor of the Chloralkali process.

Urea nitrate explosions may be initiated using a blasting cap.^[3]

Urea contains a carbonyl group. The more electronegative oxygen atom pulls electrons away from the carbon atom, forming a polar bond with greater electron density around the oxygen atom, giving it a partial negative charge. In a simplistic sense, nitric acid dissociates in aqueous solution into protons (hydrogen cations) and nitrate anions. The electrophilic proton contributed by the acid is attracted to the negatively charged oxygen atom on the urea molecule and the two form a covalent bond. The formed O-H bond is stabilized into a hydroxyl group when the oxygen abstracts an electron pair away from the central carbon atom, which leads to bond resonance between it and the two amino groups. As such, the urea cation can be thought of as a amidinium species. Paired with the spectator nitrate counteranion, it forms urea nitrate.

(NH₂)₂CO (aq) + HNO₃ (aq) → [(NH₂)₂COH]⁺[NO₃]⁻ (s)

The compound is favored by many amateur explosive enthusiasts as a principal explosive for use in larger charges. In this role it acts as a substitute for ammonium nitrate based explosives. This is due to the ease of acquiring the materials necessary to synthesize it, and its greater sensitivity to initiation compared to ammonium nitrate based explosives.

[1]
Oxley, Jimmie C.; Smith, James L.; Vadlamannati, Sravanthi; Brown, Austin C.; Zhang, Guang; Swanson, Devon S.; Canino, Jonathan (2013). "Synthesis and Characterization of Urea Nitrate and Nitrourea". Propellants, Explosives, Pyrotechnics. 38 (3): 335–344. doi:10.1002/prep.201200178.
[2]
Aaron Rowe (18 September 2007). "Chem Lab: Spray-On Test for Improvised Explosives". Wired.
[3]
"Explosives - ANFO (Ammonium Nitrate - Fuel Oil)". GlobalSecurity.org.
[4]
Rosenfeld, Louis (1999). Four Centuries of Clinical Chemistry. CRC Press. ISBN 978-90-5699-645-1.

Almog J, Burda G, Shloosh Y, Abramovich-Bar S, Wolf E, Tamiri T (November 2007). "Recovery and detection of urea nitrate in traces". J. Forensic Sci. 52 (6): 1284–90. doi:10.1111/j.1556-4029.2007.00551.x. PMID 17868267. S2CID 10228717.
Mr.X (July 2008). "Improvised Urea Nitrate". Aware EZine Gamma. Archived from the original on 2008-09-20. Retrieved 2008-11-11.

Media related to Urea nitrate at Wikimedia Commons

[Characterization-1] [1]
Oxley, Jimmie C.; Smith, James L.; Vadlamannati, Sravanthi; Brown, Austin C.; Zhang, Guang; Swanson, Devon S.; Canino, Jonathan (2013). "Synthesis and Characterization of Urea Nitrate and Nitrourea". Propellants, Explosives, Pyrotechnics. 38 (3): 335–344. doi:10.1002/prep.201200178.

[wired-2] [2]
Aaron Rowe (18 September 2007). "Chem Lab: Spray-On Test for Improvised Explosives". Wired.

[globalsecurity-3] [3]
"Explosives - ANFO (Ammonium Nitrate - Fuel Oil)". GlobalSecurity.org.

[4] [4]
Rosenfeld, Louis (1999). Four Centuries of Clinical Chemistry. CRC Press. ISBN 978-90-5699-645-1.

[2]

[3]

[1]

[4]

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Urea nitrate

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Chemistry

References

Further reading

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Identifiers


CAS Number	124-47-0^Y
3D model (JSmol)	Interactive image
ChemSpider	29035^N
ECHA InfoCard	100.004.276
PubChem CID	31295
UNII	DHJ35702MG^Y
CompTox Dashboard (EPA)	DTXSID60924672
InChI InChI=1S/CH4N2O.HNO3/c22-1(3)4/h(H4,2,3,4);(H,2,3,4)^N Key: AYTGUZPQPXGYFS-UHFFFAOYSA-N^N InChI=1/CH4N2O.HNO3/c22-1(3)4/h(H4,2,3,4);(H,2,3,4) Key: AYTGUZPQPXGYFS-UHFFFAOYAL
SMILES C(=O)(N)N.[N+](=O)(O)[O-]
Properties
Chemical formula	CH₅N₃O₄
Molar mass	123.068 g·mol⁻¹
Density	1.67±0.011 g/cm³^[1]
Melting point	157–159 °C (315–318 °F; 430–432 K)
Solubility in water	167.2±0.5 mg/mL^[1]
Solubility in Ethanol	14.2±0.1 mg/mL^[1]
Solubility in Acetone	10.4±0.2 mg/mL^[1]
Solubility in Methanol	54.8±0.9 mg/mL^[1]
Explosive data
Shock sensitivity	Low
Friction sensitivity	Low
Detonation velocity	4700 m/s
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H201, H271, H301, H304, H314, H332
Precautionary statements	P220, P233, P250, P260, P305+P351+P338
NFPA 704 (fire diamond)	2 1 3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references