Urea nitrate: Difference between revisions

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

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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.

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.

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

Chemistry

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.

References

^ ^a ^b ^c ^d ^e 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.
^ Aaron Rowe (18 September 2007). "Chem Lab: Spray-On Test for Improvised Explosives". Wired.
^ ^a ^b "Explosives - ANFO (Ammonium Nitrate - Fuel Oil)". GlobalSecurity.org.

External links

Media related to Urea nitrate at Wikimedia Commons

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

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

[1]

[2]

[3]

@@ Line 1: / Line 1: @@
+{{distinguish|nitrourea}}
 {{chembox
 | Verifiedfields = changed
-| Watchedfields = changed
+| Watchedfields  = changed
-| verifiedrevid = 426796341
+| verifiedrevid  = 426796341
+| Name           =
-| ImageFile = Urea nitrate.png
-| ImageName = Structural formulae of the ions in urea nitrate
+| ImageFile      = Urea nitrate.png
+| ImageName      = Structural formulae of the ions in urea nitrate
-| ImageFile1 = Urea-nitrate-3D-balls.png
+| ImageFile1     = Urea-nitrate-3D-balls.png
-| ImageSize1 = 220px
-| ImageName1 = Ball-and-stick models of the ions in urea nitrate
+| ImageSize1     = 220px
+| ImageName1     = Ball-and-stick models of the ions in urea nitrate
-| IUPACName =
+| IUPACName      =
-| OtherNames =
+| OtherNames     =
+| SystematicName =
-|Section1={{Chembox Identifiers
+| Section1       = {{Chembox Identifiers
-| CASNo_Ref = {{cascite|changed|??}}
+| CASNo_Ref = {{cascite|correct|CAS}}
 | CASNo = 124-47-0
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = DHJ35702MG
 |  PubChem = 31295
 |  ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
@@ Line 24: / Line 29: @@
 | StdInChIKey = AYTGUZPQPXGYFS-UHFFFAOYSA-N
 }}
-|Section2={{Chembox Properties
+| Section2       = {{Chembox Properties
+| C=1 | H=5 | N=3 | O=4
-| Formula = CH<sub>5</sub>N<sub>3</sub>O<sub>4</sub>
-| MolarMass = 123.068 g/mol
 | Appearance =
-| Density = 1.69&nbsp;g/cm<sup>3</sup>
+| Density = 1.67±0.011&nbsp;g/cm<sup>3</sup><ref name="Characterization" />
-| MeltingPtC = 163
+| MeltingPtC = 157-159
 | BoilingPt =
+| Solubility = 167.2±0.5 mg/mL<ref name="Characterization">{{cite journal | doi = 10.1002/prep.201200178 | title = Synthesis and Characterization of Urea Nitrate and Nitrourea | date = 2013 | last1 = Oxley | first1 = Jimmie C. | last2 = Smith | first2 = James L. | last3 = Vadlamannati | first3 = Sravanthi | last4 = Brown | first4 = Austin C. | last5 = Zhang | first5 = Guang | last6 = Swanson | first6 = Devon S. | last7 = Canino | first7 = Jonathan | journal = Propellants, Explosives, Pyrotechnics | volume = 38 | issue = 3 | pages = 335–344 }}</ref>
-| Solubility = 15 g/100 g
+|Solubility1 = 14.2±0.1 mg/mL<ref name="Characterization" />
-| SolubleOther = soluble in alcohol<ref>http://cameochemicals.noaa.gov/chemical/12966</ref>}}
+|Solvent1 = Ethanol
-| [[RE Factor]] = 1.05
+|Solubility2 = 10.4±0.2 mg/mL<ref name="Characterization" />
-|Section3={{Chembox Hazards
+|Solvent2 = Acetone
-| MainHazards =
+|Solubility3 = 54.8±0.9 mg/mL<ref name="Characterization" />
-| FlashPt =
+|Solvent3 = Methanol
-| AutoignitionPt =
+| SolubleOther =  }}
+| Section3       =
+| Section4       = {{Chembox Explosive
+| ShockSens = Low
+| FrictionSens = Low
+| DetonationV = 4700 m/s
+| REFactor = }}
+| Section5       = {{Chembox Hazards
+| GHSPictograms = {{GHS01}} {{GHS03}} {{GHS05}}
+| GHSSignalWord = '''DANGER'''
+| HPhrases = {{H-phrases|201|271|301|304|314|332}}
+| PPhrases = {{P-phrases|220|233|260|250|305+351+338}}
+| NFPA-F = 1
+| NFPA-H = 2
+| NFPA-R = 3
  }}
+| Section6       =
 }}
+[[File:Urea nitrate (IV).jpg|thumb|Crystals of urea nitrate]]
-'''Urea nitrate''' is a fertilizer-based [[high explosive]] that has been used in [[improvised explosive device]]s in [[Afghanistan]], [[Pakistan]], [[Iraq]], and various other [[terrorism|terrorist]] acts elsewhere in the world, like the [[1993 World Trade Center bombings]].<ref name="wired">{{cite news|
+'''Urea nitrate''' is a fertilizer-based [[high explosive]] that has been used in [[improvised explosive device]]s in [[Afghanistan]], [[Pakistan]], [[Iraq]], and various [[terrorism|terrorist]] acts elsewhere in the world such as in the [[1993 World Trade Center bombings]].<ref name="wired">{{cite news|
 url=http://blog.wired.com/wiredscience/2007/09/spray-on-test-f.html|
 title=Chem Lab: Spray-On Test for Improvised Explosives|
 author=Aaron Rowe|
 publisher=Wired
-| date =18 September 2007}}</ref>  It has a destructive power similar to better-known [[ammonium nitrate]] explosives, with a [[velocity of detonation]] between {{convert|11155|ft/s|m/s|abbr=on}} and {{convert|15420|ft/s|m/s|abbr=on}}.<ref name="globalsecurity">{{cite web|
+| date =18 September 2007}}</ref>  It has a destructive power similar to better-known [[ammonium nitrate]] explosives, with a [[velocity of detonation]] between {{convert|11155|ft/s|m/s|abbr=on|order=flip}} and {{convert|15420|ft/s|m/s|abbr=on|order=flip}}.<ref name="globalsecurity">{{cite web|
 url=http://www.globalsecurity.org/military/systems/munitions/explosives-anfo.htm|
 title=Explosives - ANFO (Ammonium Nitrate - Fuel Oil)|
-publisher=GlobalSecurity.org}}</ref>
+publisher=GlobalSecurity.org}}</ref> It has chemical formula of {{chem2|CH5N3O4}} or {{chem2|(NH2)2COHNO3}}.
 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.
-Urea nitrate explosions may be initiated using a blasting cap.<ref name="globalsecurity" />
+Urea nitrate explosions may be initiated using a [[blasting cap]].<ref name="globalsecurity" />
 ==Chemistry==
-Urea contains a [[Carbonyl|carbonyl group]]. The more electronegative oxygen atom pulls electrons away from the carbon forming a greater electron density around the oxygen, giving the oxygen a partial negative charge and forming a polar bond. When nitric acid is presented,  it ionizes. A hydrogen cation contributed by the acid is attracted to the oxygen and forms a covalent bond [electrophile H<sup>+</sup>]. The electronegative NO<sub>3</sub><sup>−</sup> ion then is attracted to the positive hydrogen ion. This forms an ionic bond and hence the compound urea nitrate.
+Urea contains a [[Carbonyl|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.
+:{{chem2 | (NH2)2CO (aq) + HNO3 (aq) -> [(NH2)2COH]+[NO3]− (s) }}
-(NH<sub>2</sub>)<sub>2</sub>CO (aq) + HNO<sub>3</sub> (aq) → (NH<sub>2</sub>)<sub>2</sub>COHNO<sub>3</sub> (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.
@@ Line 65: / Line 86: @@
 ==Further reading==
-* {{cite journal |vauthors=Almog J, Burda G, Shloosh Y, Abramovich-Bar S, Wolf E, Tamiri T |title=Recovery and detection of urea nitrate in traces |journal=J. Forensic Sci. |volume=52 |issue=6 |pages=1284–90 |date=November 2007 |pmid=17868267 |doi=10.1111/j.1556-4029.2007.00551.x |url=}}
+*{{cite journal |vauthors=Almog J, Burda G, Shloosh Y, Abramovich-Bar S, Wolf E, Tamiri T |title=Recovery and detection of urea nitrate in traces |journal=J. Forensic Sci. |volume=52 |issue=6 |pages=1284–90 |date=November 2007 |pmid=17868267 |doi=10.1111/j.1556-4029.2007.00551.x |s2cid=10228717 }}
-* {{cite journal |author=Mr.X |title=Improvised Urea Nitrate |journal=aware eZine Gamma |date=July 2008 |url=http://www.awarenetwork.org/etc/gamma/?x=5}}
+*{{cite journal |author=Mr.X |title=Improvised Urea Nitrate |journal=Aware EZine Gamma |date=July 2008 |url=http://www.awarenetwork.org/etc/gamma/?x=5 |access-date=2008-11-11 |archive-url=https://web.archive.org/web/20080920082234/http://www.awarenetwork.org/etc/gamma/?x=5 |archive-date=2008-09-20 |url-status=dead }}
+==External links==
-[[File:Urea nitrate (IV).jpg|thumb|Urea nitrate]]
+*{{Commonscatinline}}
 [[Category:Explosive chemicals]]
 [[Category:Nitrates]]
 [[Category:Ureas]]
-{{explosive-stub}}