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{{distinguish|nitrourea}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 371084475 |
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| Watchedfields = changed |
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| ImageFile = Urea nitrate.png |
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| verifiedrevid = 426796341 |
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| ImageName = Structural formulae of the ions in urea nitrate |
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| Name = |
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| ImageFile1 = Urea-nitrate-3D-balls.png |
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| ImageFile = Urea nitrate.png |
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| ImageSize1 = 220px |
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| ImageName1 = Ball-and-stick models of the ions in urea nitrate |
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| ImageName = Structural formulae of the ions in urea nitrate |
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| ImageFile1 = Urea-nitrate-3D-balls.png |
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| IUPACName = |
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| OtherNames = |
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| ImageSize1 = 220px |
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| ImageName1 = Ball-and-stick models of the ions in urea nitrate |
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| Section1 = {{Chembox Identifiers |
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| CASNo = |
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| IUPACName = |
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| PubChem = |
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| OtherNames = |
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| SMILES = }} |
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| SystematicName = |
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| Section2 = {{Chembox Properties |
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| Section1 = {{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| Formula = CH<sub>5</sub>N<sub>3</sub>O<sub>4</sub> |
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| CASNo = 124-47-0 |
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| MolarMass = 123.068 g/mol |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = DHJ35702MG |
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| PubChem = 31295 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 29035 |
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| SMILES = C(=O)(N)N.(=O)(O) |
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| InChI = 1/CH4N2O.HNO3/c2*2-1(3)4/h(H4,2,3,4);(H,2,3,4) |
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| InChIKey = AYTGUZPQPXGYFS-UHFFFAOYAL |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/CH4N2O.HNO3/c2*2-1(3)4/h(H4,2,3,4);(H,2,3,4) |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = AYTGUZPQPXGYFS-UHFFFAOYSA-N |
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}} |
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| Section2 = {{Chembox Properties |
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| C=1 | H=5 | N=3 | O=4 |
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| Appearance = |
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| Appearance = |
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| Density = 1.59 g/cc |
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| Density = 1.67±0.011 g/cm<sup>3</sup><ref name="Characterization" /> |
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| MeltingPt = |
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| MeltingPtC = 157-159 |
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| BoilingPt = |
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| BoilingPt = |
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| 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> |
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| Solubility = }} |
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|Solubility1 = 14.2±0.1 mg/mL<ref name="Characterization" /> |
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| Section3 = {{Chembox Hazards |
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|Solvent1 = Ethanol |
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| MainHazards = |
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|Solubility2 = 10.4±0.2 mg/mL<ref name="Characterization" /> |
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| FlashPt = |
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|Solvent2 = Acetone |
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| Autoignition = }} |
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|Solubility3 = 54.8±0.9 mg/mL<ref name="Characterization" /> |
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|Solvent3 = Methanol |
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| SolubleOther = }} |
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| Section3 = |
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| Section4 = {{Chembox Explosive |
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| ShockSens = Low |
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| FrictionSens = Low |
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| DetonationV = 4700 m/s |
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| REFactor = }} |
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| Section5 = {{Chembox Hazards |
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| GHSPictograms = {{GHS01}} {{GHS03}} {{GHS05}} |
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| GHSSignalWord = '''DANGER''' |
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| HPhrases = {{H-phrases|201|271|301|304|314|332}} |
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| PPhrases = {{P-phrases|220|233|260|250|305+351+338}} |
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| NFPA-F = 1 |
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| NFPA-H = 2 |
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| NFPA-R = 3 |
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}} |
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| Section6 = |
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}} |
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}} |
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] |
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'''Urea nitrate''' is a fertilizer-based ] that has been used in ]s in ], ], and various other ] acts elsewhere in the world, like the ].<ref name="wired">{{cite web| |
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'''Urea nitrate''' is a fertilizer-based ] that has been used in ]s in ], ], ], and various ] acts elsewhere in the world such as in the ].<ref name="wired">{{cite news| |
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url=http://blog.wired.com/wiredscience/2007/09/spray-on-test-f.html| |
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url=http://blog.wired.com/wiredscience/2007/09/spray-on-test-f.html| |
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title=Chem Lab: Spray-On Test for Improvised Explosives| |
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title=Chem Lab: Spray-On Test for Improvised Explosives| |
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author=Aaron Rowe| |
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author=Aaron Rowe| |
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publisher=Wired |
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publisher=Wired}}</ref> It has a destructive power similar to better-known ] explosives, with a ] between {{convert|11155|ft/s|m/s|abbr=on}} and {{convert|15420|ft/s|m/s|abbr=on}}.<ref name="globalsecurity">{{cite web| |
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| date =18 September 2007}}</ref> It has a destructive power similar to better-known ] explosives, with a ] 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| |
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url=http://www.globalsecurity.org/military/systems/munitions/explosives-anfo.htm| |
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url=http://www.globalsecurity.org/military/systems/munitions/explosives-anfo.htm| |
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title=Explosives - ANFO (Ammonium Nitrate - Fuel Oil)| |
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title=Explosives - ANFO (Ammonium Nitrate - Fuel Oil)| |
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publisher=GlobalSecurity.org}}</ref> |
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publisher=GlobalSecurity.org}}</ref> It has chemical formula of {{chem2|CH5N3O4}} or {{chem2|(NH2)2COHNO3}}. |
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Production is by ] of ] using ]. This is an exothermic reaction, so steps must be taken to control the temperature. Presence of ] during the nitration catalyzes the reaction, although this is not necessary. <ref name="globalsecurity" /> |
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Urea nitrate is produced in one step by reaction of ] with ]. This is an ], so steps must be taken to control the temperature. |
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It was discovered in 1797 by ],<ref>{{Cite book |last=Rosenfeld |first=Louis |url=https://books.google.com/books?id=KPX6Yvax9jkC&pg=PA40 |title=Four Centuries of Clinical Chemistry |date=1999 |publisher=CRC Press |isbn=978-90-5699-645-1 |language=en}}</ref> inventor of the ]. |
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Urea nitrate explosions may be initiated using a blasting cap. <ref name="globalsecurity" /> |
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Urea nitrate explosions may be initiated using a ].<ref name="globalsecurity" /> |
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==Chemistry== |
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==Chemistry== |
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Urea contains a ]. 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 ion forms a covalent bond . 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. As an ionic compound urea nitrate is highly soluble in water. |
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Urea contains a ]. 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. |
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:{{chem2 | (NH2)2CO (aq) + HNO3 (aq) -> +− (s) }} |
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(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) |
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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. |
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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. |
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==Further reading== |
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==Further reading== |
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* {{cite journal |author=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 |year=2007 |month=November |pmid=17868267 |doi=10.1111/j.1556-4029.2007.00551.x |url=}} |
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*{{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 }} |
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* {{cite journal |author=Mr.X |title=Improvised Urea Nitrate |journal=.aware eZine Gamma |year=2008 |month=July |url=http://www.awarenetwork.org/etc/gamma/?x=5}} |
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*{{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 }} |
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==External links== |
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*{{Commonscatinline}} |
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