| Revision as of 17:29, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 425314669 of page 2-Nitrodiphenylamine for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 10:24, 30 September 2024 edit JWBE (talk | contribs)Extended confirmed users10,126 edits removed Category:Nitrobenzene derivatives; added Category:2-Nitrophenyl compounds using HotCat |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 399299363 |
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| Watchedfields = changed |
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| Name = 2-Nitrodiphenylamine |
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| verifiedrevid = 477214934 |
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| ImageFile = Nitrodiphenylamine.png |
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| Name = 2-Nitrodiphenylamine |
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| ImageSize = 200px |
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| OtherNames = NDPA, 2-NDPA, 2NO2DPA, Sudan Yellow 1339, C.I. 10335, CI 10335, phenyl 2-nitrophenylamine, 2-nitro-N-phenylaniline, or N-phenyl-''o''-nitroaniline |
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| ImageName = |
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| ImageFile = Nitrodiphenylamine.png |
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| IUPACName = |
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| ImageSize = 170 |
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| Section1 = {{Chembox Identifiers |
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| ImageAlt = Skeletal formula of 2-nitrodiphenylamine |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ImageFile1 = 2-Nitrodiphenylamine-3D-balls.png |
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| ImageAlt1 = Ball-and-stick model of the 2-nitrodiphenylamine molecule |
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| PIN = 2-Nitro-''N''-phenylaniline |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 8100 |
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| ChemSpiderID = 8100 |
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| PubChem = 8407 |
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| EC_number = 204-348-6 |
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| UNNumber = 1661 |
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| ChEMBL = 1450018 |
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| DTXSID = DTXSID4025749 |
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| InChI = 1/C12H10N2O2/c15-14(16)12-9-5-4-8-11(12)13-10-6-2-1-3-7-10/h1-9,13H |
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| InChI = 1/C12H10N2O2/c15-14(16)12-9-5-4-8-11(12)13-10-6-2-1-3-7-10/h1-9,13H |
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| InChIKey = RUKISNQKOIKZGT-UHFFFAOYAD |
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| InChIKey = RUKISNQKOIKZGT-UHFFFAOYAD |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = RUKISNQKOIKZGT-UHFFFAOYSA-N |
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| StdInChIKey = RUKISNQKOIKZGT-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo = <!-- blanked - oldvalue: 119-75-5 --> |
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| CASNo = 119-75-5 |
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| SMILES = O=()C1=C(NC2=CC=CC=C2)C=CC=C1 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = DT9NA7ZDD8 |
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| SMILES = O=()C1=C(NC2=CC=CC=C2)C=CC=C1 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=12|H=10|N=2|O=2 |
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| C=12 | H=10 | N=2 | O=2 |
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| Density = |
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| Density = |
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| MeltingPt = 74 - 75 °C |
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| MeltingPtC = 74 to 75 |
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}} |
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|Section7={{Chembox Hazards |
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| GHSPictograms = {{GHS07}} |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|315|319|335}} |
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| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}} |
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'''2-Nitrodiphenylamine''' is an ] with the formula {{chem2|C6H5NHC6H4NO2}}. It is a ] derivative of ]. It is a red solid, usually found in form of flakes or powder. It is polar but ]. |
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] is used to extend the shelf-life of explosives containing nitrocellulose or nitroglycerin. Such nitrated materials release nitrogen oxides, which deteriorate the device. The diphenylamine traps NO<sub>2</sub>, affording the title compound and related species. And the title compound further traps additional nitrogen oxides.<ref>{{cite journal |doi=10.1016/0003-2670(94)85116-6 |title=Characterization of smokeless gunpowder by means of diphenylamine stabilizer and its nitrated derivatives |date=1994 |last1=Espinoza |first1=Edgard O'N. |last2=Thornton |first2=John I. |journal=Analytica Chimica Acta |volume=288 |issue=1–2 |pages=57–69 }}</ref><ref>{{cite journal |doi=10.1002/prep.201900341 |title=Estimation of the Ballistic Parameters of Double Base Gun Propellants |date=2020 |last1=Boulkadid |first1=Karim M. |last2=Trache |first2=Djalal |last3=Krai |first3=Samir |last4=Lefebvre |first4=Michel H. |last5=Jeunieau |first5=Laurence |last6=Dejeaifve |first6=Alain |journal=Propellants, Explosives, Pyrotechnics |volume=45 |issue=5 |pages=751–758 |s2cid=213752567 }}</ref> One of its major uses is to control the explosion rate of ]. |
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As a stabilizer, its major role is to eliminate the acidic nitrates and ]s produced by gradual decomposition of nitric acid esters, which would otherwise ] further decomposition. Its amount is usually 1-2% of the mixture; higher amounts than 2% degrade the propellant's ballistic properties. The amount of the stabilizer depletes with time; remaining content of less than 0.5% (with initial 2% content) requires increased surveillance of the munition, with less than 0.2% warranting immediate disposal, as the depletion of the stabilizer may lead to autoignition of the propellant.<ref>{{Cite web | url=http://chemicalland21.com/specialtychem/finechem/2-NITRODIPHENYLAMINE.htm |title = 2-Nitrodiphenylamine (O-Nitro-N-Phenylaniline)}}</ref> |
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Other stabilizers of a similar nature are ], ]. While ] (MNA also used in ]), and ] (DPA) are more commonly employed.<ref>{{cite web |url=http://www.islandgroup.com/military/propellant_stabilizers.php |title=PROPELLANT STABILIZERS |access-date=2014-06-07 |archive-url=https://web.archive.org/web/20140715002246/http://www.islandgroup.com/military/propellant_stabilizers.php |archive-date=2014-07-15 |url-status=dead }}</ref> |
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==References== |
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{{Reflist}} |
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==External links== |
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* |
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{{DEFAULTSORT:Nitrodiphenylamine}} |
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] |
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