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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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| Verifiedfields = changed |
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| verifiedrevid = 477366559 |
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| Watchedfields = changed |
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| verifiedrevid = 437302525 |
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| ImageFile = Ammonium dinitramide.png |
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| ImageFile = Ammonium dinitramide.png |
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| ImageSize = 220px |
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| ImageSize = 220px |
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| IUPACName = Ammonium dinitramide |
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| IUPACName = Azanium dinitroazanide<ref name=pubchem/> |
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| OtherNames = {{ubl|Ammonium dinitroazanide<ref name="pubchem">{{Cite web |title=Ammonium dinitramide |url=https://pubchem.ncbi.nlm.nih.gov/compound/10219428 |access-date=2024-07-18 |website=pubchem.ncbi.nlm.nih.gov}}</ref>|Ammonium dinitramide<ref name=pubchem/>}} |
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| OtherNames = |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo_Ref = {{cascite|correct|PubChem}} |
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| CASNo = <!-- blanked - oldvalue: 140456-78-6 --> |
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| CASNo = 140456-78-6 |
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| PubChem = |
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| EC_number = 604-184-9 |
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| MeSHName = |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| PubChem = 10219428 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 8394920 |
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| ChemSpiderID = 8394920 |
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| SMILES = .((=O))(=O) |
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| UNII = 8JCB80Q5K1 |
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| SMILES = .((=O))(=O) |
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| InChI = 1/N3O4.H3N/c4-2(5)1-3(6)7;/h;1H3/q-1;/p+1 |
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| InChI = 1/N3O4.H3N/c4-2(5)1-3(6)7;/h;1H3/q-1;/p+1 |
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| InChIKey = BRUFJXUJQKYQHA-IKLDFBCSAM |
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| InChIKey = BRUFJXUJQKYQHA-IKLDFBCSAM |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/N3O4.H3N/c4-2(5)1-3(6)7;/h;1H3/q-1;/p+1 |
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| StdInChI = 1S/N3O4.H3N/c4-2(5)1-3(6)7;/h;1H3/q-1;/p+1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = BRUFJXUJQKYQHA-UHFFFAOYSA-O |
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| StdInChIKey = BRUFJXUJQKYQHA-UHFFFAOYSA-O |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = {{chem2|}} |
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| H = 4 | N = 4 | O = 4 |
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| H=4 | N=4 | O=4 |
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| MolarMass = 124.06 g/mol |
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| MolarMass = 124.06 g/mol |
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| Appearance = |
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| Appearance = |
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| Density = 1.81 g/cm<sup>3</sup> |
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| Density = 1.81 g/cm<sup>3</sup> |
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| MeltingPtC = 93 |
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| MeltingPtC = 93 |
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| BoilingPt = decompose |
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| BoilingPt = decomposes at {{convert|127|C|F K|abbr=on}} |
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| Solubility = }} |
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}} |
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| Section3 = {{Chembox Hazards |
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| Section3 = {{Chembox Structure |
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| Structure_ref = <ref name=pubchem/> |
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| LattConst_a = 6.914 ] |
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| LattConst_b = 11.787 Å |
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| LattConst_c = 5.614 Å |
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| LattConst_alpha = 90.00 |
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| LattConst_beta = 100.40 |
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| LattConst_gamma = 90.00 |
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| UnitCellFormulas = 4 |
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}} |
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| Section4 = {{Chembox Thermochemistry |
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| DeltaGf = −150.6 kJ/mol |
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| DeltaHf= −148 kJ/mol<ref name="properties1" /> |
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}} |
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|Section6={{Chembox Explosive |
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| ShockSens = Low<ref name="properties1">{{cite journal |last1=Östmark |first1=H. |last2=Bemm |first2=U. |last3=Langlet |first3=A. |last4=Sandén |first4=R. |last5=Wingborg |first5=N. |title=The properties of ammonium dinitramide (ADN): Part 1, basic properties and spectroscopic data |journal=Journal of Energetic Materials |date=1 June 2000 |volume=18 |issue=2–3 |pages=123–138 |doi=10.1080/07370650008216116 |bibcode=2000JEnM...18..123O |s2cid=94304770 |url=https://www.tandfonline.com/doi/abs/10.1080/07370650008216116 |issn=0737-0652}}</ref> |
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| FrictionSens = Low |
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|Section7={{Chembox Hazards |
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| GHSPictograms = {{GHS01}}{{GHS02}}{{GHS07}}{{GHS08}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|201|228|302|371}} |
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| PPhrases = {{P-phrases|210|230|240|241|250|260|264|270|280|301+312|309+311|330|370+378|370+380|372|373|401|405|501}} |
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| MainHazards = |
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| FlashPt = |
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| Autoignition = }} |
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| NIOSH_id = 7175 |
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| Section6 = {{Chembox Explosive |
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|Section8= {{Chembox Related |
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'''Ammonium dinitramide''' ('''ADN''') is an ] with the ] {{chem2||auto=1}}. It is the ] ] of ] {{chem2|HN(NO2)2}}. It consists of ammonium ] {{chem2|+}} and dinitramide ] {{chem2|−N(NO2)2}}. ADN decomposes under heat to leave only ], ], and ]. |
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It makes an excellent ] oxidizer with a slightly higher ] than ] and, more importantly, does not leave corrosive ] fumes. This property is also of military interest because halogen-free smoke is harder to detect. It decomposes into low-molecular-mass gases, which contributes to higher performance without creating excessive temperatures if used in gun or ]s. However, the dinitramide salt is more prone to detonation under high temperatures and shock compared with the ]. |
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The ] Bofors company produced LMP-103S as a 1-to-1 substitute for ] by dissolving 65% ammonium dinitramide, {{chem2|N(NO2)2}}, in 35% water solution of ] and ammonia. LMP-103S has 6% higher specific impulse and 30% higher impulse density than hydrazine ]. Additionally, hydrazine is highly toxic and ], while LMP-103S is only moderately toxic. LMP-103S is UN Class 1.4S, allowing for transport on commercial aircraft, and was demonstrated on the ] in 2010. Special handling is not required. LMP-103S could replace hydrazine as the most commonly used monopropellant.<ref>{{Cite web |title=Green propellant LMP 103S |url=https://www.ecaps.se/rocket-fuel-1 |access-date=2024-04-25 |website=ecaps.se}}</ref><ref>{{Cite journal |last1=Persson |first1=Mathias |last2=Anflo |first2=Kjell |last3=Friedhoff |first3=Pete |date=2019 |title=Flight Heritage of Ammonium Dinitramide (ADN) Based High Performance Green Propulsion (HPGP) Systems |url=https://onlinelibrary.wiley.com/doi/10.1002/prep.201900248 |journal=Propellants, Explosives, Pyrotechnics |volume=44 |issue=9 |pages=1073–1079 |doi=10.1002/prep.201900248 |issn=0721-3115}}</ref> |
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The ADN-based monopropellant FLP-106 is reported to have improved properties relative to LMP-103S, including higher performance (] of 259 s vs. 252 s) and density (1.362 g/cm<sup>3</sup> vs. 1.240 g/cm<sup>3</sup>).<ref>{{Cite book |last1=Larsson |first1=Anders |url=http://www.intechopen.com/books/advances-in-spacecraft-technologies |title=Advances in Spacecraft Technologies |last2=Wingborg |first2=Niklas |date=2011-02-14 |publisher=InTech |isbn=978-953-307-551-8 |editor-last=Hall |editor-first=Jason |chapter=Green Propellants Based on Ammonium Dinitramide (ADN) |doi=10.5772/13640 |chapter-url=https://cdn.intechopen.com/pdfs/13473/InTech-Green_propellants_based_on_ammonium_dinitramide_adn_.pdf |doi-access=free}}</ref> |
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== History == |
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Ammonium dinitramide was invented in 1971 at the ] in the ]. Initially all information related to this compound was ] because of its use as a ], particularly in ] ]. In 1989 ammonium dinitramide was independently synthesized at ].<ref name="sri">{{cite web |url=http://www.sri.com/psd/research/adn.html |title=Dinitramide Salts: ADN Plus Other Salts |publisher=] |accessdate=2012-04-15 |url-status=dead |archiveurl=https://web.archive.org/web/20120526005446/http://www.sri.com/psd/research/adn.html |archivedate=2012-05-26}}</ref> SRI obtained US and international patents for ADN in the mid-1990s, at which time scientists from the former ] revealed that they had discovered ADN 18 years earlier.<ref name="sri"/> |
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== Propellant mixtures == |
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ADN can be mixed with conventional ] such as ] to improve its ].<ref>{{Cite journal |last1=Wang |first1=Qiong |last2=Wang |first2=Xiao-Hong |last3=Pan |first3=Qing |last4=Chang |first4=Hai |last5=Yu |first5=Hong-Jian |last6=Pang |first6=Wei-Qiang |date=3 March 2023 |title=Thermal Behaviors and Interaction Mechanism of Ammonium Dinitramide with Nitrocellulose |journal=Molecules |volume=28 |issue=5 |page=2346 |doi=10.3390/molecules28052346 |doi-access=free |pmid=36903591 |pmc=10005589 }}</ref> One of the challenges of using ADN is its ]. Hu et al. have investigated the possibility of reducing the hygroscopicity of ADN by co-crystallization with ].<ref>{{Cite journal |last1=Hu |first1=Dongdong |last2=Wang |first2=Yinglei |last3=Xiao |first3=Chuan |last4=Hu |first4=Yifei |last5=Zhou |first5=Zhiyong |last6=Ren |first6=Zhongqi |date=September 2023 |title=Studies on ammonium dinitramide and 3,4-diaminofurazan cocrystal for tuning the hygroscopicity |url=https://doi.org/10.1016/j.cjche.2023.01.006 |journal=Chinese Journal of Chemical Engineering |volume=61 |pages=157–164 |doi=10.1016/j.cjche.2023.01.006 |via=Elsevier Science Direct}}</ref> |
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There is also interest in using ADN to make liquid ]s. When ADN is co-crystalized with a ] (]), the hygroscopicity is greatly reduced, but so is its performance as an explosive.<ref>{{Cite journal |last1=Qiao |first1=Shen |last2=Li |first2=Hong-zhen |last3=Yang |first3=Zong-wei |date=June 2022 |title=Decreasing the hygroscopicity of ammonium dinitramide (ADN) through cocrystallization |journal=Energetic Materials Frontiers |volume=3 |issue=2 |pages=84–89 |doi=10.1016/j.enmf.2022.03.001 |doi-access=free }}</ref> ADN was mixed with amine nitrates in order to lower its melting point for use as a liquid monopropellant. The onset temperature for ADN was essentially unchanged, but some cross-reaction with the amine nitrates was observed.<ref>{{Cite journal |last1=Matsunaga |first1=Haroki |last2=Katoh |first2=Katsumi |last3=Habu |first3=Hiroto |last4=Noda |first4=Masaru |last5=Miyake |first5=Atsumi |date=November 2018 |title=Thermal behavior of ammonium dinitramide and amine nitrate mixtures |url=https://doi.org/10.1007/s10973-018-7875-6(01 |journal=Journal of Thermal Analysis and Calorimetry |volume=135 |pages=2677–2685 |doi=10.1007/s10973-018-7875-6(01 |doi-broken-date=13 December 2024 |via=Academic Search Ultimate}}</ref> Kim et al. have also examined mixtures of ADN with ] as a potential liquid monopropellant.<ref>{{Cite journal |last1=Kim |first1=Ju Won |last2=Bhosale |first2=Vikas Khandu |last3=Kim |first3=Kyu-Seop |last4=Lee |first4=Seung Ho |last5=Kwon |first5=Sejin |date=February 2, 2022 |title=Room-temperature catalytically reactive ammonium dinitramide–H2O2 monopropellant for microsatellites |url=https://doi.org/10.1016/j.asr.2021.11.022 |journal=Advances in Space Research |volume=69 |issue=3 |pages=1631–1644 |doi=10.1016/j.asr.2021.11.022 |via=Elsevier Science Direct}}</ref> |
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== Preparation == |
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There are at least 20 different synthesis routes that produce ammonium dinitramide. In the laboratory ammonium dinitramide can be prepared by nitration of ] or its salts (here potassium sulfamate) at low temperatures: |
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: {{chem2|KSO3NH2 + 2 ] → ] + N(NO2)2 + ]}} |
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The process is performed under red light, since the compound is decomposed by higher-energy ]. The details of the synthesis remain classified. |
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Other sources{{who?|date=February 2019}} report ammonium synthesis from ], anhydrous ], and ] (oleum) containing 20% free ]. A ] other than ] must be added before the acid dinitramide decomposes. The final product is obtained by ]. |
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Another synthesis known as the ] synthesis method requires four synthesis steps and results in a yield of up to 60%.<ref>{{cite patent |country=US |number=5714714 |pubdate=1998-02-03 |title=Process for preparing ammonium dinitramide |assign1=] |inventor1-last=Stern |inventor1-first=Alfred G. |inventor2-last=Koppes |inventor2-first=William M. |inventor3-last=Sitzmann |inventor3-first=Michael E. |inventor4=Lori A. Nock; Donna M. Cason-Smith}}</ref> ] is nitrated with ]: |
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: {{chem2|] + HNO3 → CH3CH2\sO\sC(\dO)\sNH\sNO2 + H2O}} |
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and then reacted with ammonia to form the ammonium salt of ''N''-nitrourethane: |
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: {{chem2|CH3CH2\sO\sC(\dO)\sNH\sNO2 + ] → }} |
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This is nitrated again with ] to form ethyl dinitrocarbamate and ]: |
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: {{chem2| + ] → CH3CH2\sO\sC(\dO)\sN(NO2)2 + +NO3−]]}} |
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Finally, treatment with ammonia again splits off the desired ammonium dinitramide and regenerates the urethane starting material: |
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: {{chem2|CH3CH2\sO\sC(\dO)\sN(NO2)2 + 2 NH3 → CH3CH2\sO\sC(\dO)\sNH2 + }} |
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==References== |
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{{reflist}} |
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==Further reading== |
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{{More footnotes|date=February 2012}} |
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* Modern rocket fuels> PDF> Hesiserman Online Library |
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* ''Textbook of Chemistry'' 1999 Prentice Press, New York |
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*{{cite journal |
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| journal = Propellants, Explosives, Pyrotechnics |
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| volume = 29 |
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| issue = 3 |
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| pages = 178–187 |
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| year = 2004 |
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| title = An Overview on the Synthetic Routes and Properties of Ammonium Dinitramide (ADN) and other Dinitramide Salts |
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|author1=Subbiah Venkatachalam |author2=Gopalakrishnan Santhosh |author3=Kovoor Ninan Ninan | doi = 10.1002/prep.200400043}} |
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*{{Cite journal |last1=Chen |first1=Fu-yao |last2=Xuan |first2=Chun-lei |last3=Lu |first3=Qiang-qiang |last4=Xiao |first4=Lei |last5=Yang |first5=Jun-qing |last6=Hu |first6=Yu-bing |last7=Zhang |first7=Guang-Pu |last8=Wang |first8=Ying-lei |last9=Zhao |first9=Feng-qi |last10=Hao |first10=Ga-zi |last11=Jiang |first11=Wei |date=January 2023 |title=A review on the high energy oxidizer ammonium dinitramide: Its synthesis, thermal decomposition, hygroscopicity, and application in energetic materials |journal=Defence Technology |volume=19 |pages=163–195 |doi=10.1016/j.dt.2022.04.006 |issn=2214-9147 |doi-access=free}} |
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