Ammonium dinitramide
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IUPAC name
Ammonium dinitramide
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Identifiers | |
3D model (
JSmol ) |
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ChemSpider | |
ECHA InfoCard
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100.126.585 |
EC Number |
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PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
H4N4O4 | |
Molar mass | 124.06 g/mol |
Density | 1.81 g/cm3 |
Melting point | 93 °C (199 °F; 366 K) |
Boiling point | decomposes at 127 °C (261 °F; 400 K) |
Hazards | |
GHS labelling: | |
Danger | |
H201, H228, H302, H371 | |
P210, P230, P240, P241, P250, P260, P264, P270, P280, P301+P312, P309+P311, P330, P370+P378, P370+P380, P372, P373, P401, P405, P501 | |
Thermochemistry | |
Std enthalpy of (ΔfH⦵298)formation |
-148 kJ/mol[1] |
Gibbs free energy (ΔfG⦵)
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−150.6 kJ/mol |
Explosive data | |
Shock sensitivity | Low[1] |
Friction sensitivity | Low |
Related compounds | |
Other cations
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Guanylurea dinitramide |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Ammonium dinitramide (ADN) is the ammonium salt of dinitraminic acid. ADN decomposes under heat to leave only nitrogen, oxygen, and water. The ions are the ammonium ion NH4+ and the dinitramide N(NO2)2−.
It makes an excellent
The EURENCO Bofors company produced LMP-103S as a 1-to-1 substitute for hydrazine by dissolving 65% ammonium dinitramide, NH4N(NO2)2, in 35% water solution of methanol and ammonia. LMP-103S has 6% higher specific impulse and 30% higher impulse density than hydrazine monopropellant. Additionally, hydrazine is highly toxic and carcinogenic, 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 Prisma satellite in 2010. Special handling is not required. LMP-103S could replace hydrazine as the most commonly used monopropellant.[2][3]
The ADN-based monopropellant FLP-106 is reported to have improved properties relative to LMP-103S, including higher performance (ISP of 259 s vs. 252 s) and density (1.362 g/cm3 vs. 1.240 g/cm3).[4]
History
Ammonium dinitramide was invented in 1971 at the Zelinskiy Institute of Organic Chemistry in the USSR. Initially all information related to this compound was classified because of its use as a rocket propellant, particularly in
Preparation
There are at least 20 different synthesis routes that produce Ammonium dinitramide. In the laboratory ammonium dinitramide can be prepared by nitration of sulfamic acid or its salts at low temperatures.
- KSO3NH2 + 2HNO3 → KHSO4 + NH4N(NO2)2 + H2O
The process is performed under red light, since the compound is decomposed by higher energy photons. The details of the synthesis remain classified.
Other sources[
Another synthesis known as the urethane synthesis method requires four synthesis steps and results in a yield of up to 60%.
- CH3CH2OC(O)NH2 + HNO3 → CH3CH2OC(O)NHNO2 + H2O
- CH3CH2OC(O)NHNO2 + NH3 → CH3CH2OC(O)NNO2NH4
- CH3CH2OC(O)NNO2NH4 + N2O5 → CH3CH2OC(O)N(NO2)2 + NH4NO3
- CH3CH2OC(O)N(NO2)2 + 2NH3 → CH3CH2OC(O)NH2 + NH4N(NO2)2
References
- ^ S2CID 94304770.
- ^ "Green propellant LMP 103S". ecaps.se. Retrieved 2024-04-25.
- ISSN 0721-3115.
- ISBN 978-953-307-551-8.
- ^ a b "Dinitramide Salts: ADN Plus Other Salts". SRI International. Archived from the original on 2012-05-26. Retrieved 2012-04-15.
- ^ US 5714714, Stern, Alfred G.; Koppes, William M. & Sitzmann, Michael E. et al., "Process for preparing ammonium dinitramide", published 1998-02-03, assigned to USA, Secretary of the Navy
Further reading
This article includes a list of general references, but it lacks sufficient corresponding inline citations. (February 2012) |
- Modern rocket fuels> PDF> Hesiserman Online Library
- Textbook of Chemistry 1999 Prentice Press, New York
- Subbiah Venkatachalam; Gopalakrishnan Santhosh; Kovoor Ninan Ninan (2004). "An Overview on the Synthetic Routes and Properties of Ammonium Dinitramide (ADN) and other Dinitramide Salts". Propellants, Explosives, Pyrotechnics. 29 (3): 178–187. .