Chemistry:2-Dimethylaminoethylazide
| |||
| |||
| Names | |||
|---|---|---|---|
| Preferred IUPAC name
2-Azido-N,N-dimethylethan-1-amine | |||
| Other names
Dimethyl(2-azidoethyl)amine
| |||
| Identifiers | |||
3D model (JSmol)
|
|||
| ChemSpider | |||
PubChem CID
|
|||
| |||
| |||
| Properties | |||
| (CH 3) 2NCH 2CH 2N 3 | |||
| Molar mass | 114.152 g·mol−1 | ||
| Appearance | Colorless liquid | ||
| Density | 0.9930 g/cm3 | ||
| Melting point | −68.9 °C (−92.0 °F; 204.2 K) | ||
| Boiling point | 135 °C (275 °F; 408 K) | ||
| Solubility | Acetone, ethers, alcohols, hydrocarbons, THF | ||
| Thermochemistry | |||
Std enthalpy of
formation (ΔfH⦵298) |
+586 cal/g | ||
| Hazards | |||
| Flash point | 29.4 °C (84.9 °F; 302.5 K) | ||
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 | |||
2-Dimethylaminoethylazide (DMAZ) is a liquid rocket fuel being investigated for use as a spacecraft propellent to replace the toxic, carcinogenic monomethylhydrazine.[1] It is a member of the competitive impulse non-carcinogenic hypergol (CINCH) family which were assessed as a replacement for hydrazine-derived propellants.[2][3] DMAZ was also found to be sensitive to impact, direct flame, shock wave, heat in confined space, and electrostatic discharge.[4]
Formation and reactions
DMAZ is an organic azide, which is prepared by reacting the chloride of the corresponding alkyl-amine (in this case ethylamine) with sodium azide:[1]
- NaN
3 + NH
2CH
2CH
2–Cl → NaCl + NH
2CH
2CH
2–N
3
Ideally, the complete combustion of DMAZ produces carbon dioxide, water, and nitrogen:
- 2 (CH
3)
2NCH
2CH
2N
3 + 13 O
2 → 8 CO
2 + 10 H
2O + 4 N
2
Ignition delays
During their inquiry into finding alternative hypergolic fuel, a joint effort by the Aviation and Missile Research, Development, and Engineering Center (AMRDEC), the U.S. Army Research Laboratory (ARL), and the National Aeronautics and Space Administration (NASA) determined that DMAZ could perform competitively with Aerozine-50 and is less toxic than hydrazine-based fuels.[4][5] However, DMAZ-inhibited red fuming nitric acid (IRFNA) systems have demonstrated longer ignition delays than monomethylhydrazine-IRFNA systems. In an effort to address this issue, researchers synthesized the related compounds 2-azidoethanamines – 2-azido-N-methylethanamine (MMAZ) and 2-azido-N-cyclopropylethanamine (CPAZ) in hopes of enhancing the reactivity of DMAZ's amine nitrogen to reduce ignition delays. MMAZ is not hypergolic, while CPAZ is hypergolic.[6]
According to research conducted by Army Research Laboratory, the azido group in DMAZ's lowest energy structure will prevent the transfer of protons from nitric acid to the amine lone pair acid, a chemical reaction that may be associated with a rate-limiting step in DMAZ-IRFNA ignition.[6]
However, according to a 2014 ARL report, a correlation between compound basicities and ignition delays was not observed, which indicates that the proton transfer from nitric acid to DMAZ's amine may not be a rate-controlling step in the ignition process of DMAZ-IRFNA systems.[7]
References
- ↑ 1.0 1.1 Mellor, B. (2004). "A Preliminary Technical Review of DMAZ: A Low-Toxicity Hypergolic Fuel". 557. p. 22. Bibcode: 2004ESASP.557E..22M.
- ↑ "Army Develops New Fuel". Spacedaily.com. February 23, 2000. http://www.spacedaily.com/news/fuel-00c.html.
- ↑ Michael J. McQuaid (April 2004). The Structure of Secondary 2-Azidoethanamines: A Hypergolic Fuel vs. a Nonhypergolic Fuel. Army Research Laboratory. https://apps.dtic.mil/sti/citations/ADA421464.
- ↑ 4.0 4.1 Xie, Hui; Mu, Xiaogang; Zhang, Yue; Wang, Xuanjun (May 8, 2017). "Theory investigation progress of DMAZ". AIP Conference Proceedings 1839 (1): 020016. doi:10.1063/1.4982381. Bibcode: 2017AIPC.1839b0016X.
- ↑ McQuaid, Michael (December 2003). Computationally Based Measures of Amine Azide Basicity and Their Correlation With Hypergolic Ignition Delays. Army Research Laboratory. https://apps.dtic.mil/sti/citations/ADA420016.
- ↑ 6.0 6.1 McQuaid, Michael (September 2002). Computational Characterization of 2-Azidocycloalkanamines: Notional Variations on the Hypergol 2-Azido-N,N-Dimethylethanamine (DMAZ). Army Research Laboratory. https://apps.dtic.mil/sti/citations/ADA405699.
- ↑ Chen, Chiung-Chu; McQuaid, Michael (January 2014). A Thermochemical Kinetic-Based Study of Ignition Delays for 2-Azidoethanamine-Red Fuming Nitric Acid Systems: 2 Azido-N-Methylethanamine (MMAZ) Vs. 2 Azido-N,N-Dimethylethanamine (DMAZ). Army Research Laboratory. https://apps.dtic.mil/sti/citations/ADA599206.
 |  |
