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{{Orphan|date=February 2009}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 271672001 |
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| ImageFile = DMAZ.png |
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| ImageFile = DMAZ.png |
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| ImageSize = 150px |
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| ImageSize = 150px |
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| ImageFileL1 = 2-Dimethylaminoethylazide Ball and Stick.png |
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| IUPACName = (2-Azido-ethyl)-dimethyl-amine |
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| OtherNames = |
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| ImageSizeL1 = 150px |
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| ImageFileR1 = 2-Dimethylaminoethylazide Space Fill.png |
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| Section1 = {{Chembox Identifiers |
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| ImageSizeR1 = 150px |
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| PIN = 2-Azido-''N'',''N''-dimethylethan-1-amine |
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| OtherNames = Dimethyl(2-azidoethyl)amine |
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|Section1={{Chembox Identifiers |
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| CASNo = 86147-04-8 |
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| CASNo = 86147-04-8 |
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| PubChem = |
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| PubChem = 22280928 |
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| SMILES = CN(C)CCN== |
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| SMILES = CN(C)CCN== |
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| ChemSpiderID = 11308317 |
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| InChI = 1/C4H10N4/c1-8(2)4-3-6-7-5/h3-4H2,1-2H3 |
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| InChIKey = XIXCIVDAWWCJJR-UHFFFAOYAI |
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| StdInChI = 1S/C4H10N4/c1-8(2)4-3-6-7-5/h3-4H2,1-2H3 |
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| StdInChIKey = XIXCIVDAWWCJJR-UHFFFAOYSA-N |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = {{chem2|(CH3)2NCH2CH2N3}} |
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| C=4 | H=10 | N=4 |
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| C=4|H=10|N=4 |
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| Appearance = |
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| Appearance = Colorless liquid |
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| Density = |
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| Density = 0.9930 g/cm<sup>3</sup> |
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| MeltingPt = |
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| BoilingPt = |
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| MeltingPtC = -68.9 |
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| Solubility = }} |
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| BoilingPtC = 135 |
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| Solubility = |
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| Section3 = {{Chembox Hazards |
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| SolubleOther = Acetone, ethers, alcohols, hydrocarbons, THF}} |
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| MainHazards = |
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|Section3={{Chembox Thermochemistry |
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| FlashPt = |
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| Autoignition = }} |
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| DeltaHf = +586 cal/g}} |
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|Section4={{Chembox Hazards |
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| MainHazards = |
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| FlashPtC = 29.4 |
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| AutoignitionPtC = }} |
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'''2-Dimethylaminoethylazide''' ('''DMAZ''') is a liquid fuel being investigated for use as a spacecraft propellent to replace the toxic, carcinogenic ].<ref>{{cite journal | title = A Preliminary Technical Review of DMAZ: A Low-Toxicity Hypergolic Fuel | author = Mellor, B. | journal = Proceedings of the 2nd International Conference on Green Propellants for Space Propulsion | year = 2004 | url = http://adsabs.harvard.edu/full/2004ESASP.557E..22M | pages = 22 }}</ref> |
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'''2-Dimethylaminoethylazide''' ('''DMAZ''') is a liquid ] being investigated for use as a spacecraft propellent to replace the toxic, carcinogenic ].<ref name=":2">{{cite conference |title = A Preliminary Technical Review of DMAZ: A Low-Toxicity Hypergolic Fuel | author = Mellor, B. |book-title=Proceedings of the 2nd International Conference on Green Propellants for Space Propulsion | volume = 557 | year = 2004 | bibcode = 2004ESASP.557E..22M | page = 22 }}</ref> It is a member of the competitive impulse non-carcinogenic ] (CINCH) family which were assessed as a replacement for ]-derived propellants.<ref>{{cite web|url=http://www.spacedaily.com/news/fuel-00c.html |title=Army Develops New Fuel |publisher=Spacedaily.com |date=February 23, 2000 |access-date=July 12, 2014}}</ref><ref>{{cite journal |title=The Structure of Secondary 2-Azidoethanamines: A Hypergolic Fuel vs. a Nonhypergolic Fuel |website=Defense Technical Information Center |url=https://apps.dtic.mil/sti/citations/ADA421464 | date = April 2004 | author = Michael J. McQuaid | publisher = Army Research Laboratory }}</ref> DMAZ was also found to be sensitive to impact, direct flame, shock wave, heat in confined space, and electrostatic discharge.<ref name=":0">{{Cite journal|last1=Xie|first1=Hui|last2=Mu|first2=Xiaogang|last3=Zhang|first3=Yue|last4=Wang|first4=Xuanjun|date=May 8, 2017|title=Theory investigation progress of DMAZ|journal=AIP Conference Proceedings|volume=1839|issue=1|page=020016|doi=10.1063/1.4982381|bibcode=2017AIPC.1839b0016X|doi-access=free}}</ref> |
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==Formation and reactions== |
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{{expand section|date=February 2022}} |
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DMAZ is an organic azide, which is prepared by reacting the chloride of the corresponding alkyl-amine (in this case ]) with ]:<ref name=":2" /> |
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:{{chem2|NaN3 + N(CH3)2CH2CH2\sCl → NaCl + N(CH3)2CH2CH2\sN3}} |
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Ideally, the complete combustion of DMAZ produces carbon dioxide, water, and nitrogen: |
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:{{chem2|2 (CH3)2NCH2CH2N3 + 13 O2 → 8 CO2 + 10 H2O + 4 N2}} |
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==Ignition delays== |
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During their inquiry into finding alternative hypergolic fuel, a joint effort by the ] (AMRDEC), the ] (ARL), and the ] (NASA) determined that DMAZ could perform competitively with ] and is less toxic than hydrazine-based fuels.<ref name=":0" /><ref>{{Cite journal |last=McQuaid|first=Michael|date=December 2003|title=Computationally Based Measures of Amine Azide Basicity and Their Correlation With Hypergolic Ignition Delays |website=Defense Technical Information Center |url=https://apps.dtic.mil/sti/citations/ADA420016 |publisher=Army Research Laboratory }}</ref> However, DMAZ-] (IRFNA) systems have demonstrated longer ignition delays than ]-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 ].<ref name=":1">{{Cite journal |last=McQuaid|first=Michael|date=September 2002|title=Computational Characterization of 2-Azidocycloalkanamines: Notional Variations on the Hypergol 2-Azido-N,N-Dimethylethanamine (DMAZ) |website=Defense Technical Information Center |url=https://apps.dtic.mil/sti/citations/ADA405699 |publisher=Army Research Laboratory}}</ref> |
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According to research conducted by Army Research Laboratory, the ] 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 ] in DMAZ-IRFNA ignition.<ref name=":1" /> |
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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.<ref>{{Cite journal |last1=Chen|first1=Chiung-Chu|last2=McQuaid|first2=Michael|date=January 2014|title=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) |website=Defense Technical Information Center |url=https://apps.dtic.mil/sti/citations/ADA599206 |publisher=Army Research Laboratory}}</ref> |
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==References== |
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==References== |
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{{reflist}} |
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{{reflist}} |
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== Further reading == |
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*{{Cite encyclopedia |title=Aliphatic Amines |chapter=N,N-Dimethyl-2‑azidoethylamine (DMAZ)|encyclopedia=Encyclopedia of Liquid Fuels |publisher=De Gruyter |last=Schmidt |first=Eckart W. |date=2022 |pages=156–172 |doi=10.1515/9783110750287-002 |isbn=978-3-11-075028-7}} |
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{{DEFAULTSORT:Dimethylaminoethylazide, 2-}} |
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