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Author: Subject: Make 2-Dimethylaminoethylazide
APO
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[*] posted on 11-2-2013 at 11:18
Make 2-Dimethylaminoethylazide


I want to make 2-Dimethylaminoethylazide for rocket propellant testing, but I have know idea how, it sounds like it's competitive to hydrazine.
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Hexavalent
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[*] posted on 11-2-2013 at 11:30


I'm not sure about an exact synthesis, but you might want to look into the Dutt-Wormall reaction for producing azides, where a diazonium salt reacts with a sulfonamide to give a diazoaminosulfinate intermediate, which undergoes hydrolysis to yield the azide and a sulfinic acid.



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Valentine
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[*] posted on 11-2-2013 at 12:27


1. Ethylene chlorohydrin + 2 dimethylamine --> dimethylaminoethanol + dimethylammonium chloride

2. Dimethylaminoethanol + thionyl chloride --> 2-dimethylaminoethyl chloride hydrochloride + SO2 + HCl &nbsp&nbsp&nbsp&nbsp&nbsp&nbsp&nbsp&nbsp [Organic Syntheses, Coll. Vol. 4, p.333 (1963)]

3. 2-Dimethylaminoethyl chloride hydrochloride + NaOH --> 2-Dimethylaminoethyl chloride + NaCl

+ NaN3 (to the same pot) --> 2-Dimethylaminoethylazide + NaCl

I would choose this way probably.

(If 3 wouldn't work very well, I would make 2-dimethylaminoethyl hydrazine from dimethylaminoethyl chloride and hydrazine, then I would react it with acidic NaNO2 to prepare the azide)

[Edited on 11-2-2013 by Valentine]
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kristofvagyok
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[*] posted on 11-2-2013 at 12:30


Quote: Originally posted by APO  
I want to make 2-Dimethylaminoethylazide for rocket propellant testing

You read something on wiki and instantly post it here. Great.

It is usually made from dimethylamino-ethylchloride and sodium azide in water, easy synthesis like 1x1.

The only problem is that the dimethylamino-ethylchloride is a really effective vesicant, so forget to work with this in time, else way you will have really nice blisters on your skin.




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[*] posted on 11-2-2013 at 16:44


Well, I couldn't find a source on how to make it, so why not ask a public forum. Besides if it has any power close to hydrazine and is non-carcinogenic, why shouldn't it be considered as a fuel for my rocket engine? Thanks anyways.
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