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Author: Subject: Nitration and acetone
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[*] posted on 17-7-2019 at 17:42
Nitration and acetone


About 2 years ago, I had an accident in which I mixed a small amount of fuming nitric acid and acetone inside a graduated cylinder. The mixture quickly began bubbling and fuming, and within a few seconds, the contents of the cylinder were ejected onto my ceiling, leaving a nasty blotch. I had wondered why this happened, so today I revisited it, adding acetone to a test tube containing fuming nitric acid. This time, it wasn't as violent (maybe because I added acetone to RFNA, and last time I added RFNA to acetone) but the reaction was still vigorous, ejecting plenty of RFNA and acetone from the test tube, after copious bubbling and production of nitrogen dioxide. Luckily, I worked outside this time. Anyhow, I was wondering if anyone has some sort of insight into how this happens, I'd be interested to hear it. All over the internet, there are reports of injuries and accidents involving acetone and nitric acid. So my question is: is the acetone being oxidized, or is it being nitrated? Is it oxidized directly to carbon dioxide, water and nitrogen, or is there an intermediate?


Finally, I seem to recall that I heard some reference to nitric acid being able to convert acetone to a powerful and sensitive explosive. I thought I saw that on this board. I plan to do a test in which I will attempt to see what product may be produced if I add very cold nitric acid to very cold acetone under strong stirring, and then evaporate the solution. I'll try and post some pictures/videos of the acetone/nitric acid, and this test when I get around to it. Anyway, any response or insight would be appreciated.
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Sulaiman
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[*] posted on 17-7-2019 at 22:51


Nitric acid plus acetone = formic acid plus acetic acid plus heat
if allowed to heat up then https://www.youtube.com/watch?v=uFwiZYfEsuY

Conc. nitric acid is very oxidising when hot, less so when cool (and/or diluted),
so reactions often start very slowly then suddenly run away.
(usually producing lots of NO2)




CAUTION : Hobby Chemist, not Professional or even Amateur
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Pumukli
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[*] posted on 18-7-2019 at 02:55


Isn't formic acid oxidized further immediately? (CO2, H2O, more heat)

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[*] posted on 18-7-2019 at 11:15


According to US3491160A, acetone can be destructively nitrated to nitroform be fuming nitric acid. I have used this method myself from time to time.
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[*] posted on 18-7-2019 at 13:21


Now THAT’S what I’m talking about. I’ll try it tomorrow. I’m just worried about an accident or runaway.
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[*] posted on 19-7-2019 at 10:08


Just add the acetone gradually. The reaction is quite violent (I think I preheated the nitric acid when I did it, but it was quite some years ago, so I'm not entirely certain), and I think I remember some alternate methods, possibly from other patents, which aimed to tame the reaction a little.
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