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Author: Subject: nitroethane - and again
Douchermann
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[*] posted on 17-9-2008 at 20:31


Haha well of course I like to experiment, but this reaction is sort of a one time chance, that's why I'm trying to get this going straight forward. I used up the last of my NaBr making the EtBr (and no, it's not OTC anymore here), and used up the last of my NaNO2 to make the AgNO2. I'm trying to prove to myself that this reaction is doable in my current disposition before I spend any more money on it buying more silver, NaNO2, and NaBr (I lost half of my silver due to an unexplainable event). I have done plenty of searching and have done plenty of time wasting experiments like NaEtSO4 + NaNO2, and EtBr + NaNO2 in DMSO (didn't find out about the reaction of EtBr + DMSO until afterwards). I do thank you for all of your help so far though.



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Douchermann
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[*] posted on 19-9-2008 at 20:36


hmm, I like that a lot rosco.

On another note, I attempted the vapor phase nitration of propane today with limited success... the most I got was that it smelled like burning nitromethane. However, the distillate produces no insoluble liquids upon addition of water. If I don't burn off the excess propane however, a white smoke (that doesn't condense in my 400mm liebig) will be evolved from the tube. However, it appears that this white smoke is at least somewhat flammable... perhaps the white smoke is the nitroalkane mix that isn't fond of condensing. The experiment was cut short as some liquid touched the hot glass tube and broke it...

BTW, the combustion tube is a 5ft long 1" O.D glass tube, and I build a custom 5ft long burner to accommodate for it. The tube appeared to have NO2 in it (it seemed to have a reddish tint to it). I had to keep the propane moving moderately fast to kick up enough HNO3, certainly not the recommended 15 seconds. I have no way of accurately determining the temperature, so it's basically a crap shoot at the moment. Any comments, or questions?




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Rosco Bodine
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[*] posted on 13-11-2010 at 19:17


The pyrophoric nature of vapors remaining from distillations of this particular organic nitro compound which I reported, is now something which I have seen described by others as an explosion hazard for structurally related compounds, although I do not have the citations handy. There have been other reports of explosions which occured upon venting of distillation apparatus to the atmosphere, after distillations were completed, it being evident that residual vapors inside the distillation apparatus were pyrophoric and exploded immediately upon exposure to air. So my caveat is reiterated, that at a minimum the distillation apparatus should be allowed to cool completely before opening or venting. Perhaps as a prudent additional precaution the residual vapors should be purged with a non-flammable, non-oxidizing, non-reactive gas or vapor, before opening the distillation apparatus to the air.

Additionally I have found the following article of possible interest.

Attachment: Nitroethane article - Journal_of_the_Chemical_Society circa 1906.pdf (266kB)
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Rosco Bodine
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[*] posted on 14-11-2010 at 13:24


Quote: Originally posted by Polverone  
Rosco, that is an interesting procedure. I have never heard of it before and I've read plenty of articles on nitroalkane production. Is it from a patent? Something you worked out yourself? If you have more detailed notes on procedure and yield I'd be very interested in seeing them.


Thanks to solo for helping with this illuminating reference attached. It is of course the article which was basis for my experiment forty years ago, so from memory I was a bit vague on the details, for example the sulfanilic acid as a
surfactant. I recall more correctly now ( I think ) that the sulfanilic acid actually came into use as a surfactant for
isosafrole oxidation to piperonal via aqueous sodium dichromate plus H2SO4....a parallel procedure which was somehow related in the general time frame to the nitroethane synthesis :D The details are a bit unclear to me now, as that was a time in my younger days when sexual exhaustion and other distracting activities took a tremendous toll on my powers of concentration, so
my memories of details of experiments during those years tend to be a bit muddled .....forgive me. Those were
"the good old days" if you get my meaning :D :cool:

http://www.youtube.com/watch?v=5LxC3M-Yngs&fmt=18 Harry Nilsson - Put The Lime In The Coconut (1971)

Attachment: Preparation of nitroethane JCS, 1944, 24-25 .pdf (381kB)
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[Edited on 14-11-2010 by Rosco Bodine]
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simba
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[*] posted on 1-8-2011 at 11:16


what about bubbling NO2 gas through ethyl iodide/bromide?

My only fear is that nitroethane may form an explosive mixture with the residual NO2, but I feel the amount of NO2 won't be enough to cause any harm in this case.

What are your thoughts on that?
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chucknorris
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[*] posted on 4-11-2012 at 10:47


Ok tried some NE today.

Following problems occured:

The NAETSO did not fully solved to the water, even hot one, (325ml water + 222g naetso), but remained solid particles at the bottom. Flowed through dropper funnel anyways.

The whole mixture boiled up at around 95-110C and reached dry stage at 114C. Then made salt separation, put chloroform in and separated the chloro layer and distilled it - everything came over before reaching even 110C temp. So most likely no NE was produced at all, huh?

Used CO2 as inert gas for preventing possible detonation risk.

Is my 2kw hot plate defective, I could never reach even close to 120-130c what is the normal heat level even when using al foil as radiation enhancer?
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[*] posted on 14-12-2012 at 13:50


I've just come across with this. :)

"Получение нитроэтана AgNO2 + EtBr"
"Getting nitroethane AgNO2 + EtBr"

http://tor4.su/phpBB/viewtopic.php?f=37&t=5495

Translation with Google:

"Getting nitroethane AgNO2 + EtBr

Post Ufo_i ┬╗December 15, 2007, 04:54
Nitroethane

Reagents:

Diethyl ether (150 ml) - dried over KOH and drained, not distilled.
AgNO2 (65.5 g) was stored in the dark over calcium chloride (~ 2 months).
EtBr (40.9g) - dried with calcium chloride, then do not distilled.

In 500 ml flask, wrapped with foil to protect it, pour the cooled air in the freezer and stirring tonkorasterty silver nitrite (all this in a darkened room, of course). To this mixture for 3 hours, with 4 portions added bromoethane, who was also a pre-cooled in the freezer. In between additions flask capped, stored in a refrigerator at 4 C and periodically shaken.
When the addition is complete the bulb is:

at 4C - 24 hours
at 10C - 24 hours
at room temperature - 40 hours

vstyahivaetsya and when she remembered about (3-10 a day)

Now then towed to a / b, the flask was added 300 ml of distilled water and nitroethane as an azeotrope with water. Layer containing nitroethane, separated (~ 18 g), the aqueous portion extracted with 25 ml of DCM. The extract is combined with nitroethane, dried with magnesium sulfate and dispersed by 20 cm column.

Nitroethane yield about 50% of theory"

At the end it's quite muddled :( .
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AndersHoveland
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[*] posted on 14-12-2012 at 15:06


Direct nitration is probably possible, using nitric acid, ethane gas, and a small quantity of N-hydroxyphthalimide (NHPI) as a catalyst.



I'm not saying let's go kill all the stupid people...I'm just saying lets remove all the warning labels and let the problem sort itself out.
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