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Author: Subject: Diethyl ether peroxide
zeppelin69
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[*] posted on 20-2-2007 at 20:14
Diethyl ether peroxide


I hope I dont get run off for making such a "kewl" first post, but I am curious about this compound, and I want to learn more about it. I havent been able to find anything about it though except for wikipedia's short discription as a very powerful organic peroxide.

I think I know how one would go about making it, I just want to know if it iseven resonable. Does anyone have any experince with it? I dont want anything to do with this stuff if it is going to be like having NI3 laying around in my shop though. If it is fairly mild, however, I'd like to give it a go.

[Edited on 21-2-2007 by zeppelin69]
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Ozone
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[*] posted on 20-2-2007 at 20:28


Hello,

Welcome to Science Madness.

First,

If you have diethyl ether it is likely making the peroxide via autooxidation as-we-speak. These peroxides can (and have) killed Chemists and will *vaporize* you, your house, your dog, etc. (or, at the very least, you will be in the emergency room having splinters of glass removed from your body, hands (what's left of them), eyes, etc.).

DO NOT do anything which will accelerate this!

Second,

Please use the search function displayed immediately below the Science Madness logo. You would have found this:

http://www.sciencemadness.org/talk/viewthread.php?tid=265#pi...

Cheers,

O3




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Sauron
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[*] posted on 20-2-2007 at 20:44


Anyone who uses Et2O and who has a lick of sense tries very hard not to make (or accumulate/concentrate) peroxides and to destroy them when possible.

@O3 is understating the case.

The same goes for THF, dioxane, and other ethers. The worst of them in terms of ease of autoxidation, that I know of, is di-siopropyl ether.
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XxDaTxX
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[*] posted on 20-2-2007 at 20:55


Natural selection at its finest.

Distill and collect pure ether (discard the inhibitor). Store over oxygen in a clear glass bottle in direct sunlight (maybe a big balloon filled with O2 and fitted over the neck would help). When you have a good amount for your experiment remove the balloon and allow ether to evaporate.

... Take a 3x5 index card and write "Kewl" on it. Stick it on your forehead.
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guy
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[*] posted on 20-2-2007 at 20:55


ethers form peroxides via a free radical mechanism right? So what makes the ether C-H bond so readily broken? Is it because its next to the oxygen, in that case why are alcohols more stable?

[Edited on 2/21/2007 by guy]
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Ozone
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[*] posted on 20-2-2007 at 21:01


As they say, "Word".

In my experience, di-isopropylether is the worst, followed by dioxane, THF, then Diethyl. The crappy thing is that you have to store your dioxane at rt as it freezes; this is sort of like distilling it to dryness at equivalent temperature.

O3

I'd call this detritus *if* one could ever outstate (or overstate) the hazards associated with ether peroxides.

[Edited on 21-2-2007 by Ozone]




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jon
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[*] posted on 20-2-2007 at 21:21


he does'nt get the name zepplin for nothing it has some historical connotations ya know.
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zeppelin69
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[*] posted on 20-2-2007 at 21:36


Thanks for the advice. I did do a search for diethyl ether peroxide, though nothing came up?

Anyways, I definetly wont be trying this, I knew there must have been a reason it wasnt a more popular primary.

[Edited on 21-2-2007 by zeppelin69]
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leu
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[*] posted on 20-2-2007 at 21:49


It would be best if you listened to these words of wisdom about peroxides since these compounds have injured and killed many chemists that weren't so cautious :( If you really want to know more about the peroxide formed from diethyl ether, you'd better start with studying German unless you've already mastered it, since that's the language that Rieche published his research in Z agnew Chem 44 590 (1931) and Ber 64 {B} 2335 (1931) :P



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evil_lurker
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[*] posted on 20-2-2007 at 23:53


Quote:
Originally posted by zeppelin69
Thanks for the advice. I did do a search for diethyl ether peroxide, though nothing came up?

Anyways, I definetly wont be trying this, I knew there must have been a reason it wasnt a more popular primary.

[Edited on 21-2-2007 by zeppelin69]


That explains that.

Ether peroxide is some seriously nasty stuff... for all intents and purposes its simply too unstable to be handled, let alone transported.

Over the years there have been several chemists have been seriously injured or maimed simply by unscrewing the cap off a bottle of ether that has sat on the shelf too long.
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