I was a little uneasy about writing about this one, since I was worried someone would try and make it. The image for this entry actually went through a few iterations, first, with a detailed explanation of the mechanism. Then, I cut it down to just the stepwise formation of the dimer and trimer. Then I decided it was probably better to leave bad enough alone and just show the structure:
It seems like terrorism news, like Richard Reid's (the "shoe bomber") bombing attempt, the 7/7/05 tube bombings, and, as mentioned on Pure Pedantry, yesterday's apparent thwarted UK-US flight attack, always brings up discussions of acetone peroxide.
This is probably because, as far as explosives go, acetone peroxide is one of the easiest to make. The trouble is, it has the terrible tendency of blowing up before you want it to.
Explosives come in all colors, from touch-sensitive ones like acetone peroxide and nitrogen triiodide, to far less sensitive ones, like HMX, HNIW, and octanitrocubane (previously discussed at the old blog). People who work professionally (and legitimately) with explosives would never use something like acetone peroxide, because it's simply too sensitive. The appeal is that it's a high-energy compound that's quite easy to make.
I don't work with any kind of munition (thankfully), so that's about all I know about acetone peroxide specifically. Every chemist, however, will be familiar with organic peroxides. Compounds like ethyl ether will form peroxides over time and exposure to oxygen, like ethyl ether peroxide. Many chemicals will react over time to form "organic peroxides," of the general structure R-OOH, so we have to store them with peroxide inhibitors, like BHT, and minimize oxygen exposure. The trouble here is the peroxide bond, which is quite weak, as this Chemical and Engineering news article discusses.
Many organic peroxides will turn on you, at sufficiently high concentrations. A great example is benzoyl peroxide, which is present at a <10% concentration in certain acne medications. Here, it (presumably) acts a lot like hydrogen peroxide, by an antibacterial effect. The 10% Clearasil stuff is safe - higher concentrations of benzyol peroxide are explosive, but not to the extent acetone peroxide is.
Ether peroxides can be quite explosive. For this reason, especially in industry, most ethers (especially ethyl ether, and the notorious isopropyl ether) are never stored very long. They have been responsible for lab fatalities.
Come back Monday for a slightly happier molecule. Have a good weekend.
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My old high school chem teacher (way back in the 70's) used to give this lecture on diethyl ether - citing its volitility, flammability and formation of highly unstable and explosive peroxides in the stored media. I think it was commonly used at one time to speedily dry wet glassware, although that job evolved onto acetone. All the while he did his lecture with the realization that he and everyone in the class knew about the rusty old metal can from the 50's at least with a big label "Diethyl Ether" on it, sitting on top the fume hood. You can be certain that after that lecture, nobody went anywhere near that can. Turns out it was just an old rusty can that he stuck an old 'ether' label on.
Chemists are so funny sometimes.
When I was in college, one of our chem professors came across an old bottle of picric acid, with a thick crust around the cap. Quite the excitement, had the bomb squad come out to get rid of it.
I worked in Switzerland a couple of years ago.
About a year before I arrived some apprentice laboratory assistants decided to make some acetone peroxide.
One of them lost a hand. They were probably lucky.
this is quite pretty dangerous and no none should even make it at home.. i heard that there was a militant palestinian factory which exploded accidentally.