7 ms·
Things I Won't Work With: Azidoazide Azides, More or Less (2013)
- Bjartr 4y agoAll of the posts in Derek Lowe's "Things I Won't Work With" series are excellent and worth a read. Do be sure to read the comments as well, there's some gold in there.
- kadoban 4y agoI wish there was a way to filter to just that series on this blog. Or maybe there is and I just haven't found it? I've read I think all of them before, but they're fun to reread here and there. His other writing is similarly great, but much of it is for a far more chemist audience.
- bramblerose 4y agoThe best I've found is using Google with a site: filter -- https://www.google.com/search?q=%22things+i+won%27t+work+with%22+site%3Ascience.org https://www.google.com/search?q=%22things+i+won%27t+work+wit...
- ce4 4y agohttps://hn.algolia.com/?dateRange=all&page=0&prefix=false&query=Corante.com&sort=byPopularity&type=story https://hn.algolia.com/?dateRange=all&page=0&prefix=false&qu...
- deleted 4y ago[deleted]
- bradrn 4y agoThere was indeed such a filter at one point. But alas, they seem to have removed it in their recent redesign…
- mattkrause 4y agoI still see a "Category" panel on the right-hand side, and clicking on the name of a category (like "Things I won't work with") seems to show posts just from that category. Not all of them are titled "Things I won't work with", but others seem still on-theme. If it doesn't show up in your browser, try this: https://www.science.org/topic/blog-category/things-i-wont-work-with https://www.science.org/topic/blog-category/things-i-wont-wo...
- kadoban 4y agoThank you! Yeah I think it's not visible on my browser, maybe because mobile? At least they didn't remove the functionality, just hid it :/
- mattkrause 4y agoD'oh. The whole panel vanishes when I shrink the window down (macOS Safari and Firefox on Linux).
- lelandfe 4y agoThe poor man’s responsiveness: hide the stuff that doesn’t fit
- bradrn 4y agoOh, thank you! Not sure how I missed that… (I suspect it’s a recent addition, though; I don’t recall that panel being there last time.)
- chaxor 4y agoI think FOOF is the most well known 'thing i won't work with' article
- josephcsible 4y agoI'd put that one in second place, behind ClF3.
- cratermoon 4y agoIt certainly has the most appropriate name.
- greenbit 4y agoProbably if you record the sound of it airing its grievances and play that back slowly enough, "foof" is exactly the sound it makes.
- pdntspa 4y agoI know nothing of chemistry (not even high school) and that series is AMAZING
- ce4 4y agoThe blog was formerly hosted on corante.com, search for this and you get all the early submissions on hn, too: https://hn.algolia.com/?dateRange=all&page=0&prefix=false&query=Corante.com&sort=byPopularity&type=story https://hn.algolia.com/?dateRange=all&page=0&prefix=false&qu...
- deleted 4y ago[deleted]
- Vaslo 4y agoFor those who care and that I’m not patronizing - this is the same kind of behavior you see in TNT (though way more extreme in this molecule). Basically the bonds in these molecules are so unstable they are teetering at the top of a hill and just need a nudge to roll down that hill and become far more stable and much lower energy nitrogen molecules (N2 as nitrogen a nitrogen molecule, not elemental N on the periodic table). When they roll down that hill they let off a huge amount of energy as the bonds break and reform. That energy can be translated to force, as it does in bombs. Just touching this stuff is enough to trigger the bonds to start breaking in a nasty chain reaction. Amazing they were able to characterize this stuff (that is get the x-rays, NMR specs, etc). I think the only way this stuff could be useful is if it could be somehow completely immobilized in a liquid or solid until use. Sounds insanely dangerous!
- djur 4y agoTNT is much less sensitive in some important ways. You can heat it up enough to melt and pour it without it exploding, and you can subject it to a great deal of physical shock, too. You need to set it off with another (less stable) high explosive.
- quickthrower2 4y agoAre you talking about it in Dynamite form?
- krisoft 4y agoDynamite traditionally has no TNT in it. It is nitroglycerin soaked in to some sorbent. Chemically a totally different material.
- eutectic 4y agoI think the energy in TNT mostly comes from the desire of carbon and hydrogen to join forces with the oxygen, which has a much higher activation energy than nitrogen leaving of its own accord.
- 4y ago
- UpstandingUser 4y agoI can't find it now, but my favorite of TIWWW was this chemical that just smelled terrible and did so in exceedingly small quantities. Like, a stray drop of this gets the building evacuated kind of bad, and people are asking what that smell is a mile or more downwind.
- deleted 4y ago[deleted]
- wlesieutre 4y agoThings I Won't Work With: Thioacetone https://www.science.org/content/blog-post/things-i-won-t-work-thioacetone https://www.science.org/content/blog-post/things-i-won-t-wor...
- UpstandingUser 4y agoThis is it, and holy hell it's worse than I remembered.
- pdntspa 4y ago> To convince them otherwise, they were dispersed with other observers around the laboratory, at distances up to a quarter of a mile, and one drop of either acetone gem-dithiol or the mother liquors from crude trithioacetone crystallisations were placed on a watch glass in a fume cupboard. The odour was detected downwind in seconds. How is the smell able to travel so quickly? And through walls no less?
- mrguyorama 4y agoNigel of the NileRed youtube channel has just the other day disputed this claim. Diffusion isn't very fast and the wind would have to have been going 15mph or more. He says he wants to create this compound and test it, as he has done with a few other "horrific smell" compounds. However, there's a running theory that he has kinda burnt out his nose working with certain compounds, as he seems mostly unphased by smelly chemicals that other people very much struggle working with.
- somedudetbh 4y agothere should be a feature on hackernews where anything Derek Lowe writes on any platform is automatically sent to the front page.
- mabbo 4y agoThere is- hundreds of people who immediately vote it up before even reading it.
- dralley 4y agoThis very same post even made it to the front page like 3 days ago.
- ColinWright 4y agoDo you have a link for that? This search: * https://news.ycombinator.com/from?site=science.org https://news.ycombinator.com/from?site=science.org ... doesn't show it. And this search, for the word "azides": * https://hn.algolia.com/?dateRange=all&page=0&prefix=false&query=azides&sort=byDate&type=story https://hn.algolia.com/?dateRange=all&page=0&prefix=false&qu... ... doesn't show anything in the last year.
- dralley 4y agoSorry, it actually came up near the top of the comments of a similar article from the same author https://news.ycombinator.com/item?id=32566743 https://news.ycombinator.com/item?id=32566743 I misremembered
- farisjarrah 4y agoThis is a great video on Azidoazide Azide, explosions and fire is a horrifically entertaining and educational youtube channel. I say horrific because of the chemicals that he works with. But he seems like he knows what he's doing... Hopefully... https://www.youtube.com/watch?v=-Sz4d7RQB6Y https://www.youtube.com/watch?v=-Sz4d7RQB6Y
- SV_BubbleTime 4y ago“So how does this composition get this reputation then? Well, it’s hard to make so other people don’t make it and test. And what the Germans in 2011 published is ”Hey, it’s too sensitive and we can’t test it because it’s below our threshold for sensitivity”… Which doesn’t mean suppose that’s a fucking zero then, it just means they have some cut off.” This guy is the best.
- dralley 4y agoThere is some speculation in the comments that he got a slightly different chemical.
- AdamH12113 4y agoI knew that was going to be Explosions&Fire before I even clicked the link. His videos are a lot of fun even though I can't follow most of the chemistry.
- woah 4y agoHere's a video of a guy making this stuff in jars and styrofoam cups in a dirty possum infested shed in Australia: https://www.youtube.com/watch?v=-Sz4d7RQB6Y https://www.youtube.com/watch?v=-Sz4d7RQB6Y Apparently it's not as bad as they say.
- ajackfox 4y agoI knew this was going to be Explosions & Fire before I clicked. This guy is completely insane and I love it.
- Beltiras 4y agoApparently not as insane as Klapötke et al
- deleted 4y ago[deleted]
- mcguire 4y agoI can't remember; does he have any problems with yellow chemistry in that video? :-)
- TakeBlaster16 4y ago> Apparently it's not as bad as they say. Clearly that's because he had the good sense not to put it near a spectrometer.
- christophilus 4y agoI feel like I just got put on an FBI watchlist for clicking that.
- deleted 4y ago[deleted]
- hilbert42 4y agoYes, likely that's all of us here. ...But they're probably not worried, they'd know our planned actions would be once-off and self-limiting and never come to fruition. ;-)
- nibbleshifter 4y agoTom of the YouTube channel "Explosions & Fire" actually made this stuff in his shed, its nowhere near as atrociously unstable as Derek implies it is.
- CamperBob2 4y agoI wish he had access to instrumentation that could verify that he actually made what he was trying to make. One of the comments makes a fairly convincing case that he ended up with a different compound that, while still violently explosive, was much less sensitive. Given that he DGAF that his scale doesn't work, he probably isn't interested in building an NMR spectrometer in his shed.
- nibbleshifter 4y agoFor his cubane project he has been getting stuff sent off for NMR, obviously he can't send a hilariously sensitive energetic off for that. I'm genuinely unsure what other product would be made if you react isocyanogen tetrabromide with sodium azide, you could get a mix of azide and bromide on the isocyanogen, but that's super unlikely (bromide and azide double displacement is favourable reaction in this case, the bromine being more than happy to fuck off with the sodium) and you would get a distinct bromine cloud off any detonation or deflagration of the product.
- hobofan 4y ago[2013]
- mcint 4y agoPlease mark this (2013)
- failrate 4y agoAnd that well-armored hand will probably have fewer than 5 fingers.
- erik_seaberg 4y agoHe's alluded before to > I'd call for all the chemists who've ever worked with a hexanitro compound to raise their hands, but that might be assuming too much about the limb-to-chemist ratio.
- CraftingLinks 4y agoThe author must be an avid Terry Pratchett fan. Similar writing style.
- javajosh 4y agoIt's interesting to me that so many of these horrible compounds have repeating names. Is that coincidence or is it something about chemistry?
- Bjartr 4y agoIf one of that structure in a compound is problematic, let's see what happens when we cram in as many of them as we can!
- bombcar 4y agoYep often the worst are the ones that are unstable and deform into other horrible chemicals.
- cratermoon 4y agoIn another Things I Won't Work With entry[1] he talks about cramming nitrogen complexes together, so it's definitely in the chemistry. 1 https://www.science.org/content/blog-post/things-i-won-t-work-hexanitrohexaazaisowurtzitane https://www.science.org/content/blog-post/things-i-won-t-wor...
- alkyon 4y agoAt school I synthesized a tiny amount of NI3 (nitrogen triiodide). As it was late and the substance was still dripping wet I went home leaving it under fume hood to dry. Next day I learned (to much amusement of my chemistry teacher) that it scared the hell out of a cleaning lady who managed to trigger it off accidently while cleaning the chemistry lab.
- deleted 4y ago[deleted]
- dtgriscom 4y agoI love these Derek Lowe posts. Somehow he mixes highly technical details with down-home folksiness. Examples: > Hydrogen sulfide, for example, reacts with four molecules of FOOF to give sulfur hexafluoride, 2 molecules of HF and four oxygens. . .and 433 kcal, which is the kind of every-man-for-himself exotherm that you want to avoid at all cost. and > Organometallic reagents come from large tribes, and there are always wild cousins up in the hills. A good place to look for the livelier ones is in the simplest alkyl derivatives, and you should go all the way down to the methyls if you want to know their real character. Ignore the halides. Methylmagnesium bromide you can get in multiliter kegs; they might as well sell it in Pottery Barn. and > ... compounds with lots of nitrogens in them – more specifically, compounds with a high percentage of nitrogen by weight – are a spirited bunch. They hear the distant call of the wild, and they know that with just one leap of the fence they can fly free as molecules of nitrogen gas. And that’s never an orderly process. and > perchloric anhydride (dichlorine heptoxide) [is] a liquid with a boiling point of around 80 C, and I'd like to shake the hand of whoever determined that property, assuming he has one left.
- deleted 4y ago[deleted]
- billiam 4y agoI would read literally anything he writes about chemistry.
- greenbit 4y agoKind of tangentially reminds me of "nitric acid acts on trousers", which afaict is from Ira Remsen's quote about nitric acid acting upon copper. Can't find a good link
- analog31 4y agoMy wife was a boron chemist in grad school. I've learned that any element with three sticks is bad news.
- deleted 4y ago[deleted]
- quickthrower2 4y agoWhen working with this stuff how much do they make? Can they make so little of it that an explosion is no issue but still get good data?