[HN Gopher] Things I Won't Work With: Azidoazide Azides, More or...
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Things I Won't Work With: Azidoazide Azides, More or Less
Author : ColinWright
Score : 198 points
Date : 2022-08-26 15:24 UTC (7 hours ago)
(HTM) web link (www.science.org)
(TXT) w3m dump (www.science.org)
| CraftingLinks wrote:
| The author must be an avid Terry Pratchett fan. Similar writing
| style.
| dtgriscom wrote:
| I 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]
| farisjarrah wrote:
| This 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
| AdamH12113 wrote:
| I 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.
| SV_BubbleTime wrote:
| "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 wrote:
| There is some speculation in the comments that he got a
| slightly different chemical.
| [deleted]
| billiam wrote:
| I would read literally anything he writes about chemistry.
| nibbleshifter wrote:
| Tom 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 wrote:
| I 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 wrote:
| For 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.
| woah wrote:
| Here'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
|
| Apparently it's not as bad as they say.
| christophilus wrote:
| I feel like I just got put on an FBI watchlist for clicking
| that.
| [deleted]
| tablespoon wrote:
| > Here'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
|
| > Apparently it's not as bad as they say.
|
| Maybe so, but people also do incredibly stupid shit on YouTube
| for attention, so maybe not.
| mcguire wrote:
| I can't remember; does he have any problems with yellow
| chemistry in that video? :-)
| emeraldd wrote:
| "Things I Won't Work With...." and the person who decides to
| work with it runs a channel named "Explosions&Fire" ...
|
| From the article: "We're talking high-nitrogen
| compounds here (a specialty of Klapotke's group), and the
| question is not whether such things are going to be explosive
| hazards. (That's been settled by their empirical formulas,
| which generally look like typographical errors). The question
| is whether you're going to be able to get a long enough look at
| the material before it realizes its dream of turning into an
| expanding cloud of hot nitrogen gas."
|
| Seems legit to me ...
| Scoundreller wrote:
| Oh c'mon, it's Australia. They have other marsupials there.
| cratermoon wrote:
| Also, C2N14 is probably less dangerous than _several_
| indigenous Australian animals.
| TakeBlaster16 wrote:
| > 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.
| ajackfox wrote:
| I knew this was going to be Explosions & Fire before I clicked.
| This guy is completely insane and I love it.
| mcint wrote:
| Please mark this (2013)
| hobofan wrote:
| [2013]
| alkyon wrote:
| At 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.
| failrate wrote:
| And that well-armored hand will probably have fewer than 5
| fingers.
| Vaslo wrote:
| For 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!
| eutectic wrote:
| I 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.
| djur wrote:
| TNT 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.
| ffhhj wrote:
| Can it be contained inside a diamond anvil cell?
| UpstandingUser wrote:
| I 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.
| wlesieutre wrote:
| Things I Won't Work With: Thioacetone
|
| https://www.science.org/content/blog-post/things-i-won-t-wor...
| pdntspa wrote:
| > 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?
| elmomle wrote:
| Individual molecules of air travel at speeds in the
| hundreds of meters per second
| (https://pages.mtu.edu/~suits/SpeedofSound.html). So it
| seems quite possible that individual molecules may be found
| quite far away from their origin quite quickly, even if the
| bulk is much slower in mixing (I'm not an expert here and
| would love to hear more if someone knows more about this).
|
| It sounds like this substance is bad enough that a couple
| of molecules per Litre would make the air smell awful,
| which together with the previous point may explain how the
| bad smell could be detected at such a distance so quickly.
| Stratoscope wrote:
| A fume cupboard has an exhaust fan. Think of it like an
| enclosure with a built-in fume hood.
| mrguyorama wrote:
| Nigel 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.
| elmomle wrote:
| In the thioacetone TIWWW, Lowe says that "the workers in
| the laboratory did not find the odours intolerable". It
| sounds like in higher concentrations it just overwhelms
| and numbs a strong reaction people have at even extremely
| low concentrations.
| seszett wrote:
| > _the wind would have to have been going 15mph or more_
|
| 15 mph really isn't much for wind, though? In fact that's
| about how much wind there is where I am right now, so
| that doesn't strike me as an unreasonable condition.
| mrguyorama wrote:
| The specific claim he disputed was "smelled one mile away
| almost instantly" which would be a much bigger claim.
| UpstandingUser wrote:
| This is it, and holy hell it's worse than I remembered.
| dangerlibrary wrote:
| Maybe https://www.science.org/content/blog-post/things-i-won-t-
| wor...
| mnw21cam wrote:
| There's a section of "Ignition!" where the rocket scientists
| try out mercaptans as a rocket fuel, and get exiled to the far
| end of a huge empty field for the duration of their
| experiments.
| eutectic wrote:
| Mercaptans sound like a terrible rocket fuel; heavier than
| carbon, with less energy released.
| selimthegrim wrote:
| Charles Stross even wrote a story - "A Tall Tail" roughly
| inspired by these materials.
| scrlk wrote:
| Ignition! is a fantastic read. Not related to mercaptans (or
| bad smells), but this passage from the book has always made
| me chuckle:
|
| > [Chlorine trifluoride] is, of course, extremely toxic, but
| that's the least of the problem. It is hypergolic with every
| known fuel, and so rapidly hypergolic that no ignition delay
| has ever been measured. It is also hypergolic with such
| things as cloth, wood, and test engineers, not to mention
| asbestos, sand, and water -with which it reacts explosively.
| It can be kept in some of the ordinary structural metals --
| steel, copper, aluminum, etc. -- because of the formation of
| a thin film of insoluble metal fluoride which protects the
| bulk of the metal, just as the invisible coat of oxide on
| aluminum keeps it from burning up in the atmosphere. If,
| however, this coat is melted or scrubbed off, and has no
| chance to reform, the operator is confronted with the problem
| of coping with a metal-fluorine fire. For dealing with this
| situation, I have always recommended a good pair of running
| shoes.
| kraussvonespy wrote:
| Lowe's discussion of this is called "Sand won't save you
| this time".
| nullc wrote:
| If you liked Ignition! you might also enjoy "Excuse Me Sir,
| Would You Like to Buy a Kilo of Isopropyl Bromide?"
| [deleted]
| 1-more wrote:
| Might be this one https://www.science.org/content/blog-
| post/things-i-won-t-wor...
| [deleted]
| somedudetbh wrote:
| there should be a feature on hackernews where anything Derek Lowe
| writes on any platform is automatically sent to the front page.
| mabbo wrote:
| There is- hundreds of people who immediately vote it up before
| even reading it.
| dralley wrote:
| This very same post even made it to the front page like 3
| days ago.
| ColinWright wrote:
| Do you have a link for that? This search:
|
| * 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
| &qu...
|
| ... doesn't show anything in the last year.
| dralley wrote:
| Sorry, 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
|
| I misremembered
| javajosh wrote:
| It's interesting to me that so many of these horrible compounds
| have repeating names. Is that coincidence or is it something
| about chemistry?
| cratermoon wrote:
| In 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-
| wor...
| Bjartr wrote:
| If 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 wrote:
| Yep often the worst are the ones that are unstable and deform
| into other horrible chemicals.
| Bjartr wrote:
| All 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.
| ce4 wrote:
| The 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&qu...
| pdntspa wrote:
| I know nothing of chemistry (not even high school) and that
| series is AMAZING
| kadoban wrote:
| I 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 wrote:
| The best I've found is using Google with a site: filter -- ht
| tps://www.google.com/search?q=%22things+i+won%27t+work+wit...
| ce4 wrote:
| https://hn.algolia.com/?dateRange=all&page=0&prefix=false&q
| u...
| bradrn wrote:
| There was indeed such a filter at one point. But alas, they
| seem to have removed it in their recent redesign...
| mattkrause wrote:
| I 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-
| wo...
| kadoban wrote:
| Thank 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 :/
| lelandfe wrote:
| The poor man's responsiveness: hide the stuff that
| doesn't fit
| mattkrause wrote:
| D'oh. The whole panel vanishes when I shrink the window
| down (macOS Safari and Firefox on Linux).
| chaxor wrote:
| I think FOOF is the most well known 'thing i won't work with'
| article
| josephcsible wrote:
| I'd put that one in second place, behind ClF3.
| cratermoon wrote:
| It certainly has the most appropriate name.
| greenbit wrote:
| Probably if you record the sound of it airing its
| grievances and play that back slowly enough, "foof" is
| exactly the sound it makes.
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(page generated 2022-08-26 23:00 UTC)