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Jan 09 2013

Why I am not a chemist

azidoazide

I’m not. Definitely not. But even I look at that chemical structure on the right and cringe. Or duck. Or run from the room. Something dramatic, anyway.

But there are chemists who cheerfully work with N-amino azidotetrazole? Maaadneeeesssss!

101 comments

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  1. 1
    NightShadeQueen, resident nutcase

    *cough* Octaazacubane*cough*

  2. 2
    AJ Milne

    …There are no conceivable uses for it – well, other than blowing up Raman spectrometers, which is a small market…

    (Raucous laughter…)

    In my experience, just about anyone who’s ever darkened the door of any science department has had at least one slightly off-the-wall chemistry prof, who gets this peculiar gleam in their eye when talking about things that go boom enthusiastically and with little provocation.

    (Yes, both. The things go boom enthusiastically and with little provocation, and the profs talk about them enthusiastically and with little provocation.)

    Anyway, I suppose we shouldn’t be surprised they also do research.

  3. 3
    michaeld

    Ah azides, during my undergrad years I was in one of the lab buildings studying when a group of security start coming up the stairs then people in biohazard suits eventually it came out there was an explosion on the next floor and we had to leave. We later learned it was a grad student who wasn’t careful enough with an azide (luckily no one was seriously hurt). My chemistry proffs had similar stories to tell including of one grad student who thought making a beaker full of azides to save time was a good idea.

  4. 4
    kemist, Dark Lord of the Sith

    Explosions and fires are routine hazards of organic chem – at my uni, whenever there was a legitimate fire alert, it was invariably in the chemistry department, and the rate almost doubled when people started playing around with microwaves, that is, before the advent of commercial chemistry-oriented machines, when people still used the cooking-oven types.

    You’d put your contraption (normally a pressurized schlenck tube) inside with a beaker full of water to take the excess watts, start it, drop a leaded plexiglass shield in front of it, and get the hell out of the room, peaking once in a while to see if it was cooked / exploded.

    I was lucky enough not to get serious explosions (when it happenned, it was limited to glassware and contained inside the microwave), considering that I used things like palladium catalysts mixed with flammable solvents.

    The most serious incidents in my lab were a metal powder fire and an explosion that was contained in a walk-in vent with blast doors due to a faulty thermocouple probe (the chemist to which it happened could have died had he still been inside – he now has another job.).

    I now have a much less risky career as a programmer. Apart from being poorly paid considering the risks, there are very few jobs left for organicians these days.

  5. 5
    Glen Davidson

    NNNNNNNNNNNNNNo!

    Glen Davidson

  6. 6
    joshfreeman

    Azidotetrazole? This is madness!

    Madness? THIS. IS. CHEMISTRY!

  7. 7
    hyperdeath

    At university, I knew a guy who was heavily into amateur chemistry. One of the many things he kept in his room was sodium azide. It was kept in a crudely labeled container on his bedside table.

  8. 8
    dysomniak "They are unanimous in their hate for me, and I welcome their hatred!"

    #7 and people think I’m nuts because I keep a little hexane around for organic extractions…

  9. 9
    Ogvorbis: Still failing at being human.

    Add some oxygen and you have my daughter’s entire vocabulary for a six month period when she was a toddler.

    (Sorry. Liberal arts major. That’s all I got.)

  10. 10
    epikt

    That’s why doing your chemsitry in silico is such a good idea. It’s very hard to hurt yourself running a computer simulation of a chemistry experiment gone horribly wrong.

  11. 11
    eric

    Had a friend who blew a lab wall out and took glass shrapnel to the chest and arms because he was following an (old) published synthesis, and it was wrong/incomplete.

    A triple lesson there: don’t trust everything you read. Write your experiments up correctly. Wear your goggles.

  12. 12
    miles

    GAH! I shoulda been a chemist and not a programmer.

  13. 13
    ChasCPeterson

    This is nothing but nitrogen. The atmosphere is 81% nitrogen and it hasn’t harmed me none.

  14. 14
    Fred Salvador, Onion Jumbler

    I feel I must point out at this juncture that, as sensitive and energetic as azidoazide azide might be, I’d still rather juggle a beaker of it than milk a viper or prepare a phial of ebola virus. When it comes to dodgy handlings, biology remains the field to beat :-P

  15. 15
    PZ Myers

    Oh, right. I forgot: nitrogen is just an inert gas.

  16. 16
    Louis

    What’s wrong with N-amino azidotetrazole? Seems perfectly stable to me. Xenon trioxide. Now THERE’S a fun molecule.

    Briefly.

    Louis

  17. 17
    ChasCPeterson

    Shit, there’s two carbon atoms lurking in there too. My bad.
    [I cheerfully admit to 2 semesters of Cs in Organic, and C-s in the torturous labs*. (Fortuately, I had no dreams of medical school that needed crushing.)]

    *one semester, I swear the TA’s only words of intelligible English were “please wear goggle”. (not that there’s anything wrong with that anywhere else)

  18. 18
    Louis

    Chas,

    I want it on record that I was too kind to point out your obvious error.

    Your welcome.

    Louis

  19. 19
    a_ray_in_dilbert_space

    Fred Salvador: “When it comes to dodgy handlings, biology remains the field to beat :-P”

    Ahem.

    http://en.wikipedia.org/wiki/Demon_core

    And more generally

    http://en.wikipedia.org/wiki/Criticality_accident

  20. 20
    fredfakr

    And old employee and friend was back on my campus a few weeks ago after finishing his PhD (we’re computer nerds, not chemists).
    He was recounting the two things that happened to him within a day or two of working for me that made him know he found the right job.. He had to help an Emeritus with email that wouldn’t go out.. it was going to dyson@… and the email started with “Freeman,”.
    Very exciting to a 21YO nerd.

    The second was going into a lab to help a Prof, who was holding a glass slide with some goop on it. The P.I. told him, “If I hit this with a hammer, the whole lab would go up”.
    Octanitrocubane

    The funny thing is, he was quoted in the school Press Release just prior saying “In fact you can hit octanitrocubane with a hammer and nothing happens,”.
    I lack the chemistry background [my first discarded major] to know if he was trying to reassure the University in the press release, or trying to scare my guy. :-) We took his word on it, but I always suspected that sealed glass tube of goop in his pencil cup had some in it.. just because.. wouldn’t you if you could?

  21. 21
    Tapetum, Raddled Harridan

    I peaked on interest in things that go book after a day dealing with the discovery of old, crystallized picric acid in my lab. I like my biology much better. Give me picrotoxin in DMSO any day.

    My husband, who does work with things that go “BOOM!” was not helpful about the picric acid incident. When I called him up as the nearest expert I knew and asked for advice, he told me to barricade myself behind my biggest, heaviest lab table, and chuck things at the culprit shelf until it exploded. “Once it’s exploded, it’ll be perfectly safe!” he said, cheerfully.

    The only time I’ve seen him shaken up by a near-miss was when Aldrich messed up an order, and sent him two liters of Nitroglycerin in a standard box, via UPS, which he discovered after he had stuffed the box into his backpack and jogged across campus with it (in Febuary, fortunately). The same day the Physical Chemistry Dept. of his college got a specially packaged, specially delivered HIGH EXPLOSIVES!! delivery of two liter bottles of a perfectly safe (for explosivity anyway) aromatic compound.

  22. 22
    Ogvorbis: Still failing at being human.

    Tapetum:

    One of my friends got in a little trouble (two days of in-school suspension) when she found a 1 litre glass bottle, filled it with water, and labeled it (using some purloined school chemistry labels (and I had nothing to do with her getting those labels. nothing. I was elsewhere. Really.)) with the chemical formula for nitroglycerin and, in a light grey ink (yeah, we could get that even way back then (damn kids!)) spelled out the name. Three weeks later, the chemistry teacher found it, did some testing, determined it was water, and started investigating and somehow found out who it was. We still don’t know how he found out.

  23. 23
    NitricAcid

    Ogvorbis: I did something similar in grad studies. I was submitting a term paper on a class of highly reactive compounds, one of which was often used as a demonstration by the person who made it. He’d take a sealed ampule of it, break it, and the compound would go off in a wonderful shower of sparks as soon as it saw air. So I included a sealed ampule with my paper, and a note to the prof saying that I had included a sample for his enjoyment.

    He was horrified that I had done this, mostly because, upon handing it in, I had simply slid it under his door. He came very close to stepping on it and breaking the ampule.

    When I admitted that it had contained only ground-up molecular sieves, well, that was the only time a prof ever called me a “bastard” to my face.

  24. 24
    ChasCPeterson

    I want it on record that I was too kind to point out your obvious error.
    Your welcome.

    ditto.

    oops.

  25. 25
    dianne

    I think I’m going to file this one under “secrets man was not meant to know” and forget I ever saw this post.

  26. 26
    ithgar

    Things like this make me grateful to be handling bacteria that cause gangrene.
    *shudder*

  27. 27
    RFW

    Even though it’s been 40 years since I last “did chemistry” as an occupation, and I wasn’t an organiker, I took one look at that and immediately recognized its explosive power. It really, really, really would prefer to rearrange itself as a molecule of cyanogen (CN)₂ and six molecules of nitrogen N₂. Kaboooooooooooooooom!

    I’ll take poop any day of the week.

    The world of academic chemistry is littered with horror stories. One of my fellow grad students was working on compounds of somewhat related structure. I wondered to him about their toxicity. “Oh, no, this class of azides (or whatever they were) isn’t toxic.” Clearly he had never heard of exceptions to rules. I think he survived.

    When I was an undergraduate, the story went that in one lab at another institution, they were working on derivatives of norbordienyl dibromide which turned out, as a class, to be exceptionally toxic. Several graduate students died before the research was halted and a brief article stating that published — with no mention of those who’d lost their lives.

    To finish: a professor at Dartmouth (iirc) was working with methyl mercury, got a tiny amount on her skin because of a small hole in her protective gloves, and died in consequence.

  28. 28
    RFW

    PS: there’s a moral here for all chemists, amateur and professional: some of this stuff can be exceptionally dangerous.

  29. 29
    michaelbusch

    @14 & 19:

    You can’t juggle this stuff. It blows up if you tap the sample tray.

    Re. stuff you don’t want to handle:

    Plutonium oxide forms a fine-grained powder. On inhalation, it is just about as deadly as nerve gas.

    Antimatter and high energy particle beams win the death-per-kilo competition. Fortunately, antimatter is still best counted in atoms rather than grams.

    357 kcal/mol is “only” 6.8 million J/kg. That’s equivalent to something moving at 3.7 km/s or so. Catching rockets in flight or knocking asteroids out of the way is somewhat more energetic. But then it is very easy to be a considerable distance away.

  30. 30
    Jacob Schmidt

    But even I look at that chemical structure on the right and cringe. Or duck. Or run from the room. Something dramatic, anyway.

    I don’t get this. I have no trouble with chemical structures.

    N-amino azidotetrazole looks pretty cool thou-… wait, that thing explodes from contact with infrared radiation? How the bloody hell did they make the stuff in the first place? You’d think basic molecular collisions occurring in the reaction would be enough to wreak any molecule they actually managed to form.

  31. 31
    Louis

    RFW,

    The dimethylmercury thing is true except for one key part: there was no hole in her gloves. Dimethyl mercury just goes straight through nitriles. It is definitely something I will not work with, and I’ll work with almost anything! By all accounts this lady was a excellent chemist, but methyl mercury leaves zero room for natural hand tremble error or anything. It is basically an instant death sentence, it touches you, you will die a lot sooner than expected.

    Oh and Tapetum, picric acid is a personal favourite. Clearing out an old lab we found a ~2 kilo bottle of the stuff that had been crystallising away at the back of someone’s cupboard for who knows how long. Discussions were had. The bomb squad was called.

    They were unamused.

    Louis

  32. 32
    Jacob Schmidt

    357 kcal/mol is “only” 6.8 million J/kg.

    That actually isn’t much. It’s high for an enthalpy of formation, seeing as most enthalpies of formation are negative, but much more energy is released during other everyday reactions. Octane for instance, oxidizes to release 5.33MJ/mol, or 46.7 million J/kg (table on the right).

  33. 33
    Louis

    Chas, #24,

    Well, you ruined THAT joke. ;-)

    Louis

  34. 34
    michaelbusch

    @crayzz:

    @32: The difference of course being that the high-energy hydrocarbons (and hydrogen) have a much greater activation energy for being destablized. The same for the various nitrogen-based solid rocket fuels. That said, large quantities of rocket propellant are best appreciated from a considerable distance.

    @30 and possibly @PZ as well:

    Just to clarify: N-amino azidotetrazole was the starting point. The end point was 1-diazidocarbamoyl-5-azidotetrazole. I know just enough chemical nomenclature to appreciate how scary that sounds.

  35. 35
    zekehoskin

    This is the most fun since I read the history of liquid rocket fuel development. Things that go boom, or are poisonous, or dissolve the tanks – pick at least one. My regrets, I know it was on the web, but the google djinn appears to have lost track of it.

  36. 36
    Jacob Schmidt

    The difference of course being that the high-energy hydrocarbons (and hydrogen) have a much greater activation energy for being destablized.

    Oh, I know. I was just pointing out that 357 kcal/mol isn’t that much on it’s own. It’s not a terribly energetic reaction, but it’s a fair amount of energy in a very volatile substance.

    Just to clarify: N-amino azidotetrazole was the starting point.

    Thanks for the correction. I missed that, and was to lazy to double check the name myself. I got a hold of the full text pdf of the paper that describes the substance. Should be an interesting read.

  37. 37
    Argle Bargle

    I knew there was a reason why I went into accounting rather than chemistry.

  38. 38
    AndrewD

    Zekehoskin,
    The book you are thinking of is “Ignition! An Informal History of Liquid Rocket Propellants” by John D. Clark and is available here
    http://library.sciencemadness.org/library/index.html
    Along with a lot of other interesting stuff

  39. 39
    infraredeyes

    The problem in the dimethylmercury case was that the professor wore the wrong kind of gloves. She ware latex gloves and the compound went straight through them. Nitrile gloves would have been safe. I was working in a chem. lab at the time; we threw out several cases of latex gloves when we heard about it.

  40. 40
    kemist, Dark Lord of the Sith

    GAH! I shoulda been a chemist and not a programmer.

    Believe me, you made the right career choice.

    The main source of employment for organicians (the exciting part of chemistry) are pharmas, and they’ve pretty much disappeared from the western hemisphere since 2008. The only chemistry jobs left in chemistry are in analytical chem, and they’re mind-numbingly boring. Unless you’re ok with working in India or China for one fifth of the salary.

    The world of academic chemistry is littered with horror stories.

    Indeed.

    All those people who worked with benzene, not knowing that it’s just waiting to give you leukemia. A student in my uni lost an eye when a diethylamine bottle exploded in his face from overpressure. A research professional died of aggressive uterine cancer after manipulating massive amounts of estrogens for years.

    One of my undergrad profs once applied to work into Sharpless’ lab (he’s a quite famous Nobel Prize in chemistry). Before he agreed to work there, he spoke to his students and their main complaint was that they always had blurred vision at the end of their work days because of constant exposure to osmium tetroxide (nasty, nasty stuff that attacks the cornea among other things). He decided that he’d rather work elsewhere.

  41. 41
    kemist, Dark Lord of the Sith

    Louis:

    It is definitely something I will not work with, and I’ll work with almost anything!

    What about freshly distilled nitromethane ?

  42. 42
    ironflange

    Sheesh, and I thought hydrofluoric acid was scary.

  43. 43
    riftmann

    9- Ogvirbus Add a bunch of oxygen to it and we’ll all sound like your daughter… “NOOOOOOoooo”. I unfortunately had to stop my chemistry academic studies at the Bachelor level, I wanted to go to graduate school, but my father died and took all the umpf out of me… When I see stuff like this, I wish i had gone on anyway. Yes, I’m a typical chemist nut…

  44. 44
    johnberg

    Kemist@39 – There are very exciting jobs in analytical chemistry, one of which I had for most of my career: developing analytical instrumentation and teaching people how to use it. I started off many years ago as an organiker, and for many of the reasons people have given in the comments (especially working with labmates who didn’t think safety was something they should worry about), bailed and went into the analytical business. But the background in organic chemistry has helped tremendously in understanding what people need in their instrumentation.

    I will agree that just doing analysis of matrices day after day after day can become mind numbingly boring, but creating the instruments those people use is a whole lot of fun.

  45. 45
    paulburnett

    A previous employer had a production function and a research function. The researchers’ lab ovens’ temperature controls were in degrees C while the production folks’ ovens (same brand) temperature controls were in degrees F. One day one of the researchers’ ovens died and the maintenance folks replaced it with a spare production oven. A researcher put some wet explosive material in the new oven to dry, and set the drying temperature to 200 degrees…

  46. 46
    paulburnett

    …or did I get that backwards…? Crap.

  47. 47
    NitricAcid

    I distinctly remember certain people at my university with a reputation for being unsafe. One guy did a Diels-Alder reaction with acetylene, and got black tar. Obviously, he had polymerization, and most people would toss it. Instead, he used about thirty litres of diethyl ether to extract the goop. He had this thirty litres sitting on his bench for about a month while he toyed with ways of removing his hoped-for product from it.

    Another fellow I know was thrown out of the lab when he lost his temper trying to unscrew the cap of a four-litre can of ether, and decided to loosen it by heating it with a heat gun.

  48. 48
    A. R

    FOOF. Look it up peoples.

  49. 49
    Suido

    This isn’t chemistry, it’s Discworld alchemy on steroids. Or nitromethane, or nitroglycerin, or possibly nitrous oxide, depending on how you get your kicks.

    It’s said that there are two major types of alchemists, the athletic and the intellectual. A good alchemist of the first sort was someone who could leap over the bench and be on the far side of a safely thick wall in three seconds, and a good alchemist of the second sort was someone who knew exactly when to do this.

  50. 50
    Sili

    The problem in the dimethylmercury case was that the professor wore the wrong kind of gloves. She ware latex gloves and the compound went straight through them. Nitrile gloves would have been safe. I was working in a chem. lab at the time; we threw out several cases of latex gloves when we heard about it.

    The real problem was that noöne knew that latex was so permeable to Me2Hg in 1997. Karen Wetterhahn was not some stupid undergrad – she was a world class expert in mercury.

  51. 51
    dysomniak "They are unanimous in their hate for me, and I welcome their hatred!"

    This isn’t chemistry, it’s Discworld alchemy on steroids. Or nitromethane, or nitroglycerin, or possibly nitrous oxide, depending on how you get your kicks.

    Heh, a friend and I once filled a garbage bag full of homebrewed N2O in his backyard. That was a good party. I’d like to repeat the experiment but for some reason no one wants to sell me the precursor…

  52. 52
    Xanthë, Amy of my threads

    I discovered that blog after someone pointed out Charlie Stross’ short story A Tall Tale, which is like a mix-and-match of the direst entries on the blog… some of those blog-entries are hair-raising, and pants-wettingly funny if your sense of humour runs to explosive, lethal, or extremely horrid-smelling chemistry. (And I notice, it has been frequented by several discerning Pharyngula regulars!)

  53. 53
    yubal

    OK. I cleaned my glasses twice now and it is not a dirt problem.

    Alright… I assume you managed to synthesize that crazy compound. Please let me ask one question: WHY?

    Are you nuts? Do you have to much research funding to blow on that kind of stuff?

    We got serious work to do over here. People are trying to cure malaria and HIV with new chemistry while you people synthesize insanity for academic entertainment purpose only. What are you people smoking for breakfast?

  54. 54
    Suido

    @ yubal:

    Not sure if you noticed, but there are over 7 billion people on the planet. Plenty of research topics to go around, and plenty of work being done on HIV and malaria.

    Vive la experience!

  55. 55
    Suido

    Ahem, once more with accent:

    Vive l’expérience!

  56. 56
    Fred Salvador, Onion Jumbler

    Alright… I assume you managed to synthesize that crazy compound. Please let me ask one question: WHY?

    Are you nuts? Do you have to much research funding to blow on that kind of stuff?

    We got serious work to do over here. People are trying to cure malaria and HIV with new chemistry while you people synthesize insanity for academic entertainment purpose only.

    If you’re so au fait with the universe’s fundaments that you can make such risible statements with the kind of certainty here displayed, I think it’s only fair to put the same question to you. Why use your expertise to piss on someone else’s research? Malaria, cancer, HIV, heart disease – all these things are killing people as we speak! Go now, I charge you! Go now and cure all of the things with your lateral thinking and universal knowledge of nature!

    Alternatively, admit that you have no idea why this team are performing this research, thus have no idea of it’s possible implications and applications, and are therefore simply yet another blowhard whining about something he doesn’t understand.

  57. 57
    Draken

    This is unnatural. Nitrogen is a bond between one nitrogen atom and one nitrogen atom.

  58. 58
    hyperdeath

    This is unnatural. Nitrogen is a bond between one nitrogen atom and one nitrogen atom.

    Don’t you mean three bonds.

  59. 59
    Compuholic

    [...]no idea of it’s possible implications and applications[...]

    You don’t need to be a chemist to see at least some of it. Research on explosives: Who could possibly have an interest in that…

    And I’m sure they are not in a competition to create the most unstable molecule. The stated goal of the group is to find a replacement for RDX and other explosives that are more powerful and as safe to handle as the currently used ones. They also want to reduce the quantity of toxic materials that are produced/left over from an explosion.

    Even a substance like the one mentioned in the article might be helpful in archieving that goal. I’m pretty sure that those guys know what they are doing (at least I would hope so when you are handling stuff like that).

  60. 60
    Louis

    Kemist, #40,

    I did say almost anything! I’ve prepared it a few times in solution, but haven’t distilled…it’s a gas at RTP anyway. I’ve played with the special glassware…..mmmmm special glassware….but distilling it? I can’t imagine that would go well unless one was extremely careful and lucky.

    Louis

  61. 61
    Louis

    And I read diazomethane not nitromethane. NEED COFFEE!

    I’ve prepared and distilled tiny tiny tiny quantities of nitromethane (for use as a Michael donor), but to be honest, only the one time. And let’s be very clear that it was used immediately and not stored over sieves! ;-)

    Louis

  62. 62
    Louis

    Kemist, #39,

    Great story about the Sharpless group. Yes folks, osmium tetroxide is not something one fucks about with, it doesn’t just stain the cornea, it oxidises the carbon-carbon double bonds in retinol rendering you blind (with sufficient exposure).

    Yum!

    Louis

    P.S. Molybdenum hexacrabonyl or chromium hexacarbonyl FTW. They don’t come with an MSDS sheet listing R and S phrases. They come with a booklet and a stern look from everyone in your vicinity
    .

  63. 63
    Esteleth, [an error occurred while processing this directive]

    True story:

    When I was a wee Esteleth, I got called to the office once from my middle-school classroom. There was a family friend waiting for me, who said that she was there to take me to the hospital. Because my dad was there, after getting hurt at work. She assured me that it wasn’t anything really bad, and that he was going to be fine.

    It seems that he had gotten 10 M sodium hydroxide to the face. Pressurized 10 M sodium hydroxide.

    In the end, he was fine. The scarring is minimal now. He doesn’t have to shave that side of his face anymore, but he’s never worn a beard anyway. And because he was wearing goggles, there was never any risk to his eyes. Of course, the goggles were a loss, but those are replaceable.

    The moral of the story? Wear your goddamn goggles.

    Oh? And a face that has gotten pressurized 10 M NaOH to it is not pretty.

  64. 64
    SQB

    When I was a wee Esteleth, I got called to the office once from my middle-school classroom. (…)

    I’m glad your dad was fine in the end, but I was a bit disappointed by the story. I thought that first line was a setup for how you got a stern warning not to synthesize dioxygen difluoride in the school chemistry lab any more.

  65. 65
    David Marjanović

    *cough* Octaazacubane*cough*

    That one’s still purely hypothetical.

    So far.

    The only time I’ve seen him shaken up by a near-miss was when Aldrich messed up an order, and sent him two liters of Nitroglycerin in a standard box, via UPS, which he discovered after he had stuffed the box into his backpack and jogged across campus with it (in Febuary, fortunately).

    GAAAAAAAAH!!!

    Well, I guess the nitroglycerin was wet. When it’s wet, you can’t blow it up – unlike C2N14. We actually once made some in an extra chemistry course in highschool, the teacher put a drop on the table, hit it with a hammer, and nothing happened.

    No idea how to dry it, BTW. You can’t take dry nitroglycerine out of an exsiccator!

    Antimatter and high energy particle beams win the death-per-kilo competition. Fortunately, antimatter is still best counted in atoms rather than grams.

    I’ve read there’s a movie with a quote like… “You have 20 kg of antimatter?!? ON MY PLANET!?!?!”

    wait, that thing explodes from contact with infrared radiation? How the bloody hell did they make the stuff in the first place?

    It explodes when you aim an infrared laser at it. Aiming a weaker infrared laser at it didn’t blow it up, but generated a blurry absorption spectrum.

    constant exposure to osmium tetroxide (nasty, nasty stuff that attacks the cornea

    “Attacks”? Burns it off. Literally, just only a few molecules at a time.

    …or did I get that backwards…?

    Yes (…well, I hope you didn’t). 100 °C = boiling point of water.

    FOOF. Look it up peoples.

    As you wish.

    And the obligatory mention of its close relative.

    Pressurized 10 M sodium hydroxide.

    Gah.

  66. 66
    WharGarbl

    So, this explains why my friend get’s a school supplied insurance when he went into chemical engineering major.

    Also wonder what the researchers for N-amino compound is thinking.

    Chemist A: “Hm… this compound is highly unstable/explosive.”
    Chemist B: “Let’s make it more unstable and explosive!”
    Chemist A: “That’s a GOOD plan!”

  67. 67
    David Marjanović

    I thought that first line was a setup for how you got a stern warning not to synthesize dioxygen difluoride in the school chemistry lab any more.

    Well, that would require gaseous fluorine and a heating block that went all the way to 700 °C.

    Making hydrofluoric acid should work, though.

  68. 68
    Ogvorbis: Still failing at being human.

    riftmann at 42:

    9- Ogvirbus Add a bunch of oxygen to it and we’ll all sound like your daughter… “NOOOOOOoooo”. I unfortunately had to stop my chemistry academic studies at the Bachelor level, I wanted to go to graduate school, but my father died and took all the umpf out of me… When I see stuff like this, I wish i had gone on anyway. Yes, I’m a typical chemist nut…

    Late. Sorry.

    I was attempting humour. As in, my daughter went through a stage that lasted about six months when here entire vocabulary consisted of the word, “no.” So, add some oxygen to a bunch of nitrogen, and you get NO, NO, NO, NO.

    Not a stab at anyone who went into chemistry or, for whatever reason, could not go into chemistry.

    Sorry. Not meant as an attack.

  69. 69
    WharGarbl

    @David
    On FOOF…

    When a drop of liquid 02F2 was added to liquid methane, cooled at 90°K., a white flame was produced instantaneously, which turned green upon further burning.

    … that thing can catch on FIRE at 90 K?

    Even Streng had to give up on some of the planned experiments, though (bonus dormitat Strengus?). Sulfur compounds defeated him, because the thermodynamics were just too titanic. Hydrogen sulfide, for example, reacts with four molecules of FOOF to give sulfur hexafluoride, 2 molecules of HF and four oxygens. . .and 433 kcal

    Okay, now I’m just waiting for someone insane to try it out and release a paper on that.

  70. 70
    David Marjanović

    Aaaaah yeah. Here goes:

    The authors report a whole series of salts, X-ray structures and all, which range from the “relatively stable” lithium and sodium derivatives all the way to things that couldn’t even be isolated. In the latter category is the rubidium salt, which they tried to prepare several times. In every case, the solution detonated spontaneously on standing. And by “spontaneously”, they mean “while standing undisturbed in the dark”, so there’s really just no way to deal with this stuff. It’s probably a good thing they didn’t get crystals, because someone would have tried to isolate the hideous things. The cesium salt actually did give a few crystals, which they managed to pluck from the top of the solution and get X-ray data on. A few hours later the remaining batch suddenly exploded, though, which certainly must have been food for thought.

    [Tests] put these compounds well into the “primary explosive” category. Well, the ones that they could get data on, that is: the potassium and cesium compounds blew up as they tried to get them into the testing apparatus. So it’s safe to assume that they’re a bit touchy, too.

  71. 71
    WharGarbl

    Addendum question to #68
    Given that I’m not someone with a chemical background, I’m not sure about 433 kcal number. Did he mean that the reaction is equivalent to 433 kcal/mol, or did he mean just FOUR molecules of FOOD gives off 433 kcal?

  72. 72
    David Marjanović

    So, add some oxygen to a bunch of nitrogen, and you get NO, NO, NO, NO.

    Nature News & Views article: “Plants just say NO to aggressors”

    … that thing can catch on FIRE at 90 K?

    Apparently.

  73. 73
    David Marjanović

    FOOD

    As the comments there show, it is per mole, and I love your autocorrect.

  74. 74
    WharGarbl

    @David
    #72

    As the comments there show, it is per mole, and I love your autocorrect.

    Thanks didn’t see the comment.
    And damn that auto-correct.
    Btw, I love that Chlorine Trifluoride article. Especially that quoted section on rocket fuel (and they part that says even Nazi think it’s too dangerous to use).
    ” It is also hypergolic with such things as cloth, wood, and test engineers…”
    Ouch.
    “It’s been used in the semiconductor industry to clean oxides off of surfaces, at which activity it no doubt excels.”
    Well, at least it has some use, but I really wonder what’s the thought process that went through the people who decided to use it.
    Engineer 1: “We got this highly reactive and flammable substance that will spontaneously combust with just about anything except metal coated in metal fluoride. What can we use it for?”
    Engineer 2: “Cleaning agent?”

  75. 75
    WharGarbl

    @PZ
    #15

    Oh, right. I forgot: nitrogen is just an inert gas.

    Okay, someone correct me if my layman understanding is wrong.
    The reason most nitrogen compounds are explosive is because N2 gas are inert (very low bond energy). So that ANY nitrogen compound wants to revert back to N2 gas, which release a crap-ton of binding energy when they do.

  76. 76
    David Marjanović

    Engineer 1: “We got this highly reactive and flammable substance that will spontaneously combust with just about anything except metal coated in metal fluoride. What can we use it for?”
    Engineer 2: “Cleaning agent?”

    Chemistry teacher: “What can you do with that?”
    Brother’s friend’s gleeful standard response: “Burn it!”

  77. 77
    NitricAcid

    @WharGarbl

    That’s essentially correct. It’s not that it “wants” to revert to N2 (it doesn’t have any desires, of course), but once a molecule of these kinds of compounds starts breaking down, the formation of the N2 triple bond releases a whole lot of energy, which causes all the molecules in the immediate vicinity to also break down. And they release a whole lot of energy, and so on, and so on….

    I point this out mostly because I had a fellow chemistry instructor (one with about thirty year’s seniority over me) once wondered aloud about this kind of reaction. “The molecule is unstable because of the strength of the nitrogen-nitrogen triple bond…but how does the compound know that?”

  78. 78
    Louis

    NitricAcid, #46,

    When I was but a wee undergrad, lo those many years ago, we had a chap (a postgrad) working in the fluorine/noble gas lab where I did my undergrad project, his name was Tim Nice But Dim (It was really Adrian, he was named after a TV comedy show character, and because the name was so fucking accurate it hurt). He was well known as being LETHAL.

    Major Accident number one:

    When making a batch of bromine pentafluoride he became frustrated with his apparatus, turned the pressure on the fluorine up a bit and leaned into his fume cupboard to have a bit of a look. His face was up against the plastic reaction vessel when it went pop, leaving him with (very shallow/superficial due to scale) bright red HF burns on his face (he was wearing goggles) in the shape of the red line on the Union Jack. Results: HF burn cream applied, no long term damage, he looked like a moron. Name Change = Jack.

    Major Accident number two:

    When attempting to make a batch of xenon hexafluoride he improperly evacuated/flushed his 2 inch thick zinc “bomb” reactor leaving some air in there. He ended up making a small quantity of xenon trioxide. When he returned the next morning the corner of the lab where the oven was had gone. As had a goodly portion of the corner of the ground floor of the building. Results: Head of department was mildly vexed. Name Change = Unibomber (see what we did there?)

    He successfully completed his PhD and went to work (briefly I believe) for BNFL (British Nuclear Fuels Limited). I shit you not.

    Louis

    P.S. This one time, at chemistry camp (not really), I knew a post doc with a penchant for (badly) doing Swern oxidations on the bench (i.e. not in a fume cupboard). Not incredibly toxic, but he was, for some reason I can’t quite figure out, REMARKABLY unpopular until he stopped. The size of the clue bat that had to be applied to get him to stop was….impressive. Nice bloke, dumb as a stump.

  79. 79
    Louis

    NitricAcid, #76,

    “The molecule is unstable because of the strength of the nitrogen-nitrogen triple bond…but how does the compound know that?”

    Quantum.

    ;-)

    Louis

    P.S. For all the flippancy that is actually a serious answer….

  80. 80
    kemist, Dark Lord of the Sith

    Another fellow I know was thrown out of the lab when he lost his temper trying to unscrew the cap of a four-litre can of ether, and decided to loosen it by heating it with a heat gun.

    And there I was complaining about the absolute moron who admitted to pouring benzyl bromide in the sink after my throath and eyes started swelling.

  81. 81
    RFW

    Two more academical chemistry horror stories, one of which I was involved in: lab mate was going to work with carbonyl fluoride, COF₂, the fluorine analog of phosgene. In due course, a small cylinder of the stuff arrived. Tra la la. I asked him if he’d acquired suitable protective and safety gear. Being a good ol’ boy from Alabama (really) he airily dismissed the possibility of any hazard. I told him in that case, please give me advance warning before he opened the cylinder valve so I could shut down my own equipment and go home.

    I guess my attitude impressed him. Off he went to consult the many tomes on lab safety in the library, and the next thing we knew here came magnesium oxide paste and assorted safety gear.

    A near miss, perhaps. At the end of the day, nothing bad happened.

    Second story: My brother is an organiker, and during his grad school days, one of his lab mates was in the (bad! very bad!) habit of buying a nice steak and storing it in the lab refrigerator until he went home to cook and eat it. They ganged up on him, filled a little specimen bottle with talcum powder, sprinkled some on his latest steak, labeled the jar “brucine” (a seriously poisonous alkaloid) and put it on the shelf above, tipped on its side. ha ha ha. One very luscious steak went into the trash and no more steaks were stored in the lab fridge thereafter.

    P-zed: be careful with all lab reagents, even the ones that aren’t noted as dangerous. We don’t know everything. And we’d hate to lose you.

  82. 82
    WharGarbl

    @RFW
    #80

    P-zed: be careful with all lab reagents, even the ones that aren’t noted as dangerous. We don’t know everything. And we’d hate to lose you.

    That’s a pretty good advice. You never know when two harmless reagent would do when mixed together.

  83. 83
    Louis

    On the subject of “relatively benign things that can make nasty things”:

    My lovely wife is a biochemist/cell biologist. During her PhD she phoned me up to ask my advice about something. The solvent waste in her lab had turned black-ish, the plastic container (~10L) had swollen and was hissing slightly, and there was a bit of a “funny smell”.

    I asked her if her lab put the waste acetone from washing glassware, the various aqueous wastes and the chlorinated solvents her boss used in various little synthesis side projects he had going in the same solvent waste container. She said yes. I delicately informed her that, since it was a lovely sunny day and the solvent waste had been in direct sunlight for a few weeks (they didn’t use it much) in all likelihood they had inadvertently made phosgene and that going back in the lab was possibly a bad idea.

    She called the safety officer who, being a very sensible person, evacuated that bit of the building and got the breathing apparatus out to neutralise/dispose of the stuff properly.

    Ahhhh memories!

    Louis

  84. 84
    Esteleth, [an error occurred while processing this directive]

    True story, via a friend of mine who was an EMT:

    At a Y, a cleaning person was told to clean the grout. After some unsuccessful scrubbing with conventional cleaning agents, this person decided that if Heavy Duty Agent was good Heavy Duty Agent + Different Heavy Duty Agent would be better.

    So, he took a bucket and mixed – in large volumes – bleach and hydrochloric acid.

    (*Waits for those who know chemistry to stop cringing*)

    The EMT crew got an emergency call from the Y. The arrive, thinking that it is someone who fell, hurt themself in the weight room, or perhaps a pool injury. They open the door and discovered a green cloud hovering ~5 feet off the floor. And promptly went down from chlorine gas inhalation (my friend’s comment on the topic: “Incredibly painful.”)

    Because, you see, the bucket was located underneath an HVAC intake vent…

  85. 85
    NitricAcid

    And then there was the fellow who constantly made large batches of PPN[HOs(CO)4] as his starting material, and would get it *everywhere*. Any osmium compound will stink, and this one was incredibly putrid. If you touched any bit of equipment that he had used in the preparation of this material, you would have to scrub your hands to get them to stop reeking. This would include clamps, glassware, magnets, doorknobs….

    And then there was the woman who was told to change the cap on the Schlenk tube containing methyl triflate, at the reagent had started to significantly corrode it. She did this, and promptly tossed the old one in the garbage can. I freaked out, because it needed to have the incredibly toxic methyl triflate washed off of it before being removed from the fume hood. She held it to her nose, sniffed, and said, “But it doesn’t smell!”

    And then there was the fellow who was going to do a small-scale reaction with phenyl (or butyl?) isothiocyanate (reek, reek, reek, poisonous, reek). Now, the sample we had was pretty old, so a lot of it had polymerized; you had to carefully take the liquid out with a syringe. He decided that because it looked mostly solid, it was *supposed* to be a solid, so he’d weigh it out on the balance, as far from the fume hood as possible. And just stared vacantly at me when I yelled at him to get that stuff in the fume hood. This is the same guy who would spread samples on a delicate NaCl IR plate by smearing the sample on a pestle and hitting the plate with it. You could hear him across the lab going “tik tik tik tik” like he was trying to strike sparks and light a fire.

  86. 86
    Louis

    Ahhh we chemists are a strange breed.

    1) If male, we wash our hands BEFORE taking a wee. This is very important.

    2) We tend to run towards fires/explosions then complain that they are not as big as that fire old so and so had back in the day.

    3) We think poisons, explosives and generally fucking terrifying compounds are good.

    4) Collegiate friendliness is accompanied by campaigns of bombing (sealed tubes with dry ice in them rolled under desks, nitrile gloves with dry ice in them tied up in drawers, nitrogen triiodide painted on everything, old plastic reagent containers part filled with liquid nitrogen shaken and dropped down stairwells…)

    Louis

  87. 87
    Esteleth, [an error occurred while processing this directive]

    Not just chemists, Louis. One of the EstelethSiblings used to be a chef at a 4-star restaurant.

    Told a story of a man who chopped hot peppers and then went to go wee.

    (He neglected to wash his hands beforehand)

  88. 88
    NitricAcid

    Louis- you neglected to mention pouring liquid nitrogen into labmates’ coat pockets.

  89. 89
    kemist, Dark Lord of the Sith

    And methylene blue drinks.

  90. 90
    David Marjanović

    When making a batch of bromine pentafluoride he became frustrated with his apparatus, turned the pressure on the fluorine up a bit

    !!!

    and leaned into his fume cupboard to have a bit of a look.

    !!!!!

    When attempting to make a batch of xenon hexafluoride

    …okaaaaaaay…

    Name Change = Unibomber (see what we did there?)

    Union Jack?

    He successfully completed his PhD and went to work (briefly I believe) for BNFL (British Nuclear Fuels Limited). I shit you not.

    o_O

    was in the (bad! very bad!) habit of buying a nice steak and storing it in the lab refrigerator until he went home to cook and eat it. They ganged up on him, filled a little specimen bottle with talcum powder, sprinkled some on his latest steak, labeled the jar “brucine” (a seriously poisonous alkaloid) and put it on the shelf above, tipped on its side. ha ha ha. One very luscious steak went into the trash and no more steaks were stored in the lab fridge thereafter.

    Pity about the steak, but I have to say he really deserved it. Food in a lab fridge… just… no. That’s immoral.

    She held it to her nose, sniffed, and said, “But it doesn’t smell!”

    GAAAAAAH

  91. 91
    NitricAcid

    I check for her on FaceShelf every now and then, but haven’t found her. I keep wondering if she’s still a chemist.

  92. 92
    Louis

    Nitric Acid, Re: pranks: The … was meant to indicate “and oh so much more”! ;-) The liquid nitrogen in the pocket is a good one I admit.

    Esteleth, Re: Chillies: Those are ouchie, indeed, but nothing like as horrendous as having your Mr Pokey start foaming, properly burning, stained, or damaged beyond repair. And I suppose we have to count the capsaicinoids as chemicals…despite what the “natural nutters” think. ;-)

    David, Re: Unibomber: Much simpler, he (effectively) bombed the university. From the period when this “gentleman” was active.

    Louis

  93. 93
    Louis

    Oh and yes, him going and working for BNFL terrified everyone. We were tempted to move planets. He did, however, give an excellent interview I am lead to believe…

    Louis

  94. 94
    cm's changeable moniker (quaint, if not charming)

    him going and working for BNFL terrified everyone. We were tempted to move planets

    :-)

    I too, went for a job with BNFL (pre-university summer job; nothing serious). I didn’t get it, nor did I get the job at the top secret research facility in Malvern that you can’t find on Google. Probably due to having as a reference my school’s Russian teacher who listened to Lenin’s speeches for fun.

    The late X0s-early Y0s were an interesting time. :-)

  95. 95
    Markita Lynda—threadrupt

    Osmium is bad news.

  96. 96
    michaelbusch

    @Estheleth:

    Related restaurant kitchen story: when cleaning dishes used to make high-strength chili sauce, do not use the spray attachment. Otherwise, you will have produced pepper spray. If you should do this, it is not necessary to repeat the experiment.

    @Louis:

    John Lewis, a cosmochemist, described to me techniques he was using for separating out the components of nickel-iron meteorites. The nickel and iron carbonyls were bad enough, but when he described the chlorine-carbonyls used for the platinum group metals, I decided I was glad he would be doing all of this on the other side of two air-tight barriers with vacuum in between.

  97. 97
    Tapetum, Raddled Harridan

    @Louis – was the 2L picric acid incident back in the late ’80′s at a well regarded institute near Boston but not MIT? Because if so, my husband was around for that incident. Indeed it was close in time and location to the nitroglycerin incident. The bomb squad had an interesting year that year.

    Otherwise there seems to be disturbing amounts of dried picric acid hanging around on back shelves. Mine was at least a significantly lesser amount.

    My grandfather was a chemist for Dow. He used to recount a tale of making a large beaker of particularly noxious stuff (I don’t remember exactly what, but he found it nerve-wracking, and he was generally pretty phlegmatic about things.), he was lifting this largish beaker, full near to the brim, when there’s suddenly a huge “BOOM!” and all the alarms go off.

    He swears blue he found himself standing on the front lawn, still holding the beaker (with tongs), having somehow run down three flights of stairs without spilling a drop.

    Though in the realm of scary accidents, most of my husband’s best ones can only be told to people with high level government clearances. Let’s just say there are people working in secure facilities who really, really ought not to be there.

    My lab was comparatively very tame. Lots of alcohol, DMSO, and quantities of things either poisonous or addictive. And lots of OSHA oversight, because they get nervous about places that order LSD legally.

  98. 98
    FossilFishy (NOBODY, and proud of it!)

    I love these tales. Why?

    Because I like being privy to the crazy in other people’s lives?

    Yes, that’s part of it.

    Because they point me in the direction of interesting googling, and associated superficial learning?

    Yup, that’s in there too.

    Because they make my work day with its scratching, bruising and the very rare mild burn hazards look pretty damn good by comparison?

    Oh yes indeed, that would be it!

    The only chemical hazard I face is not noticing that I’ve got some DOT fluid on my skin. It happened once and a few hours and some peeling knee scars later it was taken care of with a quick flush of water.

    The following tale came from an interview I once did. I used to hire for the bookstore I worked for and we got a lot of uni students applying for summer positions.

    My interviewing style could be best described as “Casual a Forethought.” I gave myself plenty of time, kept it light and humourous if at all possible. All the while going down my checklist of questions. The goal was to relax the candidate to the point where they might tell me something that they perhaps shouldn’t. Most often this occurred on the last question: “Tell me about a time when you screwed up at work.”

    I had one applicant say “I shouldn’t tell you this.” then proceed to relate a fascinating tale involving a centrifuge, an improperly capped vial of radioactive material, a led apron, a Geiger counter and a scared supervisor crouching behind a steel desk at other end of the room shouting instructions. They ended with the statement:

    “We were supposed to call [relevant nuclear authority who's name escapes me] about such incidents.”

    “Did you?”

    “Oh no, we never did.”

    The inflection on that “never” was chilling.

    That and everything I’ve read here makes me profoundly glad that I spent my time in the music building, far, far from the chemistry department.

  99. 99
    NitricAcid

    Hmmmm. I just succeeded at tracking down the methyl triflate sniffer, and have found that she’s currently a much more successful chemist than I am.

    Excuse me while I go mourn the remnants of my career.

  100. 100
    NitricAcid

    Of course, Dr. Heat-The-Can-Of-Ether was renowned as a spectacular chemist, even then. Despite his inability to grasp safety rules, interpersonal relationships, or basic hygiene (he went through a few years of not bathing or showering, because he had convinced himself that the natural pheremones would be more successful at getting him laid than cologne.

  101. 101
    Markita Lynda—threadrupt

    The first four people who isolated fluorine gas died. That’s enough to keep me away from it.

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