Things That Delight Me: Things I Won’t Work With

If you’re not familiar with Derek Lowe’s “In the Pipeline” blog, you should be. Whether you’re a chemist or not, his writing is witty and wonderful and breathes zing and pizazz into, uh, your breath-mask. [things I won’t work with]

On Hexanitrohexaazaisowurtzitane: [1]

Hexanitro? Say what? 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. Nitro groups, as even people who’ve never taken a chemistry class know, can lead to firey booms, and putting six of them on one molecule can only lead to such. And since there are six nitrogens and six nitro groups, the first assumption must be that these are all bonded to each other. I mean, come on, leaving the nitro groups attached to the carbons is for wimps. So that means that someone, somewhere, has perversely made a poly-N-nitro cage compound, as if they’d been dared to cram the most bond energy into the smallest space.
That, as it happens, is exactly the case. Hexanitrohexaazaisowurtzitane, or CL-20, was developed as a highly energetic, compact, and efficient explosive. What makes it unusual is not that it blows up – go find me a small hexa-N-nitro compound that doesn’t – but that it doesn’t actually blow up immediately, early, and often. No, making things that go off when someone down the hall curses at the coffee machine, that’s no problem. Making something like this that can actually be handled and stored is a real accomplishment.

Elsewhere he talks about “Hell’s Dumpster” – [2]

Now that’s a compound to be taken seriously. How do you work with something that smells like hell’s dumpster? Like this:

“The offensive odors released by cracking trithioacetone to prepare linear poly(thioacetone) are confined and eliminated by working in a large glove box with an alkaline permanganate seal, decontaminating all apparatus with alkaline permanganate, eliminating obnoxious vapors with nitrous fumes generated by a few grams of Cu in HNO3, and destroying all residues by running them into the center of a wood fire in a brazier.”

So there you have it – just install a fireplace next to your hood (what every lab needs, for sure) and remember that, in a thioacetone situation, fogging the area with brown nitrogen oxide fumes will actually improve the air.


Please do not complain if you spend your day reading Lowe and giggling to yourself. It’s not my fault; it’s his.

One of the wonderful things about the internet is that there are always wonderful (and awful) things to discover. There’s a decent chance that one of you dear readers has not yet encountered Derek Lowe’s column, in which case I may have just made your day.


  1. Raucous Indignation says

    Marcus!! What have you done to me!? I was a chemist afore medicine; you have stolen my last few fragments of free time!

    “Thief, thief, thief! Baggins! We hates it, we hates it, we hates it forever!”

  2. says

    I wonder if, on some distant planet somewhere, there is some non-carbon-based life-form who is a well-respected scientist ….. But considers hydrogen oxide something with which they would never work?

  3. Raucous Indignation says

    I’ll give you “lulz.” One day when I was cleaning out the chemical closet in the lab, I came across a jar of picric acid. A very old dry bottle of picric acid. A 1 kilogram jar of very old dry picric acid. The Material Safety Officer seemed quite taken aback when I called him about the discovery. It all turned out well. No craters on the Upper East Side!

  4. says

    But considers hydrogen oxide something with which they would never work?

    Especially not that insanely corrosive dihydrogen monoxide! You’ve got to be nuts to synthesize that!

  5. says

    Raucous Indignation@#8:
    One day when I was cleaning out the chemical closet in the lab, I came across a jar of picric acid.

    Yipe!!! That’s even “yipetastic”!

    I know someone who once found a 5gal drum of ether, and had been told to move it, so they did and they heard something “klunk” inside. Fortunately they knew enough to get the hell out of there and make phone calls.

  6. Peter B says

    I forget where I found the PDF but read

    I G N I T I O N !
    An Informal History of
    Liquid Rocket Propellants
    by John D. Clark

    Think about fluorine chemistry. F2O2 “FOOF” difluorine dioxide. Then try to imagine something worse. It’s in the book.

  7. Crimson Clupeidae says

    Peter B., that’s a great suggestion.

    I took a hybrid rocket propulsion class my Sr year in college, and some of the things I heard about the ‘good ol’ days’ were truly frightening. And of course, there’s that large crater in the former USSR where a fertilizer plant used to be….

  8. says

    Crimson Clupeidae@#13:
    I have wondered periodically whether that huge explosion in China was a similar demonstration of “the unadvisability of stockpiling certain things.”

  9. says

    Peter B@#12:
    That’s verrrrrry interesting!!! I see that hardbound copies of that book are listed for $10,000+ on amazon, and $16,000+(canadian) on Ebay. That’s a pretty collectable edition, apparently!

    $45 for Kindle on amazon.
    PDF here

  10. EnlightenmentLiberal says

    Di-oxygen di-fluoride? One of my favorite compounds, in part because it appeared in xkcd “What If?”, who also cites Derek Lowe.

    In an article about O2F2, Chemistry blogger Derek Lowe (of the excellent In The Pipeline) used phrases like “violently hideous”, “deeply alarming”, and “chemicals that I never hope to encounter”. Another article refers to fluorine as “the gas of Lucifer”, and lists chemists who were poisoned or blown up while attempting to work with it.