"The list of people who were blown up or poisoned while trying to do so is impressive"
February 24, 2010 2:16 PM   Subscribe

There are many exciting chemicals. These are the ones that Derek Lowe won't work with. Derek Lowe authors the "In The Pipeline" blog on Corante, and writes primarily about the pharmaceutical industry. However, the subset of entries marked "Things I Won't Work With" delves entertainingly into the realm of substances like dioxygen difluoride (tl;dr: it explodes. A lot.)
posted by scrump (45 comments total) 62 users marked this as a favorite
I try to avoid dihydrogen monoxide when I can.
posted by empath at 2:22 PM on February 24, 2010 [1 favorite]

posted by Mister_A at 2:24 PM on February 24, 2010 [3 favorites]

Why couldn't my chemistry textbooks have been written by this guy?
posted by reductiondesign at 2:27 PM on February 24, 2010 [3 favorites]

There are many exciting chemicals. These are the ones that Derek Lowe won't work with.

Andro, oxandrin, dianabol, winstrol, deca-durabolin, and equipoise?
posted by nathancaswell at 2:27 PM on February 24, 2010 [2 favorites]

This blog is awesome. Today, I learned how to burn asbestos.
posted by Blazecock Pileon at 2:28 PM on February 24, 2010

Ahhh-pyrophoric chemicals. Many a tale.....
posted by lalochezia at 2:31 PM on February 24, 2010

When I first read this I thought it was the baseball player talking about steroids.
posted by Melismata at 2:37 PM on February 24, 2010 [1 favorite]

When I was a kid we got a chemistry set of the type I am fairly certain they don't sell anymore. It was just a bunch of vials and jars of stuff. There were instructions, but did we read them? Of course we did not.

We just went down the basement and started mixing things with other things. I don't know what exactly we made, but it resembled napalm- it leapt out of the dish onto the floor, where it resembled a sort of scary burning jelly until stomped upon.
posted by drjimmy11 at 2:44 PM on February 24, 2010 [4 favorites]

this needs a youtube series.

"Will it vigorously oxidate?"
posted by empath at 2:46 PM on February 24, 2010 [9 favorites]

flagged for incorrect use of "tl;dr"

1) Your short paragraph was not "too long".
2) The tl;dr didn't summarize anything from your "long" text, instead it added information which didn't exist.
3) That's not tl;dr. That's not even Mexico.
4) This isn't Reddit or 4chan, fer chrissakes.
5) You had me at "blown up".
posted by Aquaman at 2:47 PM on February 24, 2010 [3 favorites]

The tl;dr referred to the linked wikipedia article on FOOF which immediately preceded the tl;dr in question. I got it.
posted by Mister_A at 2:48 PM on February 24, 2010 [1 favorite]

At seven hundred freaking degrees, fluorine starts to dissociate into monoatomic radicals, thereby losing its gentle and forgiving nature.

I think I love this sentence. Perhaps I'll try to use it somehow...

"Warning: At seven seven glasses of bourbon, quin starts to dissociate into monoatomic radicals, thereby losing his gentle and forgiving nature."

Maybe on a t-shirt?
posted by quin at 2:54 PM on February 24, 2010 [20 favorites]

Chemists are funnier than I thought. Also crazier and I was pretty sure they were crazy to begin with.
posted by tommasz at 3:06 PM on February 24, 2010 [1 favorite]

Warning: At seven seven glasses of bourbon, quin starts to dissociate into monoatomic radicals

I think after 77 glasses of bourbon, pretty much anyone would disassociate into their component bits.
posted by DecemberBoy at 3:06 PM on February 24, 2010 [3 favorites]

Also crazier and I was pretty sure they were crazy to begin with.

Remember those computer kids in the 80s that would write about how to blow things up with a can of gasoline and some tennis balls? Some of them, if they survived to adulthood, actually became chemists.
posted by DecemberBoy at 3:07 PM on February 24, 2010 [5 favorites]

I've done some fantastic stuff as demos for various chemistry events, but the really nasty stuff like this makes me pretty glad that I'm not an organic chemist!
posted by sararah at 3:28 PM on February 24, 2010

This is a great blog; one I've been reading for years. Anyone with any chemistry experience should check out his posts under category "How Not To Do It", some of which are really funny, comments included.
posted by Maximian at 3:32 PM on February 24, 2010

Hey-o! I love that blog, even if the real medicine-y parts make my eyes glaze over sometimes. Derek is a great writer.
posted by beepbeepboopboop at 3:35 PM on February 24, 2010


posted by Kronos_to_Earth at 3:38 PM on February 24, 2010

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.

Just going to hazard a guess that it's 433 kcal/mol there... I don't think you're going to exceed matter-antimatter reactions by several orders of magnitude by chemistry alone. Or anything, really.
posted by Zalzidrax at 3:41 PM on February 24, 2010 [2 favorites]

These are wonderful. Thanks!
posted by echo target at 4:04 PM on February 24, 2010

It 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, aluminium, 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 aluminium 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.

Even more awesome.
posted by The Bellman at 4:10 PM on February 24, 2010

I don't think you're going to exceed matter-antimatter reactions by several orders of magnitude by chemistry alone. Or anything, really.

Not even... love?
posted by ROU_Xenophobe at 4:10 PM on February 24, 2010 [4 favorites]

Yeah, this is a great series where I first heard the sad story of toxicologist Karen Wetterhahn's poisoning via dimethylmercury:
Karen Wetterhahn went home to her husband and two children. She should have gone straight to the hospital. For the dimethylmercury that had landed on her glove had penetrated the latex and then her skin and was already beginning a slow, unseen journey into her blood and into her brain.

But how could she have known this? There were no visible holes in her glove. The dimethylmercury, clear like water but three times as dense, hadn’t burned or otherwise announced itself as it seeped into her skin. Even the wetness of the drop or two would have been indistinguishable from the clamminess that builds up inside rubber gloves. There was no reason for Karen Wetterhahn to think that she had been exposed to dimethylmercury.
posted by benzenedream at 4:14 PM on February 24, 2010 [1 favorite]

That blog is very interesting.

I quit chemical engineering in 5th semester. The career opportunities in Mexico sucked, people were getting fired every month and their jobs gone to China, and frankly it was too difficult and I am not that good.

This is the first time I've felt any regret in a decade. Chemistry can be stupidly fun. And dangerous. Which makes it stupidly fun squared.

The man in charge of the analytical chemistry lab had been there for over 40 years and he hated all the new safety BS. A chemistry lab should be smelly and dangerous and smelly. He would give us a few grams here and there of almost anything and access to the older equipment. Beers ice cold in 3 minutes with dry ice and a recirculator, perfect coffee on a hot plate with a magnetic agitator, followed by vacum filtering.

Then came the revenge of the nerds. The law students were just across the lawn from the lab, and they treated the chem students the way you would expect. One day they were specially rude to one of the girls. We got a lot of pyrite and some strong acid. We built a bunch of hydrogen sulfide generators with Snapple bottles and condoms and hid them in the law student's trashcans. We expected just a little annoying rotten egg smell, but they had to evacuate the whole building and do an expensive search and cleanup.

Hydrogen sulfide is as pleasant as cool lemonade compared to anything in this blog. I would have gotten access to some nastier stuff in 8th semester, and I don't think I would have matured that much in a year and a half. Maybe quitting was the right decision.
posted by dirty lies at 4:18 PM on February 24, 2010 [8 favorites]

Odd that this particular post would have gotten such a disproportionate response from the intertrons but hey, it's a fantastic blog so whatever it takes. Maybe 'FOOF' nudged it over the edge.

Chemists have the best stories.
posted by Skorgu at 4:20 PM on February 24, 2010

Thanks for reminding me of this blog. I first encountered it via his post describing a liquid nitrogen dewar explosion. (Summary: you know what happens when you put some dry ice in a two-litre soda bottle and screw on the cap? Take that and multiply it by a hundred.)
posted by Johnny Assay at 5:53 PM on February 24, 2010

Once upon a time in an otherwise dull meeting, one of our management critters asked if anyone had knew anything about picric acid in a sort of nonchalant way. I wasn't sure exactly what it was but the moment he said the name all those special senses I got after being bitten by a radioactive lab rat to tingle. I offered that it was somewhat nasty and was rewarded with lots of sideways looks and an implication that I was obviously the mad bomber what bombs at midnight. (It seemed one of our suppliers sort of blew up their prep lab and was no longer making the compound for which picric acid was an intermediate any more.)

Weeks later someone asked me how I knew this stuff. I didn't really - but it was laying there, dormant, in a very special category of shit I knew I didn't know but I explained to them "Remember when you were learning all those enzymatic pathways and immunology and stuff? I was learning how not to get my hands and face blown off."
posted by Kid Charlemagne at 6:32 PM on February 24, 2010 [2 favorites]

Having once forced the evacuation of the entire building due to odor, my old lab was then blamed for every smell from that point on, even when it was just the sewer system backing up.

As far as pyrophoric chemicals go, trimethyl aluminum has always been a favorite of mine. tBuLi may smoke a little from the needle tip as you transfer it, but Me3Al usually gives a little spark as you withdraw the needle from the canister...just enough to get your heart rate really going.
posted by Dr.Enormous at 6:42 PM on February 24, 2010 [1 favorite]

> one of our management critters asked if anyone had knew anything about picric acid...

That's just how little provocation I need to tell my favorite picric acid story.

When I was in high school they moved all the chemistry labs. After the move, most of which was accomplished by a 7-months-pregnant student teacher, the head chemistry teacher discovered an ancient jar of picric acid (which this student teacher had unknowingly carted all over campus). One of the more hilarious actions picric acid can take is to crystallize on the lids and threads of old jars, so that when you unscrew the cap and break the crystals it explodes. He takes the jar, puts it in a flammables cabinet, and calls the toxic disposal people, who refer him to the bomb squad.

The bomb squad came to school at about 7am on a Saturday. Six extremely nervous men in full Kevlar suits enter the lab and painstakingly remove the jar using three ten-foot-poles (one for the jar, one for each door to the flammables cabinet). Intermediate humor: The guy holding one of the doors forgets that these cabinets have spring-loaded hinges, and lets go right after extraction -- BANG! They move the jar into a special padded carrying vessel and gingerly take it outside, Ark-of-the-Covenant style.

The bomb squad chief pulls up just as they get outside. Bare-handed, he grabs the jar of picric acid and balances it on the side of the car while he opens up his trunk. After rummaging around for a minute, he pulls out a big fireman's boot and removes one, two, three sticks of dynamite. The jar of picric acid is placed in the heel of the boot and the dynamite is placed on top along with some rags to keep it packed together. The boot itself is wedged safely against the side of the trunk by a full gas can. Pausing to re-light his cigar, he slams the trunk, jumps in the front seat, and drives away in his, yes, unmarked cruiser.
posted by range at 7:11 PM on February 24, 2010 [18 favorites]

He's thinking of turning his blog posts into a book but doesn't know where to start. If anyone here knows an agent that would be right for him, I think they ought to be introduced.
posted by Joe in Australia at 7:35 PM on February 24, 2010

"Satan's kimchee." I love it!
posted by ErWenn at 7:37 PM on February 24, 2010 [1 favorite]

Hydrogen sulfide is as pleasant.....

Err not really
posted by lalochezia at 7:39 PM on February 24, 2010

This is the kind of FPP that makes me love Metafilter. ♥
posted by JHarris at 7:52 PM on February 24, 2010 [2 favorites]

Metafilter : Satan's kimchee
posted by liza at 9:07 PM on February 24, 2010 [2 favorites]

Alternatively, this is the kind of FPP that makes me wish I had spent a lot more effort paying attention in advanced chemistry; I could have been blowing shit up on a far grander and more terrifying scale.

When someone explains that a series of experimental reactions "have surely never been run again." because they are far too stupidly dangerous to replicate? That's exactly the kind of mad-scientist super-villain shit I could have wholeheartedly embraced, had I the attention span to understand the [insert proper term for actual complicated science] involved.
posted by quin at 9:25 PM on February 24, 2010

Lalchezia, at least with hydrogen sulfide, like lemonade, they can id the body without resorting to any extraordinary measures.
posted by Kid Charlemagne at 10:53 PM on February 24, 2010 [2 favorites]

I would add diethylether peroxide. Not because it's a particularly good explosive (it's similar to TATP), but rather because it spontaneously forms in old, unstabilized ether which it's then quite tempting to attempt to redistill. This is a mistake unless you like taking a bath in boiling, burning ether. I know not one but two people who have received extensive third-degree burns from exploding ether stills (both survived, amazingly). After the second the chemistry department to gave up on recycling ether and other peroxide-forming compounds.
posted by overyield at 11:10 PM on February 24, 2010

Ah, dangerous chemical reactions! I once had a secondary school chemistry teacher with a glass eye and a couple of missing fingers. I never knew how that happened, but he certainly liked hairy experiences.

Then, in engineering school, the chemistry class had been pushed into the early Monday morning. To try to maintain the students' interest (a hard enough task in and by itself: this was mechanical engineering, and most students only had a perfunctory interest in chemistry), the professor, helped by a very Igorish assistant, put on a marvelous show, mostly involving liquid gases and all sorts of reactions that go bang. He had a surprisingly high attendance, although I doubt anybody actually learned much chemistry there.
posted by Skeptic at 5:06 AM on February 25, 2010

Chlorine trifluoride
There’s a report from the early 1950s ... of a one-ton spill of the stuff. It burned its way through a foot of concrete floor and chewed up another meter of sand and gravel beneath, completing a day that I'm sure no one involved ever forgot. That process, I should add, would necessarily have been accompanied by copious amounts of horribly toxic and corrosive by-products: it’s bad enough when your reagent ignites wet sand, but the clouds of hot hydrofluoric acid are your special door prize if you’re foolhardy enough to hang around and watch the fireworks.
posted by caddis at 6:42 AM on February 25, 2010 [2 favorites]

Karen Wetterhahn's poisoning via dimethylmercury

This event made huge waves when I was in grad school. It's hard to convey how shocking this was. I remember people going gray in safety meetings afterwards reconsidering possible exposures that had themselves experienced or asked their students to risk.

Every chemist of a certain age will have an "I almost died story": mine involved a cylinder of HF with a corroded regulator that snapped off---fortunately I was smart enough to have it in a hood and was able to close the sash without incident; my dad had an organometallic get away from him and burn the skin off his face and hair---fortunately he had a bowl of ice beside his hood for just this eventuality and was able to avoid 3rd degree burns and scars by immersing his head in it. The point of these stories is less macho bullshit, but a realization of just how freaking dangerous some of the stuff in labs are and how casual even supposedly experienced, trained and cautious workers can be.

What the Wetterhahn poisoning really brought home, especially to the profs and senior staff, was the rather high levels of risks relatively untrained students and other workers were exposed to. If even a world expert could die this way, no one was safe. The fact that everyone had an "and I almost died" story became less a badge of pride and more a sobering realization.

So, when people complain now about the dumbing down of chem labs, I can see their points sure, but I can also see the benefits of not having another grad student trying to open a cranky bottle of HF late on a weekend night with no one around to call the ambulence.
posted by bonehead at 8:35 AM on February 25, 2010 [8 favorites]

The thread about this over on Reddit has some good stories (especially this one). The guy who wrote this also did an AMA on reddit a few months ago.
posted by pwicks at 10:49 AM on February 25, 2010

The fact that everyone had an "and I almost died" story became less a badge of pride and more a sobering realization.

I started taking my own safety seriously when I got married. Then became paranoid when I had a son.

Of course, this is "paranoid" by lab chemist standards, which means that flammable toxic solvents were still sloshed around like Kool Aid, but hey...
posted by Dr.Enormous at 8:13 AM on February 26, 2010

The thread about this over on Reddit has some good stories (especially this one).

Oh my GOD.
posted by JHarris at 11:13 AM on February 26, 2010

I'm very late to this thread.

When I was a Junior in college, I was still a chemistry major. I worked as a lab assistant for a couple of years and a summer between. During that summer, while I was looking after a couple of freshman-level labs, we were also recycling and getting rid of dangerous stuff. I forget which government agency was coming to collect the garbage. I recycled ether, luckily without incident under a very old hood. I recall a few times where my boss said, "No, you are a woman of child bearing age and you won't handle these things. I'll take care of it." I don't even remember what chemicals they were, but I do know they were teratogenic.

At the time, I hadn't even considered having children. Wasn't even an option.

I watched him from a safe distance, so I could learn something, wearing more protective gear than I thought was comfortable. I'd taken some time off from school during college, so I was about 22 at the time.

This wonderful guy, who was my boss and also the head of the department and my adviser, had once cleaned glassware in benzene and later totally understood that he was likely to get pernicious anemia. He also still plays a mean banjo in the local Dixieland band, because he's a stubborn guy like that.

A group of us also got spoken to harshly for working on our projects in the labs after hours (what? we had keys... yeah, we dodged the security guys) and distilling local wine into flammable liquor. At the time, these were considered relatively normal activities, but there were some laws that had to be followed. We got a stern talking to and we promised to behave.

Thanks Dr. Jerry. And thanks for the reminder that I should send him pictures of my very healthy kids to thank him for looking after me when I was a dumb and reckless early-20s-aged girl.

All that said, chemistry was FUN! I just didn't have the skills or math for the theoretical and would have been bored at a bench. I got my degree in '92 in a bland combination of chemistry and physics with a sociology minor and have never really used any of it. Did technical writing for a few years, which was also fun in a totally different way. Now I help kids use computers, which is great and frustrating, depending on the day.
posted by lilywing13 at 2:19 AM on March 3, 2010 [3 favorites]

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