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DBL%20Hendrix%20small.png College chemistry, 1983

Derek Lowe The 2002 Model

Dbl%20new%20portrait%20B%26W.png After 10 years of blogging. . .

Derek Lowe, an Arkansan by birth, got his BA from Hendrix College and his PhD in organic chemistry from Duke before spending time in Germany on a Humboldt Fellowship on his post-doc. He's worked for several major pharmaceutical companies since 1989 on drug discovery projects against schizophrenia, Alzheimer's, diabetes, osteoporosis and other diseases. To contact Derek email him directly: Twitter: Dereklowe

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February 23, 2010

Things I Won't Work With: Dioxygen Difluoride

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Posted by Derek

The latest addition to the long list of chemicals that I never hope to encounter takes us back to the wonderful world of fluorine chemistry. I'm always struck by how much work has taken place in that field, how long ago some of it was first done, and how many violently hideous compounds have been carefully studied. Here's how the experimental prep of today's fragrant breath of spring starts:

The heater was warmed to approximately 700C. The heater block glowed a dull red color, observable with room lights turned off. The ballast tank was filled to 300 torr with oxygen, and fluorine was added until the total pressure was 901 torr. . .

And yes, what happens next is just what you think happens: you run a mixture of oxygen and fluorine through a 700-degree-heating block. "Oh, no you don't," is the common reaction of most chemists to that proposal, ". . .not unless I'm at least a mile away, two miles if I'm downwind." This, folks, is the bracingly direct route to preparing dioxygen difluoride, often referred to in the literature by its evocative formula of FOOF.

Well, "often" is sort of a relative term. Most of the references to this stuff are clearly from groups who've just been thinking about it, not making it. Rarely does an abstract that mentions density function theory ever lead to a paper featuring machine-shop diagrams, and so it is here. Once you strip away all the "calculated geometry of. . ." underbrush from the reference list, you're left with a much smaller core of experimental papers.

And a hard core it is! This stuff was first prepared in Germany in 1932 by Ruff and Menzel, who must have been likely lads indeed, because it's not like people didn't respect fluorine back then. No, elemental fluorine has commanded respect since well before anyone managed to isolate it, a process that took a good fifty years to work out in the 1800s. (The list of people who were blown up or poisoned while trying to do so is impressive). And that's at room temperature. At seven hundred freaking degrees, fluorine starts to dissociate into monoatomic radicals, thereby losing its gentle and forgiving nature. But that's how you get it to react with oxygen to make a product that's worse in pretty much every way.

FOOF is only stable at low temperatures; you'll never get close to RT with the stuff without it tearing itself to pieces. I've seen one reference to storing it as a solid at 90 Kelvin for later use, but that paper, a 1962 effort from A. G. Streng of Temple University, is deeply alarming in several ways. Not only did Streng prepare multiple batches of dioxygen difluoride and keep it around, he was apparently charged with finding out what it did to things. All sorts of things. One damn thing after another, actually:

"Being a high energy oxidizer, dioxygen difluoride reacted vigorously with organic compounds, even at temperatures close to its melting point. It reacted instantaneously with solid ethyl alcohol, producing a blue flame and an explosion. 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. When 0.2 (mL) of liquid 02F2 was added to 0.5 (mL) of liquid CH4 at 90°K., a violent explosion occurred."

And he's just getting warmed up, if that's the right phrase to use for something that detonates things at -180C (that's -300 Fahrenheit, if you only have a kitchen thermometer). The great majority of Streng's reactions have surely never been run again. The paper goes on to react FOOF with everything else you wouldn't react it with: ammonia ("vigorous", this at 100K), water ice (explosion, natch), chlorine ("violent explosion", so he added it more slowly the second time), red phosphorus (not good), bromine fluoride, chlorine trifluoride (say what?), perchloryl fluoride (!), tetrafluorohydrazine (how on Earth. . .), and on, and on. If the paper weren't laid out in complete grammatical sentences and published in JACS, you'd swear it was the work of a violent lunatic. I ran out of vulgar expletives after the second page. A. G. Streng, folks, absolutely takes the corrosive exploding cake, and I have to tip my asbestos-lined titanium hat to him.

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, which is the kind of every-man-for-himself exotherm that you want to avoid at all cost. The sulfur chemistry of FOOF remains unexplored, so if you feel like whipping up a batch of Satan's kimchi, go right ahead.

Update: note that this is 433 kcal per mole, not per molecule (which would be impossible for even nuclear fission and fusion reaction (see here for the figures). Chemists almost always thing in energetics in terms of moles, thus the confusion. It's still a ridiculous amount of energy to shed, and you don't want to be around when it happens.

So does anyone use dioxygen difluoride for anything? Not as far as I can see. Most of the recent work with the stuff has come from groups at Los Alamos, where it's been used to prepare national-security substances such as plutonium and neptunium hexafluoride. But I do note that if you run the structure through SciFinder, it comes out with a most unexpected icon that indicates a commercial supplier. That would be the Hangzhou Sage Chemical Company. They offer it in 100g, 500g, and 1 kilo amounts, which is interesting, because I don't think a kilo of dioxygen difluoride has ever existed. Someone should call them on this - ask for the free shipping, and if they object, tell them Amazon offers it on this item. Serves 'em right. Morons.

Comments (137) + TrackBacks (0) | Category: Things I Won't Work With


1. RB Woodweird on February 23, 2010 9:50 AM writes...

1. I had to go through regulatory hell just to use some TMSCN. I think I will apply to use some FOOF and watch the guys in Safety pass out from the stress.

2. FOOF is Satan's kimchi would be a good name for a band.

3. In conjuction with 1. above, I would like to order a couple of kilos of FOOF from Hangzhou Sage Chemical just to see the crater on Google Maps.

4. One of the links in the commentary leads eventually to "Galvanic Experiments on the Dead Body of a Criminal":

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2. Seminymous Coward on February 23, 2010 10:13 AM writes...

Streng also has a paper on Dioxygen Chlorine Trifluoride (O2ClF3) and several dealing with other oxygen fluorides, including everything from 1 to 6 oxygens with 2 fluorides.

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3. CanChem on February 23, 2010 10:14 AM writes...

I really like in the J. Fluor. Chem. paper how much of the reaction progress is gauged by "pings" in the reaction vessel.

And Hangzhou? Man, those guys really do have everything.

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4. Henrik Vanger on February 23, 2010 10:18 AM writes...

Some days, I addictively return to this blog just to have phrases like "whipping up a batch of Satan's kimchi" put a smile on my face. Hunter Thompson would be proud.

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5. A Nonny Mouse on February 23, 2010 10:30 AM writes...

The Chinese would probably ship it in a padded envelope like everything else.

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6. A Nonny Mouse on February 23, 2010 10:33 AM writes...

PS Makes that carbonyl difluoride, which I have been releasing in a reaction, look decidedly tame!

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7. edward on February 23, 2010 10:33 AM writes...

Hangzhou apparently has discontinued this reagent, and no other company offers to sell a kilo.

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8. p on February 23, 2010 10:37 AM writes...

Scifinder should eliminate Hangzhou from their commerical supplier list. Has anyone ever tried to order anything from them? They pop up on pretty much every compound and really pollute searches on commercially available substances.

Or, we could do as RB Woodweird says and order some of this stuff - that might end the company right there.

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9. okemist on February 23, 2010 11:11 AM writes...

There was some 1930's German papers doing fluorinations using liquid Cl2 as a solvent, you may be able to bubble O2 into the dissolved F2 to make FOOF but most likely it will just blow up the tube like EVERYTHING else we added, Hmmm...maybe try reverse addition.

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10. processchemist on February 23, 2010 11:22 AM writes...

About pollution of supplier list, some companies (chinese, of course) list almost ALL the products described in the Organic Synthese Collective. And when you ask for quotation and delivery time, price can high and dt 1-2 months from the order (and I'm not talking about 1 ton of material...)

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11. Dave on February 23, 2010 11:23 AM writes...

I'm surprised that FOOF even exists. Then, again, F will latch onto just about everything, even things that nothing else will; otherwise, how could you explain the existance of XeF8?


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12. CanChem on February 23, 2010 11:31 AM writes...


Yeah, in the first paper Derek lists the authors talk about KrF2 forming too. All these things really give me the shivers. I'm glad I've never had to work with anything more fluorinated than C6F5OH.

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13. Sili on February 23, 2010 11:50 AM writes...

If I have not said this before, I'll say it now: Turn this series into a book! There must be a publisher for it.

You have a coupla fans over at Pharyngula already (some of them non-chemists). I wasn't even the first to link you.

Speaking of links: more XMRV whining from WPI. As usual destroyed by her ERVness.

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14. David P on February 23, 2010 11:57 AM writes...

This was an awesome read. The man Streng is a marvel, not in the least part because he was able to run multiple different series of reactions with the stuff. Either that or he had a supply of remarkably unquestioning grad students.

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15. Micah S. on February 23, 2010 11:59 AM writes...

'Audible “pings” and pressure excursions occurred when liquid O2F2 dripped onto uncooled portions of the apparatus.' lol fun times

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16. Pharma Conduct Guy on February 23, 2010 12:02 PM writes...

As a formally trained analytical chemist who was forced to live a more biologically oriented existence due to career demands, reading about basic chemistry principles brings back feelings of nostalgia. Do biologists ever really think about thermodynamics for practical purposes? Is the day of the chemist long gone?

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17. Thomas McEntee on February 23, 2010 12:38 PM writes...

Speaking of KrF2 and fluorine dissociating at 700 deg C, Bezmelnitsyn, Legasov, and Chaivanov reported in 1976 the continuous preparation of KrF2 by thermal cracking of fluorine on a nickel wire at 600-700 C followed by reaction with Kr on the reactor wall at -196 C ([Dokl Chem. (Eng Trans), 235, 365ff (1977)]. Readers interested in oxidative fluorinators should check out Karl O. Christie and David A. Dixon, "A Quantitative Scale for the Oxidizing Strength of Oxidative Fluorinators", JACS, 114, 2978-85 (1992)

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18. You're Pfizered on February 23, 2010 12:58 PM writes...


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19. milkshake on February 23, 2010 1:31 PM writes...

whatever they needed the stuff for, it was not made for improving human welfare.
This reminds me, when I was in college in Prague we had iodine trichloride preparation in freshman inorganic lab (!) that involved condensing chlorine gas into a flask on a colling bath, spooning solid iodine into that golden liquid and then carefully evaporating the produced goodness until ICl3 crystallized. I did it myself but I hear that the procedure is no longer given to freshmen after one very ugly spill...

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20. Rhenium on February 23, 2010 2:10 PM writes...

The question is whether Streng is still alive. :)

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21. Bored on February 23, 2010 3:02 PM writes...

Sili is right, Derek. Turn this series into a book. It would sell, man. "Things I Won't Work With" is already a perfect title.

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22. Katherine on February 23, 2010 3:48 PM writes...

My day gets better anytime I see "Things I Won't Work With" in my RSS feed. And I never got past Chem 111.

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23. coprolite on February 23, 2010 4:01 PM writes...

Derek, they're right. The first time I read your blog was when someone (not a scientist) sent me a link to Sand Won't Save You This Time, and I pass that one along to people now to weed out the weak-minded.

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24. cicely on February 23, 2010 4:05 PM writes...

I'm one of those non-chemist Pharyngulists of whom Sili speaks, and I would buy the book in a hot second.

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25. Cellbio on February 23, 2010 4:22 PM writes...

Great piece Derek! Who knew volatile chemistry could be so funny.

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26. widget on February 23, 2010 4:23 PM writes...

This very entertaining piece has made me enormously glad I'm a biologist...a total wuss maybe, but at least I still have all my fingers! Thanks for the laughs, definitely have a flair! Totally agree with Sili and Bored--you've got a best seller here. The Dave Barry of science!

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27. Tim McDaniel on February 23, 2010 4:55 PM writes...

My only chemistry class was in one year of in high school, and I remember little of it. "Sand Won't Save You This Time" hooked me on this blog.

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28. metaphysician on February 23, 2010 5:37 PM writes...

Put me down as another person hooked by "Sand Won't Save You This Time", and another non-chemist to boot. And I concur, really, you could turn this into a book.

As for this entry. . . 433 kilocalories?! From only five molecules?! I didn't know you could *put* that much binding energy into a molecule. . .

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29. Hap on February 23, 2010 5:59 PM writes...

I was hooked at the "How Not To Do It: Liquid Nitrogen Tanks" post, though "Things I Won't Do: Isolating Ciguatoxin" was also pretty good.

433 kcal/mol is about five C-C single bonds, so it's in the realm of (unpleasant) possibility. 280 g of FOOF and 34 g H2S gets you...about a stick and half of TNT (I think that a stick of dynamite gives off about 1 MJ), with the bonus that the products aren't all that nice (I think SF6 is bulletproof, but HF gas can't be too fun), though I guess if the shock wave containing their highest concentrations is blowing by you at above the speed of sound, you don't have to worry for long.

Sounds like a good idea to pass.

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30. Vittorio Montanari on February 23, 2010 6:45 PM writes...

Actually fluorine does not need much encouragement to become atomic at any temperature, which is probably why CF3OF and CF2(OF)2 are so easily made from CO and CO2. No abstractions here, any number of kilos, if Messrs Huanzhou are not too busy making everything else let's watch them try. The legendary George Cady pretty much could not decompose CF3OF up to when CF3OF started reacting with the cylinder (it will ignite happily any organics and detonate C2F4 though). CF2(OF)2 now, you're in the far upcountry of the proverbial creek if you don't know what you're doing and never safe even if you do. Example of the beauty of the beast: my former boss DesMarteau made CF3OOCF2OF (which is the Rock of Gibraltar compared to most hypofluorites) from CF2(OF)2. It's a wonder: CF2(OF)2 oxidizes COF2 to CF3OF and is ultimately reduced to CF3OOCF2OF. I spent some time on that clean reaction back in the days and otherwise handled fluorine for a living. I miss the eerie elegance of the science and the good memories, but tell you what, do not volunteer anywhere near CF2(OF)2. Let Los Alamos handle that by remote control if they need.

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31. David Marjanović on February 23, 2010 7:11 PM writes...

Let me just jump on the "please turn it into a book" bandwagon.

Oh, and, streng is German for "strict".

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32. David Marjanović on February 23, 2010 7:17 PM writes...

Messrs Huanzhou

Hángzhōu is an ancient city in China, known for its fine silk and its violently hideous...

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33. Karl on February 23, 2010 7:31 PM writes...

"Things I Won't Work With" would certainly have a place of honor on the bookshelf, right next to my treasured copy of Clark's "Ignition!" (which has to be the funniest technical book I've ever read).

If you got together with milkshake to include some of his stories, the result might even take over the prime spot.

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34. Hap on February 23, 2010 7:37 PM writes...

I don't know the language, but I am guessing that Huanzhou is Chinese for "shoebox funeral", or "the graveyard of fluorine chemists". Maybe someone can request a site tour, as soon as the wreckage setlles to earth and the clouds of HF pass by.

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35. Doug on February 23, 2010 8:01 PM writes...

Second (or third or fourth) for the book. I was thinking it would be exactly the right thing to use in a high school to get kids interested in chemistry.

Great stuff!

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36. Anonymous BMS Researcher on February 23, 2010 8:35 PM writes...

widget on February 23, 2010 4:23 PM wrote...

> This very entertaining piece has made me
> enormously glad I'm a biologist...a total wuss
> maybe, but at least I still have all my fingers

Oh, biology has its thrills too, like BSL-4 pathogens (such as Ebola), not that I ever worked on anything that exotic! I last used a pipette in the bio labs maybe 20 years ago, now I work with computers so I am at risk of carpal tunnel.

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37. Josh on February 23, 2010 9:12 PM writes...

I have a minor in chemistry (major in zoology) but my main focus as my first job out of college was working in a BL-3 and high containment areas with anthrax, bot, serin, soman, and VX. FOOF scares me more than those....

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38. drjim on February 23, 2010 10:58 PM writes...

Duh....makes me glad I'm an EE!

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39. Curt Fischer on February 24, 2010 2:35 AM writes...

It's amazing that FOOF does not react with CO2.
When added to Dry Ice, dioxygen difluoride did not react and was only absorbed by the solid. Addition of acetone to this mixture resulted in sparking accompanied by an explosion.

Maybe he was pissed that the CO2 didn't blow and wanted to see some pretty colors, and that a bottle of acetone was close at had.

I was also touched by the acknowledgements section:
The author wishes to thank[...]Mrs. L. V. Streng [...]for their contributions in the experimental work.

That sounds like love.

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40. milkshake on February 24, 2010 3:04 AM writes...

I think Mrs Steng stood nearby with a fire extinguisher in one hand and first-aid kit in the other. She fluffed her husband's ego after each round of bloodcurdling mishaps with words "at least you are not a nuclear scientist"

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41. iridium on February 24, 2010 6:11 AM writes...

"Sand Won't Save You This Time" rules!

... it does not need to be a big book .... :)

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42. Fungus on February 24, 2010 6:45 AM writes...

A book dedicated to stories of fires and explosions in the lab (aka "war stories") would be a fantastic read. I have about 5 or 6 to share myself.

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43. Stephanie on February 24, 2010 7:14 AM writes...

Always love seeing "Things I won't work with" in my RSS feed. I'm a librarian, I'd make sure a book of these hit the bestseller list.

This post just made my day. I am not a chemist (although I spent most of my college years studying it), I always enjoyed the more, um.... explosive aspects of the discipline.

Now, I just have to figure out how to explain my giggling to my cubemates.

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44. Imants Zudans on February 24, 2010 10:03 AM writes...

What a great read! Thanks!

I like how you mentioned Hangzhou Sage Chemical. This is actually a very serious problem. For ordinary chemicals it is more difficult to catch suppliers that play these sorts of tricks. And we have seen a fair share of these. In our company we learn which supplier is relaible and which is not, avoid the ones that have a poor service. But there is no place all chemists can share this experience so that other don't make the same mistakes.
And I wonder how they decide what to put in their catalog. Random Wikipedia selection?

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45. Dave_n on February 24, 2010 10:09 AM writes...

In another life, many years ago and not in the USA, I used to work in organometallic chemistry, when "men were men and women were women" and did not worry about thermodynamics, only if it reacted well!! When someone ended their graduate career (with a PhD not a "bang"), we used to surround their reaction train with blast shields and give the newly minted PhD a switch to activate a break seal that would let air into the train. Then just before s/he pressed the button, an 8 mm camera would start rolling. Some pretty spectacular effects when fluorinated, and other energetic organ-ometallic compounds met oxygen.

In that same life time, I used to have (legal) target practice with 0.22 rifles on the "Winchester quarts" of reactants that had to be disposed of. Spectacular colors and explosions at a safe distance. Those were the days when you could own rifles and pistols in the UK. Today Health and Safety would never allow such enjoyable sport. Dave_n

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46. Sili on February 24, 2010 11:48 AM writes...

But there is no place all chemists can share this experience so that other don't make the same mistakes.
That's actually odd. In this age of 'Web 2.0', there should be an Ebay/Amazon of chemicals, where buyers can add feedback and reviews, that in turn can be voted on by other buyers. Of course such systems can be gamed, but they're not wholly useless. Permalink to Comment

47. hell to the chief on February 24, 2010 1:01 PM writes...

Of course in the old days when this stuff was published, it was common for reviewers to try and repeat the observations in the paper before publication.
So you can add "review the paper" to the list of things you would not do.

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48. Hap on February 24, 2010 2:03 PM writes...

I'm not a fan of less stringent review requirements, but I'd make an exception for that, because there is no way in hell (or anyplace else) that I would try to reproduce anything in that paper (nor in Klapotke's or Christe's work, to take two good examples) - even if I had the position and the equipment, I sure don't have the experience to do so, and I would guess that few people in chemistry do. Very few people would thus actually be able to attempt to reproduce the work, and thus review it (and likely most of those would be competitors). The work won't be published very much at all, and that would be a loss if for nothing else than the loss in entertainment value.

I like good chemical literature, but I'm not willing to die for it (and in a way that probably would remove me from the organ donor lists, thus assuring that my life would only be useful as a particularly pointed warning on what not to do.)

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49. Rustler on February 24, 2010 10:16 PM writes...


If you are ever in southern New Mexico, give me a ring. We'll go out on the outskirts of the Jornada Del Muerto and we'll sling some lead. One of my favorite targets is a 55 gallon drum into which I've put about one gallon of gasoline. On a hot July evening it makes a most satisfying fireball. Of course, you have to use the right ammunition. As a kid, I'd stretch plastic over the drum and cover it with powdered magnesium. We would pretend to re-enact the Trinity test, which happened just a few dozen miles away. It was really quite amazing. We would get the blinding flash and a miniature mushroom cloud. We'd laugh our heads off then do it again. And no radioactivity!

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50. Spectrochimico on February 25, 2010 12:37 AM writes...

The very first project I worked on in graduate school involved synthesizing halooxides for spectroscopic analysis. The senior graduate student working on the project was pregnant and wouldn't even go into the room where we ran the synthesis.

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51. BenP on February 25, 2010 2:05 AM writes...

I'm a bit confused. You quoted 433kcal per 4 ATOMS of FOOF reacted with HS?

That would be like 10^25 per mol. That exceeds the energy of splitting a uranium atom by like, a trillion.

Please tell me its 433kcal per mol.

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52. Nile on February 25, 2010 5:18 AM writes...

Makes you wonder what species exist in 'Fluorox' propellants - both in the exhaust stream, and in the storage tank. It isn't used often, for some or other reason, but it has the distinction of being the most powerful oxidiser available for bipropellants, so it's not quite 'left on the shelf'.

Yes, I'd buy a copy of 'Sand won't save you...' in book form. Would you care to do a limited-run signed special binding with scorch marks?

Having just read a samizdat copy of 'Ignition!', I can assure you that there's a market for the book. Ignore all asmonitions from the publisher that you should 'dumb it down'.

Remind me, sometime, to blog a distressing story about a large vat of Hydrofluoric acid in a British civil nuclear installation.

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53. UC on February 25, 2010 5:33 AM writes...

The 433kcal is for the reaction stoichiometry given in moles.

If I had a better table of enthalpies of formation, it would be trivial to back calculate the enthalpy of formation of FOOF, assuming it's not already in the paper (which I can't access). I'd also be guessing at the state of the H2S (probably solid).

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54. Nile on February 25, 2010 5:43 AM writes...


If I was an unscrupulous supplier (say, somewhere near Huanzhou), and I'd taken your money for an order I know damn' well I can't synthesise, I'd examine my conscience at length and take the 'What would Satan do?' approach.

The answer? Mail out a small vial of HF, lots of powdered Teflon, and a kilogram of plastique with an anti-tampering detonator. Who's to know?

Any chemist stupid enough to order the stuff can claim his Darwin award, and the world's a safer place.

A footnote, and a cover-my-ass disclaimer:

I would not normally advocate the use of letterbombs - it is very unfair on the delivery guy and illegal to boot, and you might not take the above suggestion entirely seriously - but you might want to sit down and try writing out a packaging & despatch procedure for something as hazardous as a cryogenic fluorine superoxidiser. Then ask yourself: what if some dishonest half-assed laboratory supply company tried to deliver something a tenth as dangerous? How many people died to make it?

They have *some* good suppliers in China, and some very, very bad ones.

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55. Joe on February 25, 2010 12:38 PM writes...

Sili is right, Derek. Turn this series into a book. It would sell, man. "Things I Won't Work With" is already a perfect title.

Better still, "Things that make you go BOOM!"

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56. Paul on February 25, 2010 2:45 PM writes...

Many of the compounds Streng added FOOF to are well known in the rocket propellant field. Tetrafluorohydrazine, for example, is a storable oxidizer. I imagine he was seeing if FOOF could be made to stably dissolve in another propellant component, to give it extra oomph.

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57. David Dyer-Bennet on February 25, 2010 3:08 PM writes...

+1 for the book! And I note that I'm also a fan of Ignition!, though I do not own a copy.

I come by