From daHubby Dave, my pet chemical engineer—his chioice is MIC http://en.wikipedia.org/wiki/Methyl_isocyanate.
I don’t know, CalMeachem. Yeah, thionyl chloride is fairly nasty, but I used to run a reaction where I refluxed it for a week with a catalytic amount of DMF and a substrate. I never found it that much worse to work with than TFA.
How in the world did a 2 mL spill of SOCl2 cause a building-wide evacuation? That seems like complete overkill.
We work with a similar chemical, Bromine trifluoride, on the oil patch. It is stored in a capsule that is lowered into oil wells where it is injected through a circular nozzle that sprays it in a ring inside metal tubing to cut the tube into an upper and lower section.
The stuff is ridiculously dangerous. It is handled and administered by a dedicated specialist. It will explode/burn/melt/vaporize virtually anything it touches.
Well to be perfectly honest, it was a fairly small building. All buildings on Air Force bases aren’t hangar-sized after all. This just happened to be one of the little ones. More of a “shed,” really.
Actually it was a shed specifically designed to store 2ml tubes of thionyl chloride.
And it wasn’t really an official “evacuation” so much as “going home without first cleaning up the thionyl chloride.”
In fairness, that’s considered a big deal at Wright-Patterson AFB. You do NOT go home before cleaning up the thionyl chloride. They have a sign over the sink and everything. They are serious about lab safety at Wright-Patterson AFB. All the other Air Force bases are kind of sick of hearing about it, actually.
If anyone from Wright-Patterson AFB starts getting all high and mighty, the best thing to do is ask them point blank: “Oh yeah? Well what about the THIONYL CHLORIDE?” It shuts them right down. They’re all like, “SHUT UP SHUT UP SHUT UP!!!” and then they run to the bathroom and wash their hands about ten or twelve times.
It’s all told in the exciting behind-the-scenes book, F**k You Wright-Patterson AFB! True Tales of the Base that Couldn’t Keep Track of the Thionyl Chloride.
This daughter of WV’s “Chemical Valley” knows where you’re coming from!
Wait, wait, wait… So, a capsule is lowered into a metal tube (perhaps a bore hole?), and a circular nozzle sprays it in all directions so it forms a ring on the inside of the pipe, and that alone cuts through the metal!?!
That… is… AWESOME!
This br5ingsw back memories. No Thionyl Chloride isn’t anywhere near as nasty as this stuff. That Pentaborane stuff mentioned upthread isn’t as bad as trifluorochlorine, but let me relate my story about thionyl chloride.
I was new grad student wor5king in a new lab with a new professor. I had some industrial experience though, so I new a severe problem when I smelled it. Like asterion one of my co-workers had to reflux a reaction with thionyl chloride as the solvent. The reaction probably went just fine, the problem is with the way this student chose to remove the solvent afterwards. He stuck 200 mls of it on the Roto-Vap. I’m studying in the next room and I start smelling hydrochloric acid. Thionyl chloride produces hydrochloric acid with water, so that’s what you smell. I look into the next room, and this guy is standing in the middle of a cloud of thionyl chloride like nothing is happening. I straightened him out real quick. I don’t care if you don’t notice your lungs dissintegrating, if your generating a cloud in a chemistry lab, it better damned well be contained in the hood. The next day, all of the brand new steel in the cloud was rusted brown.
As far as I know, Thionyl Chloride will not touch Teflon either. That carbon fluorine bond is just too strong. I’m not sure that trifluorochlorine won’t oxidize teflon, but it’s my best guess as to how they contain it.
I wouldnt be so sure. I’ve ran across some pickle jars that would give that stuff a run for the money 
You can rotovap thionyl chloride (I did it each time I used it for that reaction in an academic lab.) I just made sure that the rotovap was in the hood each time and then just neutralized the contents of the flask when done. We had a dedicated hood with a dedicated rotovap for anything potentially nasty, flammable, or just plain bad-smelling.
Interesting reaction I was running. As far as I can tell by doing a search, the only place the procedure is published is in the patent literature (though there are now a couple med chem journal articles by the same group where they just reference the patent.) And I could never get their workup (adding toluene and then rotovaping) to be of any real use and had to come up with my own, which had enough changes that I put the full synthesis in Master’s thesis.
I never had a RotoVap in a hood. I suppose that would have made sense for some things. When I had to remove oxalyl chloride, I just used my vacuum pump and several traps. Frankly, the stuff I was making wasn’t stable to atmospheric water, so the RotoVap wasn’t really an option.
I never had a work up that worked exactly as the procedure described. That’s just one of the costs that need to be accounted for in developing a new synthesis. It is impossible for you to precisely duplicate the conditions the original experimentor had. It also is impossible to write down everything you do presicely. Chemistry research is not the sort of thing your average MBA knows how to account for.
Chlorine Triflouride.
Its so damn nasty it oxidizes itself !
Yeah, yeah, cut me a little slack for some lame humor will ya?
Routinely, in attempts to get a well to produce, a string of tubing a few thousand meters long is assembled piece by piece and lowered into the well. So you have a tube in a tube, essentially. Once in a while, you get stuck somewhere and you simply can’t pull the tubing string out of the hole no matter how hard the rig pulls. So now you have to sever the tubing. You can do it with explosives (this is what I work with) but chemicals are much more surgical and precise in this case. It leaves a very clean cut, actually.
I saw a great video of a guy dressed in a hilarious full body rubber suit pouring a beaker of BT onto the ground. The explosive reactivity of the stuff is ridiculous. Individual droplets were exploding into little fireballs on contact with the ground. I wish I could find it.
You don’t need a strong oxidizing agent to disproportionate (oxidize itself). Aldehydes do it all the time. As far as I know chlorine trifluoride does not disproportionate.
Where’s my nerd smiley?
My joke was lamer than that…
Chlorine = oxidizer
Fluorine = oxidizer
= It oxidizes itself! Bonus points if said by the creepy Oxyclean! guy.