favorite solvent? maybe. ;)
September 24th, 2008 by Ψ*ΨIt’s been awhile since I posted a picture, hasn’t it? Here’s one for you:
This is a reaction I’m running in conc sulfuric. There’s something about using that stuff as a solvent that makes me feel like a total badass. (Thus the reason I also love Sandmeyer chemistry.) Doesn’t hurt that the starting material is crazy-fluorescent, either! 
perylene brickdust?
of course
as far as i know, the dianhydride won’t DISSOLVE in anything else
Hot DEET, molten benzophenone; methanesulfonic acid plus P2O5 (lower viscosity than H2SO4), maybe MeCN/TFA. How much worse can it be than metal phthalocyanines?
well, molten imidazole too.
ACN/TFA may be worth a shot for glassware cleaning–it would at least go through a frit much faster. might try it
ADN/TFA hydrolyzes some into HCN, so make sure you do not whiff any vapors.
It’s pretty. Much more so than those damn sugars of mine.
Very pretty indeed.
My favorite solvent is carbon disulfide. Did I say favorite? I meant holy fuck that shit smells terrible.
I thought your favorite was boiling pyrene.
No, that’s actually my favorite. CS2 is my least favorite. Boiling pyrene is so awesome I makes me crap my pants.
What response is beyond that? If you knew Max Zander, you’d like it even more. Think an eminent German scientist who sounds exactly like Dr. Strangelove. I guess that would be Cherman zientist.
How awesome would it be to have a strangelove-esque supervisor… (sigh)
I did a selective hydrolysis of a cyanobenzamide to the corresponding carboxylic acid in grad school – starting material, neat sulfuric acid, heat it up, pour on ice. It worked pretty well, which is better than lots of my chemistry.
Yours is prettier, though. If my reactions had color, something went wrong.
Pechmann condensations to make coumarins are typically done in neat sulfuric acid. Plus, your products are always glowy!
I kept trying to selectively alkylation an ethylene glycol oligomer, and DMSO/KOH was recommended as an effective system. The solution turned yellow, but since I had no idea how to get my stuff out of DMSO, I was hosed (even if I actually had the correct product).
Other people in lab made similar colors to the picture for crystal studies. Very pretty bricks – orange and neon red, but I have no idea what they dissolved in. Powder X ray diffraction, here we come…
Once upon a time I did HPLC, actually size-exclusion chromatography on various porous glass beads, of a nylon derivative and concentrated sulfuric was the mobile phase. Everything except those glass beads (as the column packing) was teflon lines or some special passivated alloy. Luckily that project only lasted a few months.
so viscous! that COULDN’T have been fun…
Favorite solvent — what a great question! How about sodium in liquid ammonia?
Sorry — that’s more of a favorite solution…fun with electrons…
I have done couple of cyclizations in conc sulfuric acid myself and some of them – isatin formation – were just as pretty as yours.
The list of solvents that dissolve everything should include triflic acid – it is expensive from Aldrich but the 3M company sells it by liter reasonably priced.
Also if you ever dump sulfuric acid reaction on ice and need to netralise the acid, use conc ammonia – much lesser exotherm than with NaOH or KOH, and you also wont have problems with crystals growing in your mix (KHSO4 and Na2SO4 decahydrate are quite poorly soluble at 0C)
Apparently 3M doesn’t sell triflic acid anymore?
Oh well, my info was so dated – from the end of the last cenury infact.
I doubt perfluorobutanesulfonic acid is as useful as TfOH, for superacid applications done in neat TfOH, Olah style. And it is expensive.
IIRC, 3M’s TfOH didn’t even have the name of the compound on the bottle…just some formula number. Still, it was quality stuff, and the wooden crates the bottles came in made for nice footstools for the little labmates.
Apropos of nothing: kitteh!!1one
There’s always time for kittehs, but, huh?
Mostly a test of the image comment plugin. Which now everyone can use. Also, kitteh!!111one
Well, I don’t have to worry about that – images (at least from unapproved sources) call the wrath of the demon Websense.
No kittehs and cheezburgers for me.
You dissolve kittehs in solvent?
Probably makes for a very cationic solution.
*Buh-DUM-Bump!*
Thank you, I’ll be here all week!
NOOOOO! kittehs are not soluble.
It’s official: You can find ANYTHING on the Internets.
but when you do nobody can hear your scream
That would be a catastrophe!
Oooooooooh Shiny!
how do you purify your neat sulfuric?
i don’t
why?
the commercial H2SO4 is crap. Before use you have to filter it carefully through a paper filter. If this does not remove the color you just add one spoon of potassium permanganate.
This is normally followed by distillation under increased pressure.
Ave!
I hope it was only a joke with that sulfuric acid being filtered through a paper filter
BTW, I am working on perylene brickdust too. Ψ*Ψ, did you brominate the stuff pictured above?
Greets
Micha