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Molecule of the Day
Benzophenone Ketyl (Dry and purple)
Posted by Molecule of the Day on April 12, 2007
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Benzophenone is a colorless solid, tetrahydrofuran is a colorless liquid, and sodium metal is unremarkable stuff.
When pure, its silvery and bright, but it tarnishes easily in the presence of oxygen or water, leaving it looking like
any other metal kinda greyish silver. If you mix the three together and boil them for a few hours (sometimes you
dont even have to do that if everythings very pure and dry), you end up with an impossibly dark royal blue-
purple solution. This is benzophenone ketyl radical (and the related benzophenone dianion reduced one step
further by one more atom of Na
0
).
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Oxygen or water will react with ketyl radical, meaning you can produce dry, oxygen-free THF. This is desirable
because many reactions wont work with even traces of water. The benzophenone actually decomposes a little
bit, producing benzene and some other contaminants, but these are present at fairly low levels (and they usually
dont interfere with your reaction).
If the still pot has to remove too much water, you end up with a clear solution again (rarely), or a rust-colored
slime (happens more often). Often boiling it for a few hours again will dry it out, but usually, you end up having to
break down the still, safely disposing of the sodium chunks. This can take a whole afternoon.
Stills are pretty dangerous, so you tend to see kegs of dry solvents used in industry. The solvents are passed
over columns of drying agents right before use to ensure theyre completely dry. Ive even seen this setup in a
few academic labs (usually younger guys). Ketyl drying might not make it another generation its already a sort
of oral tradition, and economies of scale will make other methods of getting dry solvents cheaper and cheaper.
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Comments
1. #1 Grad
April 12, 2007
See http://membership.acs.org/c/ccs/resources/CHS_10_4_distillation.pdf for some of the dangers of
stills, and a discussion of the trade offs betweens stills and column systems.
Incidentally, Ive definitely distilled solvents this way. I wouldnt expect to see this disappear from
academic laboratories (particularly the less well funded ones) until insurance mandates it. That being said,
Im a physical chemist, and we dont even have any solvent stills or stills of any kind.
2. #2 Uncle Al
April 13, 2007
Uncle Al begs to differ. There is benzophenone ketyl (blue-green) and benzophenone dianion (deep red).
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The combo is the extraordinarily huge epsilon deep purple wonder. Aside from being dry (~10 ppm
water) and free of oxygen, Na/benzopehone-distilled THF is also freed of peroxides. Any rotovap can be
a peroxide sensor once.
The only purples that come close are Crystal Violet and (CO)5[W,Mo,Cr]S=CPh2. S=CPh2 itself is an
extraordinary cerulean blue (better than vanadyl sulfate). M(CO)6 + S=CPh2 + h(nu) in solvent. No
doubt an inorganiker can pontificate as to why only one goes on.
3. #3 Molecule of the Day
April 13, 2007
Fixed, thanks.
4. #4 bogus
October 3, 2010
saanch ko aanch nahi pyaare
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