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October 27, 2010
Graphene Oxide as a Reagent
Posted by Derek
Since graphene was worth a Nobel prize this year, it's only fitting that I mention a recent application of it in chemical synthesis. A paper in Angewandte Chemie shows how graphene oxide can be used as an oxidizing reagent for organic compounds. It performs primary alcohol-to-aldehyde, secondary alcohol-to-ketone, and alkyne-to-methylene ketone reactions quite well. This doesn't seem to be due to residual metals, but is a reaction of the graphene oxide (GO) itself, which is probably a complex mixture of epoxides and who-knows-what on the carbon surface.
Interestingly, it appears that the GO can be regenerated by atmospheric oxygen as the reaction goes on (and then re-used_, so in the end, these processes are being performed by the oxygen itself. This could be an appealing method for scaleup, since it drastically reduces some possible waste streams. The turnover isn't as high as with some more traditional oxidants, but the cost might be hard to beat.
The first thing I thought of was using this material in a flow reactor, perhaps with occasional bubbling of oxygen into the solvent stream. It seems likely that as we learn to manipulate the surfaces of such materials that we'll find some very useful catalysts. . .
Comments (13)
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1. You're Pfizered on October 27, 2010 10:22 AM writes...
Nice Monopoly reference in the abstract.
Permalink to Comment2. barry on October 27, 2010 12:50 PM writes...
If graphene oxide can do it, why not graphite oxide? in the flow-reactor mode, this may compete with per-acetic acid as the next fashionable sterilant to replace chlorine in our drinking water. Of course you would have to be sure that polynuclear aromatic hydrocarbons (PAHs) aren't shed into the stream.
Permalink to Comment3. milkshake on October 27, 2010 12:51 PM writes...
My impression is that unless some bulk commodity chemicals are concerned (where every cent per pound counts) the process chemists are not that keen on using pure oxygen as a terminal oxidant on large scale because of the fire/explosion hazard. It is not nice to have organic vapors in pure oxygen - even "nonflammable" stuff like DCM burns quite nicely in pure O2.
Permalink to Comment4. processchemist on October 27, 2010 1:22 PM writes...
With a continuous reactor (fixed bed, counter corrent fluxes of air - no pure oxigen, PLEASE -and reactant in solution) it would be wonderful.
Permalink to CommentAs oxidant the only thing I like less than oxygen is ozone.
5. usedtobeatirbm on October 27, 2010 1:24 PM writes...
'....alkyne to methylene ketone...' That sounds like a hydration, not an oxidation?
Permalink to Comment6. partial agonist on October 27, 2010 4:43 PM writes...
#5, you are correct. The title of the paper is "Graphene Oxide: A Convenient Carbocatalyst for Facilitating Oxidation and Hydration Reactions"
Permalink to Comment7. gippgig on October 27, 2010 7:06 PM writes...
Hydration of an alkyne would produce a methyl ketone, not a methylene ketone.
Permalink to Comment8. gippgig on October 27, 2010 7:13 PM writes...
Oops, I was thinking of a terminal alkyne. A disubstituted alkyne would produce a methylene ketone. Disregard my previous comment.
Permalink to Comment9. tim on October 28, 2010 8:05 AM writes...
Can you combine it with an amine and acid chloride to make an amide?
Permalink to Comment10. Anonymous on October 28, 2010 8:58 AM writes...
The hotter a scientific field (with more scientific teams involved), the less likely the research findings are to be true (or useful).
Permalink to Comment11. Anonymous on October 28, 2010 12:44 PM writes...
>>3 milkshake
Non-flammable stuff like steel burns nicely under O2.
Permalink to Comment12. Anonymous on October 29, 2010 10:59 AM writes...
>>9
Only if you use stoichiometric samarium.
Permalink to Comment13. Yael Soga on March 1, 2012 2:36 PM writes...
I’m not that much of a online reader to be honest but your blogs really nice, keep it up! I'll go ahead and bookmark your website to come back down the road. Cheers
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