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Author: Subject: Toluene Directly to Benzene?
ScienceHideout
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[*] posted on 23-8-2011 at 18:41
Toluene Directly to Benzene?


I am planning a type of reduction-oxidation reaction where I can turn toluene to benzene. It is sort of a displacement...

C6H5CH3 + ??? => C6H6 + CH3???

All I need is something that will be sooo reactive it will take that methyl substituent right off the benzene ring! Or, at least it is possible in my imagination..... :P Benzene is nonpolar, toluene is polar, so stoiciometry and solubility (or miscibility) wouldn't be too much of an issue because benzene is hydrophobic. Hopefully CH3??? would be polar so it won't mix. I just need to find out what can break apart a carbon-carbon bond! Oh, brother! Any suggestions? No, I'm not crazy. And thanks in advance.


P.S. I also think Benzene would make the most beautiful name for a baby girl... who agrees? It can be shortened to Benny... I hope my wife would have a sense of humor when I decide our daughter's name will be Benzene...




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TerryFlamingo
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[*] posted on 23-8-2011 at 21:26


Oxidation of toluene, [and really, anything with a reactive proton at the benzylic position] typically results in benzoic acid: which you may be able to further oxidize to CO2 and Benzene. Although I don't know of any oxidizer that is potent enough to do so without substituting something back onto the ring.

What do you need Benzene for that Toluene is not adequate for?
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[*] posted on 23-8-2011 at 22:20


For goodness sake I wish people would use the search function.

http://www.sciencemadness.org/talk/viewthread.php?tid=4902#p...

Im assuming you need benzene as a reactant as they are few cases where toluene won't substitute.No need to reinvent the wheel,use a benzoate or benzoic acid which are relatively easy to obtain OTC.




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hkparker
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[*] posted on 24-8-2011 at 00:38


What is important about directly going from toluene to benzene? Are you trying to prove something or are you just trying to get Benzene? If you just want benzene oxidize toluene with KMnO4, acid work up to benzoic acid, dry distill with CaO.

The Benzene thread starman pointed out has some methods that might be what your looking for but oxidation, work up, and dry distillation will be your easiest way starting from toluene.

Even easier, buy benzoic acid, dry distill with CaO.




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redox
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[*] posted on 24-8-2011 at 08:02


You could try a friedel-crafts dealkylation disproportionation reaction. One could combine toluene with a lewis acid like AlCl3 or FeCl3, then fractionally distilling out the benzene. The friedel-crafts reaction is an equilibrium reaction, so distilling out benzene drives it to the right. The byproduct is xylene.



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[*] posted on 24-8-2011 at 09:00


I was hoping that I could get a nonpolar aromatic silvent for a reagent, and I was also hoping I could save of valuable reagents by doing so. I really don't want to use a whole bunch of KMnO4 to get a couple mLs of Benzene- but I have an overstock of toluene- so I was hoping that that could help...



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Bolt
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[*] posted on 24-8-2011 at 09:03


Quote: Originally posted by ScienceHideout  
No, I'm not crazy.
Well, then you must be stupid.
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[*] posted on 24-8-2011 at 09:12


Quote: Originally posted by Bolt  
Quote: Originally posted by ScienceHideout  
No, I'm not crazy.
Well, then you must be stupid.


Is there some type of rule against flaming?

BTW: I am definately looking in to the aluminum chloride now... ;)




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redox
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[*] posted on 24-8-2011 at 09:14


Somewhere there was a thread about benzene production that detailed the freidel-crafts method, just so you know.



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[*] posted on 24-8-2011 at 09:20


Quote: Originally posted by redox  
Somewhere there was a thread about benzene production that detailed the freidel-crafts method, just so you know.


Awesome! I will look for it!




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[*] posted on 24-8-2011 at 16:52


Quote: Originally posted by hkparker  
What is important about directly going from toluene to benzene? Are you trying to prove something or are you just trying to get Benzene? If you just want benzene oxidize toluene with KMnO4, acid work up to benzoic acid, dry distill with CaO.

The Benzene thread starman pointed out has some methods that might be what your looking for but oxidation, work up, and dry distillation will be your easiest way starting from toluene.

Even easier, buy benzoic acid, dry distill with CaO.


What are the yields?
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[*] posted on 25-8-2011 at 09:48


People, if you are directed to another topic, please spend your time reading that instead of posting superfluous comments here.

I'm closing this thread because this topic has been discussed ad nauseam elsewhere.




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