ScienceHideout
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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.....  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...
hey, if you are reading this, I can't U2U, but you are always welcome to send me an email!
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TerryFlamingo
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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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starman
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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.
Chemistry- The journey from the end of physics to the beginning of life.(starman)
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hkparker
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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.
My YouTube Channel
"Nothing is too wonderful to be true if it be consistent with the laws of nature." -Michael Faraday
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redox
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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.
My quite small but growing Youtube Channel: http://www.youtube.com/user/RealChemLabs
Newest video: Synthesis of Chloroform
The difference between chemists and chemical engineers: Chemists use test tubes, chemical engineers use buckets. |
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ScienceHideout
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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...
hey, if you are reading this, I can't U2U, but you are always welcome to send me an email!
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Bolt
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Well, then you must be stupid.
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ScienceHideout
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Is there some type of rule against flaming?
BTW: I am definately looking in to the aluminum chloride now... 
hey, if you are reading this, I can't U2U, but you are always welcome to send me an email!
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redox
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Somewhere there was a thread about benzene production that detailed the freidel-crafts method, just so you know.
My quite small but growing Youtube Channel: http://www.youtube.com/user/RealChemLabs
Newest video: Synthesis of Chloroform
The difference between chemists and chemical engineers: Chemists use test tubes, chemical engineers use buckets. |
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ScienceHideout
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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!
hey, if you are reading this, I can't U2U, but you are always welcome to send me an email!
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MeSynth
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| 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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vulture
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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.
One shouldn't accept or resort to the mutilation of science to appease the mentally impaired.
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