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Author: Subject: Oxidizing Xylene with potassium permanganate to phalic acid
chemkid
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[*] posted on 12-12-2007 at 15:38
Oxidizing Xylene with potassium permanganate to phalic acid


I am totally un familiar with organic synthesis, but would like to just try a few simple ones. I am interested in hydrocarbons and wanted to use xylene for something non-toxic and found this. Oxidizing xylene to phalic acid with potassium permanganate. I understand the concept behind this, its more how i would do this. Information on how i would do such a synthesis would be appreciated.

Chemkid




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[*] posted on 12-12-2007 at 15:45


Would that be 5-(5-decahydronaphthalene)-2,4-pentadiynic acid? (Dang, if I had ChemDraw I'd draw it for 'ya...)

:P!

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chemkid
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[*] posted on 12-12-2007 at 15:48


Sorry i am not much for spelling even when it rather important. I meant phthalic acid... benzene-1,2-dicarboxylic acid

EDIT: Damn it! even when i am correcting my misspelling i misspell things

[Edited on 12-12-2007 by chemkid]




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[*] posted on 12-12-2007 at 15:58


Only ortho-xylene can be oxidized to phthalic acid. It's usually done with O2 and a catalyst.

Found this on the O2 method.
http://www.freepatentsonline.com/4299977.html

This mostly refers to terephthalic acid but it's good info:
http://www.sciencemadness.org/talk/viewthread.php?fid=10&...




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[*] posted on 12-12-2007 at 16:18


there were threads on this already:

http://www.sciencemadness.org/talk/misc.php?action=search
from our search engine and this from Google:

http://www.sciencemadness.org/talk/viewthread.php?fid=10&...
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[*] posted on 13-12-2007 at 03:53


The other xylenes will certainly oxidize, as well, but to isophthalic and terephthalic acids, of course.



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[*] posted on 13-12-2007 at 07:45


Thank you for the link. I apologize for not UTFSEing. Would potassium permanganate in the same procedure work for a mixture of isomers? A mixture of acid would be fine with me. I'm not to picky. :)

Chemkid

PS: I am not using phthalic acid for anything, just wanted to try some organic synthesis w/xylene

[Edited on 13-12-2007 by chemkid]




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[*] posted on 13-12-2007 at 13:37


It should work. I'm pretty sure mixed xylenes are not in equal amounts so of course you would get an unequal amounts of the acid isomers.

I'm not currently aware of any useful synthesis with mixed o,m,p phthalic acids. Although, I'm sure there are some. Does anyone have knowledge of this? I'm not in a position to go look right now.




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