Sciencemadness Discussion Board

The Oxidation of Xylene To Benzene Or Benzoic Acid.

Jmap science - 19-10-2013 at 10:28

I could not get any toluene to make benzoic acid. Instead I got xylene. I was wondering if the oxidation of it using KMnO4 would form benzoic acid or benzene. If it forms benzene that it would also make MnO2 and potassium formate, so would it form benzene or benzoic acid?

Jmap science: jmap2112@gmail.com
Age 13

Thanks for the help!

Nicodem - 19-10-2013 at 11:18

Exhaustive alkaline permanganate oxidation of the three xylenes would give the corresponding three benzenedicarboxylic acids. See the examples in the literature.

Also UTFSE as this topic has been covered before, as for example in: http://www.sciencemadness.org/talk/viewthread.php?tid=8268

Welcome to the forum and make sure you read the forum guidelines.

plante1999 - 19-10-2013 at 13:58

From the msds I read, "Xylenes" conatin mostly p-xylene and ethyl benzene, the later will convert to terephtalic acid on the conditions you stated, the former is said to yield benzoic acid. Both acid would be in the form of the potassium salt.

EDIT, I inversed both, xylene yield teraphtalic acid.

[Edited on 19-10-2013 by plante1999]

Jmap science - 19-10-2013 at 15:12

Thanks guys, YOu think I could add sodium hydroxide in solution I could make benzene?

Jmap science - 19-10-2013 at 15:14

Would there be a trace of benzene?

plante1999 - 19-10-2013 at 15:22

I don't think so. Not in these conditions.

bfesser - 19-10-2013 at 15:51

Quote: Originally posted by Nicodem  
UTFSE as this topic has been covered before.
<strong>Jmap science</strong>, start by reading these:
<strong><a href="viewthread.php?tid=19143">The ScienceMadness Guidelines</a></strong>

<strong><a href="viewthread.php?tid=8268">1,4-benzenedicarboxylic acid from xylene by oxidation</a></strong>
<strong><a href="viewthread.php?tid=325">Benzene synthesis</a></strong>
<strong><a href="viewthread.php?tid=2223">toluene --> benzaldehyde</a></strong>

And try the forum <img src="./images/xpblue/top_search.gif" /> <a href="search.php">Search</a> function.

If you still have questions, <em>after reading everything above</em>, you can ask them in the corresponding topics.

Welcome to ScienceMadness. :)

Nicodem - 19-10-2013 at 23:50

Quote: Originally posted by Jmap science  
Thanks guys, YOu think I could add sodium hydroxide in solution I could make benzene?

Please learn to read the replies and the given references before you hit the reply button. It is the least you can do.
Quote: Originally posted by Nicodem  
Exhaustive alkaline permanganate oxidation of the three xylenes would give the corresponding three benzenedicarboxylic acids. See the examples in the literature.

Jmap science - 23-10-2013 at 15:06

I did the experiment and I mixed for 2 weeks. I then filtered and added HCL and refluxed. There was no precipitate of Tetrephalic acid :( :(:(:(:(:(:(:(:(:(:(

bfesser - 23-10-2013 at 15:31

One 'smilie' isn't enough for you? If you're looking for helpful replies, you're going to need to supply details, not a string of frowns.

P.S. Work on your spelling&mdash;'tetraphalic' doesn't mean what you think it does...

<img src="http://www.boingboing.net/filesroot/200902241402.jpg" width="400" />

...the word you're looking for is terephthalic.

bismuthate - 23-10-2013 at 15:44

I'm not suprised that you didn't obtain 4 dick-like objects from your experiment. Please provide more info I would like to know the details.
P.S. you said you mixed for weeks.... your arm must get tired.