Sciencemadness Discussion Board

Benzene via K2Cr2O7

Mirage - 9-3-2012 at 14:03

Is it possible to oxidize the alkyl substitutant with a dichromate ion to convert it into benzoic acid. I think I would add stoichiometric am mounts with toluene in sex was and then reflux just like the permanganate method. Then combine the benzoic acid with NaOH and distill the benzene.

Has anyone ever used potassium dichromate instead of permanganate?

Mirage

Mirage - 11-3-2012 at 09:04

Quote: Originally posted by Mirage  
Is it possible to oxidize the alkyl substitutant with a dichromate ion to convert it into benzoic acid. I think I would add stoichiometric amounts of potassium dichromate with toluene in excess and then reflux just like the permanganate method. Remove the layer with the potassium benzoate, and add in some HCl to precipitate the Benzoic Acid. Then combine the benzoic acid with NaOH and distill the benzene.

Has anyone ever used potassium dichromate instead of permanganate?

Mirage


Edit: Stupid autocorrect

vmelkon - 14-9-2012 at 17:33

No, but according to this, it works
http://pubs.rsc.org/en/content/articlelanding/1951/jr/jr9510...

and it is also produces benzaldehyde, and a few other compounds.
The KMnO4 method probably also produces a bunch of compounds, the majority being potassium benzoate.

Ozone - 15-9-2012 at 08:08

LOL, I think we would all like stoichiometric amounts of sex!

In any case, it works (albeit with an ugly product distribution). The KMnO4 method is most often cited in the literature.

O3

zed - 15-9-2012 at 12:34

In my neighborhood we would just buy some Sodium Benzoate. Some people use it in canning. ( I think.)

Or, you could Chlorinate Toluene, then hydrolyse it.

[Edited on 15-9-2012 by zed]

triplepoint - 15-9-2012 at 18:11

Quote: Originally posted by zed  
In my neighborhood we would just buy some Sodium Benzoate. [Edited on 15-9-2012 by zed]


buying 1 lb of benzoic acid ... $4.00

learning how to do it yourself ... priceless

vmelkon - 16-9-2012 at 07:14

Quote: Originally posted by zed  
In my neighborhood we would just buy some Sodium Benzoate. Some people use it in canning. ( I think.)

Or, you could Chlorinate Toluene, then hydrolyse it.

[Edited on 15-9-2012 by zed]


He is probably a home chemist like most of us here. Experiment to us means experience. It also means fun, enjoyment, learning.