Sciencemadness Discussion Board

Benzene from Phenol

ScienceHideout - 23-2-2014 at 20:38

C6H5OH + Zn ---> C6H6 + ZnO

I see multiple sources online that say that simply distilling this will drive the reaction and get benzene, but I cannot seem to find any instructions or procedures to make this go thru. Perhaps we should do some experimenting!

Phenol is 96 g/mol; benzene is 78; zinc is 65.5

What if we take 9.6 grams of phenol, make it into solution with n-BuOH (because of high boiling point) and add molar excess of zinc, ~10g. What would happen if we reflux this for 30 minutes, then set up for distillation. Will benzene come over at 80 C? I don't see any benzene/alcohol azeotropes. Besides- is benzene not insoluble? Maybe we can separate then distill?

Assuming 100% yield, we will get 7.8 g benzene... but because we are human we could probably expect 5 mL, right?

Any insight goes appreciated, thanks!

plante1999 - 24-2-2014 at 04:23

You should reflux the phenol without solvent. I remember having read that experiment in an old book about lecture experiments, apparently you heat zinc dust in a tube and pass hot phenol fumes that condenses in benzene.

ScienceHideout - 24-2-2014 at 05:23

Nice input! I would like to try that... just something about liquefied phenol makes me uncomfortable though. I don't know if it is the smell, the phenol that is left on the glassware, or perhaps the movie "unstoppable" but there must be another way... :D

But thanks anyways, Plante!

bfesser - 24-2-2014 at 05:50

Quote: Originally posted by ScienceHideout  
I see multiple sources online that say…
Then post them.

ScienceHideout - 24-2-2014 at 11:58

Quote: Originally posted by bfesser  
Quote: Originally posted by ScienceHideout  
I see multiple sources online that say…
Then post them.


Wikipedia and yahoo answers :P

I know, I know, those don't count... BUT... Wikipedia links to a book...
http://books.google.com/books?id=HEY9AAAAYAAJ&pg=PA199&a... <-Pg 23

EDIT:
http://chem-guide.blogspot.com/2010/04/preparation-of-benzen...
Here is another page

[Edited on 24-2-2014 by ScienceHideout]

Zyklon-A - 24-2-2014 at 12:16

Wikipedia say's, "Phenol is reduced to benzene when it is distilled with zinc dust or its vapor is passed over granules of zinc at 400 °C: C6H5OH + Zn → C6H6 + ZnO.