[discodermolide]

It is not an azeotrope it is a steam distillation. Phenol is volatile in steam, salicylic  acid not.

Just reiterate the point of the steam distillation of salicylic acid and to correct my comment. The steam distillation of salicylic acid is noted in this Org Syn procedure, http://www.orgsyn.org/orgsyn/pdfs/CV2P0531.pdf. The reason salicylic acid does not steam distill is because it is not present.

Why was carbon dioxide bubbled in? What happened?

Thanks, I was not aware that salicylic acid was steam volatile. I suppose lots of compounds you would not expect to be are also steam volatile!

[Rutherford]

"Number 3: Yes, the oxygen atoms are missing."
So, it was an typing mistake.

"The reason salicylic acid does not steam distill is because it is not present."
It's conjugated base is present, right? So why at the end salicylic acid and not its base left in the vessel?

[discodermolide]

"Number 3: Yes, the oxygen atoms are missing."
So, it was an typing mistake.

"The reason salicylic acid does not steam distill is because it is not present."
It's conjugated base is present, right? So why at the end salicylic acid and not its base left in the vessel?

I would say that salicylic acid is present as its sodium salt, as I said above.

[Rutherford]

Okay, you mean that at the end Na-salicylate is present instead of salicylic acid. Then there is a mistake in the answer (first no oxygens, then no Na). Thanks for helping.

[discodermolide]

Okay, you mean that at the end Na-salicylate is present instead of salicylic acid. Then there is a mistake in the answer (first no oxygens, then no Na). Thanks for helping.

No problem

[OC pro]

Totally agree with disco. Salicylic acid itself can be steam-distilled, I have done it already. It has to be the corresponding sodium salt.