Sciencemadness Discussion Board

Advice for Low Temperature Phenol Synthesis from Salicylic Acid

CwisGons - 12-6-2021 at 09:30

Hello everyone. I am a novice home chemist with a small simple distillation kit and hotplate. I was thinking of making phenol from salicylic acid by decarboxylation with the use of a basic copper carbonate catalyst, all of which I have access to. I based this off of this video.

https://www.youtube.com/watch?v=r-xt24lBbrs


I have more access to basic copper carbonate than other copper catalysts, and I was wondering if this could work. I put a link to a paper which details how copper catalysts serve as an effective decarboxylation catalyst. Could this work?

Attachment: xue2011.pdf (1.1MB)
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Amos - 12-6-2021 at 09:53

This decarboxylation actually works just fine without adding any catalytic materials, but you’ll still have to heat the salicylic acid at least to the boiling point of phenol

CwisGons - 12-6-2021 at 10:56

I know, but I wish to add the catalyst to make it faster and to use lower temperatures overall. Also, in every video I've seen of this procedure without catalyst they require a vacuum, which I don't have.

Texium - 12-6-2021 at 11:51

A vacuum isn't required, though it will lower the temperature needed to distill the phenol. I don't know whether adding a copper catalyst would actually help at all in this case, and even if it did, it wouldn't really matter. As Amos pointed out, the reaction takes place at the boiling point of phenol, and you'll need to heat it to that temperature anyway to distill the phenol.

UC235 - 13-6-2021 at 05:07

Copper catalysts don't work on salicylic acid alone. They need pyridine-type ligands to work. With nicotinic acid, they are already present. Unless you want to do your phenol prep with added quinoline, which is a typical solvent/co-solvent for copper decarboxylations, you will get the same result as just heating it.