Running an ozone generator into a water solution of pottasium piperate wont cause any piperonal to ppt out of the solution, since piperonal is the
least soluble of byproducts ? Any glycolic acid or glyoxal that is going to be generated as byproducts would remain into the solution. Also with this
way there would not be any danger to produce any organic peroxides since water is used as a solvent instead of acetone.
Sharing my thoughtsDraconicAcid - 12-1-2025 at 17:03
I'm pretty sure you can't form piperonal directly from the reaction with ozone. You'll make the ozonide, which you then have to decompose with a
reducing agent in order to make the aldehyde, or an oxidizing agent to make the acid.clearly_not_atara - 13-1-2025 at 09:53
IIRC you can usually use bisulfite for the workup but if you don't want the adduct Wikipedia suggests zinc powder.
I would be conscious of the risk of foaming during this reaction. The addition of calcium salts is known to reduce foaming when working with aqueous
solutions of fatty acid salts ("hard water" effect on soap) and might also work here. underground - 13-1-2025 at 15:53
Was just thinking to use a sodium bisulphate solution for purification.
I saw a video from Chemdelic "Ozonolysis Of Piperine To Piperonal...Kinda" and in the comment section:
"i was doing exact same synthesis when i was at the university... the difference was that i started with piperic acid and not piperine. the rest was
preaty much the same as in your procedure. the think i have learned is that you cant overshoot the ammount of ozone and you can just keep it running.
i was running my synthesis at the doubble the ammount of time needed. I also learned that the ozone generators produce a lot less than they state and
it is best to make a iodometric titration to determine your generation in the first place. it also helps to hook up pure oxygen to the generator as
the nitrogen is decreasing the ozone production"
So my guess is that you can just keep shooting ozone untill all piperic acid broke down to piperonal, then purify with bisulphate solution.
I have seen others run the same rxn but with styrene producing benzaldehyde, so it certainly kinda works. I guess there is just not enough research
done on this.
[Edited on 13-1-2025 by underground]DraconicAcid - 13-1-2025 at 16:02
Now I want to buy an ozone generator.....chempyre235 - 13-1-2025 at 20:36
