Sciencemadness Discussion Board

Acid/Base extraction of ASA from aspirin

Guizin239 - 2-2-2017 at 12:12

So, folks, I want to get myself some acetylsalicylic acid from some pills.
They contain 500mg of ASA, along with cellulose, talc and calcium phosphate.
I wanna know if it is feasible to react the ASA with sodium bicarbonate to make the sodium salt of aspirin, and then simply filter the solution to get rid of the fillers. Then react the filtrate with a strong acid to get ASA back. Would that work? Is there anything I should be aware of?
The extractions I've seen on Youtube usually involve acetone or isopropanol.
I wonder why that would be the case, since this method I described here seems to be a bit cheaper.
What am I missing?

DraconicAcid - 2-2-2017 at 12:17

If you add a strong acid, you risk hydrolysing the ASA to acetic acid and salicylic acid.

Guizin239 - 2-2-2017 at 12:21

Quote: Originally posted by DraconicAcid  
If you add a strong acid, you risk hydrolysing the ASA to acetic acid and salicylic acid.


Welp, I was going for that anyways.

DraconicAcid - 2-2-2017 at 12:25

Then it should work fine.

aga - 2-2-2017 at 12:29

Oh, i am so glad that you will soon be telling us how your experiment went, with photos, calculations and yield.

Do you think it will take a long time ?

I'm very eager to see how your experiment goes, especially the photos.

UC235 - 2-2-2017 at 16:27

Adding water to pills designed to expand and crumble in water will make a big mess and lots of glop. Using acetone to extract the ASA will avoid this. Buy uncoated, extra strength tablets with minimal fillers aside from modified starch, crush, and extract with warm acetone. Filter off the unexpanded starch then allow the acetone to evaporate.

For hydrolysis to salicylic acid, I recommend the one-pot hydrolysis/crystallization outlined in my prep of phenol which can be found in the Prepublication subforum.

nezza - 3-2-2017 at 02:23

Dissolve aspirin in NaOH -> Sodium acetylsalicylate. Do not heat. Sodium Carbonate might work.
Filter out insoluble materials.
Add acid in the cold to precipitate out acetylsalicylic acid.
Heating the solution will hydrolyse the aspirin.

CharlieA - 3-2-2017 at 18:29

A much "gentler" way to isolate ASA from aspirin is to wash the aspirin in cold water to remove soluble impurities, and then filter off the crude ASA. After drying the ASA, it can be recrystallized from ethyl alcohol. Reference: Supplement to Robert Bruce Thompson's "Illustrated Guide to Home Chemistry Experiments".
My recovery after 1 recrystallization was 72%; mp 133-4*C (lit. 135*C).