Sciencemadness Discussion Board

Fisher-Esterification

SodaPenguin - 30-1-2017 at 09:41

I was performing a Fisher esterificatiom trying to synthetise isopropyl benzoate. The execution was admittadly bad, I used way too much sulfuric acid and the reflux was also bad. An unexplainable pink Color was visible and when I added NaOH to neutralise the H2SO4 (I realise this is not an awesome idea as I could overshoot and get sodium benzoate) the color turned to a deep red. Do you guys have any idea what this could have been? My guess is it was probably an impurity in the H2SO4 as it was very old.

[Edited on 30-1-2017 by SodaPenguin]

NitratedKittens - 30-1-2017 at 11:33

What amounts of each chemical did you use

Texium - 30-1-2017 at 14:51

I would say that with the little information you have provided it is nigh impossible to explain what happened to give the red coloration, and that you should try again, using the correct ratios of reagents and recording all quantities. Also, don't use NaOH to neutralize the acid. It will cleave your ester and destroy your yield. If it won't separate into layers on its own, try extracting with ether if you have it available. Wash the organic phase with a bicarbonate solution a couple of times to neutralize trace amounts of acid.