How can i fix a low yield in esterification with acetic acid and ethanol?

[Ava.T]

I was trying to follow a procedure for a simple esterification using acetic acid and ethanol with a sulfuric acid catalyst, but my product yield was way lower than expected. I think I might have messed up the reflux setup, as I'm not totally confident I maintained a proper equilibrium for the reaction to complete.

[JerryL]

I tried a similar esterification once. The reflux looked fine at first, but water never seemed to leave the pot. I think the water kept accumulating and the equilibrium shifted back toward the acids, so the ester yield stayed low.

[James_S]

What helped in a later trial was realizing you really need to remove water or use excess alcohol. I didn't use a Dean Stark or drying agent, so the water hung around. Also I kept the condenser clear and tried not to flood the flask with heat, but I can't say if that changed much.

[Larry_H]

I did a quick check by weighing what I thought was the ester, but I’m not sure I did the separation right and the numbers felt off.

[Sophia_G]

Do you think the issue might be something else, like catalyst lifetime or impurities, rather than the reflux balance?