What could cause low yield in esterification with acetic acid and ethanol?

[Scott90]

I was trying to follow a procedure for a simple esterification using acetic acid and ethanol, but my final product yield was way lower than expected. I suspect my reflux setup wasn't truly airtight and I lost some of the more volatile reactants or products during heating.

[Stella.T]

That esterification stuff is fussy about water and losses. If your reflux wasn’t truly airtight, you could be losing ethanol or ethyl acetate through leaks. I chased a similar issue and realized vapors sneaking past a loose joint were the whole problem, not the chemistry itself. Still, remember the reaction sits at equilibrium and water can push it back if it builds up.

[Aurora11]

I once had a leak at a joint and a clogged condenser. It looked fine until I saw vapor escaping; after tightening the joints and replacing the gasket, the reflux behaved and the distillate returned more reliably. The apparent yield rose, but it wasn’t dramatic. It was enough to prove the leak mattered.

[VictoriaAW]

Are you sure the seal is the real bottleneck, or is the reaction just not going to completion under your conditions? The water byproduct and equilibrium matter a lot, and if you didn't remove water effectively it can stall.

[StevenM]

Sometimes I fix a bench with extra light and a clock to track how long things breathe during reflux, and I still wonder if room humidity is interfering more than we admit. I keep coming back to the same thought though: the seal matters, but the real bottleneck might be the water removal and the equilibrium, not the leak alone.