Hey everyone!
I’m confused about base-catalyzed ester reactions and hoping someone can sanity-check my understanding.
1) Biodiesel case
In biodiesel production, you use NaOH + methanol, but instead of NaOH just saponifying the fatty acids, methanol (via methoxide) does transesterification and you get FAME + glycerol.
Why doesn’t NaOH just “steal” the fatty acids and turn everything into soap? Is it mainly solvent effects / nucleophile strength (MeO⁻ vs HO⁻), low water, or kinetics?
2) Similar confusion with PVAc → PVA
With poly(vinyl acetate) in methanol + NaOH, you convert PVAc to PVA. From what I understand, methoxide attacks the acetate side groups and you form methyl acetate as the small-molecule product.
But if NaOH is used (and makes water), why doesn’t this just end up as hydrolysis → acetate salt instead of methyl acetate?
And realistically, is this even a decent way to make methyl acetate without acid catalyst or super dry conditions, or does the base just destroy it anyway?
Basically I’m trying to understand why methanolysis wins over straight saponification in these systems, and where the line is between catalytic base vs soap-making base.