Sciencemadness Discussion Board

Can formic acid self-catalyze Fischer esterification with n-propanol?

bnieto87 - 30-1-2017 at 11:58

I know that for Fischer esterification to take place, you need an acid catalyst, otherwise your reaction will take a very long time. If I have a n-propanol / formic acid mixture with n-propanol in excess (~20:1 ratio by weight), will esterification take place? I'm wondering if there's a chance that the formic acid could self-catalyze this reaction.

Additionally, there is some polyacrylic acid in the mixture, about 0.5-1.0wt%, although in such low quantities, I don't imagine it would affect any potential reactivity very much.

Boffis - 30-1-2017 at 12:05

Yes. If your formic acid is >98% and the alcohol is in large excess and reasonably dry you should get a reasonable yield. Check out Vogel's "Textbook of Organic Chemistry"

bnieto87 - 30-1-2017 at 13:36

Quote: Originally posted by Boffis  
Yes. If your formic acid is >98% and the alcohol is in large excess and reasonably dry you should get a reasonable yield. Check out Vogel's "Textbook of Organic Chemistry"


Is there anything else required for this reaction to proceed? Like elevated temperatures, etc.? For example, if they were stored together in a container for a few days, would that still yield a large amount? As it turns out, the reaction is NOT desirable, so I was really hoping someone would allay my fears and tell me "No, stupid, you need some sulfuric acid!" or something else along those lines.