Sciencemadness Discussion Board

Crotyl alcohol --> butyraldehyde?

1911 - 15-7-2011 at 13:43

At the moment I'm looking a most cost-effective synthesis for n-butanol and I think that crotonaldehyde would be way to go as it's produced from acetaldehyde by fairly simple aldol condensation. This could be reduced with sodium borohydride forming crotyl alcohol. I'm wondering right now, if crotyl alcohol is able to go through tautomerization (in any conditions) to butyraldehyde like vinyl alcohol to acetaldehyde or not. This butyraldehyde could be then reduced by sodium borohydride. If there was some catalyst to accelerate the tautomerization, the whole thing from crotonaldehyde to n-butanol could possibly be a one-pot synthesis.
I know that crotonaldehyde can be hydrogenated straight to the n-butanol but my economical situation doesn't allow the purchase of palladium metal. Also I highly doubt my abilities to construct a working hydrogenation apparatus.

Magpie - 15-7-2011 at 20:40

Have you given any thought to the biosynthesis of n-butanol from sugar? I was going to try this at one time but I would have to buy the bacteria (not expensive) and use anaerobic conditions.

Chaim Weizmann developed this technique because of a shortage of acetone during WWII if I remember correctly. n-butanol was a side product.

1911 - 16-7-2011 at 01:42

That could be rather interesting. Only I have no idea where to get such bacteria. How would one go obtaining clostridium beijerickii for instance. Are there any companies supplying bacteria for others than laboratories, companies or universities in the first place.

tmb - 16-7-2011 at 02:34

You can buy it here if you are interested:
ttp://mistralni.co.uk/catalogue/product/147/n-Butanol-n-butyl-alcohol
They ship to Finland; but maybe you should ask to make sure, as it is listed as hazardous.