Sciencemadness Discussion Board

1-butanol dehydrogenation via heated copper

Hockeydemon - 30-7-2013 at 11:55

I was hoping to dehydrogenate 1-butanol by heating up a coil of copper wire that I have laying around, and suspending it above a beaker of 1-butanol. I figured this was fairly easy, and straight forward because of this lab

However when I performed it small scale not much took place. Upon further reading it appears that this process is usually done in a tube furnace with a inert carrier gas.

Is this an impractical method without having a way to vaporize the alcohol with an inert gas to prevent ignition?

Magpie - 30-7-2013 at 13:59

Here's some interesting reading on attempts to make acetaldehyde:

http://www.sciencemadness.org/talk/viewthread.php?tid=55&...

I suspect making butraldehyde isn't all that easy either.

kch - 4-8-2013 at 18:53

Depending on how badly you need it, you could try this:

-Oxidize primary alcohol to butanoic acid using KMnO4 or Jones'
-Reflux with SOCl2 to butanoyl chloride
-Reduce with NaBH4 over dry ice to give the aldehyde


It's not really economical, but I think it's possible for the amateur to perform

Metacelsus - 5-8-2013 at 14:21

Thionyl chloride, sodium borohydride and dry ice :o ? Just use pyridinium chlorochromate!

It would probably be cheapest to just buy the butyraldehyde.

Also, you could condense acetaldehyde (good luck getting that!) to form crotonaldehyde and hydrogenate it.

http://www.organic-chemistry.org/chemicals/oxidations/pyridi...

https://en.wikipedia.org/wiki/Crotonaldehyde

https://en.wikipedia.org/wiki/Butyraldehyde

[Edit] Added sources

[Edited on 5-8-2013 by Cheddite Cheese]

kch - 5-8-2013 at 17:12

I'm learning here, bear with me :)

<!-- bfesser_edit_tag -->[<a href="u2u.php?action=send&username=bfesser">bfesser</a>: removed quote of entire preceding post]

[Edited on 6.8.13 by bfesser]