Sciencemadness Discussion Board

2-butanol from Butanone (MEK)

artemov - 14-11-2020 at 04:00

Just wondering if there is a relatively simple and not too expensive way to make 2-butanol from butanone (MEK, of which I have litres)?

I googled "butanol from butanone" and its various permutations, and I mostly get the reverse process, making butanone from 2-butanol by oxidation, except for one using LiAlH4.

Corrosive Joeseph - 14-11-2020 at 04:19

NaBH4....



/CJ

Aqua-regia1 - 14-11-2020 at 04:24

You can do hydrogenation of MEK to butene in fix bed reactor over Cu-zeolite. Hard job for beginner.
https://krex.k-state.edu/dspace/handle/2097/39274

I would preparing it via Grignard (ethylmagnesiumbromide) and acetaldehyde, solvent THF or ether. Easy peasy for experienced org. chemist. You can find a lot of preparing formula.

artemov - 14-11-2020 at 04:55

Quote: Originally posted by Corrosive Joeseph  
NaBH4....
/CJ


Hi Corrosive Joeseph! ... I watched your dimethyglyoxime video and was actually thinking of making 2-butanol from MEK to make 2-butyl nitrite! Both 1-butanol and 2-butanol are not easily available here.

Unfortunately I also can't get the hydrides easily (and cheaply :P) ...

Corrosive Joeseph - 14-11-2020 at 06:15

Quote: Originally posted by artemov  

I watched your dimethyglyoxime video


Eh, er, what.....? No, definitely wasn't me.

Well, NaBH4 is by far the best reductant for carbonyl to alcohol.
You only think you can't get any, sure you can, there must be 4 or 5 guys on here selling it right now.

IMO your only other option is a messy dissolving metal and acid reduction, but this will probably yield in the 50-60% range, the NaBH4 reduction should be up in the 80's I do think.


'Reduction of C=X to CHXH by Dissolving Metals and Related Methods - J.W. Huffman'
https://www.sciencemadness.org/whisper/files.php?pid=647822&...



/CJ

artemov - 14-11-2020 at 06:46

Quote: Originally posted by Corrosive Joeseph  
Quote: Originally posted by artemov  

I watched your dimethyglyoxime video


Eh, er, what.....? No, definitely wasn't me.

Well, NaBH4 is by far the best reductant for carbonyl to alcohol.
You only think you can't get any, sure you can, there must be 4 or 5 guys on here selling it right now.

IMO your only other option is a messy dissolving metal and acid reduction, but this will probably yield in the 50-60% range, the NaBH4 reduction should be up in the 80's I do think.


'Reduction of C=X to CHXH by Dissolving Metals and Related Methods - J.W. Huffman'
https://www.sciencemadness.org/whisper/files.php?pid=647822&...



/CJ


Oops sorry ... and thanks ... it's not cost effective. I think I'll just stick to the lower alcohols.

The video in question (Corrosive Chemistry) :P
https://www.youtube.com/watch?v=nZsheQlNAeg

Tsjerk - 14-11-2020 at 07:06

It is mentioned in the video you can use any nitrite ester.

Fery - 14-11-2020 at 07:20

artemov - you googled ;)
but did you search sciencemadness forum?
http://www.sciencemadness.org/talk/viewthread.php?tid=20317

artemov - 14-11-2020 at 07:27

Quote: Originally posted by Tsjerk  
It is mentioned in the video you can use any nitrite ester.


I find IPN a bit hard to handle due to its low bp. So I was thinking maybe 2-butyl nitrite would be better.
Quote: Originally posted by Fery  
artemov - you googled ;)
but did you search sciencemadness forum?
http://www.sciencemadness.org/talk/viewthread.php?tid=20317


Nice one! Thanks!

IPA + MEK -> Acetone + 2-butanol
Just need to find the right catalyst and the right conditions.

[Edited on 14-11-2020 by artemov]

njl - 14-11-2020 at 10:32

I think Thiourea dioxide can reduce carbonyls to alcohols.

ArbuzToWoda - 14-11-2020 at 10:55

By itself? Are you sure? Maybe activated, like described here: https://patents.google.com/patent/US4610802A/en