Godrick VanHess
Harmless
Posts: 14
Registered: 24-2-2017
Member Is Offline
Mood: Ionized
|
|
Removal of DMF (Dimethylformamide)
So I have a sensitive indole dissolved in DMF and I need to remove the DMF. I can evaporate the DMF using a rotary evaporator at 60°C which is
unfavorable for my application. I am thinking about trying to form a lower boiling azeotrope and try and evaporate that. I have found a few sources
that mention using benzene, toluene, heptane or a potential mixture of these to for said azeotrope. I was going to try using benzene - DMF azeotrope
but I would like to find an even milder method if possible. Does forming an azeotrope sound like a good idea or does anyone have a better idea short
of finding a different solvent?
|
|
|
Chemi Pharma
Hazard to Others
Posts: 350
Registered: 5-5-2016
Location: Latin America
Member Is Offline
Mood: Quarantined
|
|
DMF is water miscible. If you add enough water and after that an aprotic solvent after that, like dichloromethane, with stirring, DMF will be mixed at
the water layer and the indole will be remained dissolved at the dichloromethane layer.
Then, it's just to fractionate the layers and distill off the dichloromethane bottom layer at vacuum, with no heat at all, to don't screw up your
residual indole.
|
|
|
Dr.Bob
International Hazard
Posts: 2753
Registered: 26-1-2011
Location: USA - NC
Member Is Offline
Mood: Mildly disgruntled scientist
|
|
Good luck, DMF is tough to get off, azetropes might help a little, but a higher vacuum will help a lot more. And if you use DCM, I have always found
that it hold a good bit of DMF from water, so you miught get rid of some, but not all. I always try to rotovap off as much as possible first under
the highest vacuum I can get, then do a water workup, preferably with EtOAv or ether, which don't hold DMF as well, then evaporate and remove the last
DMF on the high vacuum overnight or 2 days. That usually works for me.
|
|
|
Godrick VanHess
Harmless
Posts: 14
Registered: 24-2-2017
Member Is Offline
Mood: Ionized
|
|
Quote: Originally posted by Dr.Bob  | | Good luck, DMF is tough to get off, azetropes might help a little, but a higher vacuum will help a lot more. And if you use DCM, I have always found
that it hold a good bit of DMF from water, so you miught get rid of some, but not all. I always try to rotovap off as much as possible first under
the highest vacuum I can get, then do a water workup, preferably with EtOAv or ether, which don't hold DMF as well, then evaporate and remove the last
DMF on the high vacuum overnight or 2 days. That usually works for me. |
Ah, yes that could explain it! We
did try extracting into DCM but the DMF apparently always appears on the NMR spectra. Unfortunately I'm stuck with the vacuum. I think I might try
extracting into a different solvent also. Did you mean EtOAc or EtOAV? (Sorry, just want to make sure I'm on the same page)
[Edited on 15-2-2018 by Godrick VanHess]
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
