Freebasing Alkaloids in non-aqueous solution (glycerol)

[Dumdumpadrum]

First time poster, long time lurker!

I'm working on an extraction route of nicotine from tobacco. I have successfully made a relatively pure oil out of steam distillate by doing a liquid-liquid extraction with DCM. It works well, but I'm putting this in my vape so I would like to run a vacuum distillation as well to get the nitrosamines out (they have a far lower BP than nicotine from what I've read).

And if I'm running a vacuum distillation anyways, why not skip the DCM all together?

The steam distillation produces a very weak aqueous solution of tobacco volatiles. To make this more manageable, I salt the nicotine (citric acid) and boil it down.

In order to get the nicotine volatile again I have to base it. How feasible is it to freebase the nicotine with a solution of NaOH in glycerol? Are there any strange caveats I should be aware of?

Glycerol chosen for it's very high vapor pressure and low cost. I want to keep water out of my vacuum pump if at all possible.

 

[Transform]

I want to keep water out of my vacuum pump if at all possible.

Use a cryogenic vapour trap (but beware of forming liquid oxygen if you end up using LN2!) You probably don't want DCM in your vacuum pump either, after all.

Are you planning to distill the nicotine out of the glycerol? You'll probably get some water coming over too, both because of glycerol's hygroscopicity and from the reaction of the NaOH with the nic citrate, specifically the OH- + R3NH+ >>> H2O + R3N bit. Dry before and/or after with something like anhydrous sodium carbonate.

Never tried this with nicotine, though - this is just general principles extrapolated to your case. I can't guarantee that NaOH in glycerol won't weirdly ravage your molecules either, even if it seems quite unlikely. If nitrosamines are still present, some of them could form highly reactive diazo compounds which may possibly alkylate your nicotine in strange ways, for example. More research necessary.