myristicinaldehyde - 14-7-2016 at 07:54
I found some old vanilla sugar packets while digging through the spice cabinet. Being too old to cook with (like really old) I decided to extract the
ethyl vanillin.
- Since sugar doesn't dissolve at all, or not enough for me to detect, in 2-propanol, I used 91% fresh from the bottle. 50g of sugar, so I added 100mL
of 2-propanol, since ethyl vanillin is highly soluble in it, but the sugar was dense.
I alllowed this to sit for 2h, mixing thorougly. This was gravity filtered, the sugar was a bit wet but it worked better then I thought it would.
-This resulted in 89mL of extract. I let this sit until it was reduced to 45mL (50mL in total, see below) out of direct light in a cool, dry place-
this took 2d. The result was a thicker, pale gold solution with a POWERFUL odor of vanilla. My hands REEK of it now, despite spilling only 1mL or so.
-Since ethyl vanillin isn't terribly water soluble, and I dont have the ability to vacuum distill the solution, I prepared 120mL of very cold (just at
freezing) water. I dumped in the alcohol solution. A fine white precipitate appeared, but the solution stayed that pale honey color and no more
precip. The problem is a miniscule fraction dropped out! When I left 5mL out to dry, I got a good amount of sticky, oily, very vanillin-like substance
with some white crystals poking out. I estimated this to be 50-100mg. I tasted it. It burns and made my mouth feel "dry", but the aroma!
Its been chilling out in the refigerator in a wrapped beaker.
The question:
Should I wait for anything more to come out? Or should I make some chloroform and use that to extract it? (I still have the sugar, I can try
extracting it again, but I have no hope- no vanilla smell left in it.)
zed - 16-7-2016 at 13:58
Not water soluble? Might be able to steam distill it. Problem is, there might not be much of it to steam distill. Cheap on e-bay though.
myristicinaldehyde - 17-7-2016 at 03:57
Yeah, it's not worth the effort to steam distill. I'll buy it instead! I was hoping for some nice easy crystallization...
PHILOU Zrealone - 17-7-2016 at 04:58
50g vanilla suggar contains between 3-10% by weight vanillin...thus 1.5-5g...that is not a lot for 45 ml isopropanol...
Why didn't you simply allowed the alcohol to almost completely evaporate...this would have yielded more crystals?
Since it is a phenol, maybe you could add the right quantity of base (NaOH, KOH and maybe NH4OH with a little water) and make a salt out of it...to
help crystallisation out of the isopropyl alcohol...
Yet I don't know if the aldehydic group will remain stable towards base (possible Cannizaro or imine formation).
Once crystallized, maybe add an acid (dilluted acetic acid or HCl) and extract with a good solvent.