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tceight

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(The organic phase does fairly reek of nicotine, btw).

that's good enough for me right there from a qualitative standpoint. My nose is all I have to go on here, and it's 'apparent' when I've got it right. :)
btw... 5N NaOH...... at that high, are you not concerned about degrading the nicotine molecules?
 

tceight

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At saturation the molecules wl be elbowing each other for space like in a crowded bar, say; the alkaloids will fly out if pass an open door (the oil).

Wouldn't it shift the balance of the equilibrium in favor of alkaloid to oil migration?
I can't say no, and don't know why, but my 'model' of how the molecules interact doesn't seem to let this fit. Nice idea if it does work that way.
 

tceight

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How about extracting everything into a volume of acidic water, neutralize with sodium carbonate then evaporate the water, then mix with oil.??
have you tried extracting tobacco with water? You gotta do it at least once, to really appreciate the non polar first step! :)
 
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I can't say no, and don't know why, but my 'model' of how the molecules interact doesn't seem to let this fit. Nice idea if it does work that way.

Your model is more FILO (first in last out). Doesn't matter there is more volume open to the alkaloids than the sugar. or that sugar is more soluble in water than the alkaloids. I can't say no, but that model is not like my model.

;)

Kardenm - Only because we are trying to avoid concentrated alkaloids for safety reasons as this is for jo public to do.
 

tceight

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Your model is more FILO (first in last out). Doesn't matter there is more volume open to the alkaloids than the sugar. or that sugar is more soluble in water than the alkaloids. I can't say no, but that model is not like my model.

;)

Kardenm - Only because we are trying to avoid concentrated alkaloids for safety reasons as this is for jo public to do.

my model is that there are different sizes/shapes/charges/ etc.
if you take a glass of water, and dissolve salt in it until it's saturated.... it can still dissolve a substantial amount of sugar too.
Then, when you are done putting in sugar, dissolve some glycerine...
Then some alcohol, or whatever.
And then there is still room left for pudding! :)
 
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my model is that there are different sizes/shapes/charges/ etc.
if you take a glass of water, and dissolve salt in it until it's saturated.... it can still dissolve a substantial amount of sugar too.

That's why I suggest sugar to compete with the alkaloids :)

Might give it a go with some waste material just to see ...

~~~

Did DVap mention the ye-ball result ? Did I miss that or is he just keeping us on our toes ?
 
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tceight

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That's why I suggest sugar to compete with the alkaloids :)

Might give it a go with some waste material just to see ...

~~~

Did DVap mention the ye-ball result ? Did I miss that or is he just keeping us on our toes ?
try taking a glass of water, and filling it up with sugar. Supersaturate it even....
take a glass of water, and saturate it with salt, keeping track of how much.
then, add that same amount to the glass of sugar. I bet it all fits.

~~~~~ it will take a while, maybe an hour to strip the solvent.
 
try taking a glass of water, and filling it up with sugar. Supersaturate it even....
take a glass of water, and saturate it with salt, keeping track of how much.
then, add that same amount to the glass of sugar. I bet it all fits.

I know I'm kinda drowning but there must be a limit.

And (thanks brokenbrains) some special cases ...
 
Regarding salt saturation:

Link

Some evidence to suggest that some salts under some solvents will do something to the distribution (beyond simply deprotonating the nicotine).

Not sure qualified to read the graph, but looks like the partition levels out at 2.0

Good find.
 

tceight

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Regarding salt saturation:

Link
Some evidence to suggest that some salts under some solvents will do something to the distribution (beyond simply deprotonating the nicotine).
great find... hours of bedtime reading fodder. Thanks!
cursory look would indicate there are anions that may do as Kin is suggesting.
 

DVap

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Alright, got a result.

After all that fooling around, I was able to get a recovered nicotine amount:

800mg. Titration was within a few percent of this figure.

Assuming my steps all did what I figured they should, this would give Conc(oil)/Conc(alkaline water) of 800mg/200mg for a partition coefficient (oil/alkaline water) of 4.

I'm not quite willing to totally commit to the assumption that everything went completely by the book... so we need to say that the partition coefficient is at least 4. If I lost just 50 mg of the nicotine in the various steps other than the oil/alkaline water step, then that would throw the partition concentrations to 850mg/150mg, or a partition coefficient of 5.7.

I feel pretty safe figuring a partition coefficient of at least 4 (solid evidence) and perhaps as high as 6. As partition coefficients go, these are pretty similar in the big picture.

This is firmly in the "good enough" range, though not ideal for too much fooling around with isolation. Other tricks/solvent systems needed for that.
 
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DVap

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How about extracting everything into a volume of acidic water, neutralize with sodium carbonate then evaporate the water, then mix with oil.??

Put the emulsion on your Christmas card list, cuz' it'll still be around come December... :)

This is actually something I've been thinking about and have fooled with in the past, but I shy away from it due to the experience with an absolutely horrid emulsion.
 

DVap

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that's good enough for me right there from a qualitative standpoint. My nose is all I have to go on here, and it's 'apparent' when I've got it right. :)
btw... 5N NaOH...... at that high, are you not concerned about degrading the nicotine molecules?

Not concerned at all. If it did happen, there would be very similar products.
 
Alright, got a result.

After all that fooling around, I was able to get a recovered nicotine amount:

800mg. Titration was within a few percent of this figure.

Assuming my steps all did what I figured they should, this would give Conc(oil)/Conc(alkaline water) of 800mg/200mg for a partition coefficient (oil/alkaline water) of 4.

I'm not quite willing to totally commit to the assumption that everything went completely by the book... so we need to say that the partition coefficient is at least 4. If I lost just 50 mg of the nicotine in the various steps other than the oil/alkaline water step, then that would throw the partition concentrations to 850mg/150mg, or a partition coefficient of 5.7.

I feel pretty safe figuring a partition coefficient of at least 4 (solid evidence) and perhaps as high as 6. As partition coefficients go, these are pretty similar in the big picture.

Not as good as we would have liked, but not too bad either. Good work nailing that DVap. Eating my pie now ...
 
As I edited into the parent post, this is in the "not ideal, but good enough" range for the procedure as written.

For a real purification, it'll take other tricks as the losses would add up quickly with oil/water.

We''ll appeciate it all the more for having had to work so hard at it :)
 
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