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One thing I'm not sure about is why the chemists say that a strong acid (low pH) is required to protonate the freebase alkaloids (which are only weak bases (or is that why) ?
never to forget DVAP, and thanks for all the guidance and info you have bestowed along the way. I would never have gotten anywhere at all without it.Don't forget, I've had the purification worked out for well over a year now.
I really really really feel I need to reproduce my result with mineral oil... you all can feel free to be confident that something's coming out, but like I quoted previously, "If at first you succeed, check your work!". I've gotta see it one more time to really believe it.
yes, while I have no articulable reason to believe otherwise, intuitively I still can't believe it's that effective.
I understand and agree fully with your concerns here DVAP. While I'm not an overly paternalistic type of person, I don't hand my kids matches to play with.
The process is effective and 'safe' as is, additional refinement's can be made without much additional risk. I'd caution against providing direction to those untrained and without the equipment/environment to go the route of pure concentrated alkaloid extraction. So far.... there has never been a death/illness associated with vaping.
For both humanitarian and political reasons... lets do all we can to keep it that way!
Those with the interest and desire will find 'the other way' on their own.
if this process is as efficient as first pass seems to indicate, Then this opens the door to a few obvious 'safe' tricks to incorporate and clean things up without exposing IDLH risks.
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tceight - are you still planning to compare mineral oil and vegetable oil ?
And also compare lab acid with ascorbic, citric and ethanoic ?
And maybe also a weaker concentration of carbonate and a weaker alkali such as bicarbonate ( to see if can extract as much and maybe with less loss of sensitive alkaloids ) ?
And also compare lab acid with ascorbic, citric and ethanoic ?
And maybe also a weaker concentration of carbonate and a weaker alkali such as bicarbonate ( to see if can extract as much and maybe with less loss of sensitive alkaloids ) ?
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Strong acid does not mean "low pH" to a chemist, but rather that it fully dissociates. A strong acid will 'donate' all it's protons, and a weak acid won't. It doesn't always reflect on what you would consider strength. For example hydroflouric acid is 'strong enough' to eat glass, but is considered a 'weak acid' to chemists.
I was going to compare veg. to mineral, but with DVAP's experiment, I don't see a benefit. Vegetable oils are a witches brew of molecules, and there is no standard. Mineral oil should provide consistent results.
Path forward at this point, is to do the extraction with mineral oil, quantify yield with a strong acid, then back to base, and re extract with citric(try 50% saturated), rebase and quantify yield with that.
If it proves greater than 90%, then we can look at maximizing 'yield' from the tobacco. This has never been a concern to me, but the option may be there now.
RE: strength of alkali... I doubt this is a concern whatsoever at a maximum possible pH11. If we were using NaOH, then I might worry.
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But carbonate in water is effectively the hydroxide, no ?
And what do you mean by "then we can look at maximizing 'yield' from the tobacco" - I thought this step was shown to be very effective already leaving only the acid step as uncertain in terms of 'yield' ?
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Which chemists say that? Perhaps it's a matter of degree?
A pH just under 6 will give about 100% single protonated nicotine.
A pH just over 3 gives about 50/50 single -vs- double protonated.
A pH just under 2 gives about 10/90 single -vs- double protonated.
With a weak acid, it's hard to get at pH down below 2 (and thus essentially all double protonated), strong acids can get down there easily... maybe that's what what those chemists are talking about?
By chemists I meant you and tceight
I get the degree of dissociation and perhaps this applies to bases too so sodium carbonate in water is only partially dissociated to give hydroxide ?
As to the 'double protonated' I need a clue - is it that nicotine has two protonation sites?
No. Unless you are talking about hydroxide as the hydroxyl or -OH, in which case Yes.
Same reason as the weak/vs strong acid description. in that case, they are both just +H.
What makes the difference is their equilibrium constants.
RE: yield..
meaning, I was maximizing concentration of the alkaloids in the oil before, not caring if I got all the alkaloids out of the tobacco. (hence using so little). "if the acid step proves greater than 90%" then we can use more oil, or double soak the tobacco, skip pressing, etc.. etc.. and not care about it. It's all about finding a point of safety, cost effectiveness, simplicity, and consistency.
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By chemists I meant you and tceight
I get the degree of dissociation and perhaps this applies to bases too so sodium carbonate in water is only partially dissociated to give hydroxide ?
As to the 'double protonated' I need a clue - is it that nicotine has two protonation sites?
Yep.. Nicotine does have 2 sites. One on the pyrrolidine ring, one on the pyridine ring. The nitrogen on the pyrrolidine ring is much easier to protonate (more basic, needs pH around 6 for 100%). The nitrogen on the pyridine ring is harder to protonate (less basic, needs pH <2 to approach 100%).
As far as solubility behavior goes, I'm not sure I've seen anything on non -vs- single -vs- double protonated. I simply work the pH to drive protonation to fairly exclusive non -vs- double.
I don't even remotely resemble that remark! I'm still in kindergarten with this stuff. :-SBy chemists I meant you and tceight
Yes.
yes
Got it (re equilibrium constants).
So as long as the acid is effective, it doesnt matter too much how much oil one has, just keep the acidified water to a small volume, right ?
I don't see a problem with squeezing out. One just gets some particulates that can be filtered out. Otherwise there will be quite a lot of lost end product.
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right. and if the solubility ratio is high enough(what DVAP mentioned) with only single protonated alkaloids, then we might be able to get by with far "less concentrated (weaker)" acid.
We know citric (pH 2.0) and ascorbic work to some extent, but don't know the actual figure. Fingers crossed it's over 90%. Over 95% of course would allow extra steps to greater purity.
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Naw.. Na2CO3 fully dissociates.
Na2CO3 ---> 2Na(+) + CO3(2-)
So what happens?
CO3(2-) + H2O ---> HCO3(-) + OH(-)
Or we can take the view:
Na2CO3 + 2 H2O ---> 2NaOH + H(+) + HCO3(-)
So even though sodium carbonate dissociates 100%, a 1M sodium carbonate solution will NOT have a pH of zero as would a 1M NaOH solution... The presence of H+ from the dissociation of H2CO3 is the reason.. it keeps the OH- concentration in check.
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