The main takeaway from addendum 4 I see is that cyclohexane was a suitable extraction solvent prior to their chemical modifications and purification steps. Cyclohexane, like butane, extracted without concern. I enjoy trying to figure out what you’re talking about but if you could be more specific that would be helpful.
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I think the amberlyst probably wouldn’t work if the THCa was deprotonated in natural form, which if I recall correctly was the theory we discussed which brought about the question “why does butane work”
That discussion was about how THCa becomes protonated in the trichome after being synthesized in the deprotonated form.
If the base form of THCa is dominant I’m not sure the cyclohexane would work well and I’m not sure the amberlyst would be able to measurably bind to it. If I’m reading it right the amberlyst is up taking the acid… the acid being THCa. Then the amberlyst is washed with strong base to remove the THCa and deprotonate it. Am I reading that wrong?
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So initially 91% THCA-A and 5% THCA-B and these are de-protonated in the plant?
The post was deleted due to an incorrect
interpretation of the active matrix group on the amberlyst
resin…see alex siegal and Magister Chem below.
My understanding is the amberlyst only becomes Positively charged after absorbing the acid. If the THCa is in basic form that can’t happen. I’m not sure what is confusing here
The protonation source could be the other fatty acids in the trichome, no? Have you looked at all of the pka of the fatty acids present in the trichome
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Patent says this:
Extract THCa with non polar.
Bind THCa to a resin by passing the ACIDIC THCa over the BASIC amberlyst resin.
Release the bound THCa using a base.
Purify again if desired using an acidic exchange resin which binds the basic salts and basically does the same purification again.
If in this patent they had added an acid FIRST then I think you’d be onto something but I don’t think they require it.
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Yes, looking through it now in detail this theory makes no sense to me.
He is claiming THCA is ionized in alkane solution? Highly unlikely.
The dimer shown is not “H+” or ionized in any way. It is plainly just two neutral molecules interacting by hydrogen bonds only… Not ionic bonds!
And then there is this business “the amberlyst is a teritary amine…alway Plus 1 charge”. That statement is very confused. A tertiary amine is neutral when not protonated. It is when it RECEIVES a proton that it becomes positive.
Very simply, the amberlyst deprotonates the THCA and then it is ionic.
If it were a quaternary amine, these statements would be correct, and then it would sense, because of the “natural state” of THCA was THCA O-, then it would interact with this hypothetical quaternary amine by ionic bonding. But that’s not, in fact, what this patent depicts.
Seems to me this is based on misreading all these papers and not the case at all.
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It’s pressure.
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You’re saying pressure is what helps dissolve?
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Magister: correct, I incorrectly thought the resin was a quaternary amine…incorrect as pointed out…The
patent is confusing where he defines his terms:
"The THCA and CBDA bound to said basic ion-exchange resin following step (i) of the process are of
the formula A and B, respectively, wherein R+ represents said ion exchange resin anion form. It should
be noted that formula A represents the ionized form (COO ) of both THCA and its isomer
(6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-4-
carboxylic acid, referred to herein as “THCA 4-COOH” and considered as an impurity in the process.
But looking at the data for resin it is a tertiary amine.
I totally agree with your criticism concerning the interpretation.
there is no identified source for the proton.
The thca leaves the synthase in the ionized form.
The synthase is excreted into the vacuole as well as the
GBGA precursor. Of course it makes no sense that the
THCA (ionic) is extracted by the butane…it is the whole point
of the discussion.
There are two dimers represented in the post.
you are only refering to the one found in the THCA crystal.
I was referring to the form coordinated by the Ca++
thanks to both you and Alex for pointing out my mistaken
thought that the resin was quaternary.
But I am wondering if you both are suggesting the proceedure will not work with a strong anion exchanger
such as a quaternary amine? If you read the entire patent and look at examples of this resin use with alcohol where they use ammonia to deprotonate the COOH…you might think a bit differently about “anion exchange”.
Admittedly the use of this resin in combination with butane makes it difficult to picture the use under these conditions. (see below #106: addendum 5)
Regards
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Pressure has a negligible contribution to a solvents ability to dissolve something. Pressure only contributes to the solubility of gasses in a liquid.
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Higher pressure in a butane solution is a direct reflection of the temperature of the solution. I understand that adding 50 psi of nitrogen is not the same as heating up my butane to 110f
imo there is no ‘dissolve’ in an organic solvent, only miscibility since there is no net positive interactions. an organic, freed by pressure from a ruptured trichome, merely floats with the stream and pressure. easy peasy.
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Pressure gets generated when a solvent is heated but the pressure generated doesn’t contribute to the solvents capacity to dissolve something, the heat does that.
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Bro…just no
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Thanks for that post. That explains it well. I already learned something today and it is still early.
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Henry’s law is exactly what I was describing…
The solubility of a gas is influenced by pressure, but pressure has no effect on a liquids’ ability to dissolve a solid.
You don’t understand what Henry’s law is then.