A working list of byproducts formed during acid catalyzed CBD conversions

I agree and I mentioned that early in the introduction. But that never is not worth noting in the context of this discussion.

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Sorry I had to take a break but I’m happy to see someone else already shared it. I meant to link accessible PDFs for everything. The other one notably missing is Mechoulam’s Hashish VII but it’s somewhat outdated (although it was the building block for much later research) and has been uploaded here in the past if you check on google scholar, if anyone wants to reference it, or I can upload it again.

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I do very much appreciate the work out into compiling and interpreting this research here.

Thank you.

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Welcome to the future @mitokid!

Thanks for the great thread @jakovsau5! Very nicely written and quite interesting.

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Thanks for compiling and sharing.

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The muriatic acid method produced the greatest number of
impurities in the sample. Specifically, this method produced both
11-hydroxy-THC and 11,500-dihydroxy-D9-THC, which were not
found in the other methods. This is interesting because this is the
procedure that could occur in the human body. The isomerization
of CBD using 0.05% HCl may occur in the human body generating
these unknown cannabinoids, which warrants further research to
be conducted on these isomers for toxicity and pharmacokinetics.
This study allows researchers to begin isolating these impurities to
study toxicity on the human body.

Looks like muriatic acid is a good starting point for the garbage challenge, pair it with hardware store heptane/toluene and some crude and we’ve got a good start

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Was it Etoh and phosphoric that was very clean? Was it ethanol and pTsa that was particularly nasty?

I think @pdxcanna is right that solvent and acid choice will be very telling with the garbage challenge.

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I would personally go with HCl. Any weakly reactive acid that leads to an incomplete conversion.

Other morning thoughts:

This preliminary list is intended to be a jumping off point. I can’t emphasize that enough. Problematically, different catalysts and different solvents can lead to unique byproducts, such as the ethoxy and methoxy HHCs that only seem present when ethanol and methanol are used as solvents respectively. I believe it would be more practical to test for byproducts that seem very common to every reaction eg 8-OH-iso-HHC, and then perhaps a few such as 11,5’-dihidroxy-THC that may signal a less desirable reaction. Because some of the research is flimsy as @roiplek was quick to mention, I would not bank on these “telltale signs” being accurate without further research on other catalysts and solvents.

From a regulatory standpoint, p-Toluenesulfonic acid seems to offer the most complete reaction with the fewest byproducts, but I would not be surprised if some of the other THCs still occur in trace quantities. Weaker acids generally seem to allow for less stable bonds but maybe someone can correct me on that. I see little reason to use other acids so in a hypothetical well regulated world where we could purchase adequately lab tested isomerized delta 8 THC from a dispensary, I would see little reason not to ban the use of other acids for commercial production (for delta 8 THC).

The particular cannabinoids I see come up consistently in research are 9α-OH-HHC and 8-OH-iso-HHC which no labs are testing for to my knowledge. These have mild THC-like effects according to at least one study. A higher purity reaction is also known to take place in an inert environment and it is not unlikely the difference in % is due to these oxygenated compounds incl 11-OH-THC and 11-OH-CBD with the former displaying psychoactivity as it as major metabolite of THC. Many of the others seem to be artifacts from either weak or incomplete reactions.

Testing for residual acids may be more practical, but we have yet to see that happening either. Is there a difficulty in testing for these residuals or is it lack of interest on the part of manufacturers? From my understanding it isn’t hard to remove the acid catalyst, but rather it is a matter of proving it succinctly with a lab result.

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So is hci or ptsa the best for conversion? I’ve used both for 8. Ptsa ftw.
Always looking for a challenge. Ive got a d9 sop and am willing to try some things to see where and what works best for mfg something clean.

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Ptsa and any alcohol produces a byproduct that can mutate your DNA, this is why ptsa is usually used with hydrocarbons in academic literature

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Right on. I should have clarified, many here already know n-hexane is a great solvent choice. Ethanol and methanol also create ethoxy and methoxy THC side reactions so they are obviously less than ideal in any scenario.

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Per my d8 trials, hexane gave the cleanest.

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This is marvelous. I’m going to shoot a video on it Very educational

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Per my trials the only time I made olivetol and cresol were with hexane

Never made it with heptane

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Just going off of what my coas from kca showed me that for my particular sop hexane worked the best.

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I did 24 hours room temp

All 4 I tested over the 24 hours popped no idea why

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I ran a 3 hour rxn. Quenched when I saw my spike normalize and begin to drop. All clear. I keep posting the same coa, but it seemed to give the cleanest. Here it is @Kingofthekush420
Clear Fraction COA.pdf (2.9 MB)

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There’s some obvious noise before the d9 peak, but kca also showed me that there were zero trash in it. So, that’s what I’ve found

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Most ppl consider those weird thc isomers bad though since we don’t know the toxicity and we can’t quantify then

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This! This is the stuff that still gets my motor turning, a well thought out piece, with comprehensive sourcing. :+1: great write up! Wish there was a high five and a hug button instead of just the love button.

Also great work on the guys refining their science and figuring the riddles out. This stuff is the future.

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