right…diamonds are precious. even sans sauce.
although making diamonds and decarbing seems like less work than distillation at some level. remind me again why we’re here?
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Thc distillate is somewhat pure but i have never seen “thc distillate” as a 99+ thc mix usually there are several other compounds in the mix as well as 80% thc.
You have the propensity to carboxylate several other compounds and cannabinoids in the distillate mix.
The overall purpose of this process is to increase the amount of crystals able to be grown from decarbed thc distillate correct?
Can you be more specific on your last statement on yields?
In my experience after the carboxyl group leaves thc has no method of attaching itself to one another. So adding the group is the only way you could actually achieve crystalline growth.
Your yield question: the carboxyl group has mass, adding it back would increase the mass of each molecule. Try this as an experement, take some thca isolate record the weight, decarbed it and record the weight. Note the difference.
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Yes of course when decarboxylating the CO2 will not attach to other molecules most likely, however when adding CO2 back onto a mix of molecules contained in thc distillate you run a risk of carboxylating other molecules in that mix.
Right right this would add an additional 44 g/mol onto the thc molecule.
Have people been able to crystallize thc when it is decarboxylated or is that the problem we are trying to solve? Because if we can isolate thc in its decarboxylated form we should do that then REcarboxylate to avoid the risk of side products/reactions.
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I beleive @Soxhlet meant that once decarbed, THC looses it’s attraction to other THC molecules. aka “it won’t crsytallize”.
yeah, I think so. I have not explicitly scoured the interwebs, but I have not stumbled across it, and that does seem to be the consensus of the opinions I’ve read.
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I see! That would make more sense.
If we cannot crystallize thc in its decarboxylated form I would suggest trying to attach a sugar onto the free alcohol with a 1:1 molar ratio of sugar to thc. Purify this reaction. Crystallize. Remove the sugar then REcarboxylate if necessary!
Or instead of sugars, could use a sulfate/phosphate group, may be even easier to attach and remove!
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What sugar structure would you suggest? I have a variety of cyclodextrins, dextrose, sucrose, fructose.
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I would start with Dextrose, mannose. Simple 6 member ring sugars. I may have to look into some carbohydrate literature if you are really serious about trying this im super down. I would steer you away from fructose because it is a non-reducing sugar.
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these guys are using biology rather than chemistry, but the end point is presumably similar…
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This topic is all over the place. You’re all correct, except for the errant typo here or there. The steric hindrance of the original position of the carboxylic acid nowithstanding, there isn’t much we can do to make a carboxylic moiety just stick to a phenolic ring wherever we want it to.
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We are not trying to attach and phenols or aromatics to the carboxylic acid…
I think you may have digested our plans differently than what we intended to do.
I guess that we are just looking at it from different angles. A phenol (benzene ring with an OH group on it) is precisely what the middle of the THC molecule is, which is where people want to “reattach” the carboxylic acid for some unknown reason. Does that make sense?
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Just a quick summary…
THCa can be crystallized, THC without the acid (carboxyl) group can not be AFAWK
The acid group adds mass, making it favorable economically. Also, if we were able to crystallize distilled THC we could possibly achieve greater purity than if we had only distilled. (I can see this being beneficial for already decarbed material)
The goal is then to reintroduce the carboxyl group, for which the following suggestions have been made:
-“Attach a sugar onto the free alcohol”
I have gone down long and deep wormholes on this topic, to little avail… But perhaps this will be a more helpful lead for someone other than I
Ive been informed this specific method will not work, but there is some promising literature down this line of thinking.
A side note, @DrJosh this is the second time I’ve seen you jump into a conversation to claim “I can do it, no problem” and then proceed to offer zero proof to back up your claim. This is far from helpful and slightly annoying. Pictures or it didn’t happen.
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@Future. Thanks for the summary.
the sugar attached to the free alcohol was not a suggestion for attaching the carboxyl group. it was the reason @Photon_noir was chastising us for wandering.
It was suggested as a way of attracting cannabinoids (now cannabosides) to each other for the purpose of purification via crystallization. with THC-gluc crystallized (and thus isolated). one could perform the required REcarb step(s) on 99+% purity and be less likely to make junk.
the paper I linked uses enzymes to add the sugar(s). with the goal of increasing water solubility & thus bioavailability. my chemistry was a loooong time ago.
Edit: mind you, after being chastised for wandering, I went back and read the thread a 1/2 dozen times. It hangs together. just. With THC-acetate thrown in there as a red herring for 10100 to get a hold of.
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one could certainly be evolved for the task in short order. the enzyme they used looks like it’s target is close enough structurally to use as a starting point.
you amplify the gene (PCR) under low fidelity conditions, and look for clones that decarb our favorite cannabinoids.
I’d wager an enzyme would be the most regio-specifc way to put the carboxyl back too. the best candidate from above might be a good starting point, under different reaction conditions, but screening through the first pool as well makes good sense.
If I could see a good way to make decarbing/REcarbing THC a life saving (and thus selectable) trait, it would be faster.
Edit: …and now we’re officially off topic. thread title is “Chemistry”!!
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@cyclopath actually OP asked about carboxylation, so I edited the title to match and hopefully draw in more conversation
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Yes sir this sure does make more sense. However sterically hindered by the alcohol group on the phenol ring and the carbon chain it is the only active site possible on that ring to attach a carboxyl group. I was thinking use some ortho/para directing groups for this reaction to even be feasible on paper.
I think this is a silly method in general to solve the problem at hand and there should be other synthetic methods to solve this problem than adding back on the carboxyl group!
Thank you for the input and thought. Let me know how you feel about the directing groups
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Attaching the sugar would possibly allow for decarbed thc to be able to form a crystal.
If anyone has schlenk line chemistry they would like me to try this on 
I would also like to try with sulfate/phosphate groups.
Future! Your Kolbe Schmidtt probably wont work, my guess is that the carbon ortho (adjacent) to the free alcohol would be sterically hindered by the alcohol/carbon chain even with the lowest pka on the thc molecule! Im down to try tho if someone has some schlenk lines for me to use!
There is possible chemistry that does not involve expensive enzymes i just dont have my academic lab at my disposal to next fall 
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and this is why I don’t do organic synthesis!
As a thought puzzle it is an interesting discussion but I agree that this is a long way to go to get a cup of coffee. Isolate the THCA before decarbing, the end.
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