Minimizing decarb of CBGa in etoh during solvent recovery

https://industrialoutlook.in/chemicals/chemical-3/

Lists a couple of those aprotic (although I kind of like calling them sorority solvents like my phone just did :rofl:) solvents too…

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I want to say thanks to everyone, I have a lot to work with now.
This really is a great community and its great learning from each other

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eyeworm, when I pull from the FFE there’s about 6-8% residual ethanol left. If its possible, what would be the steps to solvent switch before final purge to avoid any more decarb

Be sure to use well filtered solutions, and clean vessels, to avoid any presence of any solid which could catalyse decarb. :point_up:

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Dr, what other types of solids are we talking about? Could there be side chain reactions taking place contributing energy to the decarb?
I’m filtered through 20 micron, 5 micron, 1 micron socks, through 1 micron lenticular, then carbon lenticular, and carbon scrubber.

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Ok you filtration procedure seems convenient.

Magnesium oxide for instance can catalyse that.
Various kind of zeolites or clays mays as well.

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Put it in a rotovap, pull off as much ethanol as you can in a short period of time, charge 1-2L of heptane…homogenize in situ with diminished vacuum…pull full vac and distill off ethanol/heptane mixture…repeat 3x to totally replace ethanol with heptane.

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Why not do the bulk of the solvent recovery in a TFF membrane? This can be done at room temperature and should reduce the amount of solvent in the extracted mixture by quite a bit, and then you should only need a rotovap or FFE for the last portion of solvent remaining.

Less solvent to remove should mean less time exposed to whichever methodology of recovery used, and that translates to less exposure to heat and less material decarbed.

This would also require you to have access to a TFF membrane with the proper membrane material for pushing your extraction solvent through but nothing else. So this may be a restriction just due to money or equipment but something to consider.

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I suspect this is the real take home.

I’m not going to track it down right now, but I’m pretty sure there is solid data showing that ethanol speeds decarb for thc. I believe it’s published, and has been waved around here at least a couple of times.

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Could always wash the ethanol out with water at this point correct?

Protic solvents (alcohols) certainly potentiate decarb. I think we had a similar discussion on a decarb on vacuum thread a few years ago

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In a world without troubles you would be right to say ethanol is miscible in water and should be able to be washed out. But, bear in mind your cannabinoids will not be dissolved in any sort of solvent that is immiscible with water - so you’ll probably just create an emulsion…over time it might clear up with organic (cannabinoids) floating on top…but it’ll be a mess.

Our ideas can be somewhat combined…one could add water and heptane. The water will wash out much of the ethanol (some ethanol will be retained in the heptane because thats just how partitions work when something is water and organic soluble/miscible). But ideally, this should reduce emulsions since the organic stuff will go into heptane and most of the ethanol will go into water. Once you rotovap off the heptane, the ethanol will leave with it due to the azeotrope (and the fact that heptane will significantly outweigh the ethanol). Ultimately, I think this will be less effective/convenient than the solvent switch I described because there are more steps, phase cuts/possible emusions to navigate, and ethanol will still be hanging around in the heptane. Water is also a protic solvent, which we know can potentiate decarb (although limited solubility means water is probably less a problem than alcohols).

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Yes …just looking at the molecule one might expect it decarbs in a manner similar to CBDA…are these people saying you can decarb at 25 C….basically room temp?

SOMETHING FUNNY IS GOING ON.

If you bought CBGA…is it shipped dry ice…or something?
Or are we describing a phenomena where ethanol, ethanol water,
Or ethanol terp soup catalyzes CBGA decarboxylation(???)

How could CBGA be synthesized intracellularly in the plant and be exported to storage area…and stored until you hit it with EtOH…
And then mysteriously decarb.

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Ah yes sorry I meant after you have homogenized the heptane/ ethanol solution.

Unclear what rate of decarb is at such mild conditions - I haven’t messed around with it. But putting cannabinoid acids in any protic solvent will potentiate decarb, even at mild conditions. Chilling in the plant, or as a dry isolate you would see much slower decarb, if any. Give it a shot - dissolve some THCA in heptane and in ethanol and sit those vials on the windowsill - check once a week. Ethanol vial will quickly outpace heptane vial - but it shouldn’t happen in the blink of an eye at room temp.

edit: that is to say, it isn’t mysterious at all. Its been observed and documented previously.

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Well I had written something similar (identical except widowsill)
Implies UV catalysis of unknown rxns…but just on bench rt.
Having worked loads in Protic-water-ethanol solutions…w/wo added acids…I’ve never really appreciated this enhanced rate you speak of…certainly thca decarbs at significantly higher rate. At 235F than CBDA.

If you take thca and put it in Pentane capped reaction vial with min. Head space…heat to 100C/ for
24 hrs….you will find plenty of thca still in solution.
My point here is these guys are saying they decarb at 35C. And CBGA to boot…
Have I missed a discussion of CBGA decarbing at 35C? Please advise.

Wtf…extract with H20 pH12 , sonicate a zap or two, filter over some dirt of choice…
Acidify filtrate to pH 2.9…let it set 3hr…filter…rinse precip with H2O you can’t get more protic…
Plant cytoplasm …you can’t get more protic.

I keep CBDA in 95% EtOH…in refer and RT…I think you do see some decarb ….
I will have to look into the rate. Because of concentration dependent complexes of the
Carboxylic acids we should really look at rates at different concentrations…
Thanks for valuable comments.

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Carbon scrubber might be accitic and induce carboxilation

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How hot is your evaporator? Usually CBGa will start to crash once ethanol levels reach get around 10%. It would also crash below 40c in heptane. I eventually kept made a solution at a 1:1:1 ratio of ethanol, heptane, and oil before doing an inline water wash into a centrifuge at 50c. The ethanol would be gone and the heptane solution would crash immediately after coming out of the centrifuge.

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