Mostly Sunny with a chance of Precipitating Sugars

Those who have made oil-based cannabis tinctures know that when ethanol crude is introduced to lipids, sugars precipitate from the solution. I am looking to find the mechanism that causes the sugars to crash to ensure that the final product will not continue to precipitate sugars. These sugars are jamming up our processes and the solution, as I see it, lies in knowing how and why this is happening. Ultimately, we would also like to ensure that no sugars are crashing in the finished, bottled product. It isn’t harmful, but it is ugly and unprofessional.

Our basic process is as follows:

Add crude to warmed MCT. Homogenize. Let sit for a few hours. Homogenize again. Filter @ 1.5 microns. Bottle. Sell.

We will often find that sugars continue to precipitate after our final filtration. Is this process accelerated by heat? Are we not waiting long enough before filtering? What is our major malfunction?

We appreciate any guidance or assistance concerning this matter that can be provided. In all of my research, I am unable to find any papers or studies concerning this phenomena.

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Winterize it

Winterizing removes fats/waxes and is typically done with product produced using hydrocarbon extraction methods. It, it my experience, does nothing to remove sugars. Ethanol is the solvent we use to extract with, and sugars stay in suspension at all temperatures.

What I am experiencing happens when the crude is introduced to lipids. Only in a lipid solution do the sugars crash. I am looking for the mechanism by which these sugars crash from solution. I can filter these sugars out, but I need to know how to force all of the sugars to crash prior to filtration.

Even after filtration, I am finding sugars continuing to crash. Without understanding how to force them out, it doesn’t matter if I filter at 0.2 microns; the sugars continue to precipitate.

Thank you for your suggestion.

Sugars should be water soluble.

As I recall, when you tried adding water and shaking , you had trouble getting the emulsion to break. Did you try adding salt (making it a brine wash)

Maybe heat?

I believe I suggested throwing it the the freezer. Rather than using a sep funnel. I’m assuming that was a fail?

@Photon_noir?

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While sugars are indeed water soluble, I have not seen them fall out of solution with water, nor have I tried using salt. Also, removing the water from solution ads a significant amount of time. I am looking to expedite and hone the process. The freezer was also a fail.

It appears as though sugars continue to crash for a period of days or weeks when in a lipid-based solution and collect on the sidewalls and floor of whatever container it happens to be in. To expedite the process I need to know why. When I understand why, figuring out how will be exponentially easier. I want to know why. Someone out there knows; I just hope they see this. I have dug for answers and come up with nothing.

Well, there are a few tricks for sugars, if they really are sugars. One is to try Winterizing an acetone solution. This should help precipitate proteins and sugars.

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They absolutely are sugars. We have done solubility and taste tests on them. @cyclopath is very familiar with our process/problems and can attest to validity of my claims. He saw them firsthand for years.

I am also trying to avoid using, and consequently having to remove, another solvent. I want to understand why and how the sugars are precipitating in lipids so that I can expedite that process. If you can help me understand this process, I would greatly appreciate it.

That being said, I will run a small experiment with acetone winterization to see how well it removes sugars.

Thank you.

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what about dissolving the extract in a nonpolar solvent and washing against h20 in a sep funnel?

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This is another interesting suggestion that I will have to experiment with, but we don’t want to remove more than we have to from the crude. We like having a full spectrum product. The crude we produce is sold as RSO as well as used for making our ketogenic tinctures. We are doing our best to avoid the use of other solvents. Adding and then removing another solvent slows our process down.

To clarify, I do not have trouble removing the sugars with basic filtration. These sugars filter out at 11 microns just fine. The trick for us is making sure they have all crashed prior to filtration to ensure finished, bottled product does not continue to precipitate sugars. I want to know the chemistry behind the precipitation of cannabis sugars in lipids. My issue is not removing them; it is learning how and why they are crashing from solution.

Thank you for your suggestion.

Yo…those sugars are valuable.

That sugar slurry can be fermented and distilled to generate ethanol. If you come up with a sugar removal specific SOP I’d love to keep it on file.

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I am happy to share it with you when we figure it all out. There may also be a few other uses we have yet to discover…

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@cyclopath and I talked about it today to see if I might be able to help. Since you are making a “ketogenic” tincture, you can probably just wash it with water to remove the sugars. I can attest to the fact that I have been unable to emulsify water with that ketogenic solvent. That said, cooling the mixture to precipitate sugar for filtration/decanting is another valid option, unless the CBD content is too high to allow that without co-precipitation of CBD. So is @cyclopath 's carmelization/decantation tek, once the sugars have all crashed out, I suppose.

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Have you tried the Tollen test? This should tell you qualitatively whether you have any sugars (at least reducing sugars) present in your sample and its kind of fun. Great way to make a mirror inside a RBF. By far the easiest way is to introduce a nonpolar solvent maybe ethyl acetate or hexanes and wash that with water in a sep funnel. If you choice the right solvent that carries your compound well then solvent recovery/removal might be as much work as thinking warm thoughts.

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What about a liquid-liquid separation using non polar solvent and VG. Since VG is a sugar alcohol. Idk … I dont know much. Barely passed chemistry in HS lol

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Seems that MCT is hydrophilic enough that just washing against water doesn’t work well here. which is a pity. because that would be a nice simple solution. rather than adding another solvent to the process.

I’m still hoping someone with more chemistry than I have can make it work.

@QGA?

As fas as replicating the carmelizing them in MCT tek from the rice cooker days, I think your biggest issue would be having to decant out of the still.

However, if you look at your still (conical fermenter) you’ll see that there is another exit higher up (racking port), if you treat the ppt sugars like yeast and draw off from above them, you might have a win :wink:

you’d need to do some preliminary saturation tests to figure out how much MCT to add to the still at the start of the run.

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Why are you putting MCT into crude? I make a purified oil first. I then add an appropriate amount of oil and mct to form the proper concentration.

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once upon a time? to get the last of the ethanol out without a rotovap.

now? it is happening AT formulation, and on the shelf.

one way to get around that would be to add LESS MCT, while things are hot, then let it sit for ??? and so encourage the ppt to occur from a more highly saturated solution.

adding the oil before ANY ethanol was removed, then evaporating the enthanol should be no less “pure” than evaporating the ethanol first, and it is arguably less work.

it also works as a transfer solvent. much easier to move 400mg/ml in MCT around at rm temp than 65-70% cannabinoids, even fully decarbed.

the problem may actually be the regulatory framework in OR.

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@cyclopath but wouldn’t adding purified oil to MCT yield a product with far fewer contaminants than just adding MCT to unprocessed extract? When I hear crude I think raw, unpurified extract. Is there a processing step involved prior to adding the MCT that I missed?

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:slight_smile:
cryo ethanol.filter. recover ethanol. dissolve in mct.filter.bottle. hand to consumer.

vs

cyro ethanol. filter. add some mct. recover ethanol. filter (this time “sugars” are gone). add rest of mct. bottle. hand to consumer.

second is more “pure”.

no?

when I got to the product, it was RSO in Coconut Oil.
it tasted nasty. but it was effective.

by switching to cryo-ethanol & MCT, I achieved a better tasting, and more visually appealing product. one that wasn’t alternately liquid or solid on the shelf.

many of those same cryo-ethanol extracts could be processed as shatter, without any additional purification steps. so “crude” isn’t really a great moniker. although given the higher temp (-35 range) it may be more appropriate than on my watch.

edit: “Full Spectrum” anyone?!?

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