Improved chlorophyll removal method

Yeah, good call. I actually think the most likely method the blue diamonds are made is simply by adding copper acetate to ethanol/methanol to create a blue solution, dropping in some diamonds, and then precipitating them out. the resulting diamonds would be blue in color.

Of course, there would be copper impurities, but I don’t think that would be harmful. I actually stumbled across the copper chlorophyll idea from a patent that creates copper chlorphyll and isolates it as a value product itself, which is then marketed as a health supplement. The difference here is that for our purposes, we’re viewing that chlorphyll as a waste product instead of a value one

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I mean, that’s literally what’s happening. You’re exchanging the magnesium ion with the cupric ion. Any of the complicated ion exhcnage processes using membranes and resins and such have the exact same end goal. It’s just that in this example, the chemistry is simple enough that none of that is needed.

As I type this though, I wonder about using other heavy metals to do the same thing. Since one of the main factors of solubility is molecular size, exchanging the magnesium ion with a bigger ion may result in even more chlorophyll reduction. The larger chlorophyll molecule should (in theory) should make an even less soluble chlorophyl complex than the copper one. This is why the copper chlorophyll complex has lower solubility than the magnesium one, because the Cu ion is over double the size as the Mg ion.

Looking at the periodic table, silver stand out as an interesting possiblity. It’s got a 2+ charge, same as copper & magnesium, and it’s
molar mass is 107 g/mol, compared to coppers 63 g/mol and magnesium’s 29. Silver acetate can be made with a colodiol silver solution and nitric acid. Could be an interesting experiment someday.

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Aren’t all sodium ions water soluble? If we could somehow exchange the magnesium with 2 NA+ ions I bet we could water wash the chlorophyll out using LLE

I have no experience with this so I’m shooting in the dark

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thats sound logic, and you’re correct in the sense that substituting a Na ion in place of an Mg ion WILL make the chlorophyll complex more water soluble. But “more” in this case is a relative figure. The cation at the center is only a small part of the solubility of the complex. The bigger factor is the long hydrocarbon tail ATTACHED to the cation. . By exchanging the Mg ion with a Na one, you might increase the water solubility from a really really small number to a slightly more than really really small number, but chlorophyll will always be effective water insoluble.

You CAN make it into chlorophyllin by saponifying it with NaOH, and chlorophyllin IS water soluble. Be aware though that adding NaOH converts all the cannabolic acids into the salt deriviative of the hydroxide used (NaOH will convert THCA into sodium cannabinate, for example, and KOH into potassium cannabinate). That said, that may not be a bad thing, just something to be aware of.

In fact, when I do my extracts, I like to basify the crude extract and do a chloroform wash, which gives me an aqeous layer with all the salts, chlorophyllin, and various other bits of plant-based hodgepodge, and an organic layer with the terps, and the THC. I’ll then neutralize the aqeous layer and extract back into an organic layer (DCM this time). Cold crash the acids, and than recombine with the terps as desired.

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Absolutely love this thread. More chemistry please. I cant get enough of this.

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well, if you like long, nerdy posts that go deep into the chem weeds, you’re in luck, just posted this monstrosity :laughing:

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Thats exactly what I am into. :joy:

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Excellent job brother!

I wonder if inhaling the copper might become an issue?? Metal Fume Fever - an overview | ScienceDirect Topics

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Chemical CAS Number 6046-93-1 is your copper acetate? If I extract by putting dry biomass and methanol in a chest freezer that’s -20F and then mixing, wait an hour or two, separate the plant material, rinse it with some more cold methanol, filter and evaporate the crude down to manageable levels, should your procedure leave my extract relatively free of fats/waxes to then SPD?

how u doing @TheMadChemist?

As I understand it, over time, that Mg ion is replaced by a hydrogen ion. Will a Cu ion replace this? Gonna try this on some crude from old, improperly stored material

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So if there is a concern of THCA conversion, what if you decarb first? Do you think it would produce Hydroxylated Delta 9?

The reason I ask is because in a separate thread I was discussing my saponification reaction of my crude prior to water washing…and this crude is decarboxylated prior to my enzymatic and saponification reaction.

I tested my water washes, and my first water wash contained only about 20g (in 10L of wash) of Delta 9, some of that may be a bit of the hexane layer may have gotten pulled out. I can say that when I did my saponification reaction, there was definitely a lot more color in my water washes, so I may have been making chlorophyllin. I will have to test for that next.

I did test for anthocyanins though and I’m definitely washing out quite a bit of those. I’ll be doing another reaction this week and I’ll submit my water washings to test for chlorophyllin this time and see what the lab says.

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Cu chlorophylls are a bit more stable than Mg ones and are actually being sold as food colorants.

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A water softening cartridge loaded with Na-rich ion exchange resin that will preferentially bind Ca2+ and Mg2+ by relinquishing 2Na+

Conceivably you could run your ethanol solution through one to process chlorophyll in…some manner, at least

Hopefully it’s that hotfire Off-The-Shelf tek

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Very elegant - I love it, but DCM isn’t practical without recovery methods in place. Quick question on the terps - I’m experimenting with a binary solvent to simultaneously crash out the terps and THC in their respective layers. Have you seen it? Here’s the DOI: https://doi.org/10.1016/j.jclepro.2018.05.080

I had to add 100mmol of water to further polarize the polar phase; only then did the goodies crash out, developing a third phase in the sep funnel. Retail prices for isolated terps are higher than pure THC.

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Link is broken unfortunately

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Here, try this:

https://doi.org/10.1016/j.jclepro.2018.05.080

I copied that directly from the .pdf. I went to my browser, pulled up google, then pasted this DOI above. The top hit is the “science direct” version.

You’re using a molar ratio of menthol and acetic acid to extract terpenes with?

The menthol doesn’t change the profile?

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Happily, no. The E_f of the respective compounds appear to be just right. They used a 10krpm centrifuge, which I don’t have. This may be the reason why they didn’t crash back out of the DES, which is why I tried water, which worked. I’ll post photos when I get a moment.

Also, the provocative nature of this is that I’m extracting BOTH the THC and the terpenes. I’d really like to crack this. I found a second paper with similar parameters - same molar ratios.

When you say crude extract, how concentrated is your extract? How much flower was used in the pictures you show here? I tried this method with a concentrated methanol extract and the good stuff did not stay dissolved, but turned in to what looks like a black/green grease after adding the saturated copper acetate/water solution.