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TEK Ethyl acetate approach [CIELO]

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I’ve run a few cielo extractions now however I’ve been unable to crash anything out as yet. Took me a few goes to get my consistency right initially as everyone has mentioned that’s the main thing to get right. My calcium hydroxide is very very old. Maybe ten years so I thought I’d check the PH of some of my solvent pulls and they are showing 8 which seems rather low, I’m guessing my lime has changed somehow, can it react with air to form a different kind of calcium?

Ive ordered some fresh base to have another go.

All of my solvent pulls clouded up when I added citric acid however adding more acid did not do anything. Even pushing the dose up of 30mg/g to the point where the citric would not dissolve at all precipitated nothing. The solutions all clouded up and then cleared over the course of a few days.

Can ethyl acetate be used in place of xylene for a classic stb with naoh? Or will a strong base like that change the solvent in some way?
 
antichode said:
can it react with air to form a different kind of calcium?
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Yes - calcium hydroxide slowly (not necessarily that slowly, in fact) absorbs carbon dioxide from the atmosphere and transforms [back] into the carbonate. For this reason, those who work with lime products - such as lime mortar - will store it by mixing it into a paste with water and keeping it in a tightly-closed container, because CO2 penetrates the paste less readily than it can permeate the dry, powdered lime.

What pH were you expecting to see in your solvent pulls? How did you measure the "pH" of an ethyl acetate-based solution? Wouldn't it be better to check the pH of the lime paste before adding any solvent?

Ethyl acetate will react with caustic soda to form sodium acetate and ethanol, which messes up the extraction somewhat. You can produce calcium hydroxide (along with sodium chloride) by mixing lye solution with calcium chloride, however.

Lack of crystallisation with citric does rather suggest minimal mescaline getting pulled and it likely is your lime that's at fault. You could test a teaspoon of the lime powder by adding vinegar and see to what extent it fizzes because of carbonate formation. It's possible to crudely measure the volume of CO2 with the help of a balloon stretched over the test tube too. If you weigh the reagents you can make an estimate of the degree of carbonate reconversion by using this method. Further details upon request.
 
I think I was expecting a ph of 9-10 based on comments in this thread. The smart thing would have been to test the paste as you said, but I didn’t do the smart thing. No I took my brand new probe and shoved it in the solvent, got a reading and then realised I now have a damaged probe 🤦

Ok we will see what happens with some fresh calcium hydroxide. The powder is from a range of plants all of which I’ve grown and they are all plenty active so I know that’s not the problem.

Is the reaction between sodium hydroxide and ethyl acetate determined by ph? Let’s say if I basified a tea I had extracted from fresh cactus so that it was juuust basic but not overly so would the ethyl acetate still fall apart?
 
antichode said:
Is the reaction between sodium hydroxide and ethyl acetate determined by ph?
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Sort of. The rate of reaction will (in this instance) vary with the concentration of hydroxide ions in a largely linear fashion, whereas pH is a logarithmic scale. Thus, under alkaline conditions, increasing the pH by one unit will increase the OH- concentration roughly by a factor of 10 [except it's actually the H+ concentration that will have gone down by a factor of 10 since that's what pH actually indicates]. So, 1 pH unit increase equates to EA [alkaline - acid is another matter] hydrolysis going approximately ten times faster.

If your sodium hydroxide concentration is such that the amount of free hydroxide is comparable with that of calcium hydroxide paste, the ethyl acetate should survive the extraction process. During the refinement of the CIELO method it was observed that slower pulls could encounter problems and this was traced to partial hydrolysis of the EA. What this also highlights is that the rate of hydrolysis is important - you could probably get away with EA pulls from a slightly stronger NaOH-basified mixture if you were really quick about it.

I can't quote the relevant concentrations off the top of my head, sorry!
 
Thanks for the chemistry lesson, that makes sense.

I have some fresh calcium hydroxide and upon mixing I immediately smelt a strong basic cactus smell so it all seems in order. I used a bit of mechanical help for the initial paste making which I highly recommend (although I’m not at a results stage yet).


Filtered EA is resting in the fridge for now
 

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One more thing, the solubility of the NaOH, when compared to lime, has an impact on the rapidity of the hydrolysis for bulk reasons as well.

Looking forward to news of the crystallisation process!
 
antichode said:
I have some fresh calcium hydroxide and upon mixing I immediately smelt a strong basic cactus smell so it all seems in order.
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Looks good! The odour I usually notice when making paste is the smell of ammonia!
 
merkin said:
antichode said:
I have some fresh calcium hydroxide and upon mixing I immediately smelt a strong basic cactus smell so it all seems in order.
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Looks good! The odour I usually notice when making paste is the smell of ammonia!
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This will also be from the release of ammonia as well as other amines from the cactus material and not just the mescaline. It's still a positive sign that the lime is in good condition, of course.
 
Well, no sparkly stuff to show for my efforts yet unfortunately.

This is my 5th attempt and so far no success. Every time I add the citric acid I see a lot of clouding, the EA goes completely milky, the clouds slowly begin to settle over a few days and then they just disappear leaving the solvent clear with almost no residue on the bottom of the jar, not even goo.

Paste seems well based, pulls happen as intended and look the part, solvent is filtered till its crystal clear, fridge rested whereupon some minimal water is found at the bottom so this is carefully left behind. Citric acid is added and clouding happens but nothing from there. I have tried to add more citric acid after a few days of no action so Im up to 10 or sometimes 20mg/g of solvent and still no precipitation of alkaloids.

When I add the citric acid it tends to clump and get a bit 'goopy' looking on the bottom of the jar. It does eventually dissolve however the way it looks like its sticky gives me pause, should it look like that? (last picture)

Where to from here? I have 5 litres of solvent currently sitting with no action. Im thinking at this point I should try and wash it with water and separate out whatever I can get too, would this work to soak up alkaloids and citric acid? at least I could then proceed with a little a/b on whatever I get.
 

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Have you tried freezing the solvent in place of or addition to the fridge rest? Maybe there's just a lot of water in the EA originally?

My only other comment is that the green of the cloudy liquid is a really light colour. I generally find with my plants that that preceeds a low yield. Higher yield powder seems to usually appear a much darker green (and a more intense red when torch is aimed at the jar). This may have absolutely nothing to do with anything though but it holds true for me. I thought it might be chloropyll related but it has always corresponded to yield. So, if true, that would point towards low alkaloid content in your powder. The only time this observation didn't apply was with old powder which was quite brown (old) to start with. That produced a much more gold coloured solvent though.

I find with some of the older plants which are quite woody the powder tends to not be so green and the yields lower as well. Also this is exacerbated if the entire plant was used for powder (more specifically the woody core).

No other ideas I'm afraid.
 
The last picture is a second addition of citric acid (first addition happened three days prior) after it’s sat for an hour or so. It does not like to dissolve and goes a bit goopy. It’s usually dissolved after a couple more days however and by that time (5 days after initial salting) the solvent is mostly clear

The solvent is emerald green when it’s pulled I think it’s just the lighting in the photos. I do notice however that the solvent goes a more pale yellowish colour after four days or so.

This is a mixture of cactus, whole cactus skin core, everything.
 
On Merkins suggestion I froze some EA obtained from a fresh extraction, interestingly a LOT of ice formed. It was in a sealed mason jar in the freezer so I doubt its condensation. When I performed a fridge rest for 24hrs I got 10ml of water at the bottom of the jar but frozen I seem to have ended up with all of this!

As an interesting aside the ice cold EA went through the coffee filter in an instant, much faster than at room temp. Why is that?
 

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antichode said:
As an interesting aside the ice cold EA went through the coffee filter in an instant, much faster than at room temp. Why is that?
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My first thought would be that dissolved water increases the viscosity - or perhaps the surface tension - of the EA more so than the low temperature does. Either of these helps it to pass through the filter more easily.
 
Ill salt this one out and see what happens.

whats the best way to recover my other extractions? If I wash them a few times with water it should turn acidic and pick up everything right?
 
It's worth a try with the water washes. If you don't throw anything away you won't have lost it. Golden rule of extraction. The fact that nothing came out in the first place tends to suggest there won't be much in there, though. Or have you had effective brews with these specimens before?
 
All of the plants are good performers, over the years Ive weeded out anything not worthy. The last time I extracted them I got a good yield, just shy of 6g from 10kg fresh see here Dazzling Crystals - Preparation - Welcome to the DMT-Nexus

I used to run successful extractions with lime and limonene back in the day so Im somewhat familiar with how the paste should feel etc. Why no alkaloids now is leaving me a bit perplexed. Perhaps the EA has a lot of water in it.
 
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