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Ethyl acetate approach [CIELO] Options
 
Loveall
#21 Posted : 3/2/2021 4:24:20 PM

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Quick update, sample from the citric acid salting has arrived for analysis. There have been delays because of winter storms, but we expect results over the weekend.
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Loveall
#22 Posted : 3/2/2021 5:57:49 PM

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Wow, solaris analytical was able to prioritize the sample and get an immediate turn around. I cannot recomend them enough ❤️❤️❤️

Result is "a very clean mescaline sample" . Two large peaks at ~210.5 (mescaline) and ~193.6 (mescaline with the NH2 cleaved).

Yields were good too (0.8%), in line with more laborious TEKs for this same plant material.

Some words of caution and thoughts on this process

- I tested the microwave further with a lot more alkali water and longer irradiation (a few hours at low power) and yields decreased. Less water and a few minutes yielded fine as mentioned before.
- Drying ethyl acetate with MgSO4 can be a bit messy (long settling times and/or hard to filter). Anhydrous sodium sulfate could be a better choice.
- An alternative to Ca(OH)2 may be Na2CO3. It should keep the ethyl acetate relatively dry while pulling (no need for NaCl). It may also fully dry the ethyl acetate after pulling if made anhydrous (can be converted in the oven at 525C from regular washing soda I believe).
- Do we really need to microwave while basic? What about microwaving before basing? Also, what about not microwaving at all and using citric acid to salt, just make sure to dry well.
-This process is still experimental. Use a more established TEK unless you are OK with possibly not getting product.
- Tests with acetone could be done, but that may be more difficult to dry completely and may bring more impurities with it that interfere with xtalization. However, I think it is worth a try.

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benzyme
#23 Posted : 3/2/2021 6:55:16 PM

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It's super clean. I'm only getting one peak. There's a slight shoulder, but that's typical
https://i.ibb.co/zNCMJF3...-B599-492259-AB7-ED3.jpg
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shroombee
#24 Posted : 3/3/2021 5:25:57 AM

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Loveall wrote:
Result is "a very clean mescaline sample" . Two large peaks at ~210.5 (mescaline) and ~193.6 (mescaline with the NH2 cleaved).

Awesome. I was waiting for your update. Just ordered some ethyl acetate. I'll shadow your experiments and see if I can get similar results. Smile
 
Loveall
#25 Posted : 3/3/2021 1:50:24 PM

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shroombee wrote:
Loveall wrote:
Result is "a very clean mescaline sample" . Two large peaks at ~210.5 (mescaline) and ~193.6 (mescaline with the NH2 cleaved).

Awesome. I was waiting for your update. Just ordered some ethyl acetate. I'll shadow your experiments and see if I can get similar results. Smile


Awesome. Replication is very important. Thanks for volunteering to test this out. To recap what was sent to Benz:

- Mix 300g water, 25 lime, 100g cacti -> 100g of Na2CO3 may be an alternative to lime, wort testing.
- Microwave in short spurts to not over-boil and stir frequently until 75 to 100g of water are removed. Paste will go from green to tan -> I'm not sure this step is needed, should be investigated. This step should not take very long in terms of microwave time (30 minutes or so). Extended microwaving (2+ hours) seemed to lower yield.
- Stir in 80 of NaCl -> Can skip this if Na2CO3 instead of lime is being tested since the sodium carbonate helps keep water out of ethyl acetate.
- Pull with ehtyl acetate. You can shake this if you have the right lid (#4 or #5 plastic). First pull will absorb some solvent (~50 to 100g), the rest of the pulls don't absorb anymore.
- Dry compiled pulls over MgSO4. This is the trickiest part for me. Solution gets cloudy and takes a while to clear up with settling. If the MgSO4 is to fine settling is very slow. Once I blended dried MgSO4 from the oven in an electric blender and the cloudiness was horrible and persistent in ethyl acetate. Lightly ground MgSO4 seems better. I've been sifting it through a metal coffee filter and discarding what gets trough, that seems to help. -> Different drying angents that are easier to deal with can be investigated (Na2SO4, Na2CO3, K2CO3).
- Decant/filter clear solution to a new container (e.g. shallow baking dish) and add ~250mg of citric acid. No need to stir, just drop it in (it will dissolve by diffusion) and cover with an ethyl acetate resistant lid (plastic #4 or 5, glass lid, tight aluminun foil, etc). After a day in a cool location, xtals form. Check with a pH paper, add more citric acid if not acidic (extra citric just stays in solution, it is not an issue).
- Pour off ethyl acetate (should be reusable) and optionally wash xtals with dry ethyl acetate to make them white. Let the xtals dry.
- Optially, reddisolve mescaline citrate in minimal warm water and evaporate slowly while undisturbed. The result is beautiful. Note: the product Benz tested did not go through this step.

Good luck 🤞

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Loveall
#26 Posted : 3/4/2021 5:48:09 PM

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shroombee wrote:
Loveall wrote:
Result is "a very clean mescaline sample" . Two large peaks at ~210.5 (mescaline) and ~193.6 (mescaline with the NH2 cleaved).

Awesome. I was waiting for your update. Just ordered some ethyl acetate. I'll shadow your experiments and see if I can get similar results. Smile


shroombee, I summarized what seems to work so far into a wiki page. It should be clearer than my previous post. I suggest.we update that wiki as we learn about this potential process since it is easy to lose info in a long thread. I added possible changes/improvements and questions I have as notes.

If you can replicate good results we will publish it on the wiki (right now it is not linked to the main wiki, it is a loose page).
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shroombee
#27 Posted : 3/4/2021 8:29:40 PM

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Loveall wrote:
shroombee, I summarized what seems to work so far into a wiki page. It should be clearer than my previous post. I suggest.we update that wiki as we learn about this potential process since it is easy to lose info in a long thread. I added possible changes/improvements and questions I have as notes.

If you can replicate good results we will publish it on the wiki (right now it is not linked to the main wiki, it is a loose page).

Sounds good! Ethyl acetate should arrive next week. It'll probably be a couple weeks before I have enough cactus on hand to run a bunch of experiments. I don't have enough right now to run multiple experiments on the same batch to compare results.
 
Loveall
#28 Posted : 3/8/2021 3:11:12 PM

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Updates:

*Personal bioassay (555mg) gave a wonderful experience with zero stomach discomfort. Crystals were slowly dissolved in about a cup of two week old kombucha homebrew which was pleasant to drink.

*The ethyl acetate experimental TEK has been updated. 1) Microwave is now done before adding Ca(OH)2 as this seems to help yields and 2) Anhydrous CaCl2 (widely available as a de-icer) is used instead of NaCl since the resulting paste had a good consistency and the resulting extract crystalized very well after the addition of citric acid without any chemichal drying.
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Grey Fox
#29 Posted : 3/9/2021 4:08:52 AM

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Loveall wrote:

Personal bioassay (555mg) gave a wonderful experience with zero stomach discomfort.


Thumbs up
IT WAS ALL A DREAM
 
shroombee
#30 Posted : 3/10/2021 1:01:23 AM

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At the moment I have 350 grams of dried cactus chips and all of the other materials on hand. All of my chemicals and solvents are food grade, including the ethyl acetate. So I'm going to get started tonight! Will post updates regularly. Big grin
 
shroombee
#31 Posted : 3/10/2021 6:26:32 AM

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Loveall: I'm adding my detailed notes to the end of the experimental wiki. Let me know if there is a better place or method.

So far, I have followed the experimental tek exactly, except I used a plastic bowl for the microwaving as it was easier to do the mixing that way. I figured cactus and water without base would be fine for the plastic bowl. And I eventually ended up using a Kitchenaid mixer (with stainless steel bowl) when adding the lime and calcium chloride as mixing by hand was tedious in trying to ensure the mixture didn't have any unincorporated clumps of lime.

The ethyl acetate is light green after 1 hour 30 minutes pulling.

How long does your microwaving phase take? I microwaved 10 times, 30 seconds each, mixing and weighing after each burst. Total time for my microwave phase was about 10-15 minutes.

I plan to decant at 8am tomorrow, then decant again at 8pm. 8am following day, final decanting at 8pm (giving 12 hours for each of 4 pulls). I plan to salt the pulls separately to measure yield from each pull. I will measure the amount of ethyl acetate recovered from each pull and add back the same amount for additional pulls, attempting to keep the solvent volume the same between pulls. Or should I do this a different way?
 
Loveall
#32 Posted : 3/10/2021 10:03:36 AM

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shroombee wrote:
Loveall: I'm adding my detailed notes to the end of the experimental wiki. Let me know if there is a better place or method.

So far, I have followed the experimental tek exactly, except I used a plastic bowl for the microwaving as it was easier to do the mixing that way. I figured cactus and water without base would be fine for the plastic bowl. And I eventually ended up using a Kitchenaid mixer (with stainless steel bowl) when adding the lime and calcium chloride as mixing by hand was tedious in trying to ensure the mixture didn't have any unincorporated clumps of lime.

The ethyl acetate is light green after 1 hour 30 minutes pulling.

How long does your microwaving phase take? I microwaved 10 times, 30 seconds each, mixing and weighing after each burst. Total time for my microwave phase was about 10-15 minutes.

I plan to decant at 8am tomorrow, then decant again at 8pm. 8am following day, final decanting at 8pm (giving 12 hours for each of 4 pulls). I plan to salt the pulls separately to measure yield from each pull. I will measure the amount of ethyl acetate recovered from each pull and add back the same amount for additional pulls, attempting to keep the solvent volume the same between pulls. Or should I do this a different way?


Sounds like a good plan.

That time microwave time sounds about right, except my ethyl acetate comes out mostly yellow. Did your paste change color from green to tan? I usually let the microwave run until the paste swells (takes about two minutes) and stop it. Your paste became clumpy after CaCl2 which is exactly what happens to me. After some time in ethyl acetate paste does become stickier, and for the later pulls I stir.

And yes, there is some manual labor involved in making the paste. However, I think you will be pleased with the remainder of the steps.

You should get back about ~170g of from the first pull, maybe more. Don't shake it in the morning as it is now sticky, it could absorb a lot of solvent if you do shake. After letting the paste rest all night it should decant very easily since it is sticking to itself.

Do you have pH paper? You can check each pull with it. See below how my last 4 pulls looked like, (last 3 where stirred because paste was sticky.

Since you are salting separately you can drop the citric acid into the first pull tomorrow morning. I hope you see clouds forming, and that over time it clears up and leaves xtals behind 🤞. You can also test this first in a small jar with a sample of the pull. I like to not stir and let the organic acid diffuse on its own into the ethyl acetate. I'm trying room temp first, if clouds don't crash you can then move to the fridge and even freezer if needed.

Thanks for documenting your process. We can keep it as an example in the wiki page for sure.
Loveall attached the following image(s):
IMG_20210309_222124834.jpg (1,677kb) downloaded 318 time(s).
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shroombee
#33 Posted : 3/10/2021 7:31:46 PM

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I updated my log at the experimental wiki.

Loveall wrote:
Did your paste change color from green to tan?

It wasn't clearly tan. I was looking for that. I'd say it was on its way but halfway between green and tan.

Quote:
You should get back about ~170g of from the first pull, maybe more... After letting the paste rest all night it should decant very easily since it is sticking to itself.

This morning I decanted the ethyl acetate and I only recovered 90 grams of solvent from the sticky paste. Even tried using a french press, which was basically useless. The solvent is a medium emerald green color. Yes, it's very easy to decant whatever amount was not absorbed into the cactus.

pH of the solvent is basic. I tested 10 ml of the solvent with 13 mg of citric acid and immediately got some nice milky clouds. Poured the full volume of solvent into a baking dish and added enough citric acid to get pH 6. I think I should have left the solvent in a mason jar or beaker for this step, rather than pouring it into a baking dish. Need clarification in the written tek.

Comments / questions for next experiments:

1) For the second pull, I only added 90 grams of fresh solvent to the cactus with the idea we're keeping solvent volume constant for salting so we can do p = 1 - M1/M2 calcs.

2) Why was solvent recovery so low? Perhaps need to adjust microwave process and/or don't shake. When I shake cactus with limonene, the cactus absorbs a lot of the limonene. Same with ethyl acetate?

3) Should I have added calcium chloride to increase solvent recovery of pull #1?

4) I noticed the experimental tek has been updated so pulls are only 20 minutes. The fresh ethyl acetate I added quickly turned green. Assuming FB mescaline moves into the solvent at approximately the same rate as this green material, pulls could be limited to less than an hour.

5) Assuming the rest of the process plays out and I get nice crystals with decent yield, I like this tek a lot more than limonene with HCl salting. It's quicker, less equipment, less labor (including a lot less glassware to wash).

6) About 3 hours after salting with citric acid this morning, the solvent has already lost its cloudyness. I didn't want to disturb the solvent, but there appears to be a lot of clear droplets at the bottom of the dish.

 
Loveall
#34 Posted : 3/10/2021 8:32:01 PM

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shroombee wrote:

1) For the second pull, I only added 90 grams of fresh solvent to the cactus with the idea we're keeping solvent volume constant for salting so we can do p = 1 - M1/M2 calcs.


This is a good goal. I plan to do the same, but once we the process is more established.

shroombee wrote:

2) Why was solvent recovery so low? Perhaps need to adjust microwave process and/or don't shake. When I shake cactus with limonene, the cactus absorbs a lot of the limonene. Same with ethyl acetate?


I'm afraid it could have happened during that last shake when the paste started getting sticky. I'm learning that it is ok to shake at the very begining, but once the paste is sticky it can absorb solvent of shaken.

shroombee wrote:

3) Should I have added calcium chloride to increase solvent recovery of pull #1?


I would leave it as is and see what happens on the next pull with only stirring. You may get some ethyl-acetate back.

shroombee wrote:

4) I noticed the experimental tek has been updated so pulls are only 20 minutes. The fresh ethyl acetate I added quickly turned green. Assuming FB mescaline moves into the solvent at approximately the same rate as this green material, pulls could be limited to less than an hour.


Agree. The pH change could be useful too, I think that is more telling than color changes. I did update to 20 minutes because of testing and because of the stickiness of the first pull over time.

shroombee wrote:

5) Assuming the rest of the process plays out and I get nice crystals with decent yield, I like this tek a lot more than limonene with HCl salting. It's quicker, less equipment, less labor (including a lot less glassware to wash).


👍🤞

shroombee wrote:

6) About 3 hours after salting with citric acid this morning, the solvent has already lost its cloudyness. I didn't want to disturb the solvent, but there appears to be a lot of clear droplets at the bottom of the dish.


Droplets that could be water droplets? Did water get into the ethyl acetate? Was the dish sealed to the environment? Also, if using a plastic lid to keep moisture out, it may be incompatible with ethyl acetate and the lid may dissolve with the vapors and drip. If you don't get xtals and have water droplets instead, you should still be able to pull with plain water, evaporate that, dry, and wash the residue with ethyl acetate to remove excess citric acid and any color/gunk that comes through.

On your next pull using a sealed mason jar. I think you will get clouds and then xtals. Anything that crashes after the clouds is mescaline citrate in my experience, citric acid always goes into solubion 🙂.

You also mentioned in your wiki notes that the total volume of the 1st pull dropped my 40ml. I think that is from the paste compressing as it sits in ethyl acetate, that is normal and I have seen that.

Not sure why you didn't get a tan paste like I did. Maybe it doesn't matter though. My microwave is 1700W for what it's worth and I get the paste to swell in a mason jar.which required pauses because of swelling. I think the color kept on changing while paused and hot, that is why maybe I lost all the green color.



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Loveall
#35 Posted : 3/10/2021 9:15:26 PM

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Shroombee, I'm updating the TEK. Freezer seems necessary to Max out yield consistenctly if not drying the pulls, more stuff crashes when cold.

So, for your second pull, I would recommend seeing if you get xtals in the fridge. Then go to the freezer and see what happens.

We may need to dry the pulls partially. Full dry gives issues. Maybe 1% CaCl2 added and then decanted could absorb a good chunk of water before adding citric acid.
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shroombee
#36 Posted : 3/10/2021 10:40:16 PM

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Loveall wrote:
Agree. The pH change could be useful too, I think that is more telling than color changes. I did update to 20 minutes because of testing and because of the stickiness of the first pull over time.

For my current experiment, I might as well continue with the plan to do 12 hour pulls since solvent is already trapped and we want to eliminate variables. Or maybe just pull in quick succession and combine pulls to troubleshoot the process first?

So for the next experiment (new cactus), it sounds like four pulls should be done in quick succession? Shake for 20-30 minutes, let rest for 15-30 minutes, then decant? Subsequent pulls should be "stirred, not shaken" to avoid losing solvent in the cactus. Is the length of pull time also contributing to the absorption of the solvent?

Quote:
Droplets that could be water droplets? Did water get into the ethyl acetate? Was the dish sealed to the environment? Also, if using a plastic lid to keep moisture out, it may be incompatible with ethyl acetate and the lid may dissolve with the vapors and drip. If you don't get xtals and have water droplets instead, you should still be able to pull with plain water, evaporate that, dry, and wash the residue with ethyl acetate to remove excess citric acid and any color/gunk that comes through.

Upon further examination, it appears there is nothing at the bottom of the dish. No contamination with water or plastic. My lid is a silicone liner with metal band. BTW, the silicone expands. What I'm seeing is evidently a projection of tiny oil-like droplets that are on the surface. Attempting to scrape at the droplets at the bottom with a knife reveals the bottom droplets are an illusion.

Also, in the shallow baking dish the color of the solvent is more yellowish-green. Not so much a medium emerald green as I previously described.

Quote:
So, for your second pull, I would recommend seeing if you get xtals in the frig. Then go to the freezer and see what happens.

Can this be done at any time? So could the solvent clear up with no xtals, and even after waiting for days, the solvent can go to the frig then freezer? Or does the salting, frig, freezer process need to happen on a time schedule? And if the frig/freezer seems necessary for maximum yields, is there any reason I wouldn't just go ahead and put the first pull in the frig right now?
 
Loveall
#37 Posted : 3/10/2021 11:20:47 PM

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I would keep the 12 hour experiment going. I don't think anything bad will happen. I don't think time alone makes it so more water is absorbed, I think the issue was shaking after the paste became sticky (around 12:30 am according to your notes). This is my fault, at first I didn't realize the issues with shaking after the paste has enough time to become sticky.

Thinking about your earlier question, You can cut off a piece of the paste as add CaCl2 and see what happens. It may release a bunch of solvent.

So, your dish got cloudy, but no crystals formed, right? That's too bad. Yeah you can definetly throw it in the freezer directly. The fridge -> freezer sequence is just to understand what happens at different temps. Also, bigger xtals form when the temp is lowered gradually, but that is not very important now.

My 4*20 minute pulls are crashing in the freezer. So far looks good.
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shroombee
#38 Posted : 3/11/2021 12:05:06 AM

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Loveall wrote:
I think the issue was shaking after the paste became sticky (around 12:30 am according to your notes). This is my fault, at first I didn't realize the issues with shaking after the paste has enough time to become sticky.

No worries, now the tek is improved. We can tell people what NOT to do. Thumbs up

Quote:
Thinking about your earlier question, You can cut off a piece of the paste as add CaCl2 and see what happens. It may release a bunch of solvent.

I'll try that. The paste is sticky and sort of gooey. Like old school green slime for kids with dirt mixed in. I'm not familiar with this texture as limonene paste is a little different. It doesn't have this much slime component.

Quote:
So, your dish got cloudy, but no crystals formed, right? That's too bad. Yeah you can definetly throw it in the freezer directly. The fridge -> freezer sequence is just to understand what happens at different temps. Also, bigger xtals form when the temp is lowered gradually, but that is not very important now.

Right, cloudy but no crystals formed. I'm throwing it in the freezer. I tipped the dish and now realize there is an oily substance dotted across the bottom. Earlier, it didn't seem to move when I scraped at it through the solvent with a knife (and seeing some oil droplets on the surface), leading me to believe it was an illusion. But it's real. It's not water. I put a little on white paper to confirm its oily.
 
Loveall
#39 Posted : 3/11/2021 2:27:38 AM

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Well sorry it didn't Xtalize.

Less water and less green do seem to help xtalization. However very low water also has issues.

You can remove water from the next pull by using CaCl2 pellets, they will dry the extract before you salt with citric.

However, too dry and it won't Xtalize, the clouds will settle slowly as white wispy stuff.

So now I'm trying to dry with CaCl2, then as add citric acid water solutions of different concentrations. Trying to find an ideal water/citric addition that gives the best xtalization.


Also, that would could be where the mescaline citrate ended up. It should not stay in ethyl acetate after salting I think.
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shroombee
#40 Posted : 3/11/2021 7:17:25 AM

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After 12 hours I decanted pull #2. Only recovered 65.2 grams of solvent. Recall I added 90.7 grams fresh solvent after decanting pull #1, with the hopes more solvent would release for pull #2. Nope. So the cactus trapped another 25 grams of solvent.

Since there is now about 134 grams of solvent stuck in the cactus (200-90.7 from pull #1, plus 25 grams from pull #2), I figured I needed to increase the efficiency so I added ~200 grams fresh solvent for pull #3.

I tried adding 5 grams calcium chloride to about 3 tablespoons of cactus (which is a lot of CaCl2). That did not release anymore solvent. It did make the clump drier after 30 minutes so that the small clump lost some sliminess and stickiness.

Are you still combining all 4 pulls and salting at once? How much total solvent, and how much citric acid are you adding? I realized I might be adding too much. Pull #1: 169 mg added to 90.6 grams solvent. Pull #2: 49 mg added to 65.2 grams solvent. Although pH for both ended up around 6.

Are you adding the citric acid gradually and checking pH, then putting the jar in the freezer?

Loveall wrote:
Less water and less green do seem to help xtalization. However very low water also has issues.

Perhaps pulling the green with dry IPA and/or acetone in the frig (to ensure no mescaline gets pulled), then dry back to powder before making the water paste?

Quote:
Also, that would could be where the mescaline citrate ended up. It should not stay in ethyl acetate after salting I think.

I assume you're referring to the oily droplets at the bottom of the baking dish.
 
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