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Ethyl acetate approach [CIELO] Options
 
Loveall
#681 Posted : 12/25/2021 4:47:38 AM

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Loveall wrote:
I'm pretty sure we understand the mescaline citrate salt form: (MesH)H2Cit thanks to data presented by several people.

I'm going to do a titration experiment to add to this data. Also, to make sure the salt form doesn't change under different pH conditions.

For each 1g of mescaline freebase (Mes), assumimg that to first order that is the major component being titrated,

For (MesH)H2Cit: 910mg of citric are needed to produce 1.910g of xtals
For 2(MesH)HCit: 455mg of citric are needed to produce 1.455g of xtals
For 3(MesH)Cit : 303mg of citric are needed to produce 1.303g of xtals

So by keeping track of the pH as citric acid is being added, and stopping when pH paper becomes neutral, and knowing the final yield, the salt form can be known. I typically get 1.2% yield with my current powder, so I would need ~571mg of citric acid to neutralize the extract if the salt form is indeed (MesH)H2Cit. I can check at/above 190mg and 286mg to verify the extract is still alkaline on pH paper.

I also wonder if adding 190mg of citric and then giving time for xtals for form would produce the 3(MesH)Cit form and neutralize the solution over time.



I tried this out on a 100g cactus extract. Split the EA into two jars, let's call the A and B. To A, I added 190/2 = 95mg of citric, to the second 450mg (excess). Observations so far:

A: pH strip went from alkaline to nearly neutral (first image). Clouds formed and very slowly crashed as a golden honey layer at the very bottom, with some xtal shininess under a flashlight (but it is definitely mostly thick goo at this point) Is this what 3(MesH)Cit looks like crashing from EA? I'll try to isolate this precipitate and run more tests on it.
B: pH became acidic (second picture) and the usual long xtals we think are (MesH)H2Cit formed. This was just a control. They formed a lot quicker than the precipate in jar A.

This is interesting to me. I'll report back on the mysterious precipitate im A.

Last picture is a graph of citric acid (A) depronation vs pH, from the sodium citrate page on Wikipedia.
Loveall attached the following image(s):
IMG_20211224_100552012.jpg (676kb) downloaded 293 time(s).
IMG_20211224_160423201.jpg (604kb) downloaded 288 time(s).
440px-Citric_acid_speciation.svg.png (28kb) downloaded 288 time(s).
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Cheelin
#682 Posted : 12/25/2021 6:51:37 AM

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So, Loveall, help me out here. You extracted using the std process with 100g of material, then split the 900 or so mL of pulled solvent into two equal-sized batches, and added the specified amounts of citric? I must be missing something about the volumes, only 0,095g made the solution neutral?

I guess i was stoned the day they discussed deprotonation, i don’t understand the general approach, though it sounds like you know what’s up.
 
Loveall
#683 Posted : 12/25/2021 1:16:46 PM

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Cheelin wrote:
So, Loveall, help me out here. You extracted using the std process with 100g of material, then split the 900 or so mL of pulled solvent into two equal-sized batches, and added the specified amounts of citric? I must be missing something about the volumes, only 0,095g made the solution neutral?


Yeah this is it. I would expect to get ~600mg of (MesH)H2Cit in each jar if salting normally. That salt has one molecule of mescaline and one of citric, so in terms moles (~number of mescaline molecules):

600 / (211+192) = 1.49 milimoles

If one molecule of citric acid attaches to 3 molecules of mescaline only 1.49/3 milimoles of citric acid are needed to salt the extract. In mg:

192 * 1.49/3 = 95 mg

Doesn't seem like a lot, but each molecule of citric is doing triple duty for 3(MesH)Cit.

About depronation: it's simply the number of acidic hydrogen nuclei that are removed form the acid molecule in water. Aka removed protons. For HCl it can only be one (or 0), since only one is available (simple!). For molecules that can give more than one H (called polyprotic) his is highly dependent on pH. When barely neutralized polyprotic acids tend give up all they hydrogens in exchange for product molecule the less more potent by weight salts form. When excess acidity is present, more protons stay on the acid and less potent salt by weight forms. This is how (mono, bi, trip) sodium citrate salts are made in water when mixing citric acid and sodium carbonate.

Since we have been adding excess citric to EA, (low pH) it makes sense we are getting the mono-mescaline salt if things behave like they do in water.
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Cheelin
#684 Posted : 12/25/2021 4:16:44 PM

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Merry Christmas All!

Thanks Loveall.

So the more mescaline molecules bonded to a single citrate molecule, the more potent the product.

And, by deprotonating the citrate molecule in most favorable conditions (near neutral pH), the more bonding sites per citrate molecule are available.

And, using a smaller amount of citrate relative to mescaline, in a highly deprotonated state, produces multimescalated citrate molecules.

Correct?
 
Loveall
#685 Posted : 12/25/2021 5:24:21 PM

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Cheelin wrote:
Merry Christmas All!

Thanks Loveall.

So the more mescaline molecules bonded to a single citrate molecule, the more potent the product.

And, by deprotonating the citrate molecule in most favorable conditions (near neutral pH), the more bonding sites per citrate molecule are available.

And, using a smaller amount of citrate relative to mescaline, in a highly deprotonated state, produces multimescalated citrate molecules.

Correct?


Happy Siberian Shaman day 🌲🍄🎅

Yep, that's it Cheelin.

The trimescaline citrate candidate oil was easily decanted and rinsed with fresh EA. It is drying and changing color from honey to white. I'm gonna dissolve it in water and see what it evaporates to in a shallow dish.
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Cheelin
#686 Posted : 12/25/2021 5:58:32 PM

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Good luck, I’ll be interested in yield comparisons if that does turn out to be 3M citrate.

But shit, lol, i’m already up to somewhere around 60 good, albeit small, runs of current tek.


Btw, for Trichocereus growers, just released, https://trichocereus.net...Cactus%20Cultivation.pdf
 
Loveall
#687 Posted : 12/26/2021 3:01:51 PM

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Loveall wrote:
Loveall wrote:
I'm pretty sure we understand the mescaline citrate salt form: (MesH)H2Cit thanks to data presented by several people.

I'm going to do a titration experiment to add to this data. Also, to make sure the salt form doesn't change under different pH conditions.

For each 1g of mescaline freebase (Mes), assumimg that to first order that is the major component being titrated,

For (MesH)H2Cit: 910mg of citric are needed to produce 1.910g of xtals
For 2(MesH)HCit: 455mg of citric are needed to produce 1.455g of xtals
For 3(MesH)Cit : 303mg of citric are needed to produce 1.303g of xtals

So by keeping track of the pH as citric acid is being added, and stopping when pH paper becomes neutral, and knowing the final yield, the salt form can be known. I typically get 1.2% yield with my current powder, so I would need ~571mg of citric acid to neutralize the extract if the salt form is indeed (MesH)H2Cit. I can check at/above 190mg and 286mg to verify the extract is still alkaline on pH paper.

I also wonder if adding 190mg of citric and then giving time for xtals for form would produce the 3(MesH)Cit form and neutralize the solution over time.



I tried this out on a 100g cactus extract. Split the EA into two jars, let's call the A and B. To A, I added 190/2 = 95mg of citric, to the second 450mg (excess). Observations so far:

A: pH strip went from alkaline to nearly neutral (first image). Clouds formed and very slowly crashed as a golden honey layer at the very bottom, with some xtal shininess under a flashlight (but it is definitely mostly thick goo at this point) Is this what 3(MesH)Cit looks like crashing from EA? I'll try to isolate this precipitate and run more tests on it.
B: pH became acidic (second picture) and the usual long xtals we think are (MesH)H2Cit formed. This was just a control. They formed a lot quicker than the precipate in jar A.

This is interesting to me. I'll report back on the mysterious precipitate im A.

Last picture is a graph of citric acid (A) depronation vs pH, from the sodium citrate page on Wikipedia.


Product from jar A at ~neutral pH (trimescaline citrate candidate) is below. It precipitated as an orange oil. After decanting and dissolving in water it evaporated to a film that scraped up as a crystalline solid. Recovered only 265mg, but it looks like I only partially titrated the extract (or that trimescaline citrate is more sensitive to water in EA and won't precipitate as well) because after adding excess citric, the usual long monomescaline citrate needles precipitated. Also, 265mg is significantly higher than 200mg, which is what would be expected if the 95mg of citric acid precipitated the monomescaline citrate form 🙂

The trimescaline citrate is very bitter. It dissolved in water extremely easily (much faster than monomescaline citrate). It's pH in water was 6.6 (higher than the pH from the monomescaline citrate). I added 355mg of citric acid (excess) to the trimescaline citrate solution to convert it to the monomescaline citrate form. Then, I added acetone and ethyl acetate to the water and the long familiar needles formed overnight which should be monomescaline citrate precipitating. I'll measure the yield, but expect an increase in mass from the conversion.

Conclusion is very is simple: Multiple data are consistent with the monomescaline citrate forming in the CIELO Tek because of excess citric acid. We are extremely lucky that monomescaline citrate precipitates so well and in beautiful needles. The process window is huge because we just need to add excess acid which is also very soluble in EA (anywhere from (400mg to 40g of citric should work on a standard extraction, a factor of 100x 😲Pleased. On the other hand, when trying to carefully precipitate the trimescaline citrate form, a difficult oil is encountered.

Sometimes you just get lucky.
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IMG_20211225_191556808.jpg (686kb) downloaded 229 time(s).
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Cheelin
#688 Posted : 12/26/2021 3:52:00 PM

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You da man, Loveall! Lucky or not, thank you for creating this tek, and thanks to Shroombee and all the others who helped perfect it!

I’m perfectly happy with 1M Citrate, beautiful white needles or powder, of tested purity, from readily available and relatively safe materials, requiring an hour or less of simple work. Somewhere between 150 to 200mg hits my threshold, equiv of 90 to 120mg of M HCl, the difference is meaningless in terms of physical quantity.

When the word gets out on this tek, it will become a classic diy mescaline extraction tek. One that I hope substantially improves access to deep and long-lasting relief of emotional trauma, in an easy and self-help manner.

There’s a revolution starting, and you guys have contributed!
 
highlightprotein
#689 Posted : 12/26/2021 11:29:19 PM
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Hi Loveall,

Forgive my ignorance. Are you saying that if we use a much smaller amount of citric acid than we currently do (5mg/g citric acid/EA) that we will result in a more potent product (di- or tri- mesc citrate)?

Is there no concern that we might end up with a mixture of different forms of mescaline citrate, which could make dosing difficult?

If some noobie accidentially adds a very small amount of citric acid, would they end up with a more potent product? E.g., they might assume that 500mg of citrate = 310mg of hcl, whereas in can be much stronger than that.

Cheelin, my experiment was bunk because of low alkaloid cacti. I repeated it on 50g and got no yield worth mentioning. I'm getting some more cactus material soon. However I am running out of fresh EA so I don't think I can do a cold vs room temp experiment. What I want to do instead is extract 100g with ~1 quart room temp EA, and then reuse that EA over and over again on the same source powder, and find out what happens to yield over time.

In regards to the one time I got goo, I have only two explanations: 1) it was from bridgsii, or 2) it was my first experiment and I just did something wrong.

I agree with you regarding the Wiki, I would like the Wiki to have a cleanup section for noobs who get goo. A simple cleanup is just crushing the goo as much as possible and then swirling EA and dumping through a filter. A better cleanup would be by adding back lime and water and then extracting with EA.

Loveall/Cheelin, I somewhat replicated Cheelin's findings regarding the microwave and cold EA. I think they both significantly lower yield compared to the standard tek. However I'm still a noob so my experiments may not be perfectly controlled.
 
Cheelin
#690 Posted : 12/27/2021 12:20:37 AM

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Post 680 has been updated with final results.

HLP, thanks for the info.

Before reusing your EA, make sure to, at least, use the pH neutralizing method in the wiki before each reuse. I plan on doing this, PLUS, then putting the jar in my freezer for 24 hours to freeze any free water, then decant off the precipitate plug before re-use. I have more than enough product for now, so I may not be reusing the solvent for awhile.

I followed the reliming-EA-citric advice that Loveall posted. An efficient and effective method of this type needs to be developed in a much more detailed way. It will specifically have to be tailored for very small quantities of reclaim material, in terms of ingredient quantities/ratios, equipment, and timeframes. My trial run used about 0.5g of residue, 2mL water, 3g pickling lime (way too much), 10ml EA, and 0.25g citric acid, in a shotglass. The muddy mess was was difficult to stir without spilling; the little bit of EA was decanted through coffee filter once and mixed with citric in another shotglass, and has precipitated some pure white material which i am still letting passively crystallize. I’ll filter it and then compare the taste of it. I would hesitate using Loveall's alternate suggestion of adding the residue in with the other ingredients when making a batch of paste, for fear of screwing up a good batch. Worst case would be to just toss the results of a crappy run, and chalk it up to poor technique/learning curve. I don’t like that choice and I don’t want to use harsher materials, so I’ll continue to play with the small amount of crappy residue that I do have.

Good luck with your new material, my money’s on you getting great results.
 
highlightprotein
#691 Posted : 12/27/2021 1:24:50 AM
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Cheelin wrote:
Before reusing your EA, make sure to, at least, use the pH neutralizing method in the wiki before each reuse. I plan on doing this, PLUS, then putting the jar in my freezer for 24 hours to freeze any free water, then decant off the precipitate plug before re-use. I have more than enough product for now, so I may not be reusing the solvent for awhile.


I have a couple of options here. What do you guys think is best? I am going to receive a very large quantity of cactus material. I'll be able to repeat this many times, so if anyone has suggestions on the best way forward let me know.

1) just neutralize as per the wiki
2) neutralize and freeze to get rid of water
3) neutralize, brine wash, and dry with magnesium sulphate.

I'm not necessarily a fan of #1 because I think this will be adding water to the EA. Cheelin, do you think freezing will remove the water that has been absorbed into the EA? My understanding is that EA can "absorb" a certain amount of water before it will separate into two layers. I'm not clear if freezing will remove that water that gets absorbed, or if an additional brine wash and drying with magnesium sulphate would be better.

Regarding the brine wash, my understanding is that when you mix brine with EA or other polar solvent, the water that is absorbed into the EA will want to migrate out and mix with the brine. I think this is supposed to remove the vast majority of water from the EA. And then a magnesium sulphate addition is supposed to remove the tiny amount of water left over.

Of course, a brine wash and magnesium sulphate drying is quite a bit of work. If #2 is just as good then I would rather skip this step.

I tried #3 once before, but noticed that I lost quite a bit of EA to the magnesium sulphate. The drying agent turned super green and I think I lost 10% of my EA by weight. I assume that wasn't 10% water that was removed because I did the brine wash before. But this was my first time ever drying something with anhydrous magnesium sulphate, perhaps I used too much.
 
Cheelin
#692 Posted : 12/27/2021 1:33:13 AM

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Keep it simple, until you know that simple doesn’t work. Do a 15g run with #2.
 
Loveall
#693 Posted : 12/27/2021 4:48:32 AM

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All work, I've tried them all.

#1 in particular is what I've been using. Starting % of water in EA doesn't seem to matter, it simply ends up in equilibrium with the moist paste, even when starting with dry EA, what comes off the paste will have a few % water in equilibrium with the lime/water "layer" in the paste. The only difference would be that the paste is dried a little by fresh EA, but only by a few inconsequential grams of water. With reused EA the paste is not dried as everything remains in equilibrium water-wise.

There is an even simpler path I want to try, since the water doesn't pull any color from the solvent it may not be doing much other than neutralizing EA.

So to reuse the solvent, just add it to the paste. The lime should quickly neutralize the citric acid and move free base mescaline to EA as usual.

I'll try this and report back. Could it be this easy? Hope so, don't see why it wouldn't work. Will be using used paste from the slow xtalization without too much excess citric. If the dark green color doesn't get in the way things will be super easy.
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Loveall
#694 Posted : 12/27/2021 10:28:20 AM

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highlightprotein wrote:
Hi Loveall,

Forgive my ignorance. Are you saying that if we use a much smaller amount of citric acid than we currently do (5mg/g citric acid/EA) that we will result in a more potent product (di- or tri- mesc citrate)?


Yep

highlightprotein wrote:
Hi Loveall,

Is there no concern that we might end up with a mixture of different forms of mescaline citrate, which could make dosing difficult?

If some noobie accidentially adds a very small amount of citric acid, would they end up with a more potent product? E.g., they might assume that 500mg of citrate = 310mg of hcl, whereas in can be much stronger than that.


Not concerned with a mixture, one salt should precipitate based on the amount of citric. The trimescaline citrate precipitates as an oil and takes a long time to crash, don't see anyone confusing it with monomescaline, but I guess anything can happen out there. Don't know much about the dimescaline citrate thought. People simply need to add enough citric acid, if they can't do that I don't know what to say.

highlightprotein wrote:
Loveall/Cheelin, I somewhat replicated Cheelin's findings regarding the microwave and cold EA. I think they both significantly lower yield compared to the standard tek. However I'm still a noob so my experiments may not be perfectly controlled.


Agreed, both of those options have been removed from the TEK. Thanks for confirming.
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Loveall
#695 Posted : 12/27/2021 10:32:58 AM

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Cheelin wrote:
Post 680 has been updated with final results.

HLP, thanks for the info.

Before reusing your EA, make sure to, at least, use the pH neutralizing method in the wiki before each reuse. I plan on doing this, PLUS, then putting the jar in my freezer for 24 hours to freeze any free water, then decant off the precipitate plug before re-use. I have more than enough product for now, so I may not be reusing the solvent for awhile.

I followed the reliming-EA-citric advice that Loveall posted. An efficient and effective method of this type needs to be developed in a much more detailed way. It will specifically have to be tailored for very small quantities of reclaim material, in terms of ingredient quantities/ratios, equipment, and timeframes. My trial run used about 0.5g of residue, 2mL water, 3g pickling lime (way too much), 10ml EA, and 0.25g citric acid, in a shotglass. The muddy mess was was difficult to stir without spilling; the little bit of EA was decanted through coffee filter once and mixed with citric in another shotglass, and has precipitated some pure white material which i am still letting passively crystallize. I’ll filter it and then compare the taste of it. I would hesitate using Loveall's alternate suggestion of adding the residue in with the other ingredients when making a batch of paste, for fear of screwing up a good batch. Worst case would be to just toss the results of a crappy run, and chalk it up to poor technique/learning curve. I don’t like that choice and I don’t want to use harsher materials, so I’ll continue to play with the small amount of crappy residue that I do have.

Good luck with your new material, my money’s on you getting great results.


I think you mean post 679. So much work. The data is amazing, thanks so much. A note about significance: it seems like the experiential error is about +/-10mg by looking at the same condition repeated twice (0.75g salting examples). That is very solid for such a manual process to be able to repeat results within ~6%.

I see the boiling result as having less yield with a significant difference (>10% gap). The other yield differences look like they could be within the margin of error of ~10mg?

The needles vs powder for passive vs magnetic stirring is something I have also observed. Less wall material for magnetic stirring too, and shroombee mentioned the same thing. However, now a days, I just knock off any wall xtals that look significant with a knife before filtering.

I didn't get lower yields with boiling water, but I broke the congealed paste up with fresh boiling water (25 ml) right before pulling. I've found a looser paste gives better yields because the EA can get into it better (e.g. the min water paste gave lower yield). Too much water and it becomes a mess with the EA and paste merging into one (but I recovered this by adding lime and magnesium sulfate and eventually got separation and good yield). There is definetly a paste range where it is good and simply works. The range is wide, I think it goes from 280g to 330g of water for 100g of my "dry" cactus (it's really 92g dry right after it comes out of the oven at low heat). Less water and it becomes difficult to pull (too clumpy). More water and it liquifies while pulling, absorbing EA with a risk of emulsifying with it. With experience one gets a feel for it, and you have a lot of experience.

If you feel like doing more experiments I would love to see more pulls beyond the standard 5-6. I think there may be 10% or more yield with more pulls, depending on the pull technique and how loose the starting paste is. Also, using more water would be interesting, your paste looks more compact than mine, I think you may get more yields with more water.

You've already done so much work. I hope you really enjoy your mescaline, definetly earned all of it by a lot.
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Cheelin
#696 Posted : 12/27/2021 6:13:53 PM

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On my screen it’s last post on page, post 680, but close enough.

Yep, 0.01g seems to be the lower end of significance, actually pretty good for kitchen chemistry and my clumsy self. I attribute it to a good, simple tek.

There will always be stuff on the walls, but even with just a swish-3/4 pour then final swish-n-pour, the amounts to be water washed are miniscule.

You didn’t get lower yields with boiling, because you did more work than just add boiling water, lol. I do less work with ambient water and got better yield. I typically go the lazy route, if it doesn’t cost me more.

The number of pulls has been on my mind. Next wild hair will probably trigger a boatload of runs related to that, with fresh vs reused EA. I have some other things to attend to in the immediate future, so I’ll have to resist the urge for a little while.

I add the ratio/proportionate amount of water listed in the wiki, but my batches are small. Perhaps water amount should vary slightly with batch size. Might be something else to test, sometime.

But, from a lazyman’s pov, this tek is good enough for now. Pretty damn good enough!.
 
Loveall
#697 Posted : 12/27/2021 8:17:52 PM

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That's wired your data is in post 679 for me and 680 for you 🤷‍♂️

I get what you mean by wanting to be lazy, that's the best. Perhaps we should update the L on CIELO from Leisurely to Lazily 😅.

The one and only point of boiling is for solvent reuse. The dark green color from the simple Tek worries me a little for reuse, but maybe it saturated and is perfectly OK? Using boiling water and re-loosening the paste right before pulling doesn't seem like a lot of added work, and the clearer solvent could be a lot easier to reuse and easier to see issues before xtalization (e.g. small particles or water layer).

I'm seeing ~10% yield if doing 3 more pulls into a second jar. Barely worth it, but if I'm reusing solvent, why not? This is a good check everyone should do to make sure there first set of pulls into the first quart jar are good (to make sure the second jar doesn't have a lot of product).

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Cheelin
#698 Posted : 12/27/2021 8:37:14 PM

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Here’s weird, when i’m not logged in, the post is #679; when i’m logged in it’s #680.

+1 on Leisurely -> Lazy, lol.

You also worked the pulls more for the boiling treatment; it’s already quite a workout getting a good 1-min stir on quantities > than ~50g of material.

Yes, if someone demonstrates a problem with the reused solvent from the std tek, i will certainly consider darkness of solvent a relevant consideration beyond exclusively crystal quality and quantity.

Yes that is a good check, I would do it every time a new source of material is used, then compare yields of future runs (of same material) to save solvent and work. Additionally, before neutralizing solvent, a filtering should be done to capture crystals that developed after initial filtering.
 
Loveall
#699 Posted : 12/27/2021 8:55:21 PM

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Cheelin wrote:
Here’s weird, when i’m not logged in, the post is #679; when i’m logged in it’s #680.

Maybe you deleted a post at one point?

Cheelin wrote:
+1 on Leisurely -> Lazy, lol.

Looolz done 👍
💚🌵💚 Mescaline CIELO TEK 💚🌵💚
💚🌳💚DMT salt e-juice HIELO TEK💚🌳💚
💚🍃💚 Salvinorin Chilled Acetone with IPA and Naphtha re-X TEK💚🍃💚
 
Loveall
#700 Posted : 12/28/2021 7:38:42 PM

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I explored the boiling water to make the paste further. Carefully measuring yield, it does go down by ~10% or so. Not much, but not ideal. I'm not going to claim mescaline is destroyed, just that that less is recovered for whatever reason (harder to pull, destroyed, harder to xtalize, etc).

So, Cheelin I'm with you now. Will do the basic TEK and try to reuse the dark solvent. Hopefully green darkness doesn't mater and it just works.

Since water washes do nothing to improve the color (even tried NaOH), I'm going to skip that step. The paste should be able to neutralize the used solvent.
💚🌵💚 Mescaline CIELO TEK 💚🌵💚
💚🌳💚DMT salt e-juice HIELO TEK💚🌳💚
💚🍃💚 Salvinorin Chilled Acetone with IPA and Naphtha re-X TEK💚🍃💚
 
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