Lye/Limonene/Benzoic acid

[Woolmer]

I acidified 100g of phyllodes with some citric acid in 1.5L water, microwaved for 10 minutes. Added 20g NaOH in solution. After two pulls using 30-40ml limonene the yield is only sitting around 0.1% which could be normal for the broad phyllodes I suppose, or perhaps I need to use more solvent?

Some solvent has seemingly become trapped in a phyllode sludge that floated to the top after doing a warm pull. I might decant the top layer with this sludge to a seperate vessel and add more water to promote seperation as salt did not help and there is no space in the vessel to add more NaOH solution.

 

[Jan e Kharabat]

Just an update (although people have probably figured it out by now), benzoic acid can a) be easily made with sodium benzoate and HCl (and recrystallized/purified with boiling water) and b) easily soluble in naphtha and toluene (and most other non polar solvents I think). I personally like to add benzoic acid saturated naphtha into the freebase containing naphtha, I like to see the clouds! you can simply add excess amount and let it sit for a few hours, the crystals settle down and stick to the base. The crystals are more powdery, but I will try to experiment some more and find out if one can make them "prettier".
Also, as BW reported, dmt benzoate vaporizes at fairly low temperatures and can thus be directly vaporized. This... is huge! the only thing I am a bit uncertain about is the health and safety aspect, how ok is it to vaporize benzoic salts? but all in all, benzoic acid is a game changer!

 

[Loveall]

Just an update (although people have probably figured it out by now), benzoic acid can a) be easily made with sodium benzoate and HCl (and recrystallized/purified with boiling water) and b) easily soluble in naphtha and toluene (and most other non polar solvents I think). I personally like to add benzoic acid saturated naphtha into the freebase containing naphtha, I like to see the clouds! you can simply add excess amount and let it sit for a few hours, the crystals settle down and stick to the base. The crystals are more powdery, but I will try to experiment some more and find out if one can make them "prettier".
Also, as BW reported, dmt benzoate vaporizes at fairly low temperatures and can thus be directly vaporized. This... is huge! the only thing I am a bit uncertain about is the health and safety aspect, how ok is it to vaporize benzoic salts? but all in all, benzoic acid is a game changer!

I have no idea if it is safe to vaporize with direct heat. I would personally vape it in an e-juice, but I could not get it to dissolve when trying to prepare it. Too bad, because that would have been very convenient. If someone can figure out how to dissolve DMT benzoate in e-juice that would be awesome, since it is so easy get clean xtals lazily over the counter. I guess we can call crystallization from Naphtha CINLO?

 

[JCRG]

I read that lactate salts are also used to vape nicotine, perhaps it would be worthwhile to see if DMT Lactate could dissolve well in PG and/or VG?

I am assuming it would, since lactic acid contains more polar moieties than benzoic acid (3 vs 2), although I've also heard lactic acid can smell a bit like gym socks.

 

[_Trip_]

I read that lactate salts are also used to vape nicotine, perhaps it would be worthwhile to see if DMT Lactate could dissolve well in PG and/or VG?

I am assuming it would, since lactic acid contains more polar moieties than benzoic acid (3 vs 2), although I've also heard lactic acid can smell a bit like gym socks.

Check out this thread.

Lazy alkaloid salting combos (CISLO) - Collaborative Research Project - Welcome to the DMT-Nexus

 

[JCRG]

Oh that's awesome then, thanks!

 

[Woolmer]

Trying this dry tek with 50 g MHRB 5x freeze-thaw. Working really nicely so far. First pull with 80 g heated limonene yielded 0.820 g. The colour is slightly beige.

It is effortless to freeze-thaw because there is so little liquid one can easily do 5x freeze-thaws in one day if using a microwave to thaw after freezing.

 

[Loveall]

Trying this dry tek with 50 g MHRB 5x freeze-thaw. Working really nicely so far. First pull with 80 g heated limonene yielded 0.820 g. The colour is slightly beige.

It is effortless to freeze-thaw because there is so little liquid one can easily do 5x freeze-thaws in one day if using a microwave to thaw after freezing.

Great result! And I gathered it vaped well in emesh for you? Should we publish a TEK ?

 

[_Trip_]

I think benzoate deserves a tek, it's great for storage, oral use and smoking/ e-mesh vaping.
Also there appears to be multiple solvents that can be used. I'm still unsure how I feel about the orange/ lemon after taste when using limo.

 

[Loveall]

I think benzoate deserves a tek, it's great for storage, oral use and smoking/ e-mesh vaping.
Also there appears to be multiple solvents that can be used. I'm still unsure how I feel about the orange/ lemon after taste when using limo.

I can confirm toluene works. It is cheaper than limo for me and pulls very well, better than room temp naphtha (fewer pulls are needed to exahust the bark, 5 gives ~max yield for me). I like not needing to heat the solvent. Easy to neutralize and reuse also.

 

[Global_Roaming]

I acidified 100g of phyllodes with some citric acid in 1.5L water, microwaved for 10 minutes. Added 20g NaOH in solution. After two pulls using 30-40ml limonene the yield is only sitting around 0.1% which could be normal for the broad phyllodes I suppose, or perhaps I need to use more solvent?

Some solvent has seemingly become trapped in a phyllode sludge that floated to the top after doing a warm pull. I might decant the top layer with this sludge to a seperate vessel and add more water to promote seperation as salt did not help and there is no space in the vessel to add more NaOH solution.

Hey @Woolmer, did you ever get this approach to work with acacia, or did NMT cause the usual issues?

 

[Woolmer]

IIRC, a lot of the limonene never seperated again. But this is probably due to the fatty nature of the phyllodes and not the presence of NMT. The limonene that did seperate precipitated solid DMT that was easy to handle.

 

[Global_Roaming]

Interesting.

My first test using AA (without any defatting steps) resulted in lots of white precipitate after salting with an excess of benzoic acid, but it congealed in-situ into a gel-like layer. During filtering it simply melted away.

This was very reminiscent of my acacia experiences with freeze precipitations: even with defat and backsalting steps, I usually ended up with freebase crystals covered in white blobs. Upon decanting away the solvent, the blobs melted first and took most of the freebase DMT with it. Could be polymorphic DMT and/or NMT, but my money is on NMT since bioassay of the clear oil was consistent with the online reports.

For my next test I’ll defat the acidic brew and do an acetate backsalting of the combined pulls. If I still end up with these gel salts, then I’ll re-basify/pull and try CO2 separation into NMT carbamate (generating CO2 from citric acid and sodium bicarbonate, so I’ll need a bit of luck for it to work)

 

[Unfinished-Reaction]

SWIM has used Mr. Loveall's drytek method with his Chacruna Nexus leaf and got near 1% using food safe stuff.

The powdered leaf was too hard to stir with the rootbark recipe. SWIM needed to use 350ml limonene in french press with 100g powder, 150ml water, and 25g calcium hydroxide. Then the process felt just like the Cielo tek. The 2nd-4th pulls used only 175ml limonene. Since he only had enough limonene for 4 pulls instead of 5, he just stirred longer. All extracts were combined and dried with calcium chloride cacl2. (in SWIM's case 3 liters was dried with 2 1/2 tablespoons)


SWIM ran this test 4x with his gallon of limonene. He salted combined 3 liters which was from 4 extractions (lost a lot to soaked material and spills from being stupid) with 12g benzoic acid. He then fell asleep. In the morning there was a pile of white powder in the limonene that looked just like benzoic acid. He figured he oversaturated the solution. There were no other signs of crystals anywhere. So he put jar in the morning sun for an hour until very warm to touch. He swirled the jar and everything dissolved.

The next morning the jar walls were covered in crystals and after filtering he had a very nice pile of product. (lots was recollected later by rinsing the filters with hot distilled water and evaporating water in a dish. This was not benzoic acid if anyone is curious.)

Heat lamp was used on low to dry out the limonene soaked crystals eventually turning them from yellow to off white yellow tinge color.

SWIM has no idea how to clean the limonene or if he can just reuse it in the exact same tek later on.

Swim gave all credit for everything learned to Mr. Loveall.

*** Swim mentioned he was curious about using a Chacruna leaf tea boiled and reduced in place of the water in the recipe? He thought that this could make the extraction easier with less limonene and larger returns.

 

[Unfinished-Reaction]

SWIM has used Mr. Loveall's drytek method with his Chacruna Nexus leaf and got near 1% using food safe stuff.

The powdered leaf was too hard to stir with the rootbark recipe. SWIM needed to use 350ml limonene in french press with 100g powder, 150ml water, and 25g calcium hydroxide. Then the process felt just like the Cielo tek. The 2nd-4th pulls used only 175ml limonene. Since he only had enough limonene for 4 pulls instead of 5, he just stirred longer. All extracts were combined and dried with calcium chloride cacl2. (in SWIM's case 3 liters was dried with 2 1/2 tablespoons)


SWIM ran this test 4x with his gallon of limonene. He salted combined 3 liters which was from 4 extractions (lost a lot to soaked material and spills from being stupid) with 12g benzoic acid. He then fell asleep. In the morning there was a pile of white powder in the limonene that looked just like benzoic acid. He figured he oversaturated the solution. There were no other signs of crystals anywhere. So he put jar in the morning sun for an hour until very warm to touch. He swirled the jar and everything dissolved.

The next morning the jar walls were covered in crystals and after filtering he had a very nice pile of product. (lots was recollected later by rinsing the filters with hot distilled water and evaporating water in a dish. This was not benzoic acid if anyone is curious.)

Heat lamp was used on low to dry out the limonene soaked crystals eventually turning them from yellow to off white yellow tinge color.

SWIM has no idea how to clean the limonene or if he can just reuse it in the exact same tek later on.

Swim gave all credit for everything learned to Mr. Loveall.

*** Swim mentioned he was curious about using a Chacruna leaf tea boiled and reduced in place of the water in the recipe? He thought that this could make the extraction easier with less limonene and larger returns.

Notes:
-SWIM learned that exposing Limonene to sunlight for an hour is very bad and makes your Limonene yellow and too much oxidation. It is SWIM's understanding that warming limonene by other means is much better for the solvents longevity but also not good for the limonene. But had SWIM not used too much benzoic acid to begin with, SWIM may not have needed any heat in his limonene to dissolve his benzoic acid. This was SWIM's error and not anyone else's.

- a 1 gallon acidic water wash added to the limonene will remove remnants of benzoic acid in SWIMS saturated 3 liters of left over Limonene. SWIM used chat GPT4 for this info. He told chat GPT he needed to remove 7-10 grams of benzoic acid from the limonene and that is how much water was recommended. GPT-4 said that if the acidic water is not 3-4 ph that sodium benzoate may form. SWIM had read that you do not want this to happen. And if you do not remove the remaining benzoic acid from the limonene then sodium benzoate will form the moment you use the limonene in your next extraction as it turns benzoic acid to sodium benzoate when ph is above 4. Swim's understanding is that limonene has no ph so the benzoic acid is not yet changed. (If SWIM is wrong please correct his info everyone and I will remove from this post) Maybe the sodium benzoate is removed in the water wash, but to never have it created is better right?

-Swim dried his cleaned-up limonene with anhydrous magnesium sulphate and filtered later, then wondered if next time he should just use fresh limonene? If no sunlight was used and only enough benzoic acid was used for what the Chacruna could offer, then maybe the limonene could be used in a stronger form without water washing or using heat. Swim used Mr. Loveall's tek for root bark that offers much more spice than Chacruna does. In the future extractions of his Chacruna he would only use as much benzoic acid as the plant provides in extracted dmt. In Swims case this was 0.7-1.0% of plant mass extracted using his Chacruna Nexus clones.

-Swim also added 10ml of freezing cold ethyl acetate over his crystals in a funnel with coffee filter as a cleanup measure. It worked great and SWIM lost 15% but got rid of all of the sticky limonene residue and maybe some leftover benzoic acid if any was washed off with this step.

Swim is not a chemist, and chat gpt is not always correct. Comments and corrections are welcome.

 

[JCRG]

Notice that limonene has a double bond inside its ring, it is safe to assume that most double bonds in rings will not take kindly to being exposed against ultraviolet radiation, although this greatly depends on how strained the ring is.