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Author: Subject: Explosive ascaridole from epazote herb leaves
symboom
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[*] posted on 13-2-2017 at 04:41
Explosive ascaridole from epazote herb leaves


How can I extract ascaridole from espzote leaves
What is the best organic solvent what I have
Butane
Ethanol
Isopropanol
Turpintine
DCM

Before I possibly ruin the epazote I bought
By just trial and error I thought I would ask first


Epazote essential oil contains ascaridole (up to 70%), limonene, p-cymene, and smaller amounts of numerous other monoterpenes and monoterpene derivatives (α-pinene, myrcene, terpinene, thymol, camphor and trans-isocarveol). Ascaridole (1,4-peroxido-p-menth-2-ene) is rather an uncommon constituent of spices; another plant owing much of its character to this monoterpene peroxide is boldo. Ascaridole is toxic and has a pungent, not very pleasant flavor; in pure form, it is an explosive sensitive to shock. Ascaridole content is lower in epazote from Mexico than in epazote grown in Europe or Asia.[15]

Excerp from wikipedia
On epazote herb and

So I orderd some epazote what organic solvent should I use
To extract it

IUPAC name
1-Methyl-4-(1-methylethyl)-2,3-dioxabicyclo[2.2.2]oct-5-ene



[Edited on 13-2-2017 by symboom]

[Edited on 13-2-2017 by symboom]
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[*] posted on 13-2-2017 at 05:51


Tidbits
https://www.youtube.com/watch?v=zoq_3aHk70s
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Texium (zts16)
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13-2-2017 at 07:40
Ozone
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[*] posted on 13-2-2017 at 12:28


This is intriguing. The thought that a plant makes this much of an organic peroxide is kind of nuts. But, it apparently happens.

Cool.

Anyway, here is an analytical breakdown of the essential oil and an isolation procedure:

http://biomed.papers.upol.cz/pdfs/bio/2008/02/04.pdf

O3




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symboom
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[*] posted on 13-2-2017 at 14:36


Excerp from the link in the pdf



Extraction of the oil

Extraction of volatiles and semi volatiles was per-
formed. Air-dried leaves of each species (6-12 g) were
mixed with 250 ml of double distilled water (DDW)
and 0.03 g 4-isopropyl phenol as internal standard and
subjected to steam distillation for 3 hrs at atmospheric
pressure. The water distillate containing oil was distrib-
uted two times with hexane (50 ml each) with the help
of a separatory funnel. A 50-ml of 10 % sodium hydrox-
ide solution was added to the hexane layer and stirred
at room temperature for 5 minutes and the two phases
were separated. The aqueous fraction was washed with
50 ml of hexane, and the hexane fractions were combined,
dried with anhydrous sodium sulfate and were labeled as
“non-phenolic” fraction. To the basic water layer, 1 N HCl
was added with stirring until pH = 3. The solution was
then extracted three times with hexane (50 ml each). The
hexane fractions were combined and dried over anhydrous
sodium sulfate and labeled as “phenolic” fraction. The oil
was dried over anhydrous sodium sulphate and studied by
GC–MS as described previously.



Putting it into chemicals that are easier for a home chemist to aquire

Reagents
4-isopropyl phenol
Hexane
Sodium hydroxide
Sodium sulfate
HCl gas

Replacements
p-Isopropylphenol is found in cumin. p- Isopropylphenol occurs in oil of Eucalyptus

Hexane is found in?




If hexane was used maybe butane should work

[Edited on 13-2-2017 by symboom]

[Edited on 13-2-2017 by symboom]
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[*] posted on 16-7-2017 at 00:51


edit: woops, accidental necropost. Nothing to see here.

[Edited on 16-7-2017 by Mesa]
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[*] posted on 3-8-2017 at 05:42


Thanks for accidentally necro-ing the thread, seems like a really interesting project. Turns out you can get herb plants sent to you through the mail, I though that was pretty neat, so meet my two new friends! Plenty of time to think of extraction procedures while they grow up big and strong

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[*] posted on 22-9-2017 at 05:31


I have my doubts with regards to the explosiveness of the peroxide. I think the molecule looks energetically unimpressive, so please share your findings when you manage to isolate it.
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[*] posted on 9-1-2018 at 11:42


aha - i knew it, plant based explosive, knew it would be a thing some day.
anyhow ill share a trick to estimate solubility, toss whatever chemical into google followed by "xlogp3"
"xlogp3 ascaridole" gave me following value: 2.3, meaning a solvent around that would be suitable, this is what ive got noted down in the range, generally speaking DCM tends to dissolve most
now this is just for guesstimating, it doesnt always work out.
i suggest you could maybe form react the salt with an acid or even a base? if the acid salt is soluble in water usually the basic version tends to be insoluble

1.5 - DCM | Benzaldehyde | Phenol, hydroxybenzene
1.6 - Amyl alcohol, Pentanol
1.8 - Propane
1.9 - Hexanoic acid
2.0 - Benzyl Acetate | Hexanol
2.1 - Chloroform | Benzene | Methyl benzoate
2.3 - Benzyl chloride | Methyl salicylate
2.5 - Toluene | Xylene | Heptanoic acid
2.6 - Chloropentane | Ethyl benzoate
2.9 - Butane | Styrene | Glyceryl trimethacrylate




~25 drops = 1mL @dH2O viscocity - STP
Truth is ever growing - but without context theres barely any such.

https://en.wikipedia.org/wiki/Solubility_table
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[*] posted on 9-1-2018 at 13:04


Lord. I should have addressed this back then. The procedure given as:

"Extraction of volatiles and semi volatiles was per-
formed. Air-dried leaves of each species (6-12 g) were
mixed with 250 ml of double distilled water (DDW)
and 0.03 g 4-isopropyl phenol as internal standard and
subjected to steam distillation for 3 hrs at atmospheric
pressure. The water distillate containing oil was distrib-
uted two times with hexane (50 ml each) with the help
of a separatory funnel. A 50-ml of 10 % sodium hydrox-
ide solution was added to the hexane layer and stirred
at room temperature for 5 minutes and the two phases
were separated. The aqueous fraction was washed with
50 ml of hexane, and the hexane fractions were combined,
dried with anhydrous sodium sulfate and were labeled as
“non-phenolic” fraction. To the basic water layer, 1 N HCl
was added with stirring until pH = 3. The solution was
then extracted three times with hexane (50 ml each). The
hexane fractions were combined and dried over anhydrous
sodium sulfate and labeled as “phenolic” fraction. The oil
was dried over anhydrous sodium sulphate and studied by
GC–MS as described previously."

...Is complicated because the authors were using an internal standard to gauge recovery (to close the balance of mass). In essence, 6-12g air-dried leaves were mixed with 250 mL water and steam distilled. The subsequent work up was done with hexanes (or heptane from starting fluid, or light naphtha, etc.).

I'd bet that powdering the leaves and extracting with non-polar solvent (e.g. hexanes) in a soxhlet would probably work well, too. I've had good results using DCM to extract terpenes, as well, but the solvent will be less selective and further cleanup may be required.

I've got to see about getting some of these plants. The idea is still fascinating. I'd like to see if ascarindole can be used to initiate a polymerization (say, simple styrene, either thermally, or via redox couple).

O3




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symboom
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[*] posted on 9-1-2018 at 21:24


Glad to see renewed interest in this



Chemistry video storage (1000 videos so far)
https://www.mediafire.com/folder/kbll6gz9bdb4q/Videos
Natures Intellectual Organic Peroxide. >>Ascaridole <<

Oxone
Used for the production of --> CH2O/Cl2/ClO2/Br2/I2

------------------------------------->>Hydrogen Peroxide << -------------------------------------------- >> Acetylene <<
Peroxide Salts
Zinc Peroxide <\> Copper Peroxide <\>Silver Peroxide <\>Lithium Peroxide <\>Magnesium Peroxide <\>Calcium Peroxide to Calcium Superoxide
CoO2. \\ NiO2 \\ Ti/V/Cr peroxy complex \\ Triamine chromium peroxide \\ LiH \\SiO2-H2SO4 (SSA) \\ [Ni(NH3)6]

Exotic reducing agents
Ga2O TiCl2 GeCl2 && Na2S2O4
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[*] posted on 10-1-2018 at 05:20


Well, are plants aren't hard to grow! 4 months since I posted the picture earlier on in the thread, the same plants were huge. I say huge because a few days ago I cut off most of the stems and leaves, to stop them dying as they're annuals going to seed. I've kept all the overcuts in my freezer to prevent loses of Optus oil. Overkill, but whatever.

I spent the day today making enough chloroform to use my Soxhlet extractor. So I'll give this a shot soon, maybe next week. Hexane would be better, oh well.


[Edited on 10-1-2018 by Tdep]

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[*] posted on 10-1-2018 at 06:26


Chloroform will definitely get it. It will also get all of the pigments, and other stuff (surprisingly, I've found it to be a better solvent for waxes than hexanes). Hexane is a much "poorer" solvent which is more selective for the oils -- not perfect, but cleaner than the chloroform will be.

I suspect that you'll get a green/brown extract. I'd probably try cleaning it up with some silica gel (maybe not...unless it can be eluted intact from the gel: https://www.google.com/patents/US3420906).

Regardless, progress is progress, and I'm curious to see what you get.

I've found some of these plants for sale, but they like full sunlight, preferably outside...and it's cold in the NE US, so I'll probably have to wait until March, or so. Aside, several spice companies appear to sell it by the pound (dried leaves), but I'm worried about how stable the ascarindole might be throughout their (unknown) handling and processing scheme.

Nice plants!

O3




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[*] posted on 10-1-2018 at 07:17


Yeah selectivity is an issue. I really want to see it explode, but even if the oil I extract is the perfect 70% (as so claimed by some sources), the 30% other terpenes and shit will go a long way to masking the energetic properties. I mean it's only one peroxide bond in that whole molecule, even at 100% purity I really question its ability to explode. So purification is a challenge. Would be nice to be in a lab and just have hexane, run a column under nitrogen, monitor it by TLC and NMR each fraction before rotovaping them all down... I don't even have the silica or the glassware to run a column :(

Another thought, I suppose I'll have to vacuum distillation off the chloroform?I'd like to avoid that if possible because I haven't done them much, and the thought of chloroform in my pump makes me slightly nauseas, but I don't want to go through all this extraction just to destroy all the peroxide bonds removing the solvent. So is it worth the effort?

Been perfect growing weather for them here. Been quite a few brutally sunny days just when they needed it, glad I remembered to water them often, they were sometimes getting a bit cooked in those black pots
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[*] posted on 10-1-2018 at 09:32


Yeah, you'll probably get a lot of gummy, oily mess. If your worried about thermal decomp during solvent removal, you can always just warm it a little (say, 40-50 °C) in a water bath and run a stream of air (better N2) over it to blow off the solvent (can't easily recover the solvent this way).

I too question whether it would be capable of "detonation" (maybe accelerating deflagration if very pure and confined?)--OB stinks and it's a particularly stable peroxide. That's why I wanted to see if there was utility as an organic-soluble radical initiator. It's not as cool as exploding plants, but it's something.

I suspect that you'll get a mixture of peroxides (e.g. menthene-hydroperoxides and who-knows-what), too.

Interestingly, the menthadiene gives ascarindole with singlet oxygen: https://www.sigmaaldrich.com/catalog/product/aldrich/w355801... -- which might be an interesting project if the parent compound can be either obtained or synthesized.

I'm going to buy a kg of this (it's the "rawest" dried product I could find) to see if it's worth working with, peroxide-wise:

https://www.herbco.com/p-616-epazote-herb-cs.aspx

Cheers,

O3




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symboom
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[*] posted on 30-3-2018 at 11:57


natural organic compound classified as a bicyclic monoterpene that has an unusual bridging peroxide functional group. It is a colorless liquid with a pungent smell and taste that is soluble in most organic solvents. Like other low molecular weight organic peroxides, it is unstable and prone to explosion when heated or treated with organic acids.

Boldo leaf also contains 2-4% of volatile oil. Major constituents reported as: ascaridole (16-38%), 1,8-cineole (11-39%) and. p-Cymene (9-29%)

Espazote has (16-70%) ascaridole
Boldo leaf (16-38%) ascaridole

Ascaridole is also a major component of epazote (or Mexican tea, Dysphania ambrosioides, formerly Chenopodium ambrosioides) where it typically between (16-70%)of the plant's essential oil


The specific flavor of the Chilean tree boldo (Peumus boldus) primarily originates from ascaridole. .[14The content of ascaridole in the plant depends on cultivation and is maximal when the nitrogen to phosphorus ratio in the soil is about 1:4. It also changes through the year peaking around the time when the plant seeds become mature.

Espazote
Baldo

[Edited on 30-3-2018 by symboom]




Chemistry video storage (1000 videos so far)
https://www.mediafire.com/folder/kbll6gz9bdb4q/Videos
Natures Intellectual Organic Peroxide. >>Ascaridole <<

Oxone
Used for the production of --> CH2O/Cl2/ClO2/Br2/I2

------------------------------------->>Hydrogen Peroxide << -------------------------------------------- >> Acetylene <<
Peroxide Salts
Zinc Peroxide <\> Copper Peroxide <\>Silver Peroxide <\>Lithium Peroxide <\>Magnesium Peroxide <\>Calcium Peroxide to Calcium Superoxide
CoO2. \\ NiO2 \\ Ti/V/Cr peroxy complex \\ Triamine chromium peroxide \\ LiH \\SiO2-H2SO4 (SSA) \\ [Ni(NH3)6]

Exotic reducing agents
Ga2O TiCl2 GeCl2 && Na2S2O4
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