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Mister E
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[*] posted on 10-3-2018 at 11:59
Cannabinoid concentration


Living in a state where I can legally work with cannabinoids makes this an exciting time.

I'm getting read to do some short path distillation using d-limonenne as my solvent. I know it is possible to isolate cannabinoids using this method however due to the secretive nature of the cannabis world there is little in the way of actual documentation of this.

I see a few problems that I'm sure I will have to overcome.

First up is the questionable information regarding the most well known cannabiniod, tetrahydrocannabinol or THC.

The commonly excepted BP for THC is 157C however pubchem lists the BP for Drobinol (brand name Marinol, pharmaceutical grade THC) as 392F (200C) at 0.02 mm of Hg

https://pubchem.ncbi.nlm.nih.gov/compound/Dronabinol#section...

If the pubchem is correct then the true BP of THC would be 514C not 157C. However this huge difference between temperatures makes me question the BP's for all cannabinoids.

What I do know is yhe BP for d-limonenne. That is well know to be 176C.

Many people say it's overly hard or impossible to use limonene to extract cannabinoids because of their similar BP's but one person in Canada, Horatio Delbert, claims to not only do so regularly but has won several awards for his product.

Now Horatio has both answered some questions I have and added many more. He does not seem to be aware of the discrepancies in BP's nor is he willing to share detailed information. As I said the cannabis world is rather tight lipped. However he has made mention of a few things that expect I will have to figure out on my own shortly.

I know he uses a rotovap, I'm just starting out and only have a stir mantle. I'm hopeful I will be able to at least provide proof of concept with the mantle.

He has mentioned azeotropic distillation as well as having to add water to his rotovap. Could water form an azotrotic bond with limonene and reduce it's boiling point? If so does anyone know the calculation needed to determine the new BP?

I hope to be able to post my experiments here and have others who understand the science behind it do peer reviews of my work. As more and more of the world legalize cannabis use we need to have firm scientific methods to make sure concentrate products are not put on the market that are unsafe. The current levels of secrecy around production has led to too many amateurs who are not able to learn how to progress.

If anyone has any information they wish to share or any questions for me please do so. I will be starting my extraction as soon as I receive a new boiling flask, hopefully within a week.
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[*] posted on 10-3-2018 at 14:58


Quote: Originally posted by Mister E  

As I said the cannabis world is rather tight lipped


This might be true for the cannabis world, but it is not for the scientific world. Cannabis and its compounds are very well studied because of the obvious. Try to have a look around here:
https://www.ncbi.nlm.nih.gov/
Usually it is a good start; not all new articles are in their databases, but after a year or so most articles end up in there. Material and methods is often a rich source for protocols.

I found scientific articles completely un-understandable at first, but just hang on and keep on reading, at some point you will get the hang of it.
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[*] posted on 10-3-2018 at 15:01


I believe limonene is steam distillable whereas THC is not, so steam distilling would probably separate the mixture. Regular distillation would probably work too, since the actual boiling point of THC is much higher than 157 °C.

After cannabis became legal in my state at the request of a friend I made a distilled extract for him from his home-grown plant material. I first extracted the coarsely ground buds by gently swirling in -12°C 99% isopropanol (3x100 mL or so for about 14g IIRC). The solution was filtered, distilled until most of the solvent was collected, then the last solvent removed under aspirator vacuum and heating with a hot water bath until all traces of solvent were removed. The light brown extract thus acquired was then vacuum distilled through a short path at about 1 mm Hg. A clear colorless oil came over around 180-200°C. It was very viscous but not quite solid, and yellowed and darkened over time. I don't know about THC concentration, but it was judged to be very very potent.


[Edited on 11-3-2018 by Crowfjord]
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[*] posted on 10-3-2018 at 18:44


Pacific northwest eh? I'm in California and adult use is legal. I however don't know the legality of making your own concentrate. As far as I can tell, medical patients are allowed to use safe extraction methods and adults in general can use/have up to 8g, but nothing about making it as a private citizen. You surely couldn't transfer it for any kind of trade or sale b/c of the huge fines for unlicensed manufacture, transportation, distribution and sale of a controlled substance(at least not here). They would bag and tag your ass quickly given the chance, with prejudice since there are legal routes.

I'd say it is pretty weird change of pace. A friend just remarked only two days ago "it's so strange to be able to drive to town and buy pot as if your getting a gallon of milk... Crazy". Still not allowed to smoke in public or drive of course, but if it's in your pocket no problem.




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10-3-2018 at 18:53
Morgan
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[*] posted on 10-3-2018 at 19:50


Off topic but just wondering if this is dramatically effective or not?
https://therooster.com/blog/keep-calm-and-listen-neil-youngs...
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Tsjerk
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[*] posted on 10-3-2018 at 22:41


https://sci-hub.tw

Copy the DOI number from any article too here in order to avoid paying for articles. Maybe not completely legal, but hé, we are not making any money out of it anyway right?

[Edited on 11-3-2018 by Tsjerk]
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[*] posted on 11-3-2018 at 02:00


What are you trying to make: cannabinoids as chemicals of reasonable purity for experiments, or cannabis concentrate for personal use?



Smells like ammonia....
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[*] posted on 11-3-2018 at 13:52


Critical extraction with CO2 is the most effective and safest route, plums use Butane but CO2 gives a very clean extraction and is generally the preferred method. There is a forum named after a date in March (cant remember it all now!!) but some date connected with cannabis, the forum is an excellent source of information.

Where i live its totally illegal so obviously the above info came to me via someone else dream who passed it on to someone else and i then overheard it etc....... :D

[Edited on 11-3-2018 by NEMO-Chemistry]
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[*] posted on 11-3-2018 at 14:35


Here again, critical CO2 is the best known method. Extraction result in a clear oily wax.
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[*] posted on 12-3-2018 at 02:32


Are there any examples of amateurs (ones that don't buy a ready to use system) getting a super-critical CO2 extraction done?
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[*] posted on 12-3-2018 at 13:30


OP I think you are getting some things mixed up.

The procedure you describe with the limonene sounds like it is being used as an azeotropic distillation agent. In simple terms, it is being used to entrain the terpenes and carry them over out of the mixture. This allows higher boiling terpenes to be removed without raising the heat too much. In a rotovap, this would likely be very efficient. Since rotovaps have such a high surface area of evaporation, and tend to have lower separation coefficients, this method could quickly leave behind relatively pure cannabinoids in the evaporation flask. You'd probably still want to recrystallize them in the end though. To reiterate, in this procedure, the cannabinoids stay in the evaporation flask, you are not distilling those over.

A rotovap is doubly useful in this regard because they often have the ability to continually add solvent as the evaporation progresses, without having to take the apparatus apart or remove much of the vacuum.


Some notes, you would definitely need to do this under a vacuum, and I definitely I wouldn't do this procedure with a heating mantle, as it relies upon controlling the heat source well, so it'd probably be more wise to use an oil bath.

This of course isn't the only way to obtain pure cannabinoids. They could probably be isolated very easily by recrystallizing from the right solvent combination. Since terpenes tend to be liquid and having lower boiling points than the desired cannabinoids, they should be able to be easily separated by crystallization, owing to their higher solubility.

I miss living in a medical state and being able to try things like this. Personally, I don't know why people want to remove the terpenes. The terprenes are primarily what give the strain its unique profile and effects.

[Edited on 12-3-2018 by Sidmadra]
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[*] posted on 12-3-2018 at 13:40


Quote: Originally posted by Sidmadra  
OP I think you are getting some things mixed up.

The procedure you describe with the limonene sounds like it is being used as an azeotropic distillation agent. In simple terms, it is being used to entrain the terpenes and carry them over out of the mixture. This allows higher boiling terpenes to be removed without raising the heat too much. In a rotovap, this would likely be very efficient. Since rotovaps have such a high surface area of evaporation, and tend to have lower separation coefficients, this method could quickly leave behind relatively pure cannabinoids in the evaporation flask. You'd probably still want to recrystallize them in the end though. To reiterate, in this procedure, the cannabinoids stay in the evaporation flask, you are not distilling those over.

A rotovap is doubly useful in this regard because they often have the ability to continually add solvent as the evaporation progresses, without having to take the apparatus apart or remove much of the vacuum.


Some notes, you would definitely need to do this under a vacuum, and I definitely I wouldn't do this procedure with a heating mantle, as it relies upon controlling the heat source well, so it'd probably be more wise to use an oil bath.

This of course isn't the only way to obtain pure cannabinoids. They could probably be isolated very easily by recrystallizing from the right solvent combination. Since terpenes tend to be liquid and having lower boiling points than the desired cannabinoids, they should be able to be easily separated by crystallization, owing to their higher solubility.

I miss living in a medical state and being able to try things like this. Personally, I don't know why people want to remove the terpenes. The terprenes are primarily what give the strain its unique profile and effects.

[Edited on 12-3-2018 by Sidmadra]


Might the terpenes in beer/hops have any marginal effects if indeed the terpines modulate paranoia/anxiety?

Another curious tidbit (if true). Not really a scientific source and all.
"Oh the other hand, some terpenes life Myrcene from mangoes seem to turbocharge THC, which could be a good or bad thing. Possible one's effective dose might be reduced."
https://mmjdoctoronline.com/health-news/black-peppercan-cure...


[Edited on 12-3-2018 by Morgan]
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NEMO-Chemistry
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[*] posted on 12-3-2018 at 14:02


CO2 super critical is really easy at home, a plastic tube used to clean aquarium gravel, a CO2 cylidar with the tube going to the bottom so it makes dry ice, cap off both ends the plastic tube, one end make loads of 1mm holes and the other make one hole with a barbed pipe fitting.

Fill plastic tube with the erb and fill tube with liquid CO2, let it all find its way out the little holes (put a bowl under it). Simples and cheap, its done alot with Lighter gas in tins but dont do that!! really bad fire hazard in my dream.
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[*] posted on 12-3-2018 at 19:39


What kind of plastic tube should I use to hold roughly 73 atm. of pressure? "Little holes" and "super critical" don't sound like they go hand-in-hand :D
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[*] posted on 13-3-2018 at 01:04


Quote: Originally posted by Tsjerk  
Quote: Originally posted by Mister E  

As I said the cannabis world is rather tight lipped


This might be true for the cannabis world, but it is not for the scientific world. Cannabis and its compounds are very well studied because of the obvious. Try to have a look around here:
https://www.ncbi.nlm.nih.gov/
Usually it is a good start; not all new articles are in their databases, but after a year or so most articles end up in there. Material and methods is often a rich source for protocols.

I found scientific articles completely un-understandable at first, but just hang on and keep on reading, at some point you will get the hang of it.


Sadly thanks to very repressive regimes of yore even the scientific data is often contradictory. But I'll dig through the link you sent and see if there is anything decent on the subject however the discrepancies around the BP I mentioned in my OP do not come from the grower world but from reputable scientific sources.
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[*] posted on 13-3-2018 at 01:06


Quote: Originally posted by Crowfjord  
I believe limonene is steam distillable whereas THC is not, so steam distilling would probably separate the mixture. Regular distillation would probably work too, since the actual boiling point of THC is much higher than 157 °C.

After cannabis became legal in my state at the request of a friend I made a distilled extract for him from his home-grown plant material. I first extracted the coarsely ground buds by gently swirling in -12°C 99% isopropanol (3x100 mL or so for about 14g IIRC). The solution was filtered, distilled until most of the solvent was collected, then the last solvent removed under aspirator vacuum and heating with a hot water bath until all traces of solvent were removed. The light brown extract thus acquired was then vacuum distilled through a short path at about 1 mm Hg. A clear colorless oil came over around 180-200°C. It was very viscous but not quite solid, and yellowed and darkened over time. I don't know about THC concentration, but it was judged to be very very potent.


[Edited on 11-3-2018 by Crowfjord]


Nice, short path purification of a RSO. Sounds like you were making a version of the product being marketed in Colorado as "the clear"
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[*] posted on 13-3-2018 at 01:18


Quote: Originally posted by violet sin  
Pacific northwest eh? I'm in California and adult use is legal. I however don't know the legality of making your own concentrate. As far as I can tell, medical patients are allowed to use safe extraction methods and adults in general can use/have up to 8g, but nothing about making it as a private citizen. You surely couldn't transfer it for any kind of trade or sale b/c of the huge fines for unlicensed manufacture, transportation, distribution and sale of a controlled substance(at least not here). They would bag and tag your ass quickly given the chance, with prejudice since there are legal routes.

I'd say it is pretty weird change of pace. A friend just remarked only two days ago "it's so strange to be able to drive to town and buy pot as if your getting a gallon of milk... Crazy". Still not allowed to smoke in public or drive of course, but if it's in your pocket no problem.


Every state has there own set of rules. I'm able to grow smoke and do whatever except sell with my own stuff here. The state limits commercial production to "butane, CO2, and any other solvent the MCB (marijuana control board) approves in the future".

CO2 does not make a decent shatter. You can get honey oil and pre-loaded cartridges but nothing resembling a decent dab unless it has gone through further processing. Also Supercritical systems start in the mid 5 digit range.

Butane has the obvious issues with hydrocarbons and some peoples refusals to have anything to do with them. his goes so far as to there being lighters that have a piece of hemp wick attached so you use the lighter to light the wick then the wick to light your weed.

I want to follow in he footsteps of the few how have made LHO shatter. I know there are limonene isolates that reduce it to 99% pure THCa and while I would like to be able to do that my main goal is to produce a hydrocarbon free shatter that contains a decent terp profile. If this ends up by using steam distillation to create full profile terp solutions and reintroducing it after my LHO shatter has been vac purged so be it.

After I have my legal home pilot plant running I will take it before the MCB and get the approved to move forward with a legal commercial operation.
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[*] posted on 13-3-2018 at 01:24


Quote: Originally posted by ave369  
What are you trying to make: cannabinoids as chemicals of reasonable purity for experiments, or cannabis concentrate for personal use?


Yes. I would love to be able to create pure refined cannabinoids of a large variety to experiment with as so little has researched so far beyond THC and CBD. Also I want to create cannabis concentrate that is free of petrochemicals and can be added to the list of approved commercial methods.
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[*] posted on 13-3-2018 at 01:35


Quote: Originally posted by Sidmadra  
OP I think you are getting some things mixed up.

The procedure you describe with the limonene sounds like it is being used as an azeotropic distillation agent. In simple terms, it is being used to entrain the terpenes and carry them over out of the mixture. This allows higher boiling terpenes to be removed without raising the heat too much. In a rotovap, this would likely be very efficient. Since rotovaps have such a high surface area of evaporation, and tend to have lower separation coefficients, this method could quickly leave behind relatively pure cannabinoids in the evaporation flask. You'd probably still want to recrystallize them in the end though. To reiterate, in this procedure, the cannabinoids stay in the evaporation flask, you are not distilling those over.

A rotovap is doubly useful in this regard because they often have the ability to continually add solvent as the evaporation progresses, without having to take the apparatus apart or remove much of the vacuum.


Some notes, you would definitely need to do this under a vacuum, and I definitely I wouldn't do this procedure with a heating mantle, as it relies upon controlling the heat source well, so it'd probably be more wise to use an oil bath.

This of course isn't the only way to obtain pure cannabinoids. They could probably be isolated very easily by recrystallizing from the right solvent combination. Since terpenes tend to be liquid and having lower boiling points than the desired cannabinoids, they should be able to be easily separated by crystallization, owing to their higher solubility.

I miss living in a medical state and being able to try things like this. Personally, I don't know why people want to remove the terpenes. The terprenes are primarily what give the strain its unique profile and effects.

[Edited on 12-3-2018 by Sidmadra]


So your suggesting the Limonene forms an azotropic bond with the terpenes and helps in removing them to purify the final product?

I know the initial extraction from raw plant material is being done under vacuum with limonene.

Furthermore there is a recrystallizing method referred to as "winterization" using ethanol. I also know this is being done to the extract after the limonene is removed.

I agree with the idea of keeping terpenes in he mix as much as possible and plan on experimenting with steam distillation of terpenes separately so that I can reintroduce a full profile after the concentrate is purged.

I know a rotovap would be a huge help. It's at the top of the list of things I want to add. I have a mantle and I know it was done with a mantle before however it seems to be much harder. that's okay, I'll put in the hard work with what I have to form my proof of concept.

Yes everything will be done under vacuum. Both my fractional distillation and a purge in a vac chamber after.

And yes my plan was to distill off the limonene from the THC not the other way around despite the claim from some sources that THC has a lower BP than Limonene.

[Edited on 13-3-2018 by Mister E]
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[*] posted on 13-3-2018 at 01:49


Quote: Originally posted by NEMO-Chemistry  
CO2 super critical is really easy at home, a plastic tube used to clean aquarium gravel, a CO2 cylidar with the tube going to the bottom so it makes dry ice, cap off both ends the plastic tube, one end make loads of 1mm holes and the other make one hole with a barbed pipe fitting.

Fill plastic tube with the erb and fill tube with liquid CO2, let it all find its way out the little holes (put a bowl under it). Simples and cheap, its done alot with Lighter gas in tins but dont do that!! really bad fire hazard in my dream.


What you speak of is known as open blasting. While it does work with butane (your "lighter gas) it does not work with CO2 as there is no way to put the CO2 under the pressure needed for it to reach a supercritical state and effectively strip cannabinoids.
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[*] posted on 13-3-2018 at 01:49


Quote: Originally posted by Mister E  
I want to create cannabis concentrate that is free of petrochemicals and can be added to the list of approved commercial methods.


With this I can help. Use extraction with liquified gases. The industrial method is using CO2, but this requires high pressure. For home lab, butane is the most convenient gas. It remains liquid at relatively high temperatures at standard pressure yet completely boils off, not leaving any hydrocarbons behind.

Treat cannabis with liquid butane at lowered temperatures or elevated pressure. Once the extraction is complete, lower pressure or raise the temp, the butane will completely evaporate, leaving you with a viscous concentrate that could be used for both personal use and further purification.




Smells like ammonia....
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[*] posted on 13-3-2018 at 01:52


My last package showed up today but sadly one piece is broken =( so it's another week or so now till I'm ready to begin but I will check back in and post updates of my work soon.
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[*] posted on 13-3-2018 at 01:57


Quote: Originally posted by ave369  
Quote: Originally posted by Mister E  
I want to create cannabis concentrate that is free of petrochemicals and can be added to the list of approved commercial methods.


With this I can help. Use extraction with liquified gases. The industrial method is using CO2, but this requires high pressure. For home lab, butane is the most convenient gas. It remains liquid at relatively high temperatures at standard pressure yet completely boils off, not leaving any hydrocarbons behind.

Treat cannabis with liquid butane at lowered temperatures or elevated pressure. Once the extraction is complete, lower pressure or raise the temp, the butane will completely evaporate, leaving you with a viscous concentrate that could be used for both personal use and further purification.


I want to avoid butane. There are already a handful of labs here manufacturing with butane. I've seen the test result, every one of them has residual butane let over. The states requirement of a concentrate "passing" a residual solvent test is not the same as it having no hydrocarbons left behind.

My goal is to re-create the LHO (Limonene Hash Oil) product that is manufactured in the British Columbia area. Outside of that one lab I do not know of any commercial LHO manufactures. Thus the hard time finding reliable information unlike BHO where there is a ton of information and relatively inexpensive closed loop machines that are shipped out as turn key operations.
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[*] posted on 13-3-2018 at 06:16


Quote:
 For home lab, butane is the most convenient gas. It remains liquid at relatively high temperatures at standard pressure yet completely boils off, not leaving any hydrocarbons behind.


Technical butane is NOT a food and drug grade material. The cheap stuff happy home hash oil extractors frequently use is contaminated with various oily hydrocarbon crap, which does not boil off into the atmosphere so readily. Even the slightly better stuff some cigarette lighter companies tout as not wrecking the electrical ignition systems of fancy lighters is nothing you want contaminants of in your lungs.

I use butane for stage flame effects, from what I have learned maintaining the ignition systems and burners, I wouldn't be using a non FDA tested grey market product that began with a cheap butane for extraction. Cheap, easy, good: choose any two, as usual.

I have no idea what grades are available, or what contaminants will be found in cheap d-limonene. Hope being an early adopter is not something you will regret later in life. Lungs: Only two issued per customer.
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[*] posted on 13-3-2018 at 06:21


I have seen it done using a soda stream CO2 bottle, it didnt work as well as a large CO2 cylinder but it worked fine.
The only time i seen CO2 not work was with a CO2 cylinder used for Beer in pubs, these dont have the tube inside the cylinder going to the bottom, they take the gas from the head space.

This isnt my thing, but I can assure you i seen an amber potent liquid drip like nectar using CO2. And i am told (yes seriously i havnt tried the stuff) that it smokes better than Butane extracted.

Dont shoot the messenger, i am only telling you what is apparently a very common practice in some areas of the town nearest to me. Known locally as weed world :D.

The other one i have heard about but not seen was the cream fluffer gas stuff, I think they were on about Laughing gas but hard to tell with that particular group of....acquaintances

[Edited on 13-3-2018 by NEMO-Chemistry]
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