Decoding The Holy Grail: Terpene & Cannabinoid Retention: Decarb to Extraction

[Scientific]

When terpene molecules are boiled off or evaporated, is it in the form of the intact molecule? In other words, beta-caryophyllene has a molecular formula of C15H24. Do you suppose it is boiled off in a still useable form or would the heat restructure it?

I think organic chemistry and biochemistry are fascinating (especially when they relate to stuff I can relate to, like altered states of consciousness ), but I'm no chemist. But I can say that a lot of these molecules are small and simple (which I think is good for stability), and they don't have a lot of sites at which to react (also good).

Happily, myrcene (top left) looks to be especially small, simple, and non-reactive.

The double bonds (double lines in the drawing) are more likely to react than single bonds (kind of counter-intuitively). And that "CO2H," the "acid" part of chrysanthemic acid (gotta love these names!), is comparatively reactive, but I would guess that most of the terpenes that evaporate in a closed container might very well remain unaltered and then condense on the surface of the container as soon as it cooled. For that reason, I have never enclosed my material when decarboxlylating. It seems to me like low temperatures and short heating times are the only really effective way to limit losing volatiles (though maybe trapping them in oil could work? But might that not also inhibit the release of CO2? So many questions...)

 

[Bucudinkydow]

"but I would guess that most of the terpenes that evaporate in a closed container might very well remain unaltered and then condense on the surface of the container as soon as it cooled."

Thanx, Scientific. Exactly what I was hoping for. Armed with your opinion and my supposition on the fractional distillation process, I'm going to initiate an experiment this evening. If I get positive results, I'll share. If not, I'll simply disappear into oblivion! Thanx for your help.

 

[Scientific]

Armed with your opinion and my supposition on the fractional distillation process, I'm going to initiate an experiment this evening.

Oh yeah... that is a setup for distillation, isn't it? I am reminded of the early days of modern science when people where distilling essences with alembic stills. You might want to go back and read some of that stuff if you haven't already...

And "steam distillation" in which the plant material is placed in boiling water and then the steam and oils are captured and then separated out to produce the essential oil.

I found the quote I was trying to remember: "Per the Steep Hill Labs based in Berkeley, California, this terpene’s percent dictates species: if the plant has more than .5 percent myrcene, it’s will produce indica-like effects." If you have a plant that's .5% myrcene, that's 1.4 grams of myrcene in an ounce, which is more than a milliliter, so it should be captureable with good technique, I would think.

<edit> Just found this at the Steep Hill Labs blog: "Myrcene is mostly unchanged by heating."</edit>

 

[Kicknitup1]

"Sorry, I know that's going off-topic and should go on another thread, but with all of this discussion of and effort toward preserving the natural balance of the volatiles (and my bud tender down at the Pot Stop shop telling me to eat mangoes when smoking weed to augment myrcene), I had to pose the question to people who are knowledgeable and interested in this subject."

Not off topic at all. And Bucudinkydow & the rest.....you picked up something in chemistry class. They are light and the first to go. Pressure may be our friend but not a pressure cooker unfortunately. Again, there are already industrial methods of manipulating them. But, we all hoped to pull it off in a household setting.

Which reminds me...CCO must preserve some or what would be the difference in Indica & Sativa Honey, Shatter, etc?

 

[Canyon]

The latest test are back.

The short version is, the Nova decarbed 4hr infusion is capturing about 85% of cannabinoids and around 32% of the terpines if I have the math correct.

I still need to get it charted. I will post the tests, dilutions, etc by late morning with luck.

Scientific, Could I get your thoughts on decarbing under presure using a presure cooker? I am not as quick do dismiss the process as Kickn is.

 

[bebecillo]

The latest test are back.

The short version is, the Nova decarbed 4hr infusion is capturing about 85% of cannabinoids and around 32% of the terpines if I have the math correct.

I still need to get it charted. I will post the tests, dilutions, etc by late morning with luck.

Scientific, Could I get your thoughts on decarbing under presure using a presure cooker? I am not as quick do dismiss the process as Kickn is.

Huge variation if last test gave almost perfect conversion.

Regarding terpenes you could capture them if you decarboxylate your bud in water as long as you capture the steam, problem is to filter the terpenes back.

I don't live in the us so it's harder for me to contribute, but can anyone buy myrcene or another terpene, add 1ml to a glass of water or something (like adding some terpene drops and re curing your bud) and smoke a bowl? Doing so would help us check if it works and maybe the terpene profile idea wouldn't sound so crazy

Ps: check my current grow. This baby will be used for a qwet tutorial.

Greetings

 

[Scientific]

Scientific, Could I get your thoughts on decarbing under presure using a presure cooker? I am not as quick do dismiss the process as Kickn is.

Hi Canyon -- I watched the YouTube video below to get the rundown on how you decarb in a pressure cooker.

In the video, she puts the plant material in a sealed container inside a pressure cooker that gets up to 253 F (IIRC), which would mean the pressure was about 16 PSI.

I don't see an advantage of doing it that way, and it could actually be worse since higher temps can mean reduced retention of volatiles.

First, I think that temperature is higher than is necessary or desirable. I think it's well established now that we can decarboxylate at lower temperatures if we give the process more time, and to me, lower temperatures are better because fewer volatiles are lost.

Second, I don't see any benefit in pressurizing other than to raise the boiling point of the water bath.

The only reason I can think of to use a water bath is because the temperature can be more consistent and controlled. But I have decarbed effectively in a double boiler at atmospheric pressure, so no need for the pressure as far as I can see.

I decarbed in a double boiler back when I had an ancient gas stove. But my modern GE electric oven can regulate temperature pretty well all the way down to 170 F, so I just pop my weed in the oven now at 220 F for 105 minutes and that seems to work fine.

I don't cover my cannabis for the reason given in an earlier post: I suspect that any terpenes liberated by the heat will either condense on the walls of the container or just wander off if they can. The woman in the video says she likes to wait 20 minutes before opening the inner container to give the volatiles time to settle back on the plant material. I really don't think it works that way...

In short, I don't think that decarbing in a double boiler is worth the trouble when, if you want to use a double boiler, you can effectively (I think) decarb at 1 atmosphere/212F. Or you can decarb in an electric oven of recent manufacture with good electronic temperature control.

So there's my data, reasoning, and opinion. Comments from y'all?

Pressure Cooking Cannabis to Decarb it and Activate THC - YouTube

 

[FeloniousPunk]

*Oh my gosh OB, I'm sooo scared my brain will mess it up. But thank you for the well wishes I could use them. lol
This is why I'm collecting the facts now, print them out and not deviate from the plan. I hope this all works. I will let you know.

Good Morning G2HM!

I'm sure you will be as successful with the oil as with the grow. Your abilities today far exceed where you started from at the beginning of your grow. Kudos.

Continue doing what you have done and go slow. If you are really concerned about mucking it up, cut the recipe in half, or less. Your biggest risk in making the oil is losing the plant material. Doing a few smaller batches will give you both experience and confidence, without risking your whole stash. Win/win.

It also lets you experiment with dosing levels.

And don't be afraid to utilize your helper (your husband not the cat), he's there for you!

Peace.

 

[Oldbear]

Good information here.

Additional fyi - There are companies selling terpene blends - designed to match particular strains exactly.

buy terpenes dot com is one of several

Here's a random, irreverent, possibly off-the-wall, and kinda off-topic question: If terpenes are the key to the various types of high, why not just buy them pure and add them to customize your vape?

I read a pretty convincing article that said that the explanation for the legendary difference in the effects of indica and sativa is the amount of myrcene.

I remember seeing bottles of myrcene, pinene, linalool, and lots and lots of other such stuff on the shelves of the chemistry storeroom when I was taking organic chemistry (and taking the cap off a bottle of benzaldehyde and the whole room suddenly smelling like my grandmother's kitchen when she was baking almond cookies, but that's another story).

So at the extreme of better living through chemistry, it occurred to me that if the entourage effect is real, you should be able to take pure, synthetic THC (Marinol is an example I believe) and then add x percent myrcene and y percent pinene, etc. to just evenutally dial in the exact, desired effect.

At the very least, I find myself wondering what would happen if I just augmented my oil with 1%, 2%, x% myrcene.

Sorry, I know that's going off-topic and should go on another thread, but with all of this discussion of and effort toward preserving the natural balance of the volatiles (and my bud tender down at the Pot Stop shop telling me to eat mangoes when smoking weed to augment myrcene), I had to pose the question to people who are knowledgeable and interested in this subject.

 

[Bucudinkydow]

Oh yeah... that is a setup for distillation, isn't it? I am reminded of the early days of modern science when people where distilling essences with alembic stills. You might want to go back and read some of that stuff if you haven't already...

And "steam distillation" in which the plant material is placed in boiling water and then the steam and oils are captured and then separated out to produce the essential oil.

I found the quote I was trying to remember: "Per the Steep Hill Labs based in Berkeley, California, this terpene’s percent dictates species: if the plant has more than .5 percent myrcene, it’s will produce indica-like effects." If you have a plant that's .5% myrcene, that's 1.4 grams of myrcene in an ounce, which is more than a milliliter, so it should be captureable with good technique, I would think.

<edit> Just found this at the Steep Hill Labs blog: "Myrcene is mostly unchanged by heating."</edit>

Not really interested in distillation in the purest sense of the word since my goal is retention rather than separation, but I am borrowing two of the basic principles of fractional distillation:

1: Heat is used to refract certain elements of the original substance. While refraction, or separation, isn't the point of our endeavor, it's a seemingly unavoidable byproduct of decarbing and something we're going to have to embrace and learn how to counter. So why not look to the distillers for the answer for reclamation?

2: Condensation of the refracted terpenes is done with the introduction of a chillant. And I'm suspicious that this point may be the downfall of our attempt of restitution of terpenes. After decarbing in a sealed container our expectations are restoration at simple ambient temperature. Lab tests earlier in this thread pointed to the fact that terpenes do, in fact, naturally evaporate rather quickly at ambient temperatures. So why do we have expectations of condensation at similar temps that actually cause evaporation? I have no supporting evidence but my suspicion leads me to believe that the majority our precious terpenes are still suspended in air right up to the point we open our naturally cooled sealed container. Perhaps the answer lies in the methodology of the distillers; induce condensation by dropping the temps far below ambient air prior to unsealing the container.

All of this is simple conjecture on my part. I'm convinced we are in the presence of individuals far better prepped intellectually to analyze my suppositions and I'm anxious for their input. Comments welcomed.

 

[Scientific]

Not really interested in distillation in the purest sense of the word since my goal is retention rather than separation, but I am borrowing two of the basic principles of fractional distillation:

1: Heat is used to refract certain elements of the original substance. While refraction, or separation, isn't the point of our endeavor, it's a seemingly unavoidable byproduct of decarbing and something we're going to have to embrace and learn how to counter. So why not look to the distillers for the answer for reclamation?

2: Condensation of the refracted terpenes is done with the introduction of a chillant. And I'm suspicious that this point may be the downfall of our attempt of restitution of terpenes. After decarbing in a sealed container our expectations are restoration at simple ambient temperature. Lab tests earlier in this thread pointed to the fact that terpenes do, in fact, naturally evaporate rather quickly at ambient temperatures. So why do we have expectations of condensation at similar temps that actually cause evaporation? I have no supporting evidence but my suspicion leads me to believe that the majority our precious terpenes are still suspended in air right up to the point we open our naturally cooled sealed container. Perhaps the answer lies in the methodology of the distillers; induce condensation by dropping the temps far below ambient air prior to unsealing the container.

All of this is simple conjecture on my part. I'm convinced we are in the presence of individuals far better prepped intellectually to analyze my suppositions and I'm anxious for their input. Comments welcomed.

I'm with ya, crazyman. When we speak of capturing/retaining terpenes, though, I start to foresee some complicated machinery down the road. (I am reminded of ad on TV for Welch's Grape Jelly in which Fred Flintstone explained Welch's flavor condenser/recirculater apparatus with an animated diagram of the grapey goodness escaping and returning to the cooking pot. )

 

[Kicknitup1]

Scientific, that's exactly why I dismissed the pressure cooker. There is no way that I can think of to get direct pressure on the extraction. That's the only thing that may help. The PC only raises the temp of the water. Yes you can decarb with it with the correct time dialed in but that's not solving the terpene problem. And, any step that includes mixing water with the oil, I'm against. That being said, it's the only way to get the last of the oil out of the mtl. At least then, you are only involving 10-12% of the oil. I ran 32ml of oil in 7g mtl and lost 5ml. About 4 of that is in those dreggs. That's a 15% waste factor (unacceptable to me) if you don't go after it. Any better ideas about getting it out????

 

[Scientific]

any step that includes mixing water with the oil, I'm against. That being said, it's the only way to get the last of the oil out of the mtl. At least then, you are only involving 10-12% of the oil. I ran 32ml of oil in 7g mtl and lost 5ml. About 4 of that is in those dreggs. That's a 15% waste factor (unacceptable to me) if you don't go after it. Any better ideas about getting it out????

I'm curious. So what did your process involve exactly?

 

[Oldbear]

You can add individual or mixed terpenes to anything. They also sell a dilution liquid. Your question is something I want to fond out also - what effect if any of ingesting some terpenes, Being very careful with dilution minimums. There are warnings.

Huge variation if last test gave almost perfect conversion.

Regarding terpenes you could capture them if you decarboxylate your bud in water as long as you capture the steam, problem is to filter the terpenes back.

I don't live in the us so it's harder for me to contribute, but can anyone buy myrcene or another terpene, add 1ml to a glass of water or something (like adding some terpene drops and re curing your bud) and smoke a bowl? Doing so would help us check if it works and maybe the terpene profile idea wouldn't sound so crazy

Ps: check my current grow. This baby will be used for a qwet tutorial.

Greetings

 

[Bucudinkydow]

I'm with ya, crazyman. When we speak of capturing/retaining terpenes, though, I start to foresee some complicated machinery down the road. (I am reminded of ad on TV for Welch's Grape Jelly in which Fred Flintstone explained Welch's flavor condenser/recirculater apparatus with an animated diagram of the grapey goodness escaping and returning to the cooking pot. )

I remember those flintstone ads. We're getting old, Scientific. Sometimes I feel like I share the flintstone mentality with the outcome of some of my projects!

Commercial distillation and reclamation devices are far beyond most of our capabilities, probably financially and intellectually. Fortunately, the two basic premises of my theory are quite simplistic to replicate. I live by the acronym KISS. Decarb in a sealed container, i.e. one of granny's good ol' mason jars. Nothing new here; folks have been using this procedure for a long while to avoid smelling up the kitchen. Do a cold ethanol extraction. Again, nothing unique. Hopefully, where the magic is going to happen is by combining the two. The heat during decarb has theoretically vaporized our terps but we have them trapped irrelevant of their state. Without opening the container, allow it to cool and place it in the freezer. After several hours (I use 24 hrs), we're assured the trapped terpenes are, in fact, condensed. Whether on the interior of the container or settled back on our material is of no consequence. In the early days, I failed miserably in my attempts to do oil infusions so I'm not at all sure what the extraction factor of oil is. It may be equally as efficient as ethanol but I've seen research results of 87% extraction rate of terpenes using ethanol. So, introduction of some good everclear 190 is gonna get those little terp molecules irrelevant of where they're hiding.

Stay tuned, folks. It's in the works now.

 

[Chris Scorpio]

Pressure cooker just seemed like a lot of work

Now the Nova...if yer tests are correct, I'd be interested in getting one of those, not like I do a lot of decarbe, but...I like toys

 

[Scientific]

Decarb super slowly at slightly elevated temperature for better retention of volatiles?

I have read that cannabis will decarboxylate slowly over time at room temperature. (I'll guess that THCA is less stable than THC--that it "wants" to give up the CO2.)

It looks to me like the curve of decarboxylation with time and temperature can be extended out a long way, for example

Maybe 10 minutes at 300 F
Maybe 105 minutes at 220 F
So maybe 1 week at 100F ? (Like sitting on top of the water heater in the closet.)

My question (and hope) is that you might be able to decarboxylate veryslowly and thus retain significantly more volatile components.

It would be easy enough to send samples to the lab to test this, I guess.

Thoughts/comments/corrections/suggestions?

 

[Chris Scorpio]

I've used the 36hr method and worked well

Mason jar,covered, in my oven at 170deg for 36hr

Shake jar every hr 1st 12hr ish, then when ya think about it

Not sure if any of the tests had this method or not

 

[Kicknitup1]

Decarb super slowly at slightly elevated temperature for better retention of volatiles?

I have read that cannabis will decarboxylate slowly over time at room temperature. (I'll guess that THCA is less stable than THC--that it "wants" to give up the CO2.)

It looks to me like the curve of decarboxylation with time and temperature can be extended out a long way, for example

Maybe 10 minutes at 300 F
Maybe 105 minutes at 220 F
So maybe 1 week at 100F ? (Like sitting on top of the water heater in the closet.)

My question (and hope) is that you might be able to decarboxylate veryslowly and thus retain significantly more volatile components.

It would be easy enough to send samples to the lab to test this, I guess.

Thoughts/comments/corrections/suggestions?

I think I've read that long periods in any heat promotes CBN. If not, worth a try.

 

[Kicknitup1]

I'm curious. So what did your process involve exactly?

Decarbed with Nova. I was using coconut oil @165f. Stirring well every 20 min. Then strain. That's the gist of it.