Sweet Mary's Charms

Check out the 30 most common volatile organic compounds in cannabis and their physical properties at Sweet Mary's Charms:

https://thealchemistresource.thealchemistresource.com/p/v-behaviorurldefaultvmlo_30.html

To open, cut and paste, but remove the s in https.

Great stuff as always! I printed this one and will keep it as a study reference!

"Due to marijuana proscription in the 1930's, little legal research has been possible in the US and many other locations, so until fairly recently the generally accepted explanation was that it was the medicinal effects of the THC that we were experiencing when consuming cannabis products. However, with closer examination, it became apparent that each individual terpene, terpenoid, and flavonoid in the mixture contributes its medicinal effect, so that the overall effect is an entourage of the constituent effects. The whole become at least the sum of it's parts, if not greater."

"I say mostly, because there is also the issue of essential oil safety. The beloved terpenes that we seek and covet do indeed have their own medicinal and chemical properties, some of which are used to sanitize toilet bowls, strip paint, and remove metal oxides, and can come from a variety of sources, some insalubrious, sooooo as we enter this realm, it pays to pay attention."

A few general chemistry questions, as it relates to terpenes:

You noted the importance of small amounts of esters. Are these compounds always clear? Do they separate in chilled h20 or stay miscible?

What class of terpenes or organics would have a chalky/milk white color? Every time that I do a vacuum oven terpene extraction, my hydrosol has a very light white color. When I transfer to a separatory funnel and place in a 2C fridge for ~12 hours, the white layer will float to the top of the h20 (just below the terpene layer) but still be water soluble and slightly miscible. If you bump the funnel or as it slowly drains, this layer will slightly mix with water, so I have always just discarded it - Well actually, I drink the hydrosol, and sometimes think it gives me superpowers (haha, not really but I do feel pretty good in an unscientific way...)

Thanks!

Do you think Camphor could have the physical (separating) properties that I described above? If so, it sounds like I maybe need to just discard my hydrosol?

From your link above:

16.0 Camphor aka 1.7.7-trimethylbiclo(2.2.1)heptan-2-one

Camphor is a natural occurring terpene found in a many aromatic plants including Camphor Laurel wood oil an origin of natural camphor gum or natural camphor crystals. Natural camphor it used in fragrances, flavors and OTC pharmaceutical preparations. Camphor is available in a natural and a synthetic material.
Camphor is a very impactful aromatic chemical compound. It is classified as a corrosive compound and is difficult to import and ship and must be labeled accordingly. This material should be used cautiously.

Even though it is found in many aromatic plants including Lavandin oils and other lavender Vera essential oils as well as being a main constituent in certain varieties of food grade essential oils like Rosemary and Marjoram it should be used cautiously and sparingly in flavors and fragrances. RIFM and FEMA guidelines should be consulted on acceptable levels for finished goods

Camphor has been used for centuries, with various uses. It’s used for fireworks and other explosives and munitions, as a deterrent for pests, is often used as a disinfectant, insecticide and germicide. In the culinary world, is used as a flavor component for savory and camphoraceous applications.

Traditional use of camphor suggests that it has both stimulant and a sedative property. Most consumers can recognize camphor in a variety of products including mouth wash and over the counter anti-inflammatory, anti-arthritic, and anti-spasmodic sports and pain topical preparations.

16.1 Physical Properties

Chemical formula - C10 H16 O
CAS - 76-22-2
Molar mass - 152.23672000
Appearance - White to pale yellow crystalline solid
Density - 0.992 g·cm−3
Melting Point - 176.00 to 177.00 °C. @ 760.00 mm Hg
Boiling point - 204.00 to 205.00 °C. @ 760.00 mm Hg
Flash point - 148.00 °F. TCC ( 64.44 °C. )
Vapor pressure - 0.65 mm/hg @ 25C
Solubility in water - 1600 mg/L @ 25 °C
Odor - Camphoraceous

16.2 Toxicology

MSDS - https://www.sciencelab.com/msds.php?msdsId=9923284
https://pubchem.ncbi.nlm.nih.gov/compound/camphor
PEL - NA
TLV - NA
LD-50 Oral (LD50): 1310 mg/kg [Mouse]

Human Toxicology Values

Not a known carcinogen
Not a known mutagen
Not a know teratogen.
Special Remarks on Chronic Effects on Humans: May affect genetic material based on animal data. Passes through the placental barrier in human.

Special Remarks on other Toxic Effects on Humans:

Acute Potential Health Effects: Skin: Causes skin irritation. May cause epileptic seizures. Eye: Causes eye irritation.

May cause epileptic seizures. Inhalation: Causes irritation of the respiratory tract (mucous membranes)and may cause
emphysema.

May affect behavior - the brain and Central Nervous system (muscle contraction and spasticity).

May affect the heart. Ingestion: Cause irritation of the gastrointestional tract (nausea, vomiting.

May affect behavior - the brain and Central Nervous system (dizziness, convulsions, seizures, change of motor activity, rigidity). May be harmful if swallowed.

Certain medical conditions may be aggravated by exposure: kidney disorders, liver disorders, heart disorders, epilepsy. Chronic Potential Health Effects: none identified.
Non-Human Toxicology Values

(LD50): 1310 mg/kg [Mouse]

Or perhaps this one? Both are listed as crystal structure? Would crystal float to the top in chilled water but stay below an oil layer? If I wanted to isolate the crystals, could I separate with a small amount of water and simply evaporate the liquid with low heat? Can you evaporate crystals or alter the compounds at lower temps (<60C)? Is this what flash point means?

21.0 Borneol aka Borneol; Isoborneol; 1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol; 507- 70-0; (+)-Borneol; (-)-Borneol

Borneol is an easily oxidized organic compound and terpene. It is found naturally in high-concentrations in plants such as camphor, rosemary, and some mint varieties.

Organoleptically it is herbal and camphoraceous. Borneol has a minty pine like taste but is cooling and
Fresh in the right proportions.

Essential oils containing Borneol have been used for centuries in traditional Chinese medicine as a moxa for acupuncture.

Traditionally borneol has been used as an analgesic (pain reliever), anti-fungal, antioxidant, antibacterial, and has been used traditionally for anti-fibrosis suggesting that it may help to regulate the body’s response to injuries. Additionally, it has been an ingredient selected to be formulated into certain natural insect repellants including flea and mosquito remedies.

21.1 Physical Properties

Chemical formula - C10H18 O
CAS - 507-70-0
Molar mass - 154.253 g/mol
Appearance - White to off white crystals
Density - 1.011 g/cm3 (20 °C)
Melting Point - 202 deg C
Boiling point - 212 deg C
Flash point - 150 deg F (60 deg C) /closed cup/
Vapor pressure - 0.035 mm/hg @ 25C
Solubility in water - 738 mg/L at 25 deg C
Odor - Piney, camphor-like odor

21.2 Toxicology

MSDS - https://www.fishersci.ca/store/msds...8-acros-organics-4&language=en&countryCode=CA
.gov - https://pubchem.ncbi.nlm.nih.gov/compound/Borneol
PEL - NA
TLV - NA
LD-50 Oral - LD50 = 5800 mg/kg ( Rat

Human Toxicology Values

Not a known carcinogen
Not a known mutagen
Not a known teratogen
Not a known reproductive toxin
Non-Human Toxicology Values

LD50 = 5800 mg/kg ( Rat

I suspect that the white is a water soluble as opposed to an aromatic compound.

Any thoughts on the classification of water soluble? Something volatile enough to evaporate without a solvent?

Here is my best attempt yet to isolate it. Terpenes on top and white water soluble matter below. This was separated for ~16 hours at 2C. Is a picture worth 1000 words...

WaterFarmFan said:

Any thoughts on the classification of water soluble? Something volatile enough to evaporate without a solvent?

Click to expand...

There are non volatile water soluble salts present, as well as the C-15 flavanoids which are water soluble and volatile.

Gray Wolf said:

There are non volatile water soluble salts present, as well as the C-15 flavanoids which are water soluble and volatile.

Click to expand...

If you would not mind enlightening me, how would non volatile salts go from ground flower material in vacuum oven to the condensing cold trap system?

WaterFarmFan said:

If you would not mind enlightening me, how would non volatile salts go from ground flower material in vacuum oven to the condensing cold trap system?

Click to expand...

Perhaps you could further enlighten me first, by describing the process producing it.

Hehe, sorry. Here is a slightly outdated overview. I added a second Graham condenser with takeoff and receiving flask in parallel, and also added the pid controlled heated nitrogen backfill.



My basic process for terpene extraction is:

1. Using cryogenic gloves and wide mouth dewar, freeze fresh flowers in liquid nitrogen with canisters for 5-10 minutes.
2. Pulverize flowers with stainless pestle (and cryo glove) in a 2 piece stainless honey sieve over 9" stainless bowl.
3. Separate trichomes (with a small amount of flower material that falls through 600 micron sieve screen) in collection bowl from the stems (top sieve) and flower material (bottom seive) in a different bowl.
4. Pour additional LN2 in trichome bowl and place bowl into vacuum oven with vacuum pump running and vacuum needle valve open. Stainless bowl sits on a ~15 pound 1.5" thick (6"x9") block of PTFE in vacuum oven. I don't latch oven door until 7cfm pump seals vacuum in oven due to ln2 evaporating to n2 at 700 times its liquid volume. The PTFE block has amazing heat absorption properties and will keep the stainless bowl cool long after the oven temperatures start to rise.
5. For first 2 hours, perform low temp sublimation at full vacuum.
6. Next 1 hour, backfill with N2 to ~2 inHg and raise temps in the oven to 170F (to evaporate terpenes that have condensed in oven on cold places like the stainless bowl and PTFE block from #5), and after reaching temp, do a very slow collection increasing ~1 inHg per 2-3 seconds until full vacuum.
7. Next 4-5 hours, I raise my vacuum oven temps to 217F and every 15-20 minutes perform various N2 backfills, slow collections and also use a slow bleed of N2 with vacuum valve open. After a full collection (from ~2 inHg to max vacuum), I will take the bowl out and place on slab of dry ice to cool the material, and I do this a max of 2-3 times for this 4-5 hour part of the cycle. I will also place a chunk of dry ice on the PTFE slab, where the bowl sits, to provide residual cooling once process is restarted.
8. Carefully combine terpene and hydrosol mixtures from various collection points and add to separatory funnel and place into 2C fridge.
9. Rinse all glassware with warm distilled water, collect and separate as above.
10. Reassemble condensers and cold traps and repeat process for flower material. I have had better results processing the trichomes and flower material separately, think of it like trying to purge two slabs with different solvents at the same time.

I am still experimenting and finalizing an exact collection schedule and procedure. Will be creating a thread and sharing my findings soon.

WFF

The process above yields terpenes that smell almost identical to the original flowers being processed, and most importantly yield an effect similar to mama. Chem family terpenes are simply to die for!!!

I have only been doing smaller tests of a few ounces at time, but during one, I raised my oven temps to the 240-250 range with flower material for too long at a static vacuum and got the dreaded "bath water" or "gym suana" terps, which I believe now to be caused by excessive high temp h20 steam, but I also mistakenly left my fresh air valve open with N2 closed, and allowed some oxygen to backfill, so it could be high temps plus steam and O2. After I removed the material, it seemed to alter profile of the flower material in the oven, as if being drenched in water. Some sacrifices must occasionally be offered to the canna gods for progress to be made...

It is a pain in the ass to do a dismantling, full collection, subsequent rinse and reassembly, but I want to stop my process at step 5 and see how effective the sublimation is, and whether or not it is worth the time to perform this step.

I will say that I witnessed a pretty cool thing on my most recent run. The Grahams are on ~25 degree angle and this causes fluids to build up on the coiled condenser and gurgle before eventually moving down the line. I think this is a very good thing because it causes more residence time to pre-cool the air/molecules in the condenser prior to cold traps facilitating condensation.

The cool thing was that I could see water condensing at the top end and fine drops of terpenes condensing at the bottom end, as the terpenes behave different, and kinda like Spiderman cling to everything, until enough come together and decide to move along down the system to the flasks. I gauge the entire flow of the system based on action in Grahams in fact, as water condenses at the very edge of the glass coming from the hot oven, so no water forming equals time to shut off vacuum valve, backfill with N2 and allow more water, terpenes and volatile substances to evaporate from material. Dry ice (with ethanol for traps) everywhere helps me to keep what I catch.

WaterFarmFan said:

Hehe, sorry. Here is a slightly outdated overview. I added a second Graham condenser with takeoff and receiving flask in parallel, and also added the pid controlled heated nitrogen backfill.

View Image

My basic process for terpene extraction is:

1. Using cryogenic gloves and wide mouth dewar, freeze fresh flowers in liquid nitrogen with canisters for 5-10 minutes.
2. Pulverize flowers with stainless pestle (and cryo glove) in a 2 piece stainless honey sieve over 9" stainless bowl.
3. Separate trichomes (with a small amount of flower material that falls through 600 micron sieve screen) in collection bowl from the stems (top sieve) and flower material (bottom seive) in a different bowl.
4. Pour additional LN2 in trichome bowl and place bowl into vacuum oven with vacuum pump running and vacuum needle valve open. Stainless bowl sits on a ~15 pound 1.5" thick (6"x9") block of PTFE in vacuum oven. I don't latch oven door until 7cfm pump seals vacuum in oven due to ln2 evaporating to n2 at 700 times its liquid volume. The PTFE block has amazing heat absorption properties and will keep the stainless bowl cool long after the oven temperatures start to rise.
5. For first 2 hours, perform low temp sublimation at full vacuum.
6. Next 1 hour, backfill with N2 to ~2 inHg and raise temps in the oven to 170F (to evaporate terpenes that have condensed in oven on cold places like the stainless bowl and PTFE block from #5), and after reaching temp, do a very slow collection increasing ~1 inHg per 2-3 seconds until full vacuum.
7. Next 4-5 hours, I raise my vacuum oven temps to 217F and every 15-20 minutes perform various N2 backfills, slow collections and also use a slow bleed of N2 with vacuum valve open. After a full collection (from ~2 inHg to max vacuum), I will take the bowl out and place on slab of dry ice to cool the material, and I do this a max of 2-3 times for this 4-5 hour part of the cycle. I will also place a chunk of dry ice on the PTFE slab, where the bowl sits, to provide residual cooling once process is restarted.
8. Carefully combine terpene and hydrosol mixtures from various collection points and add to separatory funnel and place into 2C fridge.
9. Rinse all glassware with warm distilled water, collect and separate as above.
10. Reassemble condensers and cold traps and repeat process for flower material. I have had better results processing the trichomes and flower material separately, think of it like trying to purge two slabs with different solvents at the same time.

I am still experimenting and finalizing an exact collection schedule and procedure. Will be creating a thread and sharing my findings soon.

WFF

Click to expand...

Thanks, I missunderstood and didn't realize we were talking about an oven.

In that case, I suspect it is a combination of water and one or more of the volatiles.

IE: Water, ethanol, and terpenes produce a white residue that goes away with evaporation.

Gray Wolf said:

Thanks, I missunderstood and didn't realize we were talking about an oven.

In that case, I suspect it is a combination of water and one or more of the volatiles.

Click to expand...

From my latest observation, the pure white was predominantly captured in the back dry ice/ethanol baths, indicating a more volatile substance that is harder to condense?

I am still confused on the terpenes listed with crystal structure. How would a crystal be volatilized? After being volatilized, does it easily go back to crystal structure via condensation?

Gray Wolf said:

IE: Water, ethanol, and terpenes produce a white residue that goes away with evaporation.

Click to expand...

Do cold or very cold temperatures have an effect on this reaction?

WaterFarmFan said:

From my latest observation, the pure white was predominantly captured in the back dry ice/ethanol baths, indicating a more volatile substance that is harder to condense?

I am still confused on the terpenes listed with crystal structure. How would a crystal be volatilized? After being volatilized, does it easily go back to crystal structure via condensation?



Do cold or very cold temperatures have an effect on this reaction?

Click to expand...

Volatility depends on temperature and vapor pressure. For instance, cannabinoids are volatile organic compounds and can be in crystaline form.

Temperature would ostensibly affect the formation of emulsion layers.

I think that I just had a serious "Aha moment". So, I am checking trichomes for ripeness with 60x pocket microscope on some finishing plants, and it hit me. The cloudy matter inside trichomes exactly resembled the cloudy nature of my hydrosol. Thus, it seems logical to infer that the white compounds that I am seeing are organics from inside trichome, and the ripening (from clear to cloudy to amber) is a chemical process that largely involves terpenes and organics in combination with the changing state of the cannabinoids. Also, given the extremely volatile nature of these white compounds, unless you are using a highly efficient cold trap system with no solvents (like me), then you would not be able to see (volatiles don't condense in traps) or isolate (volatiles evaporate with solvent purge) these compounds.

It is understatement to say that only "clean" flowers of the highest quality should be used in the process that I described above. ANY pesticides, mold, mildew or other nasties will certainly volatilize in this process and be caught in the condensers and traps. Since only separation techniques are used with no solvents, these will likely contaminate the collected terpenes and have very bad effects when vaped. In short, unless you know for certain how the flowers were grown, it would be highly unethical to do this extraction tech for resell, unless of course if entire terpene batch was sampled and subjected to thorough lab analysis.

The original impetus of my efforts centered on taking world class flowers and creating a world class extract that mirrored the effect profile of the mothers. I am currently extracting terpenes, doing a -50C ethanol extraction, purge to shatter and add back terpenes for vape carts. Blind tests, which are ongoing, have noted a huge difference in effect when cannabis terpenes are added. .1ml per gram (.9 ml) of shatter is some of the most potent vape imaginable with the right strains. I have tested some Chem D hybrids that have been devastating.