Controlling Terpenes and Cannabinoids in Flower & Extract
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This talk encompasses all of our recent work from 2016-2017. Methods for optimizing & preserving terpene and cannabinoid composition is a primary focus covering all aspects from cultivation, harvest, extraction, to packaging of finished products.
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Controlling Terpenes and Cannabinoids in Flower & Extract
- 1. www.outco.com Blake Grauerholz Extraction Manager OutCo, San Diego 1 Controlling Terpenes and Cannabinoids in Flower and Extract
- 2. www.outco.com Cultivators should: 1. Take great care in the handling of plants post harvest 2. Rely on instrumentation to monitor progress Extracts should: 1. Represent the starting material 2. Deliver customized concentrate 2 Fallacies and Ignorance of Cultivation and Extraction
- 3. www.outco.com Cultivation • Optimized environment • Pest management • Clean room practices • Preventative measures • Culling of hazardous plants 3 Where to begin?
- 4. www.outco.com Harvest Practices: • Flush • Drought • Light Deprivation • PPE • Handling of Plants 4 Harvest and Transfer to Dry
- 5. www.outco.com • Arrangement of plants • Removal of leaves • Even air circulation • Sterility • Consistent RH & Temperature • Water Activity <0.65Aw 5 Drying Cannabis 101
- 6. www.outco.com • Constant sterilization of shears. • Delicate handling • Segregation of shelf product and extract material Trimming and Manicuring
- 7. www.outco.com So many molecules we should keep track of 7 What is an Extract? >140 Cannabinoids >200 Terpenes ~30 Flavonoids Alcohols, Phenols Aldehydes, Ketones Alkaloids Carbohydrates, Fatty Acids Lactones
- 8. www.outco.com Extraction: Removal of a substance from a matrix. Needs a solvent, e.g. butane, CO2, ethanol. Separation: Mechanical force, not chemical properties, dictates success, e.g. Rosin, Ice Water Hash, Kief 8 What is an Extract?
- 9. www.outco.com 9 What is an Extract?
- 10. www.outco.com 10 What is an Extract?
- 11. www.outco.com For what: • Yield per Run YpR • Yield per Week YpW • Cannabinoid Conc. CC • Terpene Content TC • Recovery Rec 11 Optimizing your Extraction (SFE) With what: • Temperature T • Pressure P • Time t • Flow Rate FR • Particle Size PS
- 12. www.outco.com For what: • Yield per Run YpR • Yield per Week YpW • Cannabinoid Conc. CC • Terpene Content TC • Recovery Rec 12 Optimizing your Extraction Process With what: • Temperature T • Pressure P • Time t • Flow Rate FR • Particle Size PS
- 13. www.outco.com For what: • Recovery Rec Optimizing your Extraction Process With what: • Time t 0 100 200 300 400 0 5 10 15 20 25 30 35 40 YieldTHC(g) Time (t) Optimizing Run TimeExperiment t (h) Rec (g) 1 4 53.0 2 8 103 3 18 263 4 34 367 Raw n/a 500 Mass Transfer Diffusion
- 14. www.outco.com For what: • Yield per Run YpR • Yield per Week YpW • Cannabinoid Conc. CC • Terpene Content TC • Recovery Rec 14 Optimizing your Extraction Process With what: • Temperature T • Pressure P • Time t • Flow Rate FR • Particle Size PS
- 15. www.outco.com Does milling destroy THC? Optimizing your Extraction Process 0% 1% 2% %decarb by Size 0 0.2 0.4 0.6 0.8 1 1.2 1.4 %wt. Terpenes by Size
- 16. www.outco.com But it does give you higher yields! Optimizing your Extraction Process 20 22 24 26 28 30 32 34 Non-Ground Food Blender 2 mm 6 mm 10 mm %Recovery Cannabinoid Recovery by Size 75 80 85 90 95 Non-Ground Food Blender 2 mm 6 mm 10 mm %Recovery Terpene Recovery by Size
- 17. www.outco.com 17 Design of Experiment to the Rescue • Test multiple factors simultaneously • Few test for whole space response surface • Higher order effects of factors • Fast and efficient
- 18. www.outco.com Expt. No. Temp. (˚C) Pres. (psi) A 34 1100 B 34 1900 C1 47 1500 C2 47 1500 D 60 1100 E 60 1900 Factor No. Factor Super - Super + Unit 1 Temperature 34 60 ˚C 2 Pressure 1100 1900 psi Temperature (˚C) Pressure (psi) Yield THC (g) 34 60 1100 1900 47 1500 0 Executing the DoE Critical Point: 304.25 K & 72.9 atm Factor No. Factor Super - Super + Sub - Sub + Unit 1 Temperature 34 60 5.0 29 ˚C 2 Pressure 1100 1900 900.0 1900 psi Expt. No. Temp. (˚C) Pres. (psi) F 5.0 900.0 G 5.0 1900 H1 17 1400 H2 17 1400 I 29 900.0 J 29 1900
- 19. www.outco.com A Taylor expansion describes the response surface. Matrix algebra solves the Taylor expansion Y=bX b=(X’X)-1X’Y a=bX 19 Calculating the Response Surface y0+ ixi+ iixi 2+ ijxixj i i i j
- 20. www.outco.com a= 14.9 xT + 123 xp + 18.4 xTxp 20 Analyzing the DoE, THC Recovery (Super)
- 21. www.outco.com 21 Analyzing the DoE, THC Recovery (Sub) a= - 7.75 xT + 126 xp + 59.3 xTxp
- 22. www.outco.com a= - 14.9 xT - 11.7 xp + 16.8 xTxp 22 Analyzing the DoE, %Terpene (Super)
- 23. www.outco.com 23 Analyzing the DoE, %Terpene (Sub) a= 11.8 xT - 16.6 xp - 12.5 xTxp
- 24. www.outco.com 24 Visual Guide to Extracts
- 25. www.outco.com SFE, 900.0 – 1900 psi, 5.0 – 60 ˚C, 22h max 25 Compare Sub- and Supercritical Response Sub Super THC Recovery 60% 80% Terpene Fraction 52% at 34% yield 63% at 82% yield
- 26. www.outco.com • THC extracts faster than THCA • THC to THCA ratio adjusted by SFE 26 Lessons learned in SFE % Decarboxylation S.M. 7h 22h Exp. B 8.0% 25% 10% Exp. J 14% 25% 14%
- 27. www.outco.com • CBD extracts faster than THC • CBD to THC ratio adjusted by SFE 27 Lessons learned in SFE CBD/THC S.M. 7h 22h Exp. A 4.1E-03 1.3E-02 5.0E-03 Exp. J 1.7E-04 1.3E-03 3.1E-03 Bonus: Decarboxylation of CBDA slower than for THCA J. of Supercritical Fluids, 2010, 603
- 28. www.outco.com • Enrichment in minor cannabinoids • CBG enrichment by SFE 28 Lessons learned in SFE CBG/total Canna. S.M. 7h 22h Exp. B 2.9% 6.% 2.9% Exp. J 3.0% 13% 4.9% J. of Supercritical Fluids, 2010, 603
- 29. www.outco.com Changing terpene profiles in SFE • Sativa: rich in monoterpenes • Indica: rich in sesquiterpenes 29 Lessons learned in SFE Hazekamp, et al.; Cannabis and Cannabinoid Research 2016, 202 7h 22h
- 30. www.outco.com Rosin Press • Optimized for yield and quality by DoE • ~72% recovery achieved • Little effect on molecular makeup 30 Other Separation Methods
- 31. www.outco.com 31 Other Separation Methods Rosin Yield Rosin Quality
- 32. www.outco.com 32 Separation affects Extract Makeup Ice Water Hash • ~80% cannabinoid potency • ~12% recovery achieved • Little effect on molecular makeup 150 micron 25 micron
- 33. www.outco.com Apeks Supercritical • Andy Joseph, President • Jeremy Sexton, Director of Engineering Fritsch • Barry Schubmehl, Application Consultant • Leos Benes, Global Lab. Serv. Manager 33 Thanks
- 34. www.outco.com 34 The Crew Dr. Markus Roggen Taylor Trah Matt Zbiec and team Thank You Social Media: @OutCo_Extracted @OutCo_CA @ColdWaterExtractions Contact: BGrauerholz@outco.com
Editor's Notes
- I am going to dive into some familiar practices in greater detail, and highlight how we are able to offer therapeutic and craft concentrates to our patients.
- The industry is full of ego and less than scientific approaches to growing and processing this plant. That is not to say that certain ideologies and practices don’t yield good results, but what is actually happening and how can we better control it? Proper and minimal handling of plants is going to prevent degradation and loss of cannabinoids. ”Old school” methods like waiting until the stem snaps, is no longer an acceptable method in determining the appropriate time to take the next step in post processing! While RH and climate within the drying room and storage vessels should be monitored, the use of scientific instrumentation should be implemented as a means of accurately determining what is occurring within the harvested material. As an extractor, it is your job to best represent the growers hard work in the finished concentrate. We don’t add any botanically derived terpenes to our products, nor do we distill our CO2 oil (160+ known cannabinoids!). The latest extraction methods being used today allow for the targeting of certain compounds, as so, being able to operate your equipment to offer extracts rich in those is important.
- Your extract is only as great as the starting material. Therefor a good cannabis oil begins in the garden. Optimized cultivation is important not only to produce a high yielding plant, but also to provide plants that are free of pests (and pesticide), allowing the plant to focus its energy on producing essential oils and cannabinoids. Sterile Environmental practices, and treatment of incoming air, water, and the use of personnel (PPE) in the garden will help mitigate issues in the start of the pipeline. If you follow social media, there is outrage surrounding a number of popular concentrate manufacturers (some with celebrity endorsement) failing their pesticide lab testing. Pesticides are of particular concern here as the extraction process concentrates pesticide in the extract. Taking care in maintaining a clean work space, protecting your employees, and having happy healthy plants will minimize the risk of outside contamination and stress prone crops. Plants unfit for extraction and consumption should be disposed of.
- The focus on high yielding, terpene rich plants continues into pre and post harvest rituals. In particular, plants destined to go to market as whole bud/smokable flower need pay special attention to post harvest handling. Leading up to harvest, typically in the final two weeks, plants undergo plain water feedings, sometimes with added sugars, to encourage the plants to utilize any stored nutrients within the rhizosphere/planting medium. This serves mainly to improve the smoking characteristics of the cured bud making for a smoother smoke which will also help to better showcase the terpene profile (harshness stems from multiple things). Prior to harvest watering is reduced or halted altogether which will lower the water activity in the plant reducing the likelihood of microbial activity in the drying process. Plants can also be left in a 48+/- hour night cycle which is said to encourage ripeness of the trichomes and also prevents the plant from taking up more water and nutrients before chop. During harvest, the plants experience a lot of contact with people and surfaces when transferred into a new environment, the drying room. Both the people and the drying room are potential sources of contamination, therefore sterile procedures in the work flow are paramount. Workers to wear PPE, sterilize shears and tools, avoid contact with doorways/floor!
- Once in the drying room, plants are de-foliated of large fan leaves, and laid out in a fashion that accommodates the plants so they do not touch. This in turn will allow for enough air flow between vegetation to provide a consistent drying throughout the room, and no bacterial growth. We recommend a food safety or HACCP (Hazard Analysis and Critical Control) approach to this particular aspect of the supply chain optimization. All air entering the room is filtered through UV “Death Wand” lighting and HEPA Filtration systems. Once sterile, moving forward, any staff working within the room must utilize clean room practices wearing coveralls (or a uniform worn strictly in this room only), and booties over shoes which are to be changed when entering/exiting the drying room. Climate control of the drying process is everything. Temperature and humidity are to be kept between 65-74F and 30-55% humidity with the latter being employed in the first 3 days to pull adequate moisture from the room quickly. For flower to be used as a direct sale item, water activity is the most important metric. To monitor this, water activity samples are taken from designated plants daily. The desired activity is <0.65Aw by 5-7 days. BUT care must be taken to not over dry the harvest (resulting in terpene loss and a harsh smoking bud) while also preventing mold growth.
- When the flowers are removed from stem and amassed in their respective storage vessels, the handling of dried resin should not be taken lightly, but handled lightly! Trichome heads will rupture and/or fall off the plant if handled roughly. Glands will dry out when coming into contact with any surface including the buckets we dry and cure in, so buds should be handled and transferred as little as possible. Buds should be held by the stem if possible, again any contact with skin/oil/surfaces will degrade the resin quality. This step can be of the upmost importance in mechanical type extraction methods where efficiencies are already low as is. The finished product enters their long-term storage/cure container. Terpene compatible food grade plastic containers.
- THC and CBD aren’t the only things that matter. A lot of CO2 extractors are running their material until it is completely spent and extracted which yields a unsightly crude oil full of undesirables (i.e. Chloryphyll, lipids, waxes etc). A current industry obsession is the distillation of cannabis oil to a pale clear yellow THC rich oil. From a different perspective, leaving cannabis extracts unrefined, will provide an oil richer in minor cannabinoids and other biomolecules that might be of medical or recreational purpose. The latest craze about ‘clarity counts’ seemingly goes counter to the national trend away from processed goods.
- As Andy just discussed – Solvent, or Mechanical
- What is the end product you are trying to achieve? Texture and viscosity are very important, NEXT SLIDE
- How you get to a desired yield, flavor, decarb, texture or viscosity can be optimized by studying the effect variables within the process have on the extract constituents.
- What are you optimizing for? You can control the variables at your disposal (refer to slide). For this talk most focus is on SFE. Can be applied to various methods such as rosin
- Having control over the highest recovery of cannabinoids is what a lot of extractors pride themselves on. Lets take a look at just this one factor – recovery vs. time or the length of the extraction process
- Same material and conditions used Start to pull other extract constituents namely chlorophyll.
- Quickly: Aside from the added benefit of increasing the amt of material you can fit into your vessel, does milling/grinding your starting material have other benefits?
- 2kg plant matter, 6 hours run time. Minor effect at varying mm. Little effect of higher rpm
- Single factor DoE is great and produces useable data, but what if we want to test multiple variables simultaneously.
- By knowing the limitations of our machine, we are able to explore the range of pressures and temperatures to dial it in. Certain factors kept constant like time and input weight of a homogenized strain mixture. We already know what particle size is desirable from our one factor design.
- We lab test all materials (pre, post ext, etc) and extracted oils and gather data based on recovery
- Dr. Roggen uses mathematica to illustrate these response surfaces
- Lower temperatures and pressures in SUPERCRITICAL range produce best results
- While our highest pressure and temperature in the Subcritcal phase yielded the best results, although with a much smaller amout recovered
- We do the majority of our extractions supercritically while utilizing Sub for THCA specific extractions.
- B- Supercritical J-Subcritcal
- Monoterpenes (mainly myrcene, alpha-pinene, beta-pinene, limonene, linalool and terpinolene) are always present in higher amounts than sesquiterpenes (mainly caryophyllene, caryophyllene oxide and humulene), because myrcene, a monoterpene, is present in such large quantities in all cannabis. The level of monoterpenes goes down quicker than that of sesquiterpenes during the drying and curing process largely due to the fact that monoterpenes evaporate more readily. So we wait until the day of an extraction to mill and process sensitive strains where we want to preserve the terpene profile of the plant.
- Using DoE for Rosin Pressure Temperature Time Actuation
- DoE used for recovery, and consumer rating/subjective quality
- Any questions unanswered today, please feel free to email me @outco.com