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Enabling fast quality assessment of
cannabis and hemp extracts and
decarboxylated formulated for improved
ROI using four letters: FTIR
Dr. Markus Roggen
Introduction
Complex Biotech Discovery Ventures
CBDV is a research venture that seeks to add fundamental scientific insight
to the field of cannabis and mushroom production.
We seek to support the cannabis and mushroom industries by
establishing a centralized hub in Vancouver, BC, for collaborative
research focused on:
• Process Design
• Process Optimization
• Process Analytics
• Formulation Research
Collaborative Research
CBDV collaborates with academic, industry and private groups around the
globe. Some highlights of those collaborations are:
• University of British Columbia, Vancouver
• Loyalist College, Belleville
• Via Innovations by Dr. Monica Vialpando
• Veridient Science by Dr. Linda Klumpers
Fundamental Collaboration
Research Topics
• Chemometrics and data analytics for process control and optimization
• Kinetic studies to understand mechanisms
• In-process analytics for process control
• Computational studies to understand mechanisms
• Process development, like crystallization
Fundamental Cannabis and Mushroom Chemistry
Research Topics
• Chemometrics and data analytics for process control and optimization
• Kinetic studies to understand mechanisms
• In-process analytics for process control
• Computational studies to understand mechanisms
• Process development, like crystallization
Fundamental Cannabis and Mushroom Chemistry
Extraction
• The goal is to separate the
desired compounds from the
cannabis plant matrix
• Various Solvent Systems
• Alcohol (mainly EtOH)
• Hydrocarbon (mainly Butane)
• Supercritical CO2
SFE Design of Experiment
SFE optimized for single separator
Cannabinoid Concentration
E
C2 C1
C3
Post-Process / Decarboxylation
• The plant produces acid cannabinoids (e.g. THCA, CBDA).
• The market desires neutral cannabinoids (e.g. THC, CBD).
• The conversion is called decarboxylation
When and How to Decarboxylate?
There is a lack of universal agreement regarding reaction conditions.
Before Extraction
Flower Matrix
After Extraction
Oil Matrix
When and How to Decarboxylate?
There is a lack of universal agreement regarding reaction conditions.
• Oven heating
• Hot plate
• Microwave
• Oil bath
• Other?
Considerations for Decarboxylation Process
0
5
10
15
20
25
30
35
0 10 20 30 40 50 60 70 80
THCA
(%)
Elapsed Time (Minutes)
• Decarboxylation reactions vary in time
• Decarboxylation is highly temperature sensitive
• Testing methods take longer than reaction
• Wrong timing costs money Decarboxylation Map
Temperature
Time
Decarb
%
Don’t Decarboxylate to Long
Problems of excess heating:
• Availability of instruments
• Higher costs of production
• Side reaction and degradation
• Lower yields
0
10
20
30
40
50
60
70
80
0
0.5
1
1.5
2
2.5
3
3.5
0 1000 2000 3000 4000 5000 6000
THC
THC
(%)
CBN
&
d8-THC
(%)
d8-THC
CBN
Elapsed Time (Minutes)
In-Process Analytics
Infrared spectroscopy is a useful tool for reaction monitoring.
BG62-64 T0
Name
Sample 023 By Administrator Date Thursday, July 12 2018
Description
1750 800
1600 1400 1200 1000
0.23
-0.01
-0.00
0.02
0.04
0.06
0.08
0.10
0.12
0.14
0.16
0.18
0.20
0.22
cm-1
A
_ Start THCA
20.87 %
End THCA
1.56 %
Why IR for Decarboxylation Monitoring?
• Small amount of sample required
• No sample preparation (in most cases),
no consumables, minimal cleaning solvent
• Fast and easy – Results in seconds
• Simple to operate – Hardware and
software
• Economical
IR spectroscopy allows to monitor the reaction almost in real time
Decarb Control with Agilent Cary FTIR
• We developed IR monitoring methods for both
crude oil and in flower.
• Crude oil: Simple spotting on crystal
• Flower:
• Quick extraction in pentane
• Spot solution on crystal
• Let solvent evaporate
Decarb Control with Agilent Cary FTIR
• IR model for Oil Analytics
X-axis: HPLC concentration
Y-axis: IR prediction
Decarb Ratio
THCA to THC
Decarb Ratio
CBDA to CBD
Decarb Control with Agilent Cary FTIR
• IR model for THCA Flower Analytics
X-axis: HPLC concentration
Y-axis: IR prediction
Decarboxylation Observation
Not all Decarboxylations are equal
0
20
40
60
80
100
0 5 10 15 20 25 30 35 40 45
Decarb
%
Minutes
Decarboxylation at 110˚C
CBDA/CBD
THCA/THC
Decarboxylation Observation
Not all Decarboxylations are equal
Computational Studies
Steric vs. Electronic: Exploring the Rate Difference in THCA and CBDA
Decarboxylation
https://doi.org/10.26434/chemrxiv.12909887.v1
Computational Studies
https://doi.org/10.26434/chemrxiv.12909887.v1
THC CBD
Computational Studies
https://doi.org/10.26434/chemrxiv.12909887.v1
THC CBD
Computational Studies
Key Findings:
• Rate determining step is the
intermolecular protonation
• Rate difference is due to steric rather
than electronic effects
https://doi.org/10.26434/chemrxiv.12909887.v1
Summary on Decarboxylation
• An integral part of cannabis processing
• Decarboxylation either before or after extraction
• Decarboxylation rates vary based on
• Temperature
• Matrix
• Water
• Type of cannabinoid
• Batch
• In-process monitoring is advised
• We demonstrated that IR is the right tool for this
Agilent Cary 630 FTIR Spectrometer
The Agilent Cary 630 FTIR spectrometer is ideal for decarboxylation
monitoring
• Ultra-compact design saves valuable bench space
• Picture-guiding software with color-coded results reduces handling
mistakes and training needs
• Rugged and robust: More uptime and less troubleshooting
Expertise
CEO: Dr. Markus Roggen
Dr. Roggen has been actively involved in the cannabis industry for over 5 years in executive
positions overseeing production, R&D and process optimization for multiple producers. Dr.
Roggen is also a trusted advisor and mentor for multiple startups, startup accelerators and
organizations.
Co-Founder: Prof. Glenn Sammis
Prof. Sammis is an Associate Professor in the Chemistry Department at the University of British
Columbia. He has built an internationally recognized research group working on the
development of novel synthetic methods for the preparation of natural products and
pharmaceuticals.
CBDV Team
Our team covers a wide range of expertise,
including analytical chemistry, process
chemistry, engineering physics, data science
and statistics.
Dr. Markus Roggen markus@cbdvl.com

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Cannabis/Hemp Decarboxylation Monitoring by IR

  • 1. Enabling fast quality assessment of cannabis and hemp extracts and decarboxylated formulated for improved ROI using four letters: FTIR Dr. Markus Roggen
  • 2. Introduction Complex Biotech Discovery Ventures CBDV is a research venture that seeks to add fundamental scientific insight to the field of cannabis and mushroom production. We seek to support the cannabis and mushroom industries by establishing a centralized hub in Vancouver, BC, for collaborative research focused on: • Process Design • Process Optimization • Process Analytics • Formulation Research
  • 3. Collaborative Research CBDV collaborates with academic, industry and private groups around the globe. Some highlights of those collaborations are: • University of British Columbia, Vancouver • Loyalist College, Belleville • Via Innovations by Dr. Monica Vialpando • Veridient Science by Dr. Linda Klumpers Fundamental Collaboration
  • 4. Research Topics • Chemometrics and data analytics for process control and optimization • Kinetic studies to understand mechanisms • In-process analytics for process control • Computational studies to understand mechanisms • Process development, like crystallization Fundamental Cannabis and Mushroom Chemistry
  • 5. Research Topics • Chemometrics and data analytics for process control and optimization • Kinetic studies to understand mechanisms • In-process analytics for process control • Computational studies to understand mechanisms • Process development, like crystallization Fundamental Cannabis and Mushroom Chemistry
  • 6. Extraction • The goal is to separate the desired compounds from the cannabis plant matrix • Various Solvent Systems • Alcohol (mainly EtOH) • Hydrocarbon (mainly Butane) • Supercritical CO2
  • 7. SFE Design of Experiment SFE optimized for single separator Cannabinoid Concentration E C2 C1 C3
  • 8. Post-Process / Decarboxylation • The plant produces acid cannabinoids (e.g. THCA, CBDA). • The market desires neutral cannabinoids (e.g. THC, CBD). • The conversion is called decarboxylation
  • 9. When and How to Decarboxylate? There is a lack of universal agreement regarding reaction conditions. Before Extraction Flower Matrix After Extraction Oil Matrix
  • 10. When and How to Decarboxylate? There is a lack of universal agreement regarding reaction conditions. • Oven heating • Hot plate • Microwave • Oil bath • Other?
  • 11. Considerations for Decarboxylation Process 0 5 10 15 20 25 30 35 0 10 20 30 40 50 60 70 80 THCA (%) Elapsed Time (Minutes) • Decarboxylation reactions vary in time • Decarboxylation is highly temperature sensitive • Testing methods take longer than reaction • Wrong timing costs money Decarboxylation Map Temperature Time Decarb %
  • 12. Don’t Decarboxylate to Long Problems of excess heating: • Availability of instruments • Higher costs of production • Side reaction and degradation • Lower yields 0 10 20 30 40 50 60 70 80 0 0.5 1 1.5 2 2.5 3 3.5 0 1000 2000 3000 4000 5000 6000 THC THC (%) CBN & d8-THC (%) d8-THC CBN Elapsed Time (Minutes)
  • 13. In-Process Analytics Infrared spectroscopy is a useful tool for reaction monitoring. BG62-64 T0 Name Sample 023 By Administrator Date Thursday, July 12 2018 Description 1750 800 1600 1400 1200 1000 0.23 -0.01 -0.00 0.02 0.04 0.06 0.08 0.10 0.12 0.14 0.16 0.18 0.20 0.22 cm-1 A _ Start THCA 20.87 % End THCA 1.56 %
  • 14. Why IR for Decarboxylation Monitoring? • Small amount of sample required • No sample preparation (in most cases), no consumables, minimal cleaning solvent • Fast and easy – Results in seconds • Simple to operate – Hardware and software • Economical IR spectroscopy allows to monitor the reaction almost in real time
  • 15. Decarb Control with Agilent Cary FTIR • We developed IR monitoring methods for both crude oil and in flower. • Crude oil: Simple spotting on crystal • Flower: • Quick extraction in pentane • Spot solution on crystal • Let solvent evaporate
  • 16. Decarb Control with Agilent Cary FTIR • IR model for Oil Analytics X-axis: HPLC concentration Y-axis: IR prediction Decarb Ratio THCA to THC Decarb Ratio CBDA to CBD
  • 17. Decarb Control with Agilent Cary FTIR • IR model for THCA Flower Analytics X-axis: HPLC concentration Y-axis: IR prediction
  • 18. Decarboxylation Observation Not all Decarboxylations are equal 0 20 40 60 80 100 0 5 10 15 20 25 30 35 40 45 Decarb % Minutes Decarboxylation at 110˚C CBDA/CBD THCA/THC
  • 19. Decarboxylation Observation Not all Decarboxylations are equal
  • 20. Computational Studies Steric vs. Electronic: Exploring the Rate Difference in THCA and CBDA Decarboxylation https://doi.org/10.26434/chemrxiv.12909887.v1
  • 23. Computational Studies Key Findings: • Rate determining step is the intermolecular protonation • Rate difference is due to steric rather than electronic effects https://doi.org/10.26434/chemrxiv.12909887.v1
  • 24. Summary on Decarboxylation • An integral part of cannabis processing • Decarboxylation either before or after extraction • Decarboxylation rates vary based on • Temperature • Matrix • Water • Type of cannabinoid • Batch • In-process monitoring is advised • We demonstrated that IR is the right tool for this
  • 25. Agilent Cary 630 FTIR Spectrometer The Agilent Cary 630 FTIR spectrometer is ideal for decarboxylation monitoring • Ultra-compact design saves valuable bench space • Picture-guiding software with color-coded results reduces handling mistakes and training needs • Rugged and robust: More uptime and less troubleshooting
  • 26. Expertise CEO: Dr. Markus Roggen Dr. Roggen has been actively involved in the cannabis industry for over 5 years in executive positions overseeing production, R&D and process optimization for multiple producers. Dr. Roggen is also a trusted advisor and mentor for multiple startups, startup accelerators and organizations. Co-Founder: Prof. Glenn Sammis Prof. Sammis is an Associate Professor in the Chemistry Department at the University of British Columbia. He has built an internationally recognized research group working on the development of novel synthetic methods for the preparation of natural products and pharmaceuticals. CBDV Team Our team covers a wide range of expertise, including analytical chemistry, process chemistry, engineering physics, data science and statistics.
  • 27. Dr. Markus Roggen markus@cbdvl.com