Cannabis/Hemp Decarboxylation Monitoring by IR

Our research into the development

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 CO 2

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 Decarboxylation reactions vary in time Decarboxylation is highly temperature sensitive Testing methods take longer than reaction Wrong timing costs money

12. Don’t Decarboxylate to Long Problems of excess heating: Availability of instruments Higher costs of production Side reaction and degradation Lower yields

13. In-Process Analytics Infrared spectroscopy is a useful tool for reaction monitoring. _ 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 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

21. Computational Studies https:// doi.org /10.26434/chemrxiv.12909887.v1 THC CBD

22. Computational Studies https:// doi.org /10.26434/chemrxiv.12909887.v1 THC CBD

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 [email protected]