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www.outco.com
Dr. Markus Roggen
VP Extraction
OutCo, San Diego
1
The Science and Economics of CO2
Extraction and Oil Manufacturing
www.outco.com
Extracts should:
1. Represent the starting material
2. Deliver customized concentrate
2
Fallacies and Ignorance of Extraction
www.outco.com
• Background on Extraction
• Univariant Optimization
• Multivariant Optimization, DoE
• Supercritical vs. Subcritical
• Other Concentrates
• More Ways to Effect Molecular Makeup
• Thanks / Product Plugs / Veneration
3
Abstract
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
4
What is an Extract?
www.outco.com
So many molecules we should keep track of
5
What is an Extract?
>140 Cannabinoids >200 Terpenes
~30 Flavonoids
Alcohols, Phenols
Aldehydes, Ketones
Alkaloids
Carbohydrates, Fatty Acids
Lactones
www.outco.com
6
What is an Extract?
www.outco.com
7
What is an Extract?
www.outco.com
• Production Yield
• Production Costs
• Extract Constitution/Quality
• Legal Aspects
8
What is the best Extraction System?
www.outco.com
For what:
• Yield per Run YpR
• Yield per Week YpW
• Cannabinoid Conc. CC
• Terpene Content TC
• Recovery Rec
9
Optimizing your Extraction (SFE)
With what:
• Temperature T
• Pressure P
• Time t
• Flow Rate FR
• Particle Size PS
www.outco.com
For what:
• Yield per Run YpR
• Yield per Week YpW
• Cannabinoid Conc. CC
• Terpene Content TC
• Recovery Rec
10
Optimizing your Extraction Process
With what:
• Temperature T
• Pressure P
• Time t
• Flow Rate FR
• Particle Size PS
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
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
www.outco.com
For what:
• Recovery Rec
Optimizing your Extraction Process
With what:
• Particle Size PS
Experiment PS (mm) Rec (g)
1 6 215
2 4 230
3 2 235
4 1 253
210
220
230
240
250
260
0 1 2 3 4 5 6 7
YpR(g)
PS (mm)
Optimizing Particle Size
www.outco.com
14
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
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
www.outco.com
a= 14.9 xT + 123 xp + 18.4 xTxp
16
Analyzing the DoE, THC Recovery (Super)
www.outco.com
17
Analyzing the DoE, THC Recovery (Sub)
a= - 7.75 xT + 126 xp + 59.3 xTxp
www.outco.com
a= - 14.9 xT - 11.7 xp + 16.8 xTxp
18
Analyzing the DoE, %Terpene (Super)
www.outco.com
19
Analyzing the DoE, %Terpene (Sub)
a= 11.8 xT - 16.6 xp - 12.5 xTxp
www.outco.com
20
Visual Guide to Extracts
www.outco.com
SFE, 900.0 – 1900 psi, 5.0 – 60 ˚C, 22h max
21
Compare Sub- and Supercritical
Response Sub Super
THC Recovery 60% 80%
Terpene Fraction 52% at 34% yield 63% at 82% yield
www.outco.com
• THC extracts faster than THCA
• THC to THCA ratio adjusted by SFE
22
Lessons learned in SFE
% Decarboxylation S.M. 7h 22h
Exp. B 8.0% 25% 10%
Exp. J 14% 25% 14%
www.outco.com
• CBD extracts faster than THC
• CBD to THC ratio adjusted by SFE
23
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
www.outco.com
• Enrichment in minor cannabinoids
• CBG enrichment by SFE
24
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
www.outco.com
Changing terpene profiles in SFE
• Sativa: rich in monoterpenes
• Indica: rich in sesquiterpenes
25
Lessons learned in SFE
Hazekamp, et al.; Cannabis and Cannabinoid Research 2016, 202
7h 22h
www.outco.com
Rosin Press
• Optimized for yield and quality by DoE
• ~72% recovery achieved
• Little effect on molecular makeup
26
Other Separation Methods
Rosin Yield Rosin Quality
www.outco.com
27
Separation affects Extract Makeup
Ice Water Hash
• ~80% cannabinoid potency
• ~25% recovery achieved
• Little effect on molecular makeup
150 micron 25 micron
www.outco.com
Apeks Supercritical
• Andy Joseph, President
• Jeremy Sexton, Director of Engineering
Fritsch
• Barry Schubmehl, Application Consultant
• Leos Benes, Global Lab. Serv. Manager
28
Thanks
www.outco.com
29
OutCo Science Team: Taylor Trah,
Blake Grauerholz, Chris Cortina, Matt
Zbiec, Travis Kennedy
OutCo Cultivation: Dr. Allison Justice
OutCo Management: Lincoln Fish,
Austin Birch, Ben Ballard
Thank You
www.outco.com
30
Oversees all Extraction, Formulation and Production at
OutCo. jointly leads OutCo’s R&D
● PhD in Organic Chemistry, ETH Zürich, Switzerland
● Postdoc in Physical Organic Chemistry, The Scripps
Research Institute, San Diego
● Mentor, Board Member, Scientific Advisor to Cannabis
Startups, Journals and the NCIA
Public Presentations:
● Emerald Conference 2017
● CannaCon Seattle 2017
● ACS Conference 2017
● CannMed (Harvard Medical School) 2017
● Terpenes & Testing Magazine 2017
Dr. Markus Roggen
Vice President, Extraction

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CSC The Science and Economics of CO2 Extraction and Oil Manufacturing

  • 1. www.outco.com Dr. Markus Roggen VP Extraction OutCo, San Diego 1 The Science and Economics of CO2 Extraction and Oil Manufacturing
  • 2. www.outco.com Extracts should: 1. Represent the starting material 2. Deliver customized concentrate 2 Fallacies and Ignorance of Extraction
  • 3. www.outco.com • Background on Extraction • Univariant Optimization • Multivariant Optimization, DoE • Supercritical vs. Subcritical • Other Concentrates • More Ways to Effect Molecular Makeup • Thanks / Product Plugs / Veneration 3 Abstract
  • 4. 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 4 What is an Extract?
  • 5. www.outco.com So many molecules we should keep track of 5 What is an Extract? >140 Cannabinoids >200 Terpenes ~30 Flavonoids Alcohols, Phenols Aldehydes, Ketones Alkaloids Carbohydrates, Fatty Acids Lactones
  • 8. www.outco.com • Production Yield • Production Costs • Extract Constitution/Quality • Legal Aspects 8 What is the best Extraction System?
  • 9. www.outco.com For what: • Yield per Run YpR • Yield per Week YpW • Cannabinoid Conc. CC • Terpene Content TC • Recovery Rec 9 Optimizing your Extraction (SFE) With what: • Temperature T • Pressure P • Time t • Flow Rate FR • Particle Size PS
  • 10. www.outco.com For what: • Yield per Run YpR • Yield per Week YpW • Cannabinoid Conc. CC • Terpene Content TC • Recovery Rec 10 Optimizing your Extraction Process With what: • Temperature T • Pressure P • Time t • Flow Rate FR • Particle Size PS
  • 11. 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
  • 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: • Particle Size PS Experiment PS (mm) Rec (g) 1 6 215 2 4 230 3 2 235 4 1 253 210 220 230 240 250 260 0 1 2 3 4 5 6 7 YpR(g) PS (mm) Optimizing Particle Size
  • 14. www.outco.com 14 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
  • 15. 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
  • 16. www.outco.com a= 14.9 xT + 123 xp + 18.4 xTxp 16 Analyzing the DoE, THC Recovery (Super)
  • 17. www.outco.com 17 Analyzing the DoE, THC Recovery (Sub) a= - 7.75 xT + 126 xp + 59.3 xTxp
  • 18. www.outco.com a= - 14.9 xT - 11.7 xp + 16.8 xTxp 18 Analyzing the DoE, %Terpene (Super)
  • 19. www.outco.com 19 Analyzing the DoE, %Terpene (Sub) a= 11.8 xT - 16.6 xp - 12.5 xTxp
  • 21. www.outco.com SFE, 900.0 – 1900 psi, 5.0 – 60 ˚C, 22h max 21 Compare Sub- and Supercritical Response Sub Super THC Recovery 60% 80% Terpene Fraction 52% at 34% yield 63% at 82% yield
  • 22. www.outco.com • THC extracts faster than THCA • THC to THCA ratio adjusted by SFE 22 Lessons learned in SFE % Decarboxylation S.M. 7h 22h Exp. B 8.0% 25% 10% Exp. J 14% 25% 14%
  • 23. www.outco.com • CBD extracts faster than THC • CBD to THC ratio adjusted by SFE 23 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
  • 24. www.outco.com • Enrichment in minor cannabinoids • CBG enrichment by SFE 24 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
  • 25. www.outco.com Changing terpene profiles in SFE • Sativa: rich in monoterpenes • Indica: rich in sesquiterpenes 25 Lessons learned in SFE Hazekamp, et al.; Cannabis and Cannabinoid Research 2016, 202 7h 22h
  • 26. www.outco.com Rosin Press • Optimized for yield and quality by DoE • ~72% recovery achieved • Little effect on molecular makeup 26 Other Separation Methods Rosin Yield Rosin Quality
  • 27. www.outco.com 27 Separation affects Extract Makeup Ice Water Hash • ~80% cannabinoid potency • ~25% recovery achieved • Little effect on molecular makeup 150 micron 25 micron
  • 28. www.outco.com Apeks Supercritical • Andy Joseph, President • Jeremy Sexton, Director of Engineering Fritsch • Barry Schubmehl, Application Consultant • Leos Benes, Global Lab. Serv. Manager 28 Thanks
  • 29. www.outco.com 29 OutCo Science Team: Taylor Trah, Blake Grauerholz, Chris Cortina, Matt Zbiec, Travis Kennedy OutCo Cultivation: Dr. Allison Justice OutCo Management: Lincoln Fish, Austin Birch, Ben Ballard Thank You
  • 30. www.outco.com 30 Oversees all Extraction, Formulation and Production at OutCo. jointly leads OutCo’s R&D ● PhD in Organic Chemistry, ETH Zürich, Switzerland ● Postdoc in Physical Organic Chemistry, The Scripps Research Institute, San Diego ● Mentor, Board Member, Scientific Advisor to Cannabis Startups, Journals and the NCIA Public Presentations: ● Emerald Conference 2017 ● CannaCon Seattle 2017 ● ACS Conference 2017 ● CannMed (Harvard Medical School) 2017 ● Terpenes & Testing Magazine 2017 Dr. Markus Roggen Vice President, Extraction

Hinweis der Redaktion

  1. 2kg plant matter, 6 hours run time.