Presented at Cannabis Science Conference 2017 in Portland, OR Now with data on both supercritical and liquid CO2 extraction of cannabis.

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Dr. Markus Roggen
VP Extraction
OutCo, San Diego
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The Science and Economics of CO2
Extraction and Oil Manufacturing

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Extracts should:
1. Represent the starting material
2. Deliver customized concentrate
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Fallacies and Ignorance of Extraction

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• Background on Extraction
• Univariant Optimization
• Multivariant Optimization, DoE
• Supercritical vs. Subcritical
• Other Concentrates
• More Ways to Effect Molecular Makeup
• Thanks / Product Plugs / Veneration
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Abstract

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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
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What is an Extract?

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So many molecules we should keep track of
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What is an Extract?
>140 Cannabinoids >200 Terpenes
~30 Flavonoids
Alcohols, Phenols
Aldehydes, Ketones
Alkaloids
Carbohydrates, Fatty Acids
Lactones

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What is an Extract?

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What is an Extract?

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• Production Yield
• Production Costs
• Extract Constitution/Quality
• Legal Aspects
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What is the best Extraction System?

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For what:
• Yield per Run YpR
• Yield per Week YpW
• Cannabinoid Conc. CC
• Terpene Content TC
• Recovery Rec
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Optimizing your Extraction (SFE)
With what:
• Temperature T
• Pressure P
• Time t
• Flow Rate FR
• Particle Size PS

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For what:
• Yield per Run YpR
• Yield per Week YpW
• Cannabinoid Conc. CC
• Terpene Content TC
• Recovery Rec
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Optimizing your Extraction Process
With what:
• Temperature T
• Pressure P
• Time t
• Flow Rate FR
• Particle Size PS

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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

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For what:
• Yield per Run YpR
• Yield per Week YpW
• Cannabinoid Conc. CC
• Terpene Content TC
• Recovery Rec
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Optimizing your Extraction Process
With what:
• Temperature T
• Pressure P
• Time t
• Flow Rate FR
• Particle Size PS

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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

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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

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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

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a= 14.9 xT + 123 xp + 18.4 xTxp
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Analyzing the DoE, THC Recovery (Super)

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Analyzing the DoE, THC Recovery (Sub)
a= - 7.75 xT + 126 xp + 59.3 xTxp

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a= - 14.9 xT - 11.7 xp + 16.8 xTxp
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Analyzing the DoE, %Terpene (Super)

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Analyzing the DoE, %Terpene (Sub)
a= 11.8 xT - 16.6 xp - 12.5 xTxp

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Visual Guide to Extracts

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SFE, 900.0 – 1900 psi, 5.0 – 60 ˚C, 22h max
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Compare Sub- and Supercritical
Response Sub Super
THC Recovery 60% 80%
Terpene Fraction 52% at 34% yield 63% at 82% yield

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• THC extracts faster than THCA
• THC to THCA ratio adjusted by SFE
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Lessons learned in SFE
% Decarboxylation S.M. 7h 22h
Exp. B 8.0% 25% 10%
Exp. J 14% 25% 14%

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• CBD extracts faster than THC
• CBD to THC ratio adjusted by SFE
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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

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• Enrichment in minor cannabinoids
• CBG enrichment by SFE
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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

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Changing terpene profiles in SFE
• Sativa: rich in monoterpenes
• Indica: rich in sesquiterpenes
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Lessons learned in SFE
Hazekamp, et al.; Cannabis and Cannabinoid Research 2016, 202
7h 22h

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Rosin Press
• Optimized for yield and quality by DoE
• ~72% recovery achieved
• Little effect on molecular makeup
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Other Separation Methods
Rosin Yield Rosin Quality

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Separation affects Extract Makeup
Ice Water Hash
• ~80% cannabinoid potency
• ~25% recovery achieved
• Little effect on molecular makeup
150 micron 25 micron

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Apeks Supercritical
• Andy Joseph, President
• Jeremy Sexton, Director of Engineering
Fritsch
• Barry Schubmehl, Application Consultant
• Leos Benes, Global Lab. Serv. Manager
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Thanks

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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

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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