This document summarizes information from a presentation on cannabis extraction. It discusses defining extracts and what constitutes an extract in terms of cannabis compounds. It also examines optimizing extraction processes by exploring factors like temperature, pressure, time and their effects on yield, cannabinoid concentration and terpene content. The document compares subcritical and supercritical extraction methods and shares lessons learned from experiments. It also briefly discusses other separation techniques like rosin presses and ice water hash.

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Dr. Markus Roggen
VP Extraction
OutCo, San Diego
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Extraction Research Result

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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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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

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But it does give you higher yields!
Optimizing your Extraction Process
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30
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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

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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 Taylor expansion describes the response surface.
Matrix algebra solves the Taylor expansion
Y=bX
b=(X’X)-1X’Y
a=bX 17
Calculating the Response Surface
y0+ ixi+ iixi
2+ ijxixj
i i i j

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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

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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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The Crew
Blake Grauerholz
Taylor Trah
Matt Zbiec
Chris Cortina
and team
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
www.slideshare.net/MarkusRoggen