# US 11,110,372 B2 · Cold extraction method for cannabinoids and terpenes from cannabis by organic solvents

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- Number: US 11,110,372 B2
- Document ID: US11110372B2
- Status: Granted
- Kind: B2
- Application number: 16/999,846
- Filed: 2020-08-21
- Published: 2020-12-24
- Granted: 2021-09-07
- Earliest claimed: 2018-08-08
- Assignees: Neptune Wellness Solutions Inc.
- Applicants: Neptune Wellness Solutions Inc.
- Inventors: Fereshteh Farokhi; Pierre St-Jean; Etienne Villeneuve
- Web page: https://patentgrep.com/patent/US11110372B2

## CPC

- A23L 33/105: Plant extracts, their artificial duplicates or their derivatives
- B01D 11/0288: {Applications, solvents}
- A61K 31/658: {o-phenolic cannabinoids, e.g. cannabidiol, cannabigerolic acid, cannabichromene or tetrahydrocannabinol}
- A61K 36/3482: {Cannabis}
- B01D 11/0207: {Control systems}
- B01D 11/0265: {Applying ultrasound}
- B01D 11/0292: {Treatment of the solvent}
- C11B 1/10: by extracting
- A61K 2236/33: involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K 2236/50: Methods involving additional extraction steps
- A61K 2300/00: Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
- B01D 11/0257: {using mixing mechanisms, e.g. stirrers, jets (B01D11/0242 takes precedence)}
- B01D 11/028: {Flow sheets}
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- C11B: PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES (drying-oils C09F)

## Abstract

The invention relates to methods of producing extracts from cannabis plant material, where the extracts comprise cannabinoids and terpenes. The methods comprise extracting fresh or dried plant material with a cold organic solvent. The methods allow for the extraction of cannabinoids and terpenes, while leaving behind impurities such as waxes and chlorophyll that are commonly found in extractions with room temperature (RT) or warm solvent extraction methods. The methods can produce extracts having more than 90% cannabinoids.

## Claims

### Claim 1

A method of preparing a cannabis extract comprising:
a. providing cannabis plant material comprising stems, leaves, seeds, flowers or a combination thereof in an extraction chamber;
b. contacting an organic solvent at a temperature of between about 0° C. and −80° C. with the cannabis plant material;
c. extracting at least one bioactive molecule from the cannabis plant material into the organic solvent for a first period of time, thereby producing an organic solvent comprising a cannabis extract, wherein the extraction step takes place at between about 0° C. and −80° C.;
d. filtering or centrifuging the organic solvent and the cannabis plant material to remove solid materials; and
e. recovering the cannabis extract from the organic solvent; thereby producing the cannabis extract.

### Claim 2 (depends on 1)

The method of claim 1, wherein the cannabis plant material is heated to a temperature of between 110 to 145° C. prior to step (a).

### Claim 3 (depends on 2)

The method of claim 2, wherein the cannabis plant material is heated for about 40 to 75 minutes.

### Claim 4 (depends on 1)

The method of claim 1, wherein the first period of time is no more than 1 hour.

### Claim 5 (depends on 1)

The method of claim 1, comprising sonicating the organic solvent and the cannabis plant material for a second period of time, wherein the second period of time occurs:
(1) prior to step (c), or
(2) during step (c), and is the same as the first period of time.

### Claim 6 (depends on 5)

The method of claim 5, wherein the second period of time is about 10 minutes.

### Claim 7 (depends on 1)

The method of claim 1, wherein the organic solvent is at a temperature of between about 0° C. and −70° C., about 0° C. and −60° C., about 0° C. and −50° C., about 0° C. and −40° C., about 0° C. and −30° C., about 0° C. and −20° C., about 0° C. and −10° C., about −10° C. and −80° C., about −10° C. and −60° C., about −10° C. and −50° C., about −10° C. and −40° C., about −20° C. and −60° C., or about −20° C. and −50° C.

### Claim 8 (depends on 1)

The method of claim 1, wherein the organic solvent is selected from the group consisting of ethanol, acetone, and ethyl acetate.

### Claim 9 (depends on 1)

The method of claim 1, comprising returning the organic solvent comprising the cannabis extract from step (d) to the extraction chamber and repeating steps (b) through (d).

### Claim 10 (depends on 9)

The method of claim 9, wherein un-extracted cannabis plant material is added to the extraction chamber prior to repeating steps (c) and (d).

### Claim 11 (depends on 1)

The method of claim 1, wherein step (e) comprises evaporation of the organic solvent.

### Claim 12 (depends on 1)

The method of claim 1, wherein the cannabis extract is subject to one or more additional purification methods.

### Claim 13 (depends on 12)

The method of claim 12, wherein the one or more additional purification methods comprise molecular distillation or high-performance liquid chromatography (HPLC).

### Claim 14 (depends on 1)

The method of claim 1, wherein the cannabis plant material is Cannabis sativa, Cannabis indica, Cannabis ruderalis or a hybrid thereof.

### Claim 15 (depends on 1)

The method of claim 1, wherein the cannabis plant material is industrial hemp.

### Claim 16 (depends on 1)

The method of claim 1, wherein the at least one bioactive molecule comprises a cannabinoid, a flavonoid or a terpene.

### Claim 17 (depends on 16)

The method of claim 16, wherein the cannabinoid comprises Δ9-tetrahydrocannabinol (THC), cannabidiol (CBD), tetrahydrocannabinolic acid (THCA), cannabidiolic acid (CBDA), cannabigerolic acid (CBGA), cannabichromenenic acid (CBCA), cannabigerovarinic acid (CBGVA), tetrahydrocanabivarinic acid (THCVA), cannabidivarinic acid (CBDVA), cannabichromevarinic acid (CBCVA), cannabinol (CBN), cannabigerol (CBG), cannabichromene (CBC), cannabicyclol (CBL), cannabivarin (CBV), tetrahydrocannabivarin (THCV), cannabidivarin (CBDV), cannabichromevarin (CBCV), cannabigerovarin (CBGV), cannabigerol monomethylether (CBGM), cannabielsoin (CBE), cannabicitran (CBT), or a combination thereof.

### Claim 18 (depends on 16)

The method of claim 16, wherein the cannabinoid comprises THC, THCA, CBD, CBDA or a combination thereof.

### Claim 19 (depends on 1)

A method of making a cannabis extract composition, comprising:
a. providing the cannabis extract produced by the method of claim 1, and
b. mixing the cannabis extract with a pharmaceutically acceptable carrier, diluent or excipient.

### Claim 20 (depends on 19)

The method of claim 19, wherein the composition is formulated as a liquid, gel, softgel, powder, tablet, caplet, capsule, gelcap, food additive, drop, beverage, pill, lozenge, rinse, paste gum, cream, ointment, lotion, salve, balm or paste.