# US 10,870,632 B2 · Process for producing an extract containing tetrahydrocannabinol and cannabidiol from cannabis plant material, and cannabis extracts

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- Number: US 10,870,632 B2
- Document ID: US10870632B2
- Status: Granted
- Kind: B2
- Application number: 14/276,165
- Filed: 2014-05-13
- Published: 2014-09-04
- Granted: 2020-12-22
- Earliest claimed: 2000-10-17
- Assignees: Bionorica Ethics GmbH
- Applicants: Bionorica Ethics GmbH
- Inventors: Adam Mueller
- Web page: https://patentgrep.com/patent/US10870632B2

## CPC

- C07D 311/80: Dibenzopyrans; Hydrogenated dibenzopyrans
- A61K 31/35: having six-membered rings with one oxygen as the only ring hetero atom
- A61K 36/3482: {Cannabis}
- A61P 25/26: Psychostimulants, e.g. nicotine, cocaine
- Y02P 20/54: using solvents, e.g. supercritical solvents or ionic liquids
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

The invention relates to a method for producing an extract from cannabis plant matter, containing tetrahydrocannabinol, cannabidiol and optionally the carboxylic acids thereof. According to said method, the dried pint matter is ground and subjected to a CO2 extraction and the primary extract obtained is separated. The invention method permits Δ8 or Δ9 tetrahydrocannabinol to be selectively obtained both from industrial hemp and from drug-producing hemp, optionally after dissolving the primary extract in ethanol, separating undesirable waxes and removing the solvent under reduced pressure.

## Claims

### Claim 1

A process for producing an extract containing Tetrahydrocannabinol (THC) and/or cannabidiol (CBD), and optionally the carboxylic acids thereof, from a cannabis plant material or a primary extract thereof, said process comprising:
(1) subjecting the cannabis plant material or primary extract thereof to CO2 in liquefied form under subcritical pressure and temperature conditions to extract cannabinoid components; and
(2) reducing the pressure and/or temperature to separate tetrahydrocannabinol and/or cannabidiol, and optionally the carboxylic acids thereof, from the CO2.

### Claim 2 (depends on 1)

The process according to claim 1, further comprising subjecting the CO2 extracted from step (2) to increased pressure and temperature and recycling said CO2 to step (1).

### Claim 3 (depends on 1)

The process according to claim 1, wherein in step (1) the CO2 in liquefied form is at a pressure of 70 bar or less.

### Claim 4 (depends on 3)

The process according to claim 3, wherein in step (1) the CO2 in liquefied form is at a temperature of between about 20° C. to about 30° C.

### Claim 5 (depends on 1)

The process according to claim 1, wherein in step (1) the CO2 in liquefied form is at a pressure of about 60 bar.

### Claim 6 (depends on 1)

The process according to claim 1, wherein in step (2) the CO2 in liquefied form is at a pressure of about 55 bar or less.

### Claim 7 (depends on 3)

The process according to claim 3, wherein in step (2) the CO2 in liquefied form is at a pressure of about 55 bar or less and a temperature of about 20° C. or less.

### Claim 8 (depends on 1)

The process according to claim 1, which further comprises separating monoterpenes and sequiterpenes from the tetrahydrocannabinol and cannabidiol using a separator.

### Claim 9 (depends on 1)

The process according to claim 1, wherein the cannabis plant material contains 0.5% or less of Δ9-THC based on the dry plant mass.

### Claim 10 (depends on 1)

The process according to claim 1, wherein an adsorbent for extracting components other than tetrahydrocannabinol, cannabidiol and optionally the carboxylic acids thereof is arranged downstream in terms of the CO2 flow.

### Claim 11 (depends on 10)

The process according to claim 10, wherein the adsorbent is selected from the group consisting of silica gel, diatomaceous earth, bentonites, bleaching earth, activated carbons, magnesium oxide and alumina, as well as mixtures thereof.

### Claim 12 (depends on 11)

The process according to claim 11, wherein the absorbent is for extracting components selected from the group consisting of alkaloids, flavonoids, monoterpenes, sesquiterpenes, and chlorophylls.

### Claim 13 (depends on 1)

The process according to claim 1, further comprising a step of decarboxylating cannabinoid carboxylic acids in the cannabis plant material or primary extract thereof.

### Claim 14

A process for producing an extract containing Tetrahydrocannabinol (THC) and/or cannabidiol (CBD) from a cannabis plant material or a primary extract thereof, said process comprising:
(1) decarboxylating cannabinoid carboxylic acids in the cannabis plant material or primary extract thereof;
(2) subjecting the decarboxylated cannabis plant material or primary extract thereof to CO2 in liquefied form under subcritical pressure and temperature conditions to extract cannabinoid components; and
(3) reducing the pressure and/or temperature to separate tetrahydrocannabinol and/or cannabidiol from the CO2.

### Claim 15 (depends on 14)

The process according to claim 14, further comprising subjecting the CO2 extracted from step (3) to increased pressure and temperature and recycling said CO2 to step (2).

### Claim 16 (depends on 14)

The process according to claim 14, wherein in step (2) the CO2 in liquefied form is at a pressure of 70 bar or less.

### Claim 17 (depends on 16)

The process according to claim 16, wherein in step (2) the CO2 in liquefied form is at a temperature of between about 20° C. to about 30° C.

### Claim 18 (depends on 14)

The process according to claim 14, wherein in step (2) the CO2 in liquefied form is at a pressure of about 60 bar.

### Claim 19 (depends on 14)

The process according to claim 14, wherein in step (3) the CO2 in liquefied form is at a pressure of about 55 bar or less.

### Claim 20 (depends on 16)

The process according to claim 16, wherein in step (3) the CO2 in liquefied form is at a pressure of about 55 bar or less and a temperature of about 20° C. or less.

### Claim 21 (depends on 14)

The process according to claim 14, which further comprises separating monoterpenes and sequiterpenes from the tetrahydrocannabinol and cannabidiol using a separator.

### Claim 22 (depends on 14)

The process according to claim 14, wherein the cannabis plant material contains 0.5% or less of Δ9-THC based on the dry plant mass.

### Claim 23 (depends on 14)

The process according to claim 14, wherein an adsorbent for extracting components other than tetrahydrocannabinol, cannabidiol and optionally the carboxylic acids thereof is arranged downstream in terms of the CO2 flow.

### Claim 24 (depends on 23)

The process according to claim 23, wherein the adsorbent is selected from the group consisting of silica gel, diatomaceous earth, bentonites, bleaching earth, activated carbons, magnesium oxide and alumina, as well as mixtures thereof.

### Claim 25 (depends on 24)

The process according to claim 24, wherein the absorbent is for extracting components selected from the group consisting of alkaloids, flavonoids, monoterpenes, sesquiterpenes, and chlorophylls.