THCA-Amine Salt Precipitation for Cannabis Purification

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Solution Overview

Problem

Conventional methods for extracting and purifying tetrahydrocannabinol (THC) and cannabidiol (CBD) from Cannabis sativa plant biomass are inefficient, costly, and result in substantial loss or transformation of target compounds, with existing solvents being toxic and difficult to remove completely, leading to inconsistent and reproducible quality of cannabinoid extracts.

Innovation Solution

The method involves using amine salts, such as THCA-amine salts, to precipitate and purify THC from organic solvent solutions, utilizing amines like DMEA, piperidineethanol, and DBU to form insoluble salts that can be washed and recrystallized to achieve high purity, followed by decarboxylation to produce THC oil.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional organic solvent extraction methods are used to extract THC and CBD from Cannabis sativa, then the extraction process can be performed with simple equipment and操作流程, but the yields are poor and inconsistent, and the target compounds suffer substantial loss or transformation

Engineering Contradiction:
Improveextraction yieldVSAvoidloss of target compounds
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The patent changes the chemical parameters of the extraction system by using supercritical CO2 instead of conventional organic solvents, and by adjusting pH levels during purification. This transforms the extraction mechanism from solvent-based dissolution to supercritical fluid extraction, which maintains compound integrity and improves yield consistency without substantial loss of target compounds

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent utilizes the phase transition properties of CO2 between supercritical and gaseous states to achieve extraction and subsequent easy separation. By controlling pressure and temperature, CO2 transitions to a supercritical state for extraction, then returns to gaseous state for removal, leaving pure cannabinoids without solvent residue and minimizing compound loss

Inventive Principle:
Principle #36Phase transitions

2Ease of manufacture

If conventional organic solvents are used for extraction, then the extraction process is simple to perform, but the solvents are toxic and difficult to remove completely from the extracted materials

Engineering Contradiction:
Improveextraction process simplicityVSAvoidtoxicity of extraction solvents
Core Design Contradiction:
Ease of manufactureVSObject-affected harmful factors

Solution Approach 1:

The patent replaces persistent toxic organic solvents with CO2, which can be easily vented and discarded after extraction. The CO2 is used in supercritical state for extraction then returned to gaseous state and completely removed from the product, eliminating solvent residue concerns and toxicity issues while maintaining process simplicity

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

Solution Approach 2:

The patent uses CO2 as an inert extraction medium that does not react with cannabinoids or terpenes. The inert nature of CO2 prevents chemical transformations and degradation of target compounds, while its ease of removal eliminates toxic residue concerns, providing a safe extraction environment

Inventive Principle:
Principle #39Inert atmosphere (Inert environment)

3Device complexity

If conventional extraction and purification methods are used, then the process can be performed with standard equipment, but the quality of cannabinoid extracts is inconsistent and not reproducible

Engineering Contradiction:
Improveequipment requirementsVSAvoidquality consistency
Core Design Contradiction:
Device complexityVSReliability

Solution Approach 1:

The patent employs precise control of critical parameters including temperature, pressure, and pH levels throughout the extraction and purification process. By maintaining these parameters within specific ranges, the process achieves reproducible results and consistent quality across different batches, overcoming the variability inherent in conventional methods

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent replaces mechanical filtration and multiple purification steps with pH-controlled precipitation and supercritical fluid extraction. This substitution reduces the number of unit operations and equipment needed while improving quality consistency through more controlled and predictable separation mechanisms

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

4Device complexity

If conventional purification methods are used to remove solvents from extracted materials, then the process can be performed with simple equipment, but there is significant simultaneous loss of target molecules

Engineering Contradiction:
Improvepurification equipmentVSAvoidloss of target molecules during solvent removal
Core Design Contradiction:
Device complexityVSLoss of substance

Solution Approach 1:

The patent uses the phase transition of CO2 from supercritical to gaseous state to remove the extraction solvent. This transition allows complete solvent removal through simple pressure reduction and warming, eliminating the need for complex evaporation equipment and preventing target molecule loss that occurs during high-temperature solvent evaporation

Inventive Principle:
Principle #36Phase transitions

Solution Approach 2:

The patent extracts cannabinoids using supercritical CO2, then removes the CO2 solvent through phase transition to gaseous state. This clean separation takes out the solvent completely without requiring additional purification equipment or exposing the cannabinoids to conditions that would cause degradation or loss

Inventive Principle:
Principle #2Taking out (Extraction)

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

This approach allows for the efficient separation and purification of THC with minimal loss, achieving high-purity THC products and overcoming the limitations of conventional extraction methods by ensuring consistent and reproducible quality of cannabinoid extracts.

Implementation Method 1

adding and mixing into the standardized solvent-solubilized crude extract a selected volume of a selected amine whereby the amine reacts with THCA in an acid-base reaction, thereby forming and precipitating a crude THCA-amine salt

Methodology Applied
Scientific EffectAcid-base reaction: Chemical Bonding

Implementation Method 2

separating and recovering the precipitated crude THCA-amine salt from the standardized solvent-solubilized crude extract; washing the recovered crude THCA-amine salt with a selected second organic solvent one or more times

Methodology Applied
Scientific EffectWashing/Filtering: Filter (physical)

Implementation Method 3

re-solubilizing the washed THCA-amine salt in a selected third organic solvent; crystalizing the solubilized THCA-amine salt by cooling and optionally adding a selected antisolvent, to thereby produce a purified crystallized THCA-amine salt

Methodology Applied
Scientific EffectRecrystallization: Crystallisation

Implementation Method 4

decarboxylating the purified crystallized THCA-amine salt to thereby produce an oil comprising trans-delta-9-tetrahydrocannabinol (THC)

Methodology Applied
Scientific EffectDecarboxylation: Chemical Bonding

Data Source

PatentEP3877374B1Methods for extraction, processing, and purification of a selected family of target compounds from cannabis
Publication Date: 2024.03.20 NECTAR HEALTH SCI INC
  • EP3877374B1 patent drawingFigure 1A~1C
  • EP3877374B1 patent drawingFigure 2A~2C
  • EP3877374B1 patent drawingFigure 3A~3C

AI summary

Disclosed are methods for separating, recovering, and purifying tetrahydrocannabinolic acid (THCA) salts from an organic solvent solution comprising a mixture of cannabinoids. The methods comprise solubilizing the mixture of cannabinoids in a selected C5-C7 hydrocarbon solvent, adding thereto a selected amine to thereby precipitate a THCA-amine salt therefrom, dissolving the recovered THCA-amine salt in a selected solvent and then adding thereto a selected antisolvent to thereby recrystallize a purified THCA-amine salt therefrom. The recrystallized THCA-amine salt may be decarboxylated to form a mixture of Δ9-tetrahydrocannabinol (Δ9-THC) and amine. The Δ9-THC amine mixture may be acidified to separate the amine from Δ9-THC. The recovered Δ9-THC may be concentrated to produce a highly purified Δ9-THC. Also disclosed are THCA-amine salts produced with amines selected from groups of diamines, amino alcohols, and tertiary amines.