Cannabinoid Carboxylic Acid Salt Purification

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Current methods for producing pure neutral cannabinoids are laborious, prone to impurity formation, and lack efficiency, particularly in the purification of cannabinoid carboxylic acids which are ideal precursors for obtaining pure cannabinoids.

Innovation Solution

A method involving the production of crystalline and soluble salts of cannabinoid carboxylic acids through chemical reaction or extraction from Cannabis sativa, followed by mixing with suitable organic or inorganic bases in solvents to precipitate sparingly soluble salts, which can be purified by recrystallization and decomposed to yield pure neutral cannabinoids.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If complex purification processes such as preparative chromatography are used to produce pure neutral cannabinoids, then manufacturing precision is improved, but device complexity and loss of time increase

Engineering Contradiction:
Improvepurity of neutral cannabinoidsVSAvoidcomplexity of purification process
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The invention extracts and utilizes cannabinoid carboxylic acids as intermediate compounds from the decarboxylation process, separating them from the complex mixture before final purification. This extraction step simplifies the overall purification process by removing impurities early in the sequence, reducing the need for complex chromatographic steps while maintaining high purity of the final neutral cannabinoid product

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention performs preliminary decarboxylation to convert cannabinoid carboxylic acids into neutral cannabinoids, and further preliminary purification steps to remove impurities before the final isolation. By performing these actions in advance, the subsequent purification requires less complex equipment and procedures, resolving the contradiction between purity and process complexity

Inventive Principle:
Principle #10Preliminary action

2Manufacturing precision

If multiple purification steps including chromatography and vacuum distillation are employed, then manufacturing precision is improved, but loss of time increases

Engineering Contradiction:
Improvepurity of neutral cannabinoidsVSAvoidproduction time
Core Design Contradiction:
Manufacturing precisionVSLoss of time

Solution Approach 1:

The invention merges multiple purification operations into a integrated process flow where decarboxylation, filtration, and concentration steps are combined sequentially. By merging these operations that can be performed in a single reaction vessel or connected system, the invention reduces the total time required while maintaining the purity benefits of multiple purification steps

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The invention skips certain intermediate isolation steps by performing sequential reactions and purifications without isolating each intermediate product. The process rushes through multiple purification stages by maintaining continuous flow or sequential batch operations, significantly reducing the time loss associated with repeated isolation and re-dissolution cycles while still achieving high purity through the combined effect of multiple purification mechanisms

Inventive Principle:
Principle #21Skipping (Rushing through)

3Manufacturing precision

If crystallizable precursors are produced through complex processes including recrystallization and saponification, then manufacturing precision is improved, but device complexity and susceptibility to impurity formation increase

Engineering Contradiction:
Improvepurity of cannabinoid precursorsVSAvoidcomplexity of precursor production process
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The invention converts the potentially harmful effect of impurity formation during complex purification processes into a benefit by using selective crystallization of cannabinoid carboxylic acid salts. The process exploits the differential solubility and crystallization behavior of various compounds to separate impurities from the desired product, transforming what would be a source of contamination into a purification mechanism that simplifies the overall process

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

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 method allows for the economical and efficient production of pure, crystalline salts of cannabinoid carboxylic acids, reducing the effort required and susceptibility to impurities, enabling the simple and effective conversion to pure neutral cannabinoids.

Implementation Method 1

reacting them with a suitable organic base, inorganic base and/or a suitable inorganic or organic salt in a suitable solvent

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Implementation Method 2

followed by mixing with suitable organic or inorganic bases in solvents to precipitate sparingly soluble salts

Methodology Applied
Scientific EffectPrecipitation: Precipitation

Implementation Method 3

which can be purified by recrystallization

Methodology Applied
Scientific EffectRecrystallization: Crystallisation

Implementation Method 4

decomposed to yield pure neutral cannabinoids

Methodology Applied
Scientific EffectThermal decomposition: Thermolysis

Implementation Method 5

the so-called 'neutral cannabinoids' are formed by decarboxylation, i.e., the removal of CO2

Methodology Applied
Scientific EffectDecarboxylation: Decomposition (biological)

Data Source

PatentEP2760444B1Cannabinoid carboxylic acids, salts of cannabinoid carboxylic acids, and the production and uses of same
Publication Date: 2020.04.22 THC PHARM GMBH THE HEALTH CONCEPT
  • EP2760444B1 patent drawing
  • EP2760444B1 patent drawing
  • EP2760444B1 patent drawing

AI summary

The invention relates to a compound selected from the group consisting of all stereoisomers and their mixtures of the compounds of general formulas (1)-(4), in which R1 is a straight-chained, branched or cyclic hydrocarbon group with up to 12 C-atoms and X+ is selected from the group consisting of H+, NH4 +, mono, di or trivalent metal cations, NH4 +, primary, secondary, tertiary or quaternary organic ammonium ions with up to 48 C-atoms, which can carry even more functional groups, hydrazinium ion (N2H5 +), hydroxylammonium ion (NH3OH+), guanidinium ion (CN3H6 +), and organic derivatives of (N2H5 +), NH3OH+, and CN3H6 +, which can carry even more functional groups, and similar. A method is also provided for producing these compounds, comprising the following steps: producing synthetic cannabinoid carboxylic acids in a chemical reaction, or extracting natural cannabinoid carboxylic acids from plant material or cell cultures of Cannabis sativa, and adding a suitable inorganic base, a suitable organic base and/or a suitable inorganic or organic salt in a suitable solvent, to the cannabinoid carboxylic acids or cannabinoid carboxylic acid-rich extracts produced in this manner.