Converting THC to CBN with Benzoquinone Reagents

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Solution Overview

Problem

Current methods for obtaining cannabinol (CBN) are limited, as it is typically sourced from complex biomass mixtures where it is present in low quantities, making isolation challenging and inefficient.

Innovation Solution

Converting THC-rich cannabinoid mixtures into CBN-rich mixtures using benzoquinone reagents like thymoquinone or tetrachloro-1,4-benzoquinone under mild reaction conditions, avoiding the need for expensive and hazardous purification methods.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If CBN is sourced from complex biomass mixtures, then CBN can be obtained from natural sources, but CBN is present in low quantities making isolation challenging and inefficient

Engineering Contradiction:
ImproveCBN quantityVSAvoidIsolation efficiency
Core Design Contradiction:
Quantity of substanceVSProductivity

Solution Approach 1:

Instead of extracting CBN from biomass (traditional approach), the patent inverts the approach by converting THC-rich mixtures into CBN using benzoquinone reagents. This reverse strategy transforms the problem from extraction to synthesis, achieving high CBN quantities without the inefficiencies of natural extraction.

Inventive Principle:
Principle #13The other way round (Inversion)

Solution Approach 2:

The patent changes the chemical parameters by introducing benzoquinone reagents that catalyze the conversion of THC to CBN. This parameter change (chemical transformation) enables efficient CBN production from abundant THC sources, overcoming the low quantity limitation of natural biomass extraction.

Inventive Principle:
Principle #35Parameter changes

2Quantity of substance

If purification methods are used to obtain CBN from biomass, then CBN can be isolated, but expensive and hazardous purification methods are required

Engineering Contradiction:
ImproveCBN quantityVSAvoidPurification cost and complexity
Core Design Contradiction:
Quantity of substanceVSEase of manufacture

Solution Approach 1:

The patent converts the harmful/complex purification process into a beneficial simple chemical transformation. By using benzoquinone reagents to directly convert THC to CBN, the method eliminates the need for expensive and hazardous purification steps, turning a problematic process into an efficient solution.

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

Solution Approach 2:

The benzoquinone reagent acts as an intermediary that facilitates the conversion of THC to CBN. This intermediary substance enables the transformation without requiring complex purification methods, simplifying the manufacturing process while achieving high CBN quantities.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Quantity of substance

If traditional CBN extraction from biomass is used, then CBN can be obtained, but the process is time-consuming and not scalable

Engineering Contradiction:
ImproveCBN quantityVSAvoidExtraction time
Core Design Contradiction:
Quantity of substanceVSLoss of time

Solution Approach 1:

The patent performs preliminary action by using THC-rich mixtures (which are readily available from established extraction methods) as the starting material. This preliminary preparation eliminates the need for time-consuming CBN extraction from biomass, as the conversion process is much faster and more scalable.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent changes the temporal parameter by implementing a chemical conversion process that occurs much faster than traditional extraction. The benzoquinone-mediated transformation of THC to CBN significantly reduces processing time, enabling scalable production without the time losses associated with biomass extraction.

Inventive Principle:
Principle #35Parameter changes

4Productivity

If harmful solvents like benzene are used in CBN production, then CBN can be synthesized, but harmful substances are introduced into the process

Engineering Contradiction:
ImproveCBN production efficiencyVSAvoidHarmful solvents
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The patent extracts/eliminates harmful solvents like benzene from the CBN production process. By using benzoquinone reagents in alternative reaction systems, the method removes harmful substances while maintaining or improving production efficiency, creating a safer manufacturing process.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent replaces harmful, expensive, and environmentally damaging solvents with safer, more benign reagents. The benzoquinone-based system uses less hazardous materials that can be easily handled and disposed of, eliminating the need for complex safety infrastructure required for benzene-based processes.

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

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 effectively increases the CBN content in the mixture while reducing THC content, achieving scalable production of CBN-rich cannabinoid mixtures without requiring harmful solvents like benzene, thus overcoming the challenges of low CBN availability.

Implementation Method 1

converting THC-rich cannabinoid mixtures into CBN-rich cannabinoid mixtures

Methodology Applied
Scientific EffectOxidation: Oxidation

Data Source

PatentUS11472786B2Methods for converting THC-rich cannabinoid mixtures into CBN-rich cannabinoid mixtures
Publication Date: 2022.10.18 CANOPY GROWTH CORP
  • US11472786B2 patent drawing
  • US11472786B2 patent drawing
  • US11472786B2 patent drawing

AI summary

Disclosed herein is a method of converting a THC-rich cannabinoid mixture that comprises at least about 20% THC into a CBN-rich cannabinoid mixture that comprises at least about 2.0% CBN. The method comprises contacting the cannabinoid mixture with a benzoquinone reagent under reaction conditions comprising: (i) a reaction temperature that is within a target reaction-temperature range; and (ii) a reaction time that is within a target reaction-time range, such that at least a portion of the of the THC in the THC-rich cannabinoid mixture is converted into CBN.