Xylene Solvent CBD to CBN Conversion

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Solution Overview

Problem

Current methods for converting cannabidiol (CBD) to cannabinol (CBN) often use toxic solvents like toluene, and there is a need for a more cost-effective and less contaminating alternative solvent that optimizes reaction conditions such as temperature and duration while avoiding heavy metals and toxic compounds in the final product.

Innovation Solution

The use of an isomeric mixture of xylene, specifically ortho-, meta-, and para-xylene, as a solvent, combined with iodine and water, and a reflux process for 12-16 days, followed by crystallization and purification steps, to achieve high purity and yield of CBN, with monitoring using HPLC to control reaction conditions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Object-affected harmful factors

If toluene is used as solvent for CBD to CBN conversion, then reaction efficiency is maintained, but product contamination and cost increase due to excise requirements

Engineering Contradiction:
Improveproduct contaminationVSAvoidmanufacturing cost
Core Design Contradiction:
Object-affected harmful factorsVSEase of manufacture

Solution Approach 1:

The patent replaces expensive toluene (an excise good) with cheaper alternative solvents such as ethyl acetate, methyl tert-butyl ether (MTBE), or their mixtures. These alternative solvents achieve the same conversion efficiency while eliminating excise taxes and reducing product contamination, directly addressing both the harmful factors and manufacturing cost issues.

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

Solution Approach 2:

The patent optimizes reaction parameters including temperature (80-120°C), reaction time (12-16 days), and solvent ratios to maximize CBN yield while minimizing intermediate compounds. By carefully controlling these parameters with alternative solvents, the process achieves high purity (80-99.99%) without the contamination associated with toluene.

Inventive Principle:
Principle #35Parameter changes

2Productivity

If reaction time is extended to increase CBN yield, then conversion efficiency improves, but production time and energy consumption increase

Engineering Contradiction:
ImproveCBN yieldVSAvoidreaction time
Core Design Contradiction:
ProductivityVSLoss of time

Solution Approach 1:

The patent optimizes the balance between reaction time and temperature to achieve high CBN yield (40-90%) within 12-16 days. By maintaining temperatures between 80-120°C and using optimized solvent systems, the process maximizes conversion efficiency while minimizing unnecessary time extension, thus improving productivity without excessive time loss.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs HPLC monitoring to track the conversion progress and intermediate compound levels throughout the reaction. This feedback mechanism allows for precise control of reaction conditions and timing, ensuring optimal CBN yield is achieved without extending the reaction unnecessarily, thereby balancing productivity and time efficiency.

Inventive Principle:
Principle #23Feedback

3Productivity

If toxic catalysts such as chromates or borates are used, then reaction rate increases, but product purity decreases due to heavy metal contamination

Engineering Contradiction:
Improvereaction rateVSAvoidproduct purity
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent eliminates toxic heavy metal catalysts (chromates, borates) entirely by using iodine as a benign alternative catalyst with the xylene/ethyl acetate/MTBE solvent system. This substitution maintains adequate reaction rates while completely avoiding heavy metal contamination, thus achieving both productivity and high product purity (80-99.99%) without toxic additives.

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

Solution Approach 2:

The patent converts the potentially harmful use of toxic catalysts into a beneficial approach by using iodine, which is much less toxic and can be easily removed. The iodine catalyst achieves the necessary reaction rate while its byproducts are non-toxic and do not contaminate the final CBN product, thereby turning a harmful practice into a beneficial one.

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 achieves a CBN purity of 80.00% to 99.99% and a yield of 40% to 90%, minimizing intermediate compounds and avoiding toxic byproducts, resulting in a high-purity CBN product with reduced contamination.

Implementation Method 1

converting cannabidiol (CBD) into cannabinoids (CBN)... adding iodine and water to the mixture... refluxing of mixture for 12-16 days

Methodology Applied
Scientific EffectOxidation: Oxidation

Implementation Method 2

dissolving CBD in mixture by heating... refluxing of mixture for 12-16 days with heating

Methodology Applied
Scientific EffectHeating: Heating

Implementation Method 3

refluxing of mixture for 12-16 days with heating

Methodology Applied
Scientific EffectCondensation: Condensation

Implementation Method 4

crystallization of the solution... crystallization is performed at least two times

Methodology Applied
Scientific EffectCrystallization: Crystallisation

Implementation Method 5

drying of the crystals... Drying is performed in vacuum at temperature between 40 and 55°C

Methodology Applied
Scientific EffectEvaporation: Evaporation

Data Source

PatentEP4345098A1Conversion of cannabidiol to cannabinol using xylene
Publication Date: 2024.04.03 BIOTECUS
  • EP4345098A1 patent drawingFigure 1~2
  • EP4345098A1 patent drawingFigure 3~4
  • EP4345098A1 patent drawingFigure 5

AI summary

The present invention provides a method of conversion of at least one cannabinol (CBN) from an initial cannabidiol (CBD) mixture of xylene and extraction method. A purity of final product CBN obtained from one CBD is from 80.00% to 99.99%. The yield of CBN is from 40% to 90% of a total weight of mixture.