Caryophyllene Oxide Production With Catalyst-Free Atmospheric Oxidation
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Solution Overview
Problem
Existing methods for oxidizing beta-caryophyllene require catalysts, enzymes, and solvents, are slow, and lack efficient processes for producing high-purity caryophyllene oxides with diverse sensory profiles.
Innovation Solution
A method involving the oxidation of beta-caryophyllene using atmospheric oxygen at controlled temperatures (60-150°C) without catalysts or solvents, followed by distillation and optional crystallization, to produce a mixture of caryophyllene oxides with enhanced sensory properties.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If catalysts, enzymes or solvents are used for oxidation of beta-caryophyllene, then the oxidation reaction can proceed, but the process becomes more complex and requires additional reagents that may leave residues
Solution Approach 1:
The invention extracts and eliminates the need for catalysts, enzymes, and solvents from the oxidation process. By using atmospheric oxygen alone as the oxidant, the process removes harmful or complex auxiliary substances while maintaining effective oxidation of beta-caryophyllene to caryophyllene oxide.
Solution Approach 2:
The process enables beta-caryophyllene to undergo auto-oxidation using atmospheric oxygen without requiring external catalysts or enzymes. The system serves itself by utilizing naturally present oxygen in the air to drive the oxidation reaction, eliminating the need for additional chemical agents.
2Productivity
If traditional oxidation methods are used, then caryophyllene oxide can be produced, but the process is slow and requires several weeks
Solution Approach 1:
The invention changes the reaction parameters by controlling temperature (60-150°C) and oxygen exposure conditions to accelerate the oxidation process. By optimizing these parameters, the reaction time is reduced from several weeks to a much shorter duration while maintaining high conversion efficiency.
Solution Approach 2:
The process maintains continuous oxidation by keeping the reaction mixture exposed to atmospheric oxygen under controlled conditions. This continuous exposure ensures sustained reaction progress without interruption, significantly reducing the overall time required compared to batch methods with long idle periods.
3Manufacturing precision
If high purity beta-caryophyllene oxide (>95% 1R,4R,6R,10S-isomer) is required, then the fragrance application is limited, but sensory diversity is reduced
Solution Approach 1:
The invention produces an asymmetric mixture of caryophyllene oxide isomers rather than a single symmetric pure isomer. This deliberate asymmetry in the product composition creates diverse sensory profiles while maintaining sufficient overall purity, allowing the product to meet both quality and versatility requirements.
Solution Approach 2:
The oxidation process produces a universal mixture of caryophyllene oxide isomers that can serve multiple fragrance applications. The mixed isomer composition provides versatile sensory characteristics suitable for different perfume and flavor applications, making the product multi-functional rather than specialized for a single use.
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
The method achieves high yields of caryophyllene oxides within a week, avoiding unwanted by-products and enabling a more intense and diverse flavor/fragrance profile compared to traditional methods.
Implementation Method 1
oxidizing beta-caryophyllene with oxygen, in particular atmospheric oxygen
Implementation Method 2
heating of the obtained reaction mixture from step (i) to a temperature in a range from 110 to 150° C.
Implementation Method 3
distillation of the obtained reaction mixture from step (i) or (ii) to obtain a fraction comprising caryophyllene oxides
Implementation Method 4
crystallization of the fraction comprising caryophyllene oxides from step (iii)
Data Source
AI summary
The present invention relates to a method for oxidizing beta-caryophyllene with oxygen, in particular atmospheric oxygen, which avoids the use of catalysts, enzymes and solvents. Furthermore, the present invention provides a mixture comprising certain caryophyllene oxides as well as their use as a flavor and/or fragrance. The present invention also relates to products and semi-finished products comprising the mixture according to the invention.