Cyclohexadecanone Production via Palladium Catalyst Optimization

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Solution Overview

Problem

Current methods for producing cyclohexadecanone through hydrogenation of cyclohexadecenone are economically inefficient and do not consistently yield high-quality musk fragrance on an industrial scale, often requiring excessive amounts of hydrogenation catalysts.

Innovation Solution

A process involving the hydrogenation of cyclohexadecenone in the presence of metallic palladium, with a reduced palladium-to-cyclohexadecenone weight ratio of below 1:5000, using palladium on activated charcoal as a catalyst, and employing specific reaction conditions such as temperature and hydrogen pressure to achieve high yield and quality.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If very large amounts of hydrogenation catalysts are employed, then the hydrogenation reaction can proceed, but the production cost increases significantly and economic efficiency deteriorates

Engineering Contradiction:
Improvehydrogenation reaction efficiencyVSAvoidproduction cost
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent changes the key parameter of catalyst amount from conventional large amounts to a specific optimized range (0.001-0.01 wt% of substrate weight). This parameter optimization resolves the contradiction by finding the minimum effective catalyst quantity that maintains reaction efficiency while dramatically reducing production costs compared to conventional methods using much larger catalyst amounts.

Inventive Principle:
Principle #35Parameter changes

2Productivity

If conventional hydrogenation methods are used, then production can be carried out, but the yield is insufficient and perfumery quality is not consistently achieved

Engineering Contradiction:
Improveproduction capacityVSAvoidperfumery quality
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent optimizes multiple parameters simultaneously: catalyst amount (0.001-0.01 wt%), temperature (20-100°C), and hydrogen pressure (1-10 atm). This multi-parameter optimization resolves the contradiction by achieving both high productivity through efficient reaction conditions and high manufacturing precision through controlled parameters that prevent side reactions and maintain perfumery quality.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs dynamic reaction conditions where temperature and pressure can be adjusted during the hydrogenation process. This dynamic approach allows the reaction to proceed efficiently while maintaining control over product quality, resolving the contradiction between productivity and manufacturing precision by adapting conditions to optimize both objectives.

Inventive Principle:
Principle #15Dynamics

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 process results in cyclohexadecanone with a high perfumery quality and yield, suitable for industrial production, with the ability to maintain odoriferous quality and achieve almost quantitative yields, making it economically and technically advantageous.

Implementation Method 1

hydrogenation of cyclohexadecenone in the presence of metallic palladium

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

hydrogenation of cyclohexadecenone to produce cyclohexadecanone

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Implementation Method 3

palladium on activated charcoal as a catalyst

Methodology Applied
Scientific EffectAdsorption: Adsorption

Data Source

PatentUS7674765B2Method for producing cyclohexadecanone
Publication Date: 2010.03.09 SYMRISE GMBH & CO KG

AI summary

The invention relates to a method for producing cyclohexadecanone by hydrogenating cyclohexadecenone, to mixtures of aromatic substances, and to products containing the inventive cyclohexadecanone.