Solvent-Free Phenol Hydrogenation for Cyclohexanone Selectivity

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Solution Overview

Problem

Conventional hydrogenation processes for producing cyclohexanones from phenols suffer from moderate selectivity and require solvent disposal, leading to environmental concerns and increased energy consumption.

Innovation Solution

A method involving the hydrogenation of phenols in the presence of a catalyst comprising a catalytically active transition metal, a metal oxide support, and an inorganic metal salt promoter, conducted without a solvent, to achieve high selectivity and efficiency in producing cyclohexanones.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional hydrogenation processes are used to produce cyclohexanones from phenols, then the production process can be implemented, but the selectivity for cyclohexanone over cyclohexanol is only moderate

Engineering Contradiction:
ImproveselectivityVSAvoidyield
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The patent changes multiple parameters of the hydrogenation process including using a specific catalyst composition (Pd on alumina with Cs2CO3 promoter), optimizing reaction temperature (80-250°C), pressure (1-10 atm), and solvent-free conditions to achieve high selectivity (85-95%) and yield (90-98%) simultaneously

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs a composite catalyst system consisting of palladium metal dispersed on alumina support with cesium carbonate as a promoter, creating a multi-component catalytic system that enhances both selectivity and activity for the hydrogenation reaction

Inventive Principle:
Principle #40Composite materials

2Ease of manufacture

If conventional hydrogenation processes are used, then the reaction can proceed, but solvent disposal is required which causes environmental concerns

Engineering Contradiction:
Improveprocess simplicityVSAvoidenvironmental impact
Core Design Contradiction:
Ease of manufactureVSObject-generated harmful factors

Solution Approach 1:

The patent extracts and eliminates the solvent component from the hydrogenation process, conducting the reaction in a solvent-free system where phenol is hydrogenated directly without requiring additional solvents, thereby eliminating solvent disposal requirements and environmental concerns

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The reaction system uses the reactants themselves (phenol and hydrogen) without requiring external solvents, making the system self-sufficient and eliminating the need for solvent management and disposal infrastructure

Inventive Principle:
Principle #25Self-service

3Temperature

If steam is used for heating in the hydrogenation process, then the reaction can be maintained, but energy consumption increases

Engineering Contradiction:
Improvereaction temperatureVSAvoidenergy consumption
Core Design Contradiction:
TemperatureVSUse of energy by moving object

Solution Approach 1:

The patent replaces the conventional steam heating system with direct electrical heating of the reactor, substituting a thermal-mechanical energy transfer system with a more efficient direct electrical-to-thermal conversion system, thereby reducing energy losses and overall energy consumption

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

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 high conversion rates and selectivity for cyclohexanones while minimizing waste generation and energy consumption, thereby improving the efficiency and environmental sustainability of the process.

Implementation Method 1

The catalyst includes a catalytically active transition metal, a support containing an oxide, and a promoter containing an inorganic metal salt

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

The catalyst includes a catalytically active transition metal, a support containing an oxide (e.g., a metal oxide)

Methodology Applied
Scientific EffectAdsorption: Adsorption

Implementation Method 3

reducing an optionally substituted phenol in the presence of a catalyst using hydrogen in a reactor

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Data Source

PatentEP3323801B1Methods of preparing cyclohexanone and derivatives
Publication Date: 2020.06.24 INTERNATIONAL FLAVORS & FRAGRANCES INC
  • EP3323801B1 patent drawing
  • EP3323801B1 patent drawing

AI summary

The present invention provides a method of preparing an optionally substituted cyclohexanone comprising contacting an optionally substituted phenol and a catalyst in a hydrogen atmosphere. High yield and selectivity are achieved in a substantially solvent free system.