Solid Acid Catalyst for Cyclohexanone Condensation

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Solution Overview

Problem

Current processes for producing 2-(cyclohex-1′-enyl)cyclohexanone using various catalysts face issues such as high equipment corrosion, excessive energy consumption, low yield, and environmental concerns due to the use of strong acids, and require high reaction temperatures, which are costly and inefficient.

Innovation Solution

A novel solid acidic catalyst represented by the empirical formula AlxSyOz is used for the auto-condensation of cyclohexanone, prepared by soaking Al(OH)3 in a sulfuric acid solution and calcining it at 450°C, which is added in a 2% weight ratio to the reaction solution and operates at temperatures between 100°C to 160°C, allowing for improved yield and reduced equipment corrosion.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If sulfuric acid is used as catalyst, then conversion of cyclohexanone is improved, but equipment corrosion increases and environmental pollution occurs

Engineering Contradiction:
Improveconversion of cyclohexanoneVSAvoidequipment corrosion
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The patent replaces expensive, corrosive sulfuric acid with a solid acid catalyst (amorphous silica-alumina) that can be easily disposed of or regenerated. The solid catalyst avoids equipment corrosion issues while maintaining catalytic activity, and can be separated from the reaction mixture by simple filtration, eliminating the need for complex neutralization and waste treatment systems.

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

Solution Approach 2:

The patent changes the physical state of the catalyst from liquid (sulfuric acid) to solid (amorphous silica-alumina), fundamentally altering the catalyst's properties. This phase change eliminates corrosion problems while maintaining catalytic function. The solid catalyst also changes the reaction conditions, allowing operation at lower temperatures and simpler equipment design.

Inventive Principle:
Principle #35Parameter changes

2Speed

If concentrated sulfuric acid is used as catalyst, then reaction rate is improved, but side reactions increase and by-products increase

Engineering Contradiction:
Improvereaction rateVSAvoidside reactions
Core Design Contradiction:
SpeedVSObject-generated harmful factors

Solution Approach 1:

The patent changes the catalyst from concentrated sulfuric acid to solid amorphous silica-alumina, which fundamentally alters the reaction pathway. The solid catalyst provides a more controlled catalytic surface that promotes the desired condensation reaction while minimizing unwanted side reactions. This parameter change allows the reaction to proceed at lower temperatures with better selectivity.

Inventive Principle:
Principle #35Parameter changes

3Object-generated harmful factors

If diluted sulfuric acid is used as catalyst, then side reactions are reduced, but water content increases and convertibility decreases

Engineering Contradiction:
Improveside reactionsVSAvoidconvertibility of reaction
Core Design Contradiction:
Object-generated harmful factorsVSProductivity

Solution Approach 1:

The patent replaces diluted sulfuric acid with a solid acid catalyst that does not require water for dilution. The solid catalyst maintains high catalytic activity without introducing excess water into the system, thereby avoiding the trade-off between reducing side reactions and maintaining convertibility. The solid catalyst can be easily separated and regenerated.

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

4Productivity

If high reaction temperature is used, then conversion of cyclohexanone is improved, but energy consumption increases

Engineering Contradiction:
Improveconversion of cyclohexanoneVSAvoidenergy consumption
Core Design Contradiction:
ProductivityVSUse of energy by moving object

Solution Approach 1:

The patent changes the catalyst type, which fundamentally alters the temperature requirements of the reaction. The solid acid catalyst (amorphous silica-alumina) is active at lower temperatures compared to traditional sulfuric acid catalysts. This parameter change allows the reaction to proceed with high conversion at reduced temperatures, thereby decreasing energy consumption while maintaining productivity.

Inventive Principle:
Principle #35Parameter changes

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 process achieves higher conversion and selectivity of 2-(cyclohex-1′-enyl)cyclohexanone with increased reaction rate and yield, while maintaining mild reaction conditions and reducing equipment corrosion, making it a more efficient and cost-effective method compared to existing technologies.

Implementation Method 1

a process for producing 2-(cyclohex-1′-enyl)cyclohexanone by an auto-condensation of cyclohexanone at a certain temperature in the presence of a certain solid acidic catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

the auto-condensation of cyclohexanone will produce two kinds of resonance isomers (I) and (II), of which 2-(cyclohex-1′-enyl)cyclohexanone (II) is usually predominant

Methodology Applied
Scientific EffectAcid-catalyzed condensation: Chemical Bonding

Implementation Method 3

prepared by soaking Al(OH)3 in a sulfuric acid solution and calcining it at 450°C

Methodology Applied
Scientific EffectAbsorption: Absorption (physical)

Implementation Method 4

prepared by soaking Al(OH)3 in a sulfuric acid solution and calcining it at 450°C

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Implementation Method 5

prepared by soaking Al(OH)3 in a sulfuric acid solution and calcining it at 450°C

Methodology Applied
Scientific EffectCalcination: Heat Treatment

Data Source

PatentUS8519192B2Process for producing 2-(cyclohex-1'-enyl)cyclohexanone
Publication Date: 2013.08.27 CHINA PETROCHEM DEVMENT
  • US8519192B2 patent drawing

AI summary

The present invention discloses a process for producing 2-(cyclohex-1′-enyl)cyclohexanone by an auto-condensation of cyclohexanone at a certain temperature in the presence of a certain solid acidic catalyst.