Cyclohexanone Production Process with Side-Product Extraction

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Solution Overview

Problem

The conventional process for producing cyclohexanone from phenol results in increased energy consumption and decreased separation efficiency over time, leading to capacity reduction and increased production costs, due to the accumulation of undesirable side-products like dicyclohexyl, which also poses environmental concerns.

Innovation Solution

Rerouting a specific fraction of the product stream containing cyclohexanone and other useful substances, along with undesirable side-products, into a different production process, such as cyclohexane oxidation or adipic acid production, to reduce energy consumption and improve production capacity without wasting valuable products.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional distillation process is used to recover cyclohexanone from phenol, then cyclohexanone can be obtained with high purity (≥99 wt. %), but energy consumption increases and separation efficiency decreases over time due to accumulation of side-products like dicyclohexyl

Engineering Contradiction:
Improvecyclohexanone purityVSAvoidenergy consumption
Core Design Contradiction:
Manufacturing precisionVSUse of energy by moving object

Solution Approach 1:

The patent extracts and removes side-products (particularly dicyclohexyl) from the distillation system by routing a portion of the bottom fraction from the main distillation column to a secondary distillation column. This extraction prevents the accumulation of harmful substances that would otherwise increase energy consumption and reduce separation efficiency in the main column, while maintaining high cyclohexanone purity in the primary product stream.

Inventive Principle:
Principle #2Taking out (Extraction)

2Manufacturing precision

If conventional distillation process is used to recover cyclohexanone from phenol, then cyclohexanone can be obtained with high purity (≥99 wt. %), but production capacity decreases over time due to accumulation of side-products

Engineering Contradiction:
Improvecyclohexanone purityVSAvoidproduction capacity
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The patent extracts and removes side-products (particularly dicyclohexyl) from the distillation system by routing a portion of the bottom fraction from the main distillation column to a secondary distillation column. This extraction prevents the accumulation of harmful substances that would otherwise increase energy consumption and reduce separation efficiency in the main column, while maintaining high cyclohexanone purity in the primary product stream.

Inventive Principle:
Principle #2Taking out (Extraction)

3Manufacturing precision

If conventional distillation process is used to recover cyclohexanone from phenol, then cyclohexanone can be obtained with high purity (≥99 wt. %), but separation efficiency decreases over time due to accumulation of side-products like dicyclohexyl

Engineering Contradiction:
Improvecyclohexanone purityVSAvoidseparation efficiency
Core Design Contradiction:
Manufacturing precisionVSReliability

Solution Approach 1:

The patent extracts and removes side-products (particularly dicyclohexyl) from the distillation system by routing a portion of the bottom fraction from the main distillation column to a secondary distillation column. This extraction prevents the accumulation of harmful substances that would otherwise increase energy consumption and reduce separation efficiency in the main column, while maintaining high cyclohexanone purity in the primary product stream.

Inventive Principle:
Principle #2Taking out (Extraction)

4Use of energy by moving object

If side-products like dicyclohexyl are removed from the process, then energy consumption is reduced and production capacity is maintained, but additional distillation equipment and process complexity are required

Engineering Contradiction:
Improveenergy consumptionVSAvoiddistillation system complexity
Core Design Contradiction:
Use of energy by moving objectVSDevice complexity

Solution Approach 1:

The patent extracts and removes side-products (particularly dicyclohexyl) from the distillation system by routing a portion of the bottom fraction from the main distillation column to a secondary distillation column. This extraction prevents the accumulation of harmful substances that would otherwise increase energy consumption and reduce separation efficiency in the main column, while maintaining high cyclohexanone purity in the primary product stream.

Inventive Principle:
Principle #2Taking out (Extraction)

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 approach effectively reduces the accumulation of side-products like dicyclohexyl, maintaining low energy consumption and high production capacity, while minimizing environmental impact and avoiding the need for additional recovery facilities.

Implementation Method 1

separating at least part of the product stream, or at least part of the product stream from which one or more components having a lower boiling point than cyclohexanone have been removed, into a first fraction comprising cyclohexanone and a second fraction comprising phenol, cyclohexanol and RSP, using distillation

Methodology Applied
Scientific EffectDistillation: Distillation

Implementation Method 2

hydrogenating phenol to form a product stream comprising cyclohexanone, phenol and side-products, including cyclohexanol and recycling side product (RSP)

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Data Source

PatentUS8389773B2Cyclohexanone production process with impurities removal
Publication Date: 2013.03.05 CAP III
  • US8389773B2 patent drawing
  • US8389773B2 patent drawing
  • US8389773B2 patent drawing

AI summary

The present invention relates to a method for preparing cyclohexanone from phenol in a first process, the first process being a cyclohexanone production process comprising hydrogenating phenol to form a product stream comprising cyclohexanone, phenol and side-products (RSP), including cyclohexanol and undesirable side-product; separating at least part of the product stream having a lower boiling point than cyclohexanone have been removed, into a first fraction comprising cyclohexanone and a second fraction comprising phenol, cyclohexanol and RSP, using distillation; and separating the second fraction into a third fraction, rich in cyclohexanol and comprising RSP, and a fourth fraction, rich in phenol and comprising RSP, using distillation. The invention further relates to an installation for carrying out a method of the invention.