Epsilon Caprolactam Production via Atmospheric Cyclization

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Solution Overview

Problem

Current processes for producing epsilon caprolactam from 6-aminocaproic acid are inefficient, requiring high temperatures, pressures, and catalysts, leading to incomplete conversion and the presence of oligomers in the final product, making them unsuitable for industrial-scale production.

Innovation Solution

A process involving pre-treatment of 6-aminocaproic acid followed by continuous contact with superheated steam and a catalyst in a cyclization reactor at atmospheric pressure, ensuring complete conversion to epsilon caprolactam without oligomer formation, using a phosphoric acid catalyst and a condensation-rectification column for purification.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional processes are used to produce epsilon caprolactam from 6-aminocaproic acid, then high temperatures and pressures are required, but conversion is incomplete and oligomers are formed

Engineering Contradiction:
Improveconversion completenessVSAvoidreaction temperature
Core Design Contradiction:
ReliabilityVSTemperature

Solution Approach 1:

The invention changes the reaction parameters by using atmospheric pressure instead of high pressure, and by introducing a specific catalyst system (phosphoric acid or polyphosphoric acid) to enable complete conversion at lower temperatures (150-250°C), thus resolving the contradiction between conversion completeness and temperature requirements

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention introduces phosphoric acid or polyphosphoric acid as a catalyst intermediary that facilitates the cyclization reaction of 6-aminocaproic acid to epsilon caprolactam, enabling complete conversion without requiring high temperatures and pressures, and preventing oligomer formation

Inventive Principle:
Principle #24Intermediary (Mediator)

2Productivity

If high temperatures and pressures are applied, then reaction rate increases, but energy consumption increases and oligomers are formed

Engineering Contradiction:
Improvereaction rateVSAvoidenergy consumption
Core Design Contradiction:
ProductivityVSUse of energy by moving object

Solution Approach 1:

The catalyst (phosphoric acid or polyphosphoric acid) acts as an intermediary that lowers the activation energy barrier, enabling the reaction to proceed at high rates at atmospheric pressure and moderate temperatures (150-250°C), thus achieving high productivity without high energy consumption

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The invention changes the pressure parameter from high pressure to atmospheric pressure, and uses the catalyst to maintain high reaction rates at these milder conditions, thereby reducing energy consumption while preserving productivity

Inventive Principle:
Principle #35Parameter changes

3Reliability

If conventional catalysts are used, then reaction proceeds at high temperature, but oligomers are formed in the product

Engineering Contradiction:
Improveproduct purityVSAvoidreaction temperature
Core Design Contradiction:
ReliabilityVSTemperature

Solution Approach 1:

The invention uses phosphoric acid or polyphosphoric acid as a selective catalyst intermediary that promotes the desired cyclization reaction to epsilon caprolactam while suppressing side reactions that lead to oligomer formation, achieving high product purity at lower temperatures

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The catalyst provides localized active sites that selectively facilitate the cyclization of 6-aminocaproic acid to epsilon caprolactam, ensuring high product purity by preventing oligomer formation through controlled local reaction pathways

Inventive Principle:
Principle #3Local quality

4Use of energy by moving object

If atmospheric pressure is used, then energy consumption decreases, but complete conversion may not be achieved without catalyst

Engineering Contradiction:
Improveenergy consumptionVSAvoidconversion completeness
Core Design Contradiction:
Use of energy by moving objectVSReliability

Solution Approach 1:

The catalyst (phosphoric acid or polyphosphoric acid) serves as an intermediary that enables complete conversion of 6-aminocaproic acid to epsilon caprolactam at atmospheric pressure by providing an alternative reaction pathway with lower activation energy, thus achieving both low energy consumption and high conversion completeness

Inventive Principle:
Principle #24Intermediary (Mediator)

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 achieves complete conversion of 6-aminocaproic acid to epsilon caprolactam with minimal oligomer formation, reducing energy consumption and enabling industrial-scale production with high product quality.

Implementation Method 1

continuous contact with superheated steam and a catalyst in a cyclization reactor

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

continuous contact with superheated steam

Methodology Applied
Scientific EffectSteam heating: Heating

Implementation Method 3

condensation-rectification column for purification

Methodology Applied
Scientific EffectCondensation: Condensation

Implementation Method 4

condensation-rectification column for purification

Methodology Applied
Scientific EffectRectification: Distillation

Data Source

PatentUS11753372B2Process for the production of epsilon caprolactam from 6-aminocaproic acid
Publication Date: 2023.09.12 AQUAFIL SPA
  • US11753372B2 patent drawing
  • US11753372B2 patent drawing
  • US11753372B2 patent drawing

AI summary

A new process for the production of epsilon caprolactam (CPL) from 6-aminocaproic acid (6-ACA) can be obtained either from traditional petro chemical processes or can be obtained from biochemical processes. With the proposed process, the reaction time for conversion of 6-aminocaproic acid to the Nylon 6 monomer is shorter and significant energy savings are possible which is advantageous for industrial scale production. The conversion of 6-aminocaproic acid to the Nylon 6 monomer runs at atmospheric pressure and in the final product epsilon caprolactam with no oligomers formation of significance is obtained.