Conjugated Diene Production via Liquid Phase Dehydration

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Solution Overview

Problem

Current methods for producing conjugated dienes have low selectivity and high production costs due to the need for high temperatures and energy-intensive dehydration processes, which can lead to decomposition and inefficiencies.

Innovation Solution

A two-stage process involving the reaction of α-olefin and formaldehyde to produce γ,δ-unsaturated alcohol, followed by a dehydration reaction at 135 to 210°C in the presence of an acidic catalyst, with continuous feeding and intermittent removal of reactants and products, optimizing reaction conditions to enhance selectivity and stability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Temperature

If vapor phase dehydration is performed at high temperatures to vaporize the raw material, then the dehydration reaction can proceed, but a large quantity of heat source is required and decomposition of the γ,δ-unsaturated alcohol may occur

Engineering Contradiction:
Improvereaction temperatureVSAvoidheat source requirement
Core Design Contradiction:
TemperatureVSUse of energy by moving object

Solution Approach 1:

The invention changes the physical state parameter of the reaction system from vapor phase to liquid phase, allowing the dehydration reaction to proceed at lower temperatures (100-180°C) without requiring vaporization of the raw material, thereby reducing heat source requirements and preventing decomposition

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention introduces an acidic catalyst as an intermediary substance that enables the dehydration reaction to proceed efficiently at lower temperatures in the liquid phase, eliminating the need for high temperature vaporization while maintaining reaction effectiveness

Inventive Principle:
Principle #24Intermediary (Mediator)

2Temperature

If vapor phase dehydration is performed under reduced pressure to vaporize the raw material, then the dehydration reaction can proceed, but the method cannot be immediately applied from the industrial viewpoint due to complexity

Engineering Contradiction:
Improvereaction temperatureVSAvoidprocess complexity
Core Design Contradiction:
TemperatureVSDevice complexity

Solution Approach 1:

The invention changes the pressure parameter from reduced pressure to atmospheric or elevated pressure, and changes the phase from vapor to liquid, simplifying the equipment requirements and making the process immediately applicable to industrial continuous production without complex vacuum systems

Inventive Principle:
Principle #35Parameter changes

3Device complexity

If a one-stage reaction from α-olefin and formaldehyde is used to produce conjugated diene, then the production process is simple, but the selectivity of isoprene is low at about 73% and production amount of high boiling point byproducts is high

Engineering Contradiction:
Improveprocess complexityVSAvoidselectivity
Core Design Contradiction:
Device complexityVSManufacturing precision

Solution Approach 1:

The invention segments the one-stage reaction into two distinct stages: first producing γ,δ-unsaturated alcohol from α-olefin and formaldehyde with high selectivity, then dehydrating it to produce conjugated diene. This segmentation improves overall selectivity while maintaining industrial applicability through continuous processing

Inventive Principle:
Principle #1Segmentation

4Use of energy by moving object

If liquid phase dehydration is performed at lower reaction temperatures, then energy consumption is reduced, but the disclosed method cannot be immediately applied from the industrial viewpoint due to lack of continuous reaction method description

Engineering Contradiction:
Improveenergy consumptionVSAvoidindustrial applicability
Core Design Contradiction:
Use of energy by moving objectVSEase of manufacture

Solution Approach 1:

The invention implements continuous liquid phase dehydration where γ,δ-unsaturated alcohol and water are continuously fed into the reactor and the produced conjugated diene and water are continuously removed, enabling industrial-scale production at lower temperatures with improved energy efficiency and manufacturability

Inventive Principle:
Principle #20Continuity of useful action

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 selectivity and stability in producing conjugated dienes, reducing energy consumption and minimizing byproduct formation, thus improving industrial viability.

Implementation Method 1

subjecting the γ,δ-unsaturated alcohol to a dehydration reaction at 135 to 210° C. in the presence of an aqueous solution of an acidic catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS11198657B2Method for producing conjugated diene
Publication Date: 2021.12.14 KURARAY CO LTD
  • US11198657B2 patent drawing
  • US11198657B2 patent drawing
  • US11198657B2 patent drawing

AI summary

A method for producing a conjugated diene, including a step A of allowing an α-olefin and formaldehyde to react with each other to produce a γ,δ-unsaturated alcohol in the presence of an alcohol; and a step B of subjecting the γ,δ-unsaturated alcohol to a dehydration reaction at 135 to 210° C. in the presence of an aqueous solution of an acidic catalyst.