Direct Synthesis of Methacrolein from Ethers

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Solution Overview

Problem

Current (meth)acrolein synthesis processes face challenges such as high environmental impact, significant investments, and operating costs due to reliance on fossil-based raw materials and energy-intensive dehydration reactions, with limitations in scalability and catalyst durability.

Innovation Solution

A direct synthesis process using a reactive mixture of ethers or hemiacetals derived from linear alcohols, combined with oxygen and a non-reactive diluent gas, in the presence of a molybdenum-based oxidation catalyst, facilitating a one-step reaction at controlled temperatures and pressures to produce (meth)acrolein with improved selectivity and reduced water generation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Object-affected harmful factors

If glycerol dehydration route is used to produce acrolein, then renewable raw material is utilized, but catalyst deactivates quickly requiring regular regenerations and additional investment costs

Engineering Contradiction:
Improveenvironmental impactVSAvoidcatalyst durability
Core Design Contradiction:
Object-affected harmful factorsVSReliability

Solution Approach 1:

The invention changes the chemical parameters by using different raw materials (ethers and acetals instead of glycerol) and modifies the reaction conditions (gas phase oxidation at 200-400°C) to achieve a process that produces less water and avoids catalyst deactivation issues while maintaining environmental benefits

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention extracts the problematic dehydration step from the process by using oxidation of ethers/acetals instead, thereby eliminating the catalyst deactivation issue associated with glycerol dehydration while retaining the ability to produce acrolein from renewable sources

Inventive Principle:
Principle #2Taking out (Extraction)

2Productivity

If glycerol dehydration is performed in gas phase, then acrolein is produced, but energy consumption is high due to fossil fuel dependency

Engineering Contradiction:
Improveacrolein productionVSAvoidenergy consumption
Core Design Contradiction:
ProductivityVSUse of energy by moving object

Solution Approach 1:

The invention changes the energy parameters by conducting the reaction in the liquid phase at milder temperatures (20-150°C) compared to conventional gas phase dehydration, thereby reducing energy consumption and fossil fuel dependency while maintaining productivity

Inventive Principle:
Principle #35Parameter changes

3Productivity

If aldolization route using acetaldehyde and formalin is used, then acrolein is synthesized, but significant investment is required for synthesis units and raw material storage

Engineering Contradiction:
Improveacrolein synthesisVSAvoidsynthesis unit complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The invention extracts and eliminates the complex multi-step aldolization process by directly oxidizing ethers or acetals to acrolein in a single step, thereby removing the need for separate synthesis units for acetaldehyde and formalin and simplifying the overall process configuration

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

Instead of building up acrolein through sequential aldolization steps from simpler molecules, the invention inverts the approach by directly oxidizing carbon-oxygen bonded compounds (ethers/acetals) to acrolein, thereby simplifying the process flow and reducing equipment requirements

Inventive Principle:
Principle #13The other way round (Inversion)

4Productivity

If oxidation of propylene is used to produce acrolein, then acrolein is manufactured, but fossil raw materials are consumed and transport costs increase

Engineering Contradiction:
Improveacrolein productionVSAvoidenvironmental impact
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The invention changes the raw material parameters by using renewable-derived ethers and acetals (from C1-C3 alcohols) instead of fossil-based propylene, thereby reducing environmental impact and transport costs while maintaining acrolein production capability

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

This process simplifies the synthesis by reducing investment and operating costs, minimizing water production, and enhancing product concentration, while using renewable raw materials to lower environmental impact.

Implementation Method 1

in the presence of a solid oxidation catalyst chosen from molybdenum-based catalysts

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

reaction of a reactive mixture comprising at least one compound chosen from ethers, acetals or hemiacetals derived from linear alcohols, oxygen and a non-reactive diluent gas

Methodology Applied
Scientific EffectOxidation: Oxidation

Data Source

PatentEP3126318B1Process for direct synthesis of (METH)acrolein from ethers and/or acetals
Publication Date: 2018.03.21 ARKEMA FRANCE SA

AI summary

The subject matter of the present invention is a process for direct synthesis of (meth)acrolein from a reactive mixture comprising at least one compound chosen from ethers, acetals or hemiacetals derived from linear alcohols comprising from 1 to 3 carbon atoms. Examples of compounds are dimethyl ether, diethyl ether, methyl ethyl ether, dimethoxymethane, diethoxymethane, dipropoxymethane, 1,1-dimethoxyethane or 1,1-diethoxyethane. The process of the invention comprises two successive phases: oxidation then aldol condensation, which can be carried out in the presence of a solid oxidation catalyst chosen from molybdenum-based catalysts and optionally of an aldol condensation catalyst. These two phases are carried out in a reaction system comprising a single reactor or optionally two reactors in cascade.