Methacrolein Distillation for MMA Yield and Catalyst Life

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Solution Overview

Problem

Conventional processes for producing methyl methacrylate (MMA) face issues such as low yields, high by-product formation, excessive waste generation, and catalyst deactivation due to elevated water content and formaldehyde reactivity, leading to increased costs and maintenance needs.

Innovation Solution

A novel process involving the preparation of methacrolein from propanal and formaldehyde, followed by distillation in the presence of methanol, and subsequent oxidative esterification with oxygen using a heterogeneous noble metal catalyst, which includes an additional distillation step to reduce methacrylic acid content and extend catalyst life, thereby increasing yield and reducing auxiliary base consumption.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional gas phase oxidation of isobutylene or TBA is used to produce methacrolein, then the process can be implemented on production scale, but yields are below 90% and complex isolation steps are required due to by-product formation

Engineering Contradiction:
Improvemethacrolein yieldVSAvoidisolation process complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent changes the physical state parameter from gas phase to liquid phase oxidation, and modifies the catalyst system from conventional heterogeneous catalysts to a specific cobalt-manganese-bromide catalyst system in liquid phase, achieving higher yields (above 90%) and simplified isolation steps

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent replaces the conventional gas phase mechanical oxidation process with a liquid phase chemical oxidation process using a specific catalyst system, substituting the oxidation mechanism to achieve better product formation and reduce by-products

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

2Ease of operation

If water content is not reduced in methacrolein before oxidative esterification, then the process is simpler, but methacrylic acid formation increases and catalyst service life decreases

Engineering Contradiction:
Improveprocess simplicityVSAvoidcatalyst service life
Core Design Contradiction:
Ease of operationVSDuration of action of stationary object

Solution Approach 1:

The patent performs preliminary water removal from methacrolein before the oxidative esterification step, eliminating the harmful effect of water on catalyst life and methacrylic acid formation, thereby allowing the use of simpler distillation processes without compromising catalyst performance

Inventive Principle:
Principle #10Preliminary action

3Ease of operation

If formaldehyde and conversion products are not removed before oxidative esterification, then the process is simpler, but catalyst deactivation occurs and plant occupation time decreases

Engineering Contradiction:
Improveprocess simplicityVSAvoidplant occupation time
Core Design Contradiction:
Ease of operationVSDuration of action of moving object

Solution Approach 1:

The patent performs preliminary removal of formaldehyde and its conversion products (oligomers and polymers) from methacrolein before oxidative esterification, preventing catalyst deactivation and extending plant occupation time, while using simpler distillation processes

Inventive Principle:
Principle #10Preliminary action

4Productivity

If acid and amine catalysts are used in high amounts for Mannich reaction, then the reaction proceeds efficiently, but large amounts of waste products are generated

Engineering Contradiction:
Improvereaction efficiencyVSAvoidwaste product amount
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The patent changes the catalyst system from conventional acid-amine catalysts requiring high amounts to a catalytic system using minimal amounts of acid and amine, combined with preliminary water removal, achieving both efficient reaction and reduced waste product formation

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 enhances MMA yield, reduces waste and catalyst deactivation, and allows for more efficient operation with lower energy requirements and environmental impact, while minimizing the formation of harmful by-products and extending plant occupation time.

Implementation Method 1

isolating crude methacrolein by distillation in a first distillation column

Methodology Applied
Scientific EffectDistillation: Distillation

Implementation Method 2

oxidatively esterifying the methacrolein obtained from step C) with methanol and oxygen in the presence of a heterogeneous noble metal-containing oxidation catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 3

oxidatively esterifying the methacrolein obtained from step C) with methanol and oxygen

Methodology Applied
Scientific EffectOxidation: Oxidation

Data Source

PatentUS9580374B2Method for producing methacrolein and the conditioning/draining thereof for direct oxidative esterification
Publication Date: 2017.02.28 ROHM GMBH
  • US9580374B2 patent drawing
  • US9580374B2 patent drawing

AI summary

The present invention relates to a process for preparing methyl methacrylate by direct oxidative esterification of methacrolein and the preparation of methacrolein. It is a feature of this novel process that it was possible to distinctly increase the yield and the efficiency of the process compared to the prior art through a sequence of different distillation steps.