Methacrylic Acid Ester Hydrolysis via Heterogeneous Catalysis

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Solution Overview

Problem

Current methods for producing methacrylic acid face challenges such as low yields, high energy consumption, and the generation of waste acid, with existing processes often requiring multiple steps and intermediate isolation, which complicates and economizes the production.

Innovation Solution

A process involving the conversion of acetone cyanohydrin to methacrylamide, followed by esterification with alcohols to form methacrylic acid esters, and subsequent hydrolysis using heterogeneous catalysts to produce methacrylic acid, optimizing the methacrylic acid ester/H2O ratio and eliminating the need for sulfuric acid, thereby reducing waste and energy usage.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional oxidation processes are used to produce methacrylic acid from hydrocarbon gases, then the production process is straightforward, but the yields are rather low

Engineering Contradiction:

ImproveyieldVSAvoidprocess complexity

Core Design Contradiction:

ProductivityVSEase of manufacture

Solution Approach 1:

The process is divided into multiple distinct steps: hydrolysis of acetone cyanohydrin to methacrylamide, esterification to methacrylic acid esters, and hydrolysis to methacrylic acid. Each step is optimized independently to maximize overall yield while maintaining operational simplicity

Inventive Principle:

Principle #1Segmentation

Solution Approach 2:

Methacrylamide and methacrylic acid esters are used as intermediate compounds to transform the starting material into the final product through controlled reactions, enabling higher yields compared to direct oxidation methods

Inventive Principle:

Principle #24Intermediary (Mediator)

2Manufacturing precision

If multiple reaction steps with intermediate isolation are implemented, then the purity of methacrylic acid is improved, but the process complexity and manufacturing costs increase

Engineering Contradiction:

ImprovepurityVSAvoidprocess complexity

Core Design Contradiction:

Manufacturing precisionVSDevice complexity

Solution Approach 1:

The esterification and hydrolysis steps are combined in a continuous process where methacrylic acid esters are directly hydrolyzed to methacrylic acid without isolating intermediates, reducing equipment complexity while maintaining high purity through controlled reaction conditions and heterogeneous catalysis

Inventive Principle:

Principle #5Merging (Combining)

Solution Approach 2:

Temperature, pressure, and catalyst type are optimized for each reaction step to achieve high purity methacrylic acid. Heterogeneous catalysts are used to facilitate separation and reduce contamination, enabling high purity without complex isolation procedures

Inventive Principle:

Principle #35Parameter changes

3Productivity

If sulfuric acid is used as catalyst in the hydrolysis step, then the reaction efficiency is improved, but waste acid production and corrosion issues increase

Engineering Contradiction:

Improvereaction efficiencyVSAvoidwaste acid production

Core Design Contradiction:

ProductivityVSObject-generated harmful factors

Solution Approach 1:

Heterogeneous catalysts with extended service life are used instead of consumable sulfuric acid, eliminating the need for continuous acid addition and neutralization, thereby preventing waste acid generation while maintaining high reaction efficiency through catalytic activity

Inventive Principle:

Principle #27Cheap short-living objects (Disposable)

Solution Approach 2:

The catalyst system is designed to avoid the harmful byproducts of sulfuric acid neutralization. By using heterogeneous catalysts, the process eliminates salt waste and corrosion issues while maintaining productivity, converting a potentially harmful chemical approach into a cleaner catalytic process

Inventive Principle:

Principle #22Blessing in disguise (Convert harm into benefit)

4Speed

If high temperatures are used in the reaction steps, then the reaction rate is improved, but the energy consumption increases

Engineering Contradiction:

Improvereaction rateVSAvoidenergy consumption

Core Design Contradiction:

SpeedVSUse of energy by moving object

Solution Approach 1:

The reaction temperature is optimized to balance reaction rate and energy consumption. Heterogeneous catalysts enable the reactions to proceed at moderate temperatures with high efficiency, avoiding excessive energy input while maintaining productive reaction rates throughout the multi-step process

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 achieves higher yields and purities of methacrylic acid (>99.5%) with reduced waste acid production and energy consumption, simplifying the industrial-scale implementation and minimizing corrosion issues.

Implementation Method 1

Hydrolysis of the methacrylic acid ester to methacrylic acid using heterogeneous catalysts

Methodology Applied

Scientific EffectCatalysis: Catalysis

Implementation Method 2

Esterification of methacrylamide in the presence of alkanols to the corresponding methacrylic acid ester

Methodology Applied

Scientific EffectEsterification: Chemical Bonding

Implementation Method 3

Conversion of acetone cyanohydrin to methacrylamide

Methodology Applied

Scientific EffectHydrolysis: Hydrolysis

Data Source

PatentEP2714640B1Process for preparing methacrylic acid

Publication Date: 2018.08.29 ROHM GMBH

Figure 1

AI summary

The present invention relates to a process for preparing methacrylic acid based on the hydrolysis of methacrylic esters.