Solid Acid Catalyst Hydrolysis of Methyl Methoxyacetate

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Current methods for producing glycolic acid and methyl glycolate face challenges such as pollution, high production costs, and low conversion efficiency due to the use of chloroacetic acid hydrolysis, formaldehyde carbonylation, and oxalate hydrogenation/hydrolysis methods, while the potential of methyl methoxyacetate from dimethoxymethane carbonylation has not been fully utilized.

Innovation Solution

A method involving the hydrolysis of methyl methoxyacetate and methoxyacetic acid using a solid acid catalyst, specifically an acidic molecular sieve, to efficiently convert dimethoxymethane into glycolic acid and methyl glycolate, leveraging the carbonylation reaction's low temperature and high atomic economy, and allowing for the reuse of methoxyacetic acid to reduce waste and costs.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If the chloroacetic acid hydrolysis method is used to prepare glycolic acid, then the production process is simple, but it causes heavy pollution and produces a large amount of waste salt

Engineering Contradiction:
Improveproduction process simplicityVSAvoidpollution and waste salt
Core Design Contradiction:
Ease of manufactureVSObject-generated harmful factors

Solution Approach 1:

The patent replaces the harmful chloroacetic acid route with a green carbonylation process using dimethoxymethane and carbon monoxide. The solid acid catalyst enables hydrolysis without producing waste salt, converting an environmentally harmful process into a clean one while maintaining production efficiency

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

Solution Approach 2:

The patent changes the chemical parameters by using different raw materials (dimethoxymethane instead of chloroacetic acid) and different reaction conditions (solid acid catalyst at moderate temperatures). This parameter change eliminates the formation of harmful byproducts while achieving the desired glycolic acid production

Inventive Principle:
Principle #35Parameter changes

2Quantity of substance

If the formaldehyde carbonylation method is used to prepare glycolic acid, then the raw materials are cheap and easily available, but the device is easily corroded and product purification is difficult

Engineering Contradiction:
Improveraw material availabilityVSAvoiddevice corrosion and purification difficulty
Core Design Contradiction:
Quantity of substanceVSDevice complexity

Solution Approach 1:

The patent uses a solid acid catalyst that can be easily replaced and does not require complex corrosion-resistant equipment. The catalyst itself is relatively inexpensive and the reaction conditions are mild enough to avoid severe设备 corrosion, eliminating the need for expensive specialized reactors

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

Solution Approach 2:

The patent changes the reaction parameters by using solid acid catalysts at moderate temperatures and pressures, which reduces equipment corrosion compared to the harsh conditions required by formaldehyde carbonylation. The product purification is simplified by the selective catalysis and easier separation of products

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If the oxalate hydrogenation/hydrolysis method is used to prepare glycolic acid, then the production process can be implemented, but the catalyst has low conversion efficiency and poor stability

Engineering Contradiction:
Improveprocess implementabilityVSAvoidconversion efficiency and catalyst stability
Core Design Contradiction:
Ease of manufactureVSProductivity

Solution Approach 1:

The patent extracts and eliminates the problematic hydrogenation step from the oxalate route. By directly carbonylating dimethoxymethane to form methyl methoxyacetate, then hydrolyzing it, the process removes the unstable hydrogenation catalyst and replaces it with a stable solid acid catalyst system that maintains high conversion efficiency

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent changes the reaction pathway parameters by replacing the hydrogenation/hydrolysis sequence with a carbonylation/hydrolysis sequence. The solid acid catalyst operates at optimal temperatures and pressures that maximize conversion efficiency and stability, overcoming the limitations of the oxalate hydrogenation method

Inventive Principle:
Principle #35Parameter changes

4Ease of manufacture

If methyl methoxyacetate from DMM carbonylation is not applied to prepare glycolic acid, then the DMM carbonylation process remains isolated, but the potential of methyl methoxyacetate is not fully utilized

Engineering Contradiction:
Improveprocess independenceVSAvoidraw material waste
Core Design Contradiction:
Ease of manufactureVSLoss of substance

Solution Approach 1:

The patent merges the DMM carbonylation process with the glycolic acid production process. Methyl methoxyacetate, which would otherwise be a dead-end product, is integrated into the glycolic acid synthesis pathway through solid acid-catalyzed hydrolysis. This combines two processes into a unified production route, eliminating material waste and creating economic value from the carbonylation intermediate

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The patent makes methyl methoxyacetate serve multiple functions: it is both the product of DMM carbonylation and the precursor for glycolic acid production. The solid acid catalyst system enables this dual utility, allowing the same intermediate to fulfill both process roles and preventing material waste

Inventive Principle:
Principle #6Universality (Multi-functionality)

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 provides an environmentally friendly and economical pathway for producing glycolic acid and methyl glycolate, suitable for continuous production in traditional reactors, with high selectivity and conversion rates, expanding the use of methyl methoxyacetate and methoxyacetic acid from the coal chemical industry.

Implementation Method 1

allowing raw materials including the methyl methoxyacetate, the methoxyacetic acid, and water to contact and react with a catalyst to produce the glycolic acid and the methyl glycolate, wherein the catalyst is a solid acid catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

a method for preparing glycolic acid and methyl glycolate through hydrolysis of methyl methoxyacetate and methoxyacetic acid

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Data Source

PatentEP4279477B1Method for preparing glycolic acid and methyl glycolate through hydrolysis of methyl methoxyacetate and methoxyacetic acid
Publication Date: 2024.10.23 DALIAN INSTITUTE OF CHEMICAL PHYSICS CHINESE ACADEMY OF SCIENCES
  • EP4279477B1 patent drawingFigure 1

AI summary

The present application discloses a method for preparing glycolic acid and methyl glycolate through hydrolysis of methyl methoxyacetate and methoxyacetic acid. The method includes: allowing raw materials including methyl methoxyacetate, methoxyacetic acid, and water to contact and react with a catalyst to produce glycolic acid and methyl glycolate, where the catalyst is at least one selected from the group consisting of a solid acid catalyst, a liquid acid catalyst, a solid base catalyst, and a liquid base catalyst. The method for preparing glycolic acid and methyl glycolate in the present application can be implemented by a traditional fixed-bed reactor, tank reactor, or catalytic distillation reactor under an atmospheric pressure, which is very suitable for continuous production. When used in combination with methanol and formaldehyde condensation to prepare dimethoxymethane (DMM) and DMM carbonylation to prepare methyl methoxyacetate, the method in the present application can allow efficient, environmentally-friendly, and economical conversion of methanol (a platform chemical in the coal chemical industry) into glycolic acid and methyl glycolate.