Glycolide Depolymerization Impurity Control

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Solution Overview

Problem

The production of high-molecular weight polyglycolic acid from glycolide is hindered by impurities in commercially produced glycolic acid oligomers, including nitrogen-containing substances that slow down the depolymerization reaction and increase viscosity, making it difficult to achieve stable and efficient glycolide production.

Innovation Solution

A process involving repetitive or continuous feeding of glycolic acid oligomer into a depolymerization system with an organic solvent, where the concentration of depolymerization-obstructing substances, such as diglycolic acid and nitrogen-containing compounds, is controlled to no more than 15 wt.% to suppress adverse effects, and the use of a polar organic solvent with specific boiling and molecular weight ranges for efficient glycolide formation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If commercially produced glycolic acid oligomer is used as starting material for glycolide production, then the process can be economically viable, but impurities including nitrogen-containing substances and hydroxyl group-free carboxylic acids adversely affect the depolymerization reaction

Engineering Contradiction:
Improveeconomic viability of glycolide productionVSAvoidadverse effects of impurities on depolymerization
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The patent applies preliminary action by purifying the glycolic acid oligomer before using it in the depolymerization process. Specifically, the oligomer is treated to remove hydroxyl group-free carboxylic acids and nitrogen-containing substances in advance, so that the depolymerization reaction can proceed efficiently without interference from these impurities. This preliminary purification step enables the use of commercially produced oligomer while mitigating the harmful effects of impurities.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent extracts and removes specific impurities from the glycolic acid oligomer mixture. Hydroxyl group-free carboxylic acids and nitrogen-containing substances are selectively extracted or removed through purification processes, leaving behind the desired glycolic acid oligomer that can undergo efficient depolymerization. This extraction approach directly addresses the harmful effects of impurities while maintaining the economic viability of using commercial starting materials.

Inventive Principle:
Principle #2Taking out (Extraction)

2Adaptability or versatility

If impurity carboxylic acids are present in the depolymerization system, then the process can proceed with commercially available oligomer, but the reaction velocity decreases and viscosity increases

Engineering Contradiction:
Improveuse of commercially available glycolic acid oligomerVSAvoidreaction velocity and viscosity control
Core Design Contradiction:
Adaptability or versatilityVSProductivity

Solution Approach 1:

The patent applies parameter changes by controlling the concentration of impurities in the depolymerization system. Through purification treatments, the levels of hydroxyl group-free carboxylic acids and nitrogen-containing substances are reduced to specific ranges that allow efficient depolymerization. This parameter control enables the use of commercially available oligomer while maintaining optimal reaction velocity and viscosity characteristics throughout the process.

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If nitrogen-containing substances are present in the oligomer, then the production process can utilize common glycolic acid synthesis methods, but the depolymerization is obstructed and viscosity increases

Engineering Contradiction:
Improveutilization of common glycolic acid synthesis methodsVSAvoiddepolymerization obstruction by nitrogen-containing substances
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The patent applies preliminary action by removing nitrogen-containing substances from the glycolic acid oligomer before the depolymerization process. Common glycolic acid synthesis methods that may introduce nitrogen-containing impurities are used to produce the oligomer, followed by a purification step that specifically removes these nitrogen-containing substances. This ensures that the depolymerization can proceed reliably without obstruction from nitrogen-containing contaminants.

Inventive Principle:
Principle #10Preliminary 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 approach stabilizes the depolymerization process, allowing for the effective and prolonged production of glycolide by reducing the impact of impurities, thereby improving the efficiency and yield of the glycolide production process.

Implementation Method 1

depolymerizing the glycolic acid oligomer under heating to produce glycolide

Methodology Applied
Scientific EffectDepolymerization:

Implementation Method 2

a depolymerization system containing an organic solvent

Methodology Applied
Scientific EffectSolvation: Solvation

Data Source

PatentUS7812181B2Process for producing glycolide and glycolic acid oligomer for production of glycolide
Publication Date: 2010.10.12 KUREHA CORPORATION

AI summary

Glycolide production through depolymerization of glycolic acid oligomer is stabilized by controlling impurities in the glycolic acid oligomer to allow economical and effective production of glycolide. More specifically, the depolymerization system is controlled to suppress an effective concentration (x+100y wt. %) of depolymerization-obstructing substances calculated as a total of a concentration calculated as diglycolic acid (of x wt. %) of hydroxyl group-free impurity carboxylic acids (A) and 100 times a concentration calculated as ammonia (of y wt. %) of nitrogen-containing substances (B), respectively with respect to the starting glycolic acid oligomer in the depolymerization system, to at most 15 wt. %.