Glycolide Production via Mild Oxidation of Glycolaldehyde Dimer

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Solution Overview

Problem

Current methods for producing glycolide, a precursor for Poly(Glycolic Acid) (PGA), are inefficient and require high temperatures and pressures, leading to increased costs and energy consumption, and lack sustainable bio-based sources.

Innovation Solution

A novel process that converts glycolaldehyde dimer into glycolide using an oxidation step with a mild oxidizing agent under atmospheric pressure and moderate temperature, favoring the formation of glycolide over monomerization, allowing for a single reaction step in a single reactor with high yield and selectivity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If the state of the art two-step process is used to produce glycolide, then glycolide can be obtained through polycondensation and depolymerization, but high temperatures and sub-atmospheric pressures are required which increase energy consumption and equipment costs

Engineering Contradiction:
Improveglycolide productionVSAvoidenergy consumption
Core Design Contradiction:
ReliabilityVSUse of energy by moving object

Solution Approach 1:

The invention changes the reaction parameters from high temperature (190-250°C) and sub-atmospheric pressure to mild temperature (20-100°C) and atmospheric pressure. This is achieved by using a one-step oxidation process with oxidizing agents like hydrogen peroxide or oxygen in the presence of catalysts, fundamentally altering the process conditions to reduce energy consumption while maintaining reliable glycolide production

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention replaces the mechanical/thermal system (high temperature heating and vacuum pressure reduction equipment) with a chemical system using oxidation reactions. Instead of relying on thermal energy input and pressure control, the process uses chemical oxidation with catalysts to achieve glycolide formation under mild conditions, substituting mechanical/thermal processes with chemical transformations

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

2Reliability

If the state of the art two-step process is used to produce glycolide, then glycolide can be obtained through polycondensation and depolymerization, but high-pressure equipment is required which increases equipment costs

Engineering Contradiction:
Improveglycolide productionVSAvoidequipment requirements
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The invention changes the pressure parameter from sub-atmospheric (vacuum) conditions to atmospheric pressure operation. The oxidation-based one-step process does not require vacuum equipment for water removal or pressure control, eliminating the need for complex vacuum systems and high-pressure equipment while ensuring reliable glycolide production under simple atmospheric conditions

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention extracts and eliminates the need for complex high-pressure and vacuum equipment from the process. By using oxidation reactions that proceed readily at atmospheric pressure without requiring vacuum conditions for water removal, the process removes the dependency on expensive and complex pressure control equipment, simplifying the overall device requirements

Inventive Principle:
Principle #2Taking out (Extraction)

3Use of energy by moving object

If a one-step oxidation process is used to produce glycolide from glycolaldehyde dimer, then energy consumption is reduced and equipment requirements are simplified, but the method requires new reaction conditions and oxidizing agents

Engineering Contradiction:
Improveenergy consumptionVSAvoidreaction conditions
Core Design Contradiction:
Use of energy by moving objectVSAdaptability or versatility

Solution Approach 1:

The invention uses oxidizing agents (hydrogen peroxide, oxygen, or organic peracids) that can serve multiple functions: they oxidize the glycolaldehyde dimer to glycolide, and in the case of hydrogen peroxide and oxygen, they are environmentally benign and leave no harmful residues. This multi-functionality allows the process to operate under mild conditions with reduced energy consumption while maintaining versatility in reagent selection

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

Solution Approach 2:

The invention changes the reaction conditions to mild temperature (20-100°C) and atmospheric pressure, which are more adaptable and easier to control than the previous high-temperature vacuum conditions. These new parameters reduce energy consumption and simplify equipment requirements while the use of catalysts and various oxidizing agents provides flexibility and adaptability in the reaction system

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 reduces energy consumption, eliminates the need for high-pressure equipment, and utilizes bio-based resources, providing a more efficient and sustainable method for producing glycolide, improving the yield and stability of the glycolide product.

Implementation Method 1

The process uses glycolaldehyde (GA) dimer as reactant. According to the present invention a novel process is provided for producing glycolide, which process comprises an oxidation step of contacting glycolaldehyde dimer with an oxidizing agent to produce a glycolide product.

Methodology Applied
Scientific EffectOxidation: Oxidation

Data Source

PatentUS11603362B2Process for preparing glycolide
Publication Date: 2023.03.14 HALDOR TOPSOE AS
  • US11603362B2 patent drawing
  • US11603362B2 patent drawing
  • US11603362B2 patent drawing

AI summary

According to the present invention a process is provided for producing glycolide which comprises contacting glycolaldehyde dimer with an oxidizing agent to produce a glycolide product. Preferably, the process is carried out in an aprotic environment, such as in a reaction mixture comprising the glycolaldehyde dimer, the oxidizing agent, the glycolide product and an aprotic solvent.