Cyclic Ester Production via Sulfonic Acid Stabilizer

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Solution Overview

Problem

Methods for producing cyclic esters through depolymerization often result in high impurity content in the distilled glycolide, leading to inefficiencies and reduced purity.

Innovation Solution

Incorporating a sulfonic acid compound as a thermal stabilizer in the production process, alongside a polyalkylene glycol diether and a solubilizing agent, to suppress the formation of by-products and enhance production efficiency during the depolymerization of aliphatic polyesters.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If depolymerization of aliphatic polyester is performed to produce cyclic ester, then cyclic ester is obtained, but a large quantity of impurity is contained in the distilled glycolide

Engineering Contradiction:
Improvepurity of cyclic esterVSAvoidformation of by-products
Core Design Contradiction:
Manufacturing precisionVSObject-generated harmful factors

Solution Approach 1:

A sulfonic acid compound is introduced as an intermediary substance (thermal stabilizer) that mediates between the aliphatic polyester and the depolymerization process. This stabilizer suppresses unwanted side reactions and by-product formation while enabling the main depolymerization reaction to proceed efficiently, thereby improving cyclic ester purity without sacrificing production rate

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The invention changes the chemical composition parameter of the reaction system by adding a sulfonic acid compound. This parameter change modifies the reaction pathway to favor cyclic ester formation while suppressing by-product generation, resolving the contradiction between purity and production efficiency

Inventive Principle:
Principle #35Parameter changes

2Productivity

If conventional depolymerization method is used, then production process is simple, but production efficiency is low due to high impurity content

Engineering Contradiction:
Improveproduction efficiency of cyclic esterVSAvoidpurity of distilled glycolide
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The sulfonic acid compound acts as a mediating agent that enhances both productivity and purity simultaneously. By suppressing by-product formation during depolymerization, it enables higher production efficiency while maintaining high cyclic ester purity, resolving the contradiction between these two parameters

Inventive Principle:
Principle #24Intermediary (Mediator)

3Stability of the object's composition

If solubilizing agent is added to enhance solubility of aliphatic polyester, then solubility is improved, but specific compound names relating to sulfones or sulfonic acids are not described and effect on by-products is unknown

Engineering Contradiction:
Improvesolubility of aliphatic polyesterVSAvoidcomplexity of production process
Core Design Contradiction:
Stability of the object's compositionVSDevice complexity

Solution Approach 1:

The sulfonic acid compound serves multiple functions simultaneously: it acts as a thermal stabilizer to suppress by-product formation, and also functions as a solubilizing agent to enhance polyester solubility. This multi-functionality reduces the need for separate additives and simplifies the overall production process while achieving both improved solubility and reduced impurities

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

The method effectively reduces the formation of by-products in the cyclic ester, thereby improving production efficiency and maintaining high purity levels of the resulting glycolide.

Implementation Method 1

use of a sulfonic acid compound as a thermal stabilizer can suppress formation of by-products to be contained in a cyclic ester

Methodology Applied
Scientific EffectThermal stabilization:

Implementation Method 2

a polyalkylene glycol diether represented by Formula (1) below and having a boiling point from 230 to 450° C. and a molecular weight from 150 to 450

Methodology Applied
Scientific EffectSolvation: Solvation

Implementation Method 3

a step (II) of producing a mixture (II) in a state of solution by heating the mixture (I) under normal pressure or reduced pressure to a temperature at which depolymerization reaction of the aliphatic polyester starts

Methodology Applied
Scientific EffectHeating: Heating

Implementation Method 4

a step (III) of producing a distillate (III) by continuing the heating of the mixture (II) and distilling a cyclic ester formed by the depolymerization reaction together with the polyalkylene glycol diether

Methodology Applied
Scientific EffectDistillation: Distillation

Data Source

PatentUS11078179B2Method for producing cyclic ester
Publication Date: 2021.08.03 KUREHA CORPORATION
  • US11078179B2 patent drawing
  • US11078179B2 patent drawing
  • US11078179B2 patent drawing

AI summary

In a method for producing a cyclic ester according to an embodiment of the present invention, a mixture (I) containing an aliphatic polyester, a specific polyalkylene glycol diether, and a sulfonic acid compound as a thermal stabilizer is prepared and heated in predetermined conditions to obtain a mixture (II) in a state of solution. Furthermore, heating of the mixture (II) is continued to distill, together with the polyalkylene glycol diether, a cyclic ester formed by the depolymerization reaction, and thus a distillate (III) is obtained. The cyclic ester is recovered from the distillate (III). At this time, a specific solubilizing agent is added to at least one of the mixture (I) or (II). In this production method, the sulfonic acid compound as the thermal stabilizer is contained in the mixtures (I) and (II) and the distillate (III).