Cyclic Polyester Oligomer Distillation-Assisted Cyclization

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Solution Overview

Problem

Current processes for producing cyclic polyester oligomers suffer from high melting points of oligomeric species, leading to degradation and discoloration during polymerization, and require complex equipment and harsh conditions, which are not suitable for large-scale commercial operations.

Innovation Solution

A distillation-assisted cyclization (DA-C) process that separates and removes diol byproducts during the cyclization step, allowing for the production of cyclic polyester oligomers with furanic units under milder conditions, reducing the need for complex equipment and minimizing degradation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional polycondensation reactions are used to produce cyclic polyester oligomers, then polymerization can be achieved, but high temperatures and harsh conditions are required causing degradation and discoloration of thermally sensitive oligomers

Engineering Contradiction:

Improvepolymerization completionVSAvoiddegradation and discoloration

Core Design Contradiction:

ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The invention changes the reaction parameters by using ring-opening polymerization instead of conventional polycondensation, enabling the reaction to proceed at lower temperatures (below the melting point of cyclic oligomers) while achieving complete polymerization without degradation or discoloration of the thermally sensitive furanic units

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention utilizes the melting phase transition of cyclic oligomers as a process control mechanism, heating the reaction mixture to melt the solid cyclic oligomers (e.g., cyclic dimer with melting point of about 370°C) to enable homogeneous reaction, then maintaining the reaction at temperatures below the melting point to prevent degradation during polymerization

Inventive Principle:

Principle #36Phase transitions

2Ease of operation

If high temperatures are used to melt cyclic oligomers prior to polymerization, then polymerization can proceed, but degradation and discoloration occur

Engineering Contradiction:

Improvepolymerization processabilityVSAvoiddegradation and discoloration

Core Design Contradiction:

Ease of operationVSObject-affected harmful factors

Solution Approach 1:

The invention changes the temperature parameter strategy by separating the melting step (heating to melt solid cyclic oligomers) from the polymerization step (maintaining temperature below melting point), thereby achieving processability without exposing the thermally sensitive furanic units to degrading high temperatures

Inventive Principle:

Principle #35Parameter changes

3Manufacturing precision

If conventional purification methods (chromatography, distillation, extraction) are used to remove impurities from cyclic polyester oligomers, then purity can be improved, but large quantities of solvents, long times, and complex equipment are required

Engineering Contradiction:

Improveoligomer purityVSAvoidpurification equipment complexity

Core Design Contradiction:

Manufacturing precisionVSDevice complexity

Solution Approach 1:

The invention extracts and removes unwanted linear oligomeric species through selective precipitation by adding water to the reaction mixture, causing the linear species to precipitate while the desired cyclic oligomers remain in solution, thereby simplifying purification equipment requirements while achieving high purity

Inventive Principle:

Principle #2Taking out (Extraction)

Solution Approach 2:

The invention changes the purification approach by using temperature and solvent addition parameters to control the solubility and precipitation behavior of different oligomeric species, enabling simple filtration-based purification instead of complex chromatography or distillation equipment

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

The DA-C process achieves higher purity and yield of cyclic oligomers with lower viscosity and shorter reaction times, enabling more efficient and cost-effective production suitable for large-scale commercial operations.

Implementation Method 1

A distillation-assisted cyclization (DA-C) process that separates and removes diol byproducts during the cyclization step

Methodology Applied

Scientific EffectEvaporation: Evaporation

Implementation Method 2

A distillation-assisted cyclization (DA-C) process that separates and removes diol byproducts during the cyclization step

Methodology Applied

Scientific EffectDistillation: Distillation

Data Source

PatentUS11149111B2Process to prepare a cyclic oligomer and a cyclic oligomer obtainable thereby and a process to polymerize it

Publication Date: 2021.10.19 SULZER MANAGEMENT AG

AI summary

A process to prepare a (iv) cyclic polyester oligomer composition includes a cyclic polyester oligomer having furanic units and two to five repeat units. The process includes (a) reacting a monomer composition including: (i) a bifunctional furan-derivative and (ii) a diol in an linear oligomerization step to produce a (iii) linear oligomer composition including a linear oligomer species, (b) reacting the (iii) linear oligomer composition in a distillation-assisted cyclization (DA-C) step to form a (iv) cyclic polyester oligomer composition and a (v) diol byproduct. The (v) diol byproduct is removed by evaporation in the distillation-assisted cyclization (DA-C) step.