Lignin-Based Polyols via Cationic Ring Opening Polymerization

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Solution Overview

Problem

Existing methods for manufacturing lignin-based polyols through ring opening polymerization of oxiranes require high temperatures and pressures, leading to increased production costs and the formation of homopolymer by-products, making them inefficient for industrial scaling.

Innovation Solution

Cationic ring opening polymerization of oxiranes in the presence of lignin and organic solvents catalyzed by acidic catalysts, allowing for mild reaction conditions and reduced homopolymer synthesis, resulting in lignin-based polyols suitable for industrial use.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If basic catalysis is used for ring opening polymerization of oxiranes with lignin, then the reaction proceeds at high temperatures (above 80°C, generally above 100°C, reaching up to 180°C), but this leads to increased production costs and formation of oxirane homopolymer by-products

Engineering Contradiction:
Improvereaction completenessVSAvoidproduction cost
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent changes the fundamental reaction parameter from basic catalysis to cationic ring opening polymerization conditions, enabling the reaction to proceed at mild temperatures (below 80°C, preferably below 60°C, and in some cases at room temperature or even 0°C). This parameter change resolves the contradiction by achieving complete reaction without requiring high temperatures that increase costs and produce homopolymer by-products

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs a composite system combining lignin with oxiranes under cationic polymerization conditions in the presence of organic solvents. This composite approach allows the reaction to proceed selectively at mild temperatures, preventing homopolymer formation while ensuring complete conversion, thus resolving the contradiction between reaction completeness and manufacturing ease

Inventive Principle:
Principle #40Composite materials

2Reliability

If basic catalysis is used for ring opening polymerization of oxiranes with lignin, then the reaction proceeds to completion, but homopolymerization always occurs resulting in a mixture of oxyalkylated lignin and homopolymer

Engineering Contradiction:
Improveconversion rateVSAvoidproduct purity
Core Design Contradiction:
ReliabilityVSManufacturing precision

Solution Approach 1:

The patent changes the catalytic mechanism from basic to cationic, which fundamentally alters the reaction pathway. This parameter change enables selective reaction with lignin hydroxyl groups while preventing oxirane homopolymerization, achieving both complete conversion and high product purity by eliminating the harmful side reaction

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces organic solvents as intermediaries in the cationic ring opening polymerization process. These solvents facilitate the cationic mechanism and help control the reaction selectivity, ensuring that oxiranes react with lignin rather than polymerizing independently, thus achieving both complete conversion and high purity

Inventive Principle:
Principle #24Intermediary (Mediator)

3Productivity

If high reaction temperatures (above 100°C, up to 180°C) are used for ring opening polymerization, then the reaction proceeds efficiently, but propylene oxide reacts above its boiling point requiring pressure conditions

Engineering Contradiction:
Improvereaction efficiencyVSAvoidreaction pressure
Core Design Contradiction:
ProductivityVSStress or pressure

Solution Approach 1:

The patent changes the temperature parameter from high (above 100°C) to mild (below 80°C, preferably below 60°C, and in some cases at room temperature or 0°C). This parameter change resolves the contradiction by enabling efficient reaction without exceeding propylene oxide's boiling point, thus eliminating the need for pressure conditions while maintaining high productivity

Inventive Principle:
Principle #35Parameter changes

4Ease of manufacture

If cationic ring opening polymerization is used instead of basic catalysis, then mild reaction conditions (temperature and pressure) are achieved, but the process requires acidic catalysts and organic solvents

Engineering Contradiction:
Improveproduction costVSAvoidprocess complexity
Core Design Contradiction:
Ease of manufactureVSDevice complexity

Solution Approach 1:

The patent changes the catalytic system from basic to cationic, which simplifies the process by enabling mild temperature and pressure conditions. Although this introduces acidic catalysts and organic solvents, the overall process complexity is reduced by eliminating high-pressure equipment and temperature control systems, making the process easier to manufacture and scale

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 method reduces production costs, minimizes oxirane homopolymer formation, and enhances the reactivity of lignin-based polyols for applications in polyurethanes, polycarbonates, and polyesters, while maintaining high conversion rates.

Implementation Method 1

cationic ring opening polymerization of oxiranes in the presence of lignin and in an organic solvent or mixture of organic solvents using acidic catalysts

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

ring opening polymerization (ROP) of oxiranes in the presence of lignin

Methodology Applied
Scientific EffectRing opening polymerization: Chemical Bonding

Data Source

PatentUS12195491B2Lignin-based polyols
Publication Date: 2025.01.14 FUNDACION TECNALIA RESEARCH & INNOVATION
  • US12195491B2 patent drawing
  • US12195491B2 patent drawing
  • US12195491B2 patent drawing

AI summary

The present invention relates to a process to manufacture lignin-based polyols (LBP) by ring opening polymerization (ROP) of oxiranes in the presence of lignin and in an organic solvent or mixture thereof using acidic catalysts. The LBP are suitable to manufacture polyurethanes, polycarbonates and polyesters.