Waste Rubber Depolymerization to Selective C5-C7 Cycloalkenes

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Solution Overview

Problem

Chemical recycling of waste rubber is limited by complicated technology, harsh reaction conditions, low selectivity, and yield, and mechanical recycling deteriorates rubber properties, restricting its use to low-performance applications.

Innovation Solution

Depolymerization of double bond-containing polymers using an isomerization catalyst and a metathesis catalyst with a N-heterocyclic carbene ligand to produce (C5-C7)cycloalkene, employing a ruthenium complex and phosphine ligand catalysts under controlled conditions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Loss of substance

If chemical recycling methods (thermal decomposition, hydrolysis, ozone decomposition) are used to recover olefin-based products from waste rubber, then product recovery is achieved, but the process requires complicated and sophisticated technology with harsh reaction conditions, resulting in low selectivity and yield

Engineering Contradiction:
Improveproduct recoveryVSAvoidprocess complexity
Core Design Contradiction:
Loss of substanceVSDevice complexity

Solution Approach 1:

The patent changes the reaction parameters by using mild reaction conditions (room temperature or slightly elevated temperatures, atmospheric pressure) compared to conventional harsh methods. The key parameter change is the introduction of specific catalysts (Grubbs catalysts or Schrock catalysts for metathesis, and isomerization catalysts) that enable the reaction to proceed under gentle conditions, thereby simplifying the process while maintaining high selectivity and yield for producing (C5-C7)cycloalkene from waste rubber

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces catalysts as intermediaries to mediate the depolymerization and transformation of waste rubber. Specifically, metathesis catalysts (Grubbs or Schrock catalysts) and isomerization catalysts are used as intermediary substances that facilitate the chemical transformation without being consumed, enabling selective production of cycloalkene under mild conditions and avoiding the need for complicated harsh treatment processes

Inventive Principle:
Principle #24Intermediary (Mediator)

2Loss of substance

If conventional chemical decomposition is used, then waste rubber is converted to products, but selectivity and yield of the desired product are low, resulting in complicated mixtures

Engineering Contradiction:
Improvewaste rubber conversionVSAvoidproduct selectivity
Core Design Contradiction:
Loss of substanceVSManufacturing precision

Solution Approach 1:

The patent employs specific catalysts as intermediaries to achieve selective transformation. The metathesis catalyst (Grubbs or Schrock catalyst) selectively catalyzes the metathesis reaction of double bonds in waste rubber to form cyclic structures, while the isomerization catalyst selectively isomerizes double bonds. This catalytic mediation ensures high selectivity for (C5-C7)cycloalkene production, avoiding the formation of complicated mixtures that result from non-selective conventional decomposition methods

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent changes the reaction conditions to mild temperatures and atmospheric pressure, which, combined with selective catalysis, enhances the precision of the reaction. These parameter changes prevent side reactions and ensure that the transformation of waste rubber to (C5-C7)cycloalkene proceeds with high selectivity and yield, producing a purified product rather than complicated mixtures

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

High selectivity and yield of (C5-C7)cycloalkene production, enabling effective chemical recycling of waste rubber into high-value cycloalkene compounds.

Implementation Method 1

depolymerizing a double bond-containing polymer in the presence of an isomerization catalyst and a metathesis catalyst having a N-heterocyclic carbene ligand to prepare (C5-C7)cycloalkene

Methodology Applied
Scientific EffectOlefin metathesis: Chemical Bonding

Implementation Method 2

depolymerizing a double bond-containing polymer in the presence of an isomerization catalyst and a metathesis catalyst

Methodology Applied
Scientific EffectCatalytic isomerization: Catalysis

Data Source

PatentUS20260015302A1Method for preparing cycloalkene from double bond-containing polymer and method for recycling waste rubber using the same
Publication Date: 2026.01.15 KOREA ADVANCED INST OF SCI & TECH
  • US20260015302A1 patent drawing
  • US20260015302A1 patent drawing
  • US20260015302A1 patent drawing

AI summary

Provided are a method for preparing cycloalkene including: depolymerizing a double bond-containing polymer in the presence of an isomerization catalyst and a metathesis catalyst having a N-heterocyclic carbene ligand to prepare (C5-C7)cycloalkene, and a method for recycling waste rubber using the same.