Cyclic Monothiocarbonate Route for Controlled Polysulfide End Groups

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Solution Overview

Problem

There is a demand for economic processes that allow the easy preparation of polysulfides with higher functionality, particularly in the synthesis of compounds with thiol groups.

Innovation Solution

A process involving the reaction of a five-membered cyclic monothiocarbonate with a starter compound containing thiol or hydroxy groups, using a catalyst with a tertiary amino, guanidino, or phosphine group to transfer these groups into alkylene thiol or alkoxylate groups, producing compounds with alkylene and thiol or thiolate groups, including polyalkylenesulfides.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If conventional methods are used to prepare polysulfides with higher functionality, then the synthesis process becomes complex and requires hazardous materials, but the invention provides an easy and economic method with controlled end-group functionality

Engineering Contradiction:

Improveease of preparationVSAvoidprocess complexity

Core Design Contradiction:

Ease of manufactureVSDevice complexity

Solution Approach 1:

The synthesis process is segmented into a single selective reaction step where a five-membered cyclic monothiocarbonate reacts with a starter compound containing thiol or hydroxy groups. This segmentation eliminates the need for multiple reaction steps and hazardous materials, achieving both ease of manufacture and controlled end-group functionality.

Inventive Principle:

Principle #1Segmentation

Solution Approach 2:

The five-membered cyclic monothiocarbonate acts as an intermediary compound that enables the formation of polysulfides with controlled end-group functionality. This intermediary approach allows for selective reaction and eliminates the need for hazardous materials while maintaining process simplicity.

Inventive Principle:

Principle #24Intermediary (Mediator)

2Manufacturing precision

If multiple reaction steps are used to achieve controlled end-group functionality, then the synthesis time increases, but the invention achieves this in a single selective reaction step

Engineering Contradiction:

Improveend-group functionality controlVSAvoidsynthesis time

Core Design Contradiction:

Manufacturing precisionVSLoss of time

Solution Approach 1:

Multiple reaction steps that were traditionally required to achieve controlled end-group functionality are merged into a single selective reaction step. The five-membered cyclic monothiocarbonate reacts directly with the starter compound in one step, simultaneously achieving both manufacturing precision and time efficiency.

Inventive Principle:

Principle #5Merging (Combining)

Solution Approach 2:

The five-membered cyclic monothiocarbonate is pre-designed with specific structural features that enable selective reaction and controlled end-group functionality from the outset. This preliminary design eliminates the need for subsequent modification steps, reducing synthesis time while maintaining precision.

Inventive Principle:

Principle #10Preliminary action

3Productivity

If hazardous materials are used in polysulfide synthesis, then the reaction efficiency may be improved, but the invention eliminates hazardous materials while maintaining economic viability

Engineering Contradiction:

Improvereaction efficiencyVSAvoidhazardous materials

Core Design Contradiction:

ProductivityVSObject-affected harmful factors

Solution Approach 1:

The invention converts the traditional approach of using hazardous materials to improve reaction efficiency into a benign process. The five-membered cyclic monothiocarbonate and starter compound react selectively under mild conditions, eliminating hazardous materials while maintaining economic viability and acceptable reaction efficiency.

Inventive Principle:

Principle #22Blessing in disguise (Convert harm into benefit)

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 provides an easy and economic method for synthesizing polysulfides with controlled end-group functionality, allowing for the production of polyalkylenesulfides and copolymers with defined structures, without the need for hazardous materials and in a single selective reaction step.

Implementation Method 1

using a catalyst with a tertiary amino, guanidino, or phosphine group to transfer these groups into alkylene thiol or alkoxylate groups

Methodology Applied

Scientific EffectCatalysis: Catalysis

Implementation Method 2

a compound with at least one five-membered cyclic monothiocarbonate group is reacted with a starter selected from compounds with at least one thiol group, or from compounds with at least one hydroxy group, to obtain a compound with at least one alkylene group and at least one thiol or thiolate group and carbon dioxide

Methodology Applied

Scientific EffectDecarboxylation: Decomposition (biological)

Data Source

PatentEP3959194B1Process for the preparation of compounds with at least one alkylene group and at least one thiol or thiolate group

Publication Date: 2025.12.03 BASF SE

AI summary

Provided is a process for the synthesis of a compound with at least one alkylene group and at least one thiol or thiolate group, wherein a compound with at least one five-membered cyclic monothiocarbonate group is reacted with a starter selected from a compound with at least one thiol group, from a compound with at least one hydroxy group or from a basic inorganic compound to obtain a compound with at least one alkylene group and at least one thiol or thiolate group and carbon dioxide.