Spirocyclic Ammonium Salt Composition for Lower Melting Points

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Solution Overview

Problem

Existing spirocyclic ammonium salts have high melting points, which can be a disadvantage in various applications.

Innovation Solution

The development of spirocyclic ammonium salts with specific alkylene chains and exocyclic substituents, combined with certain anions, to lower the melting point.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Temperature

If conventional spirocyclic ammonium salts are used, then they exhibit good catalytic activity and electrochemical performance, but they have high melting points which limit their applicability

Engineering Contradiction:

Improvemelting pointVSAvoidapplicability in electrochemical applications and catalysis

Core Design Contradiction:

TemperatureVSAdaptability or versatility

Solution Approach 1:

The patent applies parameter changes by modifying the molecular structure of spirocyclic ammonium salts through introducing exocyclic substituents (alkyl, cycloalkyl, or aryl groups) on the alkylene chains. This structural parameter change reduces the melting point from conventional high values to below 100°C, while preserving the core spirocyclic ammonium structure that provides catalytic and electrochemical functionality. The anion selection (perfluoroalkylsulfonate, bis(perfluoroalkylsulfonyl)imide, etc.) further tunes the melting point parameter.

Inventive Principle:

Principle #35Parameter changes

2Temperature

If the spirocyclic ammonium salt structure is modified to lower melting point, then melting point is reduced, but structural complexity increases

Engineering Contradiction:

Improvemelting pointVSAvoidmolecular structure complexity

Core Design Contradiction:

TemperatureVSDevice complexity

Solution Approach 1:

The patent applies segmentation by dividing the molecule into distinct functional segments: the core spirocyclic ammonium cation structure and the exocyclic substituents on the alkylene chains. The exocyclic substituents are positioned as separate branches off the main ring systems, allowing independent optimization of each segment. This modular segmentation enables melting point reduction through substituent engineering while maintaining the integrity and functionality of the core spirocyclic structure.

Inventive Principle:

Principle #1Segmentation

3Temperature

If exocyclic substituents are introduced on alkylene chains, then melting point is reduced, but synthesis complexity increases

Engineering Contradiction:

Improvemelting pointVSAvoidsynthesis process

Core Design Contradiction:

TemperatureVSEase of manufacture

Solution Approach 1:

The patent applies preliminary action by pre-installing exocyclic substituents on the N-heterocyclic alkyl compound (A) or the α,ω-dihaloalkyl compound (B) before the spirocyclization reaction. This preliminary substitution allows the substituents to be incorporated into the final spirocyclic ammonium salt structure during the one-pot synthesis, avoiding post-synthetic modification steps. The substituents are already in place on the starting materials, so they are automatically positioned correctly when the spirocycle forms.

Inventive Principle:

Principle #10Preliminary action

Data Source

PatentEP4663638A1Spirocyclic ammonium salt and process for preparing the same

Publication Date: 2025.12.17 COVESTRO DEUTSCHLAND AG

AI summary

The invention relates to a spirocyclic ammonium salt containing at least one spirocyclic ammonium cation and at least one anion, and to a process for producing the spirocyclic ammonium salt. The invention further relates to the use of such a spirocyclic ammonium salt as a catalyst for the oligomerization of monomeric organic isocyanates with an NCO functionality > 1, in electrochemistry to improve the electrochemical activity of lithium-ion batteries, or as an ionic liquid.