Acetoxy Siloxane Production via Superacid Catalysis

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Solution Overview

Problem

Existing methods for producing end-equilibrated acetoxy group-bearing siloxanes, such as trifluoromethanesulfonic acid siloxanes, face challenges in achieving immediate equilibrium kinetics, leading to delayed processing due to high proportions of siloxane cycles that take time to adjust during storage.

Innovation Solution

A process involving the use of cyclic siloxanes, superacid catalysts like trifluoromethanesulfonic acid, acetic anhydride, and acetic acid to accelerate the equilibrium adjustment, specifically by controlling the proportion of Si atoms from Q units and using specific siloxane mixtures with D and T units, along with hydrolysis and condensation reactions, to produce end-equilibrated siloxanes with reduced cyclic content.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional methods using trifluoromethanesulfonic acid are used to prepare acetoxy group-bearing siloxanes, then the siloxanes meet quality requirements after storage, but the equilibration kinetics are slow and processing is delayed

Engineering Contradiction:
Improvequality requirementsVSAvoidequilibration kinetics
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The patent changes the chemical parameters of the reaction system by introducing acetic acid as an additional catalyst alongside trifluoromethanesulfonic acid. This parameter change accelerates the equilibration kinetics significantly, allowing the siloxanes to reach equilibrium within hours rather than requiring weeks of storage time, thus resolving the contradiction between meeting quality requirements and improving productivity

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

Acetic acid acts as an intermediary substance that facilitates the equilibration process. It mediates between the reactants and the final product by providing an additional catalytic pathway that speeds up the formation of acetoxy group-bearing siloxanes, enabling immediate further processing without prolonged storage

Inventive Principle:
Principle #24Intermediary (Mediator)

2Stability of the object's composition

If cyclic siloxanes with high D and T unit content are used, then the siloxane matrix structure is achieved, but siloxane cycles remain that require extended storage for equilibration

Engineering Contradiction:
Improvesiloxane matrix structureVSAvoidstorage time for equilibration
Core Design Contradiction:
Stability of the object's compositionVSLoss of time

Solution Approach 1:

By modifying the reaction conditions through the addition of acetic acid and controlling the proportion of Si atoms from Q units (≤10 mass%, preferably ≤5 mass%), the patent accelerates the equilibration process. This allows cyclic siloxanes with high D and T unit content to reach equilibrium rapidly without extended storage, resolving the contradiction between maintaining siloxane matrix structure and reducing equilibration time

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent performs preliminary equilibration during the synthesis process itself by using superacid catalysis with acetic acid addition. This preliminary action ensures that the siloxanes are already equilibrated at the end of the reaction, eliminating the need for extended post-preparation storage time while maintaining the desired siloxane matrix structure

Inventive Principle:
Principle #10Preliminary action

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 approach allows for the immediate isolation of reactive siloxanes with significantly reduced cyclic content, facilitating faster processing and meeting quality requirements by achieving equilibrium within a shorter timeframe.

Implementation Method 1

are reacted using superacid, in particular trifluoromethanesulfonic acid, as catalyst with acetic anhydride

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

with the addition of acetic acid, wherein the cyclic-branched siloxanes of the D/T type used are mixtures of cyclic-branched siloxanes

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Implementation Method 3

along with hydrolysis and condensation reactions, to produce end-equilibrated siloxanes

Methodology Applied
Scientific EffectCondensation: Condensation

Data Source

PatentEP3744754B1Method for producing siloxanes bearing acetoxy groups
Publication Date: 2024.10.02 EVONIK OPERATIONS GMBH

AI summary

A process for the production of preferably trifluoromethanesulfonic acid, end-equilibrated, acetoxy-group-bearing siloxanes is described, in which cyclic siloxanes, in particular comprising D4 and/or D5, and/or cyclic branched siloxanes of the D/T type are reacted with acetic anhydride and with the addition of acetic acid, preferably using trifluoromethanesulfonic acid as a catalyst, wherein the cyclic branched siloxanes of the D/T type are mixtures of cyclic branched siloxanes of the D/T type, which, in addition to siloxanes having D and T units, also contain siloxanes with Q units.