CuCl/Ti(O)(acac)2 Catalyst for Meyer-Schuster Rearrangement

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Solution Overview

Problem

Current methods for producing specific α,β-unsaturated aldehydes with conjugated C-C double bonds are not efficient, lacking a reliable and improved process for their synthesis.

Innovation Solution

A transition metal-based catalyzed Meyer-Schuster rearrangement using Cu and/or Ti catalysts, specifically CuCl/Ti(O)(acac)2, is employed to convert secondary and tertiary propargyl alcohols into α,β-unsaturated aldehydes under mild conditions in a one-pot reaction, utilizing compounds of formula (II) as starting materials.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional methods are used to produce α,β-unsaturated aldehydes, then production can proceed with existing processes, but the efficiency and reliability of producing specific compounds with conjugated C-C double bonds are insufficient

Engineering Contradiction:

Improveproduction efficiencyVSAvoidreliability of synthesis process

Core Design Contradiction:

ProductivityVSReliability

Solution Approach 1:

The patent changes the chemical parameters by introducing a copper(I) chloride catalyst system with specific ligands (NH4PF6, AgBF4) and controlling the solvent system (CH2Cl2/MeOH/H2O mixture) and temperature (reflux conditions), which transforms the reaction pathway to reliably produce conjugated α,β-unsaturated aldehydes with high efficiency

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The patent employs a composite catalyst system combining copper(I) chloride with specific ligands and co-catalysts (AgBF4), creating a multi-component catalytic system that enhances both the reliability and efficiency of the rearrangement reaction compared to simple catalyst systems

Inventive Principle:

Principle #40Composite materials

2Productivity

If strong bases followed by strong acids are used for rearrangement, then the reaction can proceed, but the reaction conditions become harsh and may affect product quality

Engineering Contradiction:

Improvereaction rateVSAvoidharsh reaction conditions

Core Design Contradiction:

ProductivityVSObject-affected harmful factors

Solution Approach 1:

The patent uses readily available, inexpensive reagents such as copper(I) chloride, ammonium hexafluorophosphate, and silver tetrafluoroborate that can be easily handled and disposed of, replacing expensive or hazardous catalysts while maintaining high reaction efficiency under mild conditions

Inventive Principle:

Principle #27Cheap short-living objects (Disposable)

Solution Approach 2:

The patent changes the reaction parameters by using mild acidic conditions (HFOP generated in situ from NH4PF6 and CuCl) instead of strong bases followed by strong acids, maintaining high productivity while eliminating harsh reaction conditions that could harm product quality

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 achieves good selectivity and yield, allowing for the production of α,β-unsaturated aldehydes, which can be used as intermediates for compounds like Vitamin A acetate, under mild reaction conditions and with a preferred catalyst ratio of Cu:Ti.

Implementation Method 1

A transition metal-based catalyst is used (or a mixture of transition metal based catalysts) for the process according to the present invention, wherein the transition metal is Cu and/or Ti

Methodology Applied

Scientific EffectCatalysis: Catalysis

Data Source

PatentEP3207016B1Method for producing specific alpha,beta-unsaturated aldehydes by rearrangement process

Publication Date: 2018.08.01 DSM IP ASSETS BV

AI summary

The present invention relates to an improved method for producing specific α,β-unsaturated aldehydes.