Alkenone Solvent Reaction Medium for Halogenated Precursor Synthesis

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Solution Overview

Problem

Current methods for preparing halogenated alkenones and their precursors face challenges in selectivity and yield, often resulting in material loss and complex separation processes.

Innovation Solution

A process involving the reaction of a carboxylic acid halide with a vinyl ether in a liquid reaction medium containing an alkenone or its halogenated precursor, where the alkenone or halogenated precursor acts as a solvent, optimizing the reaction conditions to enhance selectivity and yield, and subsequent dehydrohalogenation to form the alkenone.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional solvents are used for the reaction of carboxylic acid halide with vinyl ether, then the reaction can proceed, but selectivity and yield are reduced and separation becomes complex

Engineering Contradiction:
ImproveselectivityVSAvoidseparation complexity
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The alkenone product serves as its own solvent for the reaction. The reaction is performed by adding carboxylic acid halide to a reaction medium containing vinyl ether and alkenone, where the alkenone acts as the reaction medium. This self-service approach eliminates the need for separate solvent removal and simplifies separation processes while maintaining high selectivity and yield.

Inventive Principle:
Principle #25Self-service

Solution Approach 2:

The invention changes the physical and chemical parameters of the reaction medium by using the alkenone product itself as the solvent. This parameter change optimizes the reaction conditions to achieve high selectivity and yield while simultaneously simplifying the separation process, as the product is already in the desired medium.

Inventive Principle:
Principle #35Parameter changes

2Productivity

If conventional solvents are used for the reaction, then the reaction can proceed, but material loss increases and by-products are formed

Engineering Contradiction:
ImproveyieldVSAvoidmaterial loss
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The alkenone product serves as its own solvent, creating a reaction medium that is already optimized for product stability and minimizes unwanted side reactions. This approach reduces material loss by avoiding solvent-related by-products and simplifies the process by eliminating the need for separate solvent recovery steps.

Inventive Principle:
Principle #25Self-service

Solution Approach 2:

Instead of using a separate solvent that may cause side reactions or require complex removal, the invention converts the product itself into the solvent medium. This turns what would be a waste stream into a functional component of the reaction system, reducing material loss and improving yield.

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

3Ease of operation

If base is used in excess as solvent, then the reaction can proceed, but separation and disposal of by-products becomes difficult

Engineering Contradiction:
Improvereaction feasibilityVSAvoidby-product disposal
Core Design Contradiction:
Ease of operationVSObject-generated harmful factors

Solution Approach 1:

The alkenone product serves as its own solvent, eliminating the need for excess base as solvent. This self-service approach maintains reaction feasibility while avoiding the generation of harmful by-products associated with base solvent systems, thereby simplifying disposal requirements.

Inventive Principle:
Principle #25Self-service

Solution Approach 2:

The invention extracts the solvent function from the base component and transfers it to the alkenone product itself. This separation of functions removes the harmful by-product generation associated with base solvents while maintaining the necessary reaction conditions.

Inventive Principle:
Principle #2Taking out (Extraction)

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 simplifies product separation, reduces by-product formation, and improves the yield and purity of halogenated alkenones, allowing for more efficient production and utilization of the precursors as solvents in subsequent processes.

Implementation Method 1

reacting a carboxylic acid halide with a vinyl ether in a liquid reaction medium comprising an alkenone or a halogenated precursor of the alkenone

Methodology Applied
Scientific EffectSolvation: Solvation

Implementation Method 2

subsequent dehydrohalogenation to form the alkenone

Methodology Applied
Scientific EffectDehydrohalogenation:

Data Source

PatentEP2451763B1Process for the manufacture of halogenated precursors of alkenones in the presence of a solvent
Publication Date: 2015.03.04 SOLVAY SA
  • EP2451763B1 patent drawing
  • EP2451763B1 patent drawing

AI summary

The invention relates to a process for preparing a halogenated precursor of an alkenone, which comprises reacting a carboxylic acid halide with a vinyl ether in a liquid reaction medium comprising an alkenone or a halogenated precursor of the alkenone, and also relates to a process for preparing an alkenone, which comprises (a) reacting a carboxylic acid halide with a vinyl ether by introducing vinyl ether into a liquid reaction medium containing carboxylic acid halide to form a halogenated precursor of the alkenone and (b) eliminating hydrogen halide from said precursor to form the alkenone.