Fluorine-Containing Ether Synthesis via Partial Conversion Control

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Solution Overview

Problem

Existing methods for synthesizing fluorine-containing ether face challenges such as side reactions producing unsaturated bonds, which complicate separation and increase costs due to the need for expensive catalysts or high-energy processes.

Innovation Solution

A method involving the reaction of a fluorine-containing alkyl alcohol with a fluorinated olefin in the presence of an inorganic basic compound, where the reaction is terminated at a conversion ratio of 25-75% to inhibit side reactions and facilitate high-purity ether production through simple distillation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If the reaction is allowed to proceed to high conversion ratio to maximize yield, then the productivity is improved, but side reactions producing unsaturated bond by-products increase making separation difficult

Engineering Contradiction:
Improveyield of fluorine-containing etherVSAvoidpurity of fluorine-containing ether
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The reaction is intentionally stopped at partial conversion (25-75%) rather than allowing complete conversion. This partial action prevents the accumulation of by-products that would form at higher conversions, thereby maintaining high purity while still achieving acceptable yield through selective termination of the reaction process

Inventive Principle:
Principle #16Partial or excessive action

2Manufacturing precision

If a phase transfer catalyst or secondary/tertiary alcohol is used to suppress side reactions and improve purity, then the manufacturing precision is improved, but the cost increases

Engineering Contradiction:
Improvepurity of fluorine-containing etherVSAvoidcost of production
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The harmful basic compound responsible for dehydrohalogenation side reactions is completely removed from the reaction system. By eliminating the source of the problem rather than using expensive additives to suppress it, the method achieves high purity without increasing production costs

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The method uses inexpensive inorganic basic compounds (alkali metal hydroxides or carbonates) that can be easily disposed of or neutralized, replacing expensive phase transfer catalysts or secondary/tertiary alcohols. The cheap basic compound performs its function and is then discarded without requiring recovery or special handling

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

3Ease of operation

If chlorine addition and high temperature processing are used to modify unsaturated bond by-products for easier separation, then the ease of operation is improved, but the device complexity and energy consumption increase

Engineering Contradiction:
Improveease of separationVSAvoidapparatus requirements
Core Design Contradiction:
Ease of operationVSDevice complexity

Solution Approach 1:

Instead of treating the harmful unsaturated bond by-products after formation, the method prevents their formation in the first place by controlling reaction conditions. The potential harm of by-product formation is converted into benefit by using the same basic compound under controlled conditions to promote only the desired etherification reaction

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

Solution Approach 2:

The reaction parameters (temperature, pressure, concentration, conversion ratio) are optimized to favor the etherification reaction while suppressing dehydrohalogenation. By changing these parameters, the method achieves selective product formation without requiring complex separation apparatus or high-energy processing steps

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 approach yields high-purity fluorine-containing ether with reduced costs and simplified steps, allowing for easy separation and recycling of starting materials, thereby enhancing the efficiency and cost-effectiveness of the process.

Implementation Method 1

a method in which fluorine-containing alkyl alcohol is allowed to react with fluorinated olefin in water in the presence of a basic compound such as an alkali metal compound to prepare fluorine-containing ether

Methodology Applied
Scientific EffectNucleophilic substitution: Chemical Bonding

Implementation Method 2

the reaction mixture is allowed to stand, an organic layer and a water layer are separated

Methodology Applied
Scientific EffectLiquid-liquid extraction: Liquid-Liquid Extraction

Implementation Method 3

an organic layer and a water layer are separated

Methodology Applied
Scientific EffectDensity difference: Density Gradient

Implementation Method 4

fluorine-containing ether is collected by distillation

Methodology Applied
Scientific EffectDistillation: Distillation

Data Source

PatentEP2305626B1Method for producing fluorine-containing ether
Publication Date: 2015.08.05 DAIKIN INDUSTRIES LTD
  • EP2305626B1 patent drawing
  • EP2305626B1 patent drawing
  • EP2305626B1 patent drawing

AI summary

There is provided a method of preparing a high purity fluorine-containing ether which inhibits a side reaction generating an unsaturated bond and assures low cost and simple steps. When preparing the fluorine-containing ether by allowing a fluorine-containing alkyl alcohol to react with a fluorinated olefin in the presence of a basic compound, a reaction is terminated at a stage before a conversion ratio of the fluorine-containing alkyl alcohol reaches 75 %.