Purified Fluorine-Containing Ether Production via Halogen Adduct Separation

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Solution Overview

Problem

Existing methods for producing fluorine-containing ether compounds, such as HFE-356 mec, are inefficient and do not achieve high purity levels, leading to the need for improved production processes.

Innovation Solution

A method involving the reaction of a fluorine-containing olefin compound with a halogenating agent and/or oxidant, followed by separation of halogen adducts and oxides, to produce a purified fluorine-containing ether compound, utilizing steps (A) and (B) to achieve high purity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If existing methods are used to produce fluorine-containing ether compounds, then production can proceed with simple processes, but the purity of the product remains low and production efficiency is poor

Engineering Contradiction:
Improvepurity of fluorine-containing ether compoundVSAvoidcomplexity of production process
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The production process is divided into multiple distinct steps: (A) reacting fluorine-containing olefin with halogenating agent and oxidant to form halogen adduct/oxide, (B) separating the halogen adduct/oxide from the mixture, and (C) recovering the purified fluorine-containing ether compound. This segmentation allows each step to be optimized independently, achieving high purity (>95 mass %) while maintaining reasonable process complexity through systematic organization.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The invention extracts and removes impurities (halogen adducts and oxides) from the reaction mixture through separation step (B). By specifically targeting and removing these harmful byproducts, the process achieves high purity fluorine-containing ether compound while the extraction step is designed to be efficient rather than overly complex.

Inventive Principle:
Principle #2Taking out (Extraction)

2Productivity

If existing production methods are used, then process simplicity is maintained, but production efficiency and productivity are poor

Engineering Contradiction:
Improveproduction efficiency of fluorine-containing ether compoundVSAvoidcomplexity of production process
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The production method employs continuous reaction and separation processes where the fluorine-containing olefin continuously reacts with halogenating agent and oxidant, and the resulting mixture is continuously separated to remove impurities. This continuous operation eliminates idle time between batches and maintains high productivity, with the multi-step process organized to flow efficiently from reaction through separation to recovery.

Inventive Principle:
Principle #20Continuity of useful action

Solution Approach 2:

The invention discards harmful byproducts (halogen adducts and oxides) through separation step (B) while recovering the desired fluorine-containing ether compound in high purity form. The recovery step (C) ensures maximum utilization of the starting materials, improving overall productivity by minimizing waste and maximizing product yield from the reaction process.

Inventive Principle:
Principle #34Discarding and recovering

3Stability of the object's composition

If existing methods are used to produce fluorine-containing ether compounds, then simple reaction conditions are used, but the stability of the product is insufficient

Engineering Contradiction:
Improvestability of fluorine-containing ether compoundVSAvoidcomplexity of production process
Core Design Contradiction:
Stability of the object's compositionVSDevice complexity

Solution Approach 1:

The invention converts the harmful byproducts (halogen adducts and oxides) formed during reaction into separable impurities that can be efficiently removed. By designing the reaction to produce distinct, separable byproducts rather than complex mixtures, the process achieves stable, high-purity product while the separation step handles the removal of converted harmful substances in a controlled manner.

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

Solution Approach 2:

The production method utilizes specific parameter choices including the selection of halogenating agents and oxidants that produce separable byproducts, controlling reaction conditions to favor formation of removable impurities, and adjusting separation parameters to achieve >95 mass % purity. These parameter optimizations ensure product stability while keeping the process reasonably simple through targeted rather than exhaustive approaches.

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

The method enables the production of a composition comprising a fluorine-containing ether compound with purity greater than 95 mass %, effectively removing impurities and improving the stability and efficiency of the production process.

Implementation Method 1

reacting with a halogenating agent and/or oxidant to convert the fluorine-containing olefin compound represented by the formula (2) to a halogen adduct and/or oxide

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Implementation Method 2

separating the halogen adduct and/or oxide from the composition obtained in the step (A) to obtain a composition comprising a purified fluorine-containing ether compound

Methodology Applied
Scientific EffectSeparation: Distillation

Data Source

PatentUS20260062372A1Method for producing composition containing purified fluorine-containing ether compound
Publication Date: 2026.03.05 DAIKIN INDUSTRIES LTD

AI summary

The present disclosure provides a method for producing a composition comprising a purified fluorine-containing ether compound represented by formula (1): CHX1X2CF2OX3, wherein X1 and X2 are the same or different and each represents a hydrogen atom, a fluorine atom, or a trifluoromethyl group, and X3 represents a C1-6 alkyl group, provided that not both X1 and X2 are trifluoromethyl groups.