Stabilizer Removal in Fluorination of C3 Halogenated Hydrocarbons

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Solution Overview

Problem

The use of stabilizers in halogenated hydrocarbons can lead to catalyst deactivation during fluorination, reducing the production efficiency of fluorine-containing haloolefins, as the stabilizer's presence inhibits decomposition or polymerization but exceeds a level that shortens the catalyst's lifetime.

Innovation Solution

Removing the stabilizer from halogenated hydrocarbons before the fluorination step, utilizing a difference in boiling point for efficient distillation, thereby reducing the stabilizer's amount and preventing catalyst deactivation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Stability of the object's composition

If a stabilizer is added to halogenated hydrocarbon to prevent decomposition or polymerization, then the stability of the halogenated hydrocarbon is improved, but the lifetime of the catalyst is shortened due to catalyst deactivation

Engineering Contradiction:
Improvestability of halogenated hydrocarbonVSAvoidlifetime of catalyst
Core Design Contradiction:
Stability of the object's compositionVSDuration of action of moving object

Solution Approach 1:

The stabilizer is extracted and removed from the halogenated hydrocarbon before the fluorination reaction. This is achieved by not adding stabilizer to the reaction feed and by separating any stabilizer that may be present in the starting materials, thereby preventing catalyst deactivation while maintaining product stability through other means

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The removal of stabilizer is performed as a preliminary action before the fluorination reaction begins. By eliminating the stabilizer beforehand, the catalyst is protected from deactivation before it can cause harm, allowing the reaction to proceed with full catalyst activity throughout its lifetime

Inventive Principle:
Principle #10Preliminary action

2Stability of the object's composition

If stabilizer is present in halogenated hydrocarbon, then decomposition or polymerization is inhibited, but production efficiency is reduced due to catalyst deactivation

Engineering Contradiction:
Improveinhibition of decomposition or polymerizationVSAvoidproduction efficiency
Core Design Contradiction:
Stability of the object's compositionVSProductivity

Solution Approach 1:

The stabilizer is extracted from the system before the reaction, eliminating its harmful effect on catalyst activity. This allows the fluorination reaction to proceed at maximum efficiency without the stabilizer interfering with catalyst function, while alternative stabilization methods are employed during the reaction

Inventive Principle:
Principle #2Taking out (Extraction)

3Stability of the object's composition

If stabilizer amount exceeds certain level, then storage stability is improved, but catalyst lifetime is shortened

Engineering Contradiction:
Improvestorage stabilityVSAvoidcatalyst lifetime
Core Design Contradiction:
Stability of the object's compositionVSDuration of action of moving object

Solution Approach 1:

The stabilizer is completely removed or reduced to trace levels before the fluorination reaction. This extraction ensures that even though the halogenated hydrocarbon may have been stored with stabilizer for stability, the reaction feed contains negligible stabilizer, thus preserving catalyst lifetime

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The concentration of stabilizer is changed from a significant level (used for storage stability) to a trace or zero level (for reaction efficiency). This parameter change is achieved through removal processes before the reaction, allowing the system to optimize for catalyst lifetime during the reaction phase

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 extends the catalyst's lifetime, maintains high conversion and selectivity of the fluorine-containing haloolefin compound even during long-term reactions, improving production efficiency by inhibiting catalyst deactivation and stabilizer-induced decomposition.

Implementation Method 1

when the starting material is decomposed during storage or reaction, thereby producing an active intermediate such as a radical or an acid component (may e.g. be referred to as "radical" hereinafter), the radical is captured by a polymerization inhibitor, which serves as a stabilizer

Methodology Applied
Scientific EffectRadical capture: Absorption (physical)

Implementation Method 2

utilizing a difference in boiling point for efficient distillation

Methodology Applied
Scientific EffectDistillation: Distillation

Data Source

PatentEP3199510B1Method for producing haloolefin compound and method for removing stabilizer
Publication Date: 2022.07.20 DAIKIN INDUSTRIES LTD

AI summary

The present invention provides a method for producing a fluorine-containing haloolefin compound, the method easily inhibiting catalyst deactivation, and the method being capable of inhibiting a decrease in conversion and selectivity in the reaction, even when the reaction is continued for a long period of time. The present invention is a method for producing a fluorine-containing haloolefin compound via a step of fluorinating a C3 halogenated hydrocarbon. The method comprises a step of removing a stabilizer contained in the C3 halogenated hydrocarbon before the fluorination step.