Hexafluoro-1,3-butadiene Production via Zinc Dehalogenation and Solvent Recovery

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Solution Overview

Problem

Existing methods for producing hexafluoro-1,3-butadiene result in significant industrial waste due to the formation of organic solvents, metal salts, and unreacted compounds, making them unsuitable for industrial-scale production.

Innovation Solution

A method involving the reaction of a halogenated butane with zinc in an organic solvent, followed by separation and aftertreatment steps to recover solvents and produce a highly pure aqueous zinc halide, reducing waste and enabling efficient production of hexafluoro-1,3-butadiene.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If dechlorination reaction is performed in organic solvents (dioxane, 2-propanol) with metal (magnesium, zinc), then hexafluoro-1,3-butadiene can be produced, but a large amount of mixture containing organic solvent, metal salt, and unreacted compound is formed as industrial waste

Engineering Contradiction:
Improveproduction methodVSAvoidindustrial waste
Core Design Contradiction:
Ease of manufactureVSLoss of substance

Solution Approach 1:

The patent applies the principle of discarding and recovering by separating and recovering the organic solvent and metal salt from the reaction mixture through distillation and other separation techniques. The recovered organic solvent is reused in subsequent reactions, while the metal salt is processed to recover zinc or other metals. This eliminates the need to discard these materials as waste, directly addressing the technical contradiction between ease of manufacture and waste generation.

Inventive Principle:
Principle #34Discarding and recovering

2Productivity

If traditional dechlorination methods are used, then hexafluoro-1,3-butadiene production is achieved, but the process is unsuitable for industrial production due to large waste generation

Engineering Contradiction:
Improveindustrial production suitabilityVSAvoidindustrial waste
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The patent implements self-service by creating a closed-loop system where the organic solvent and metal catalyst are continuously recovered and reused within the same production process. The reaction system serves itself by regenerating its own components, eliminating the need for external waste treatment facilities and making the process suitable for industrial production where waste disposal is a major constraint.

Inventive Principle:
Principle #25Self-service

3Ease of manufacture

If dechlorination reaction is performed in organic solvents with metal, then hexafluoro-1,3-butadiene is produced, but separation and treatment of the reaction mixture is complex and wasteful

Engineering Contradiction:
Improvereaction methodVSAvoidseparation process
Core Design Contradiction:
Ease of manufactureVSDevice complexity

Solution Approach 1:

The patent replaces complex mechanical separation systems with a simplified process based on the inherent properties of the reaction components. By selecting organic solvents and metals that form easily separable products, and by using distillation which exploits volatility differences, the complex separation and treatment process is replaced with a more straightforward thermal separation method, reducing device complexity while maintaining ease of manufacture.

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

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 minimizes industrial waste, allows for the recovery of organic solvents and zinc halides, and produces hexafluoro-1,3-butadiene safely and inexpensively, with high purity, making it industrially applicable.

Implementation Method 1

a reaction step of reacting a halogenated butane represented by chemical formula, CF2X1—CF2X2, with zinc in an organic solvent

Methodology Applied
Scientific EffectDehalogenation reaction: Chemical Bonding

Implementation Method 2

a separation step of separating hexafluoro-1,3-butadiene from a reaction product, an aftertreatment step of adding water to a reaction product residue after the separation, and removing the organic solvent to give an aqueous solution of zinc halide

Methodology Applied
Scientific EffectDistillation: Distillation

Data Source

PatentEP3632883B1Production method for hexafluoro-1,3-butadiene
Publication Date: 2023.06.21 RESONAC CORP

AI summary

Provided is a method that is for producing hexafluoro-1,3-butadiene, discharges small amounts of industrial wastes, and is industrially applicable. The method for producing hexafluoro-1,3-butadiene includes a reaction step of reacting a halogenated butane represented by chemical formula, CF2X1-CFX2-CFX3-CF2X4 (X1, X2, X3, and X4 are each independently a halogen atom other than a fluorine atom) in an organic solvent in the presence of zinc to eliminate the halogen atoms, X1, X2, X3, and X4, other than the fluorine atoms to generate hexafluoro-1,3-butadiene, giving a reaction product containing the hexafluoro-1,3-butadiene, and an aftertreatment step of separating the hexafluoro-1,3-butadiene from the reaction product produced in the reaction step, then adding water to a reaction product residue after the separating, and removing the organic solvent, giving an aqueous solution of zinc halide.