Trans-1,1,1,4,4,4-hexafluoro-2-butene Preparation via Composite Catalyst

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Solution Overview

Problem

Existing methods for preparing trans-1,1,1,4,4,4-hexafluoro-2-butene suffer from low selectivity to trans products, high energy consumption, and generation of significant waste.

Innovation Solution

A preparation method involving the preheating of trans-2-ethoxy-1,1,1,4,4,4-hexafluoro-2-butene, followed by reaction with hydrogen in the presence of a catalyst comprising an aluminum-magnesium composite oxide and a group VIII transition metal, achieving high selectivity (up to 99%) and moderate reaction conditions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional methods (coupling with copper powder or alkaline deiodination) are used to prepare trans-1,1,1,4,4,4-hexafluoro-2-butene, then the product can be obtained, but the selectivity to trans products is low (around 50%) and chemical quantities of metal elements or bases are required

Engineering Contradiction:
Improvetrans product selectivityVSAvoidcatalyst composition complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent changes the catalytic parameters by using a specific aluminum-magnesium composite oxide catalyst with controlled composition ratios (Al2O3:MgO = 95:5 to 90:10 by weight) and optimized reaction conditions (temperature 100-200°C, pressure 0.1-1.0 MPa, H2/substrate ratio 1:1 to 1:5), achieving trans selectivity of 95-99% without requiring complex multi-component catalysts or large amounts of metal bases

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs a composite catalyst material consisting of aluminum-magnesium composite oxide with integrated group VIII transition metals (Ni, Pd, Pt, Rh, Ru, Co), where the composite structure provides both high trans selectivity and catalytic activity, eliminating the need for separate metal base additives while maintaining 95-99% trans product selectivity

Inventive Principle:
Principle #40Composite materials

2Productivity

If high-temperature pyrolysis process (600-725°C) is used to prepare E-HFO-1336mzz, then the reaction can proceed, but the energy consumption is very high

Engineering Contradiction:
Improvereaction rateVSAvoidenergy consumption
Core Design Contradiction:
ProductivityVSUse of energy by moving object

Solution Approach 1:

The patent fundamentally changes the reaction temperature parameter from conventional high-temperature pyrolysis (600-725°C) to moderate conditions (100-200°C) by introducing the aluminum-magnesium composite oxide catalyst, which enables the reaction to proceed at lower temperatures with high trans selectivity (95-99%), dramatically reducing energy consumption while maintaining productivity

Inventive Principle:
Principle #35Parameter changes

3Manufacturing precision

If hydrogenation of hexafluorobutyne is used to prepare E-HFO-1336mzz, then the product can be obtained, but the cis-selectivity is better than trans and waste alkali is produced

Engineering Contradiction:
Improveproduct cis-trans selectivityVSAvoidwaste alkali generation
Core Design Contradiction:
Manufacturing precisionVSLoss of substance

Solution Approach 1:

The patent changes the reaction parameters by using aluminum-magnesium composite oxide catalyst with group VIII transition metals, operating at controlled temperatures (100-200°C) and H2/substrate ratios (1:1 to 1:5), which shifts the selectivity toward trans products (95-99%) while avoiding the waste alkali generation problem of conventional hydrogenation methods

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 achieves high trans selectivity (up to 99%) with moderate reaction temperatures and reduced waste production, enhancing the process efficiency and environmental sustainability.

Implementation Method 1

reacting with hydrogen in the presence of a catalyst to obtain trans-1,1,1,4,4,4-hexafluoro-2-butene

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Implementation Method 2

in the presence of a catalyst comprising an aluminum-magnesium composite oxide and a group VIII transition metal

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS20250074848A1Preparation method of trans-1,1,1,4,4,4-hexafluoro-2-butene
Publication Date: 2025.03.06 GUANGDONG POWER GRID CO LTD
  • US20250074848A1 patent drawing
  • US20250074848A1 patent drawing
  • US20250074848A1 patent drawing

AI summary

The present invention belongs to the technical field of fluorine chemical industry, specifically relates to a preparation method of trans-1,1,1,4,4,4-hexafluoro-2-butene, comprising the following steps: preheating trans-2-ethoxy-1,1,1,4,4,4-hexafluoro-2-butene, mixing with hydrogen, reacting to obtain trans-1,1,1,4,4,4-hexafluoro-2-butene under the action of a catalyst. The selectivity of trans 1,1,1,4,4,4-hexafluoro-2-butene prepared by the preparation method of the present invention can reach 99%, the preparation method adopts moderate reaction temperature and produces less three wastes. The trans 1,1,1,4,4,4-hexafluoro-2-butene prepared by the preparation method has great application value in electric power, electrical appliances and electronics industries.