Hydrofluorobutadiene Synthesis via Copper-Mediated Coupling
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Solution Overview
Problem
Current methods for producing hydrofluorobutadiene are hindered by the use of expensive metal catalysts, high-temperature reactions, and limited substrate availability, making them unsuitable for mass production.
Innovation Solution
A method involving a coupling reaction of halogenated olefins with a reduced amount of zero-valent metal, such as copper, in the presence of a metal salt, which allows for the production of hydrofluorobutadiene at high yield and low cost.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If a coupling reaction using expensive palladium catalyst is used, then the synthesis of hydrofluorocarbon can be achieved, but the production cost increases significantly
Solution Approach 1:
The patent replaces expensive palladium catalyst with cheap copper powder as the zero-valent metal source. The copper powder is consumed in the reaction (4 equivalents relative to substrate), acting as a sacrificial reagent that enables the coupling reaction without requiring expensive noble metal catalysts, thus resolving the contradiction between synthesis capability and production cost
Solution Approach 2:
The patent changes the metal type parameter from palladium to copper, and adjusts the metal-to-substrate ratio parameter to 4 equivalents. This parameter change allows the use of inexpensive copper instead of expensive palladium while maintaining the coupling reaction's effectiveness through optimized stoichiometry
2Reliability
If cyclization reaction between tetrafluoroethylene and acetylene is used, then 1,1,4,4-tetrafluoro-1,3-butadiene can be synthesized, but high temperature of 600°C is required
Solution Approach 1:
The patent replaces the high-temperature thermal cyclization mechanism with a copper-mediated coupling reaction mechanism. Instead of relying on thermal energy (600°C) to drive the cyclization, the reaction proceeds through copper-catalyzed coupling at much lower temperatures, substituting a thermal process with a chemically-mediated process
Solution Approach 2:
The patent fundamentally changes the reaction mechanism parameter from thermal cyclization to copper-mediated coupling. This parameter change allows the same product (1,1,4,4-tetrafluoro-1,3-butadiene) to be synthesized at dramatically lower temperatures by changing the reaction pathway from high-temperature cyclization to low-temperature coupling
3Productivity
If 4 equivalents of activated copper are used on 1,1-difluoroiodoethylene, then hydrofluorobutadiene can be obtained at high yield of 88%, but the amount of metal used is excessive
Solution Approach 1:
The patent introduces copper(I) halide as an intermediary substance that mediates the coupling reaction. The copper(I) halide forms a catalytic cycle that enables the coupling to proceed with only 1 equivalent of zero-valent metal, rather than requiring 4 equivalents as stoichiometric reagent. The intermediary copper salt allows the metal to function catalytically rather than stoichiometrically
Solution Approach 2:
The patent changes the metal-to-substrate ratio parameter from 4:1 to 1:1 by introducing copper(I) halide as an intermediary. This parameter change transforms the reaction from requiring stoichiometric amounts of metal (4 equivalents) to requiring only catalytic amounts (1 equivalent), thereby reducing metal consumption while maintaining high yield
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 enables high-yield, low-cost production of hydrofluorobutadiene using a reduced amount of zero-valent metal, overcoming the limitations of previous methods by eliminating the need for expensive catalysts and high-temperature conditions.
Implementation Method 1
a coupling reaction of halogenated olefins with a reduced amount of zero-valent metal, such as copper, in the presence of a metal salt
Data Source
AI summary
An object of the present invention is to provide a simple, low-cost, and industrial method of producing a compound having a polyene skeleton containing hydrogen and fluorine and/or chlorine. A method of producing a halogenated diene represented by formula (1): A1A2C═CA3-CA4=CA5A6 [A1, A2, A5, and A6 are each independently hydrogen, fluorine, chlorine, a (perfluoro)alkyl group having 1 to 3 carbon atoms, or a (perfluoro)alkenyl group; A3 and A4 are each independently hydrogen, fluorine, or chlorine; at least one of A1 to A6 is hydrogen; at least one of A1 to A6 is fluorine or chlorine] comprises a step of subjecting the same or different halogenated olefin(s) represented by formula (2): A7A8C═CA9X [A7 and A8 are each independently hydrogen, fluorine, chlorine, a (perfluoro)alkyl group having 1 to 3 carbon atoms, or a (perfluoro)alkenyl group; A9 is each independently hydrogen, fluorine, or chlorine; X is bromine or iodine] to a coupling reaction in the presence of a zero-valent metal and a metal salt.