Z-1336mzz Synthesis via Copper Catalyst and Segmented Intermediates
Find Innovative SolutionsGenerate Solutions
Solution Overview
Problem
There is a need for an efficient and economical process to produce (Z)-1,1,1,4,4,4-hexafluoro-2-butene (Z-1336mzz), which is used as a refrigerant and has low ozone depletion potential and global warming potential.
Innovation Solution
The process involves contacting a halogenated alkane with an olefin in the presence of a mononitrile and a catalyst comprising copper (II) chloride, followed by fluorination and dehydrochlorination steps to produce Z-1336mzz from readily available starting materials like CF3CCl3 and CCl4.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If conventional methods are used to produce Z-1336mzz, then the production cost is high, but the manufacturing efficiency and economy are poor
Solution Approach 1:
The patent changes the reaction parameters by using copper(II) chloride as a catalyst and conducting the reaction in acetonitrile solvent at controlled temperatures, which significantly improves the manufacturing efficiency and economy of Z-1336mzz production while reducing production costs
Solution Approach 2:
The patent introduces an intermediate compound (1,1,1,3,3-pentachloro-4,4,4-trifluorobutane) in the synthesis pathway, which serves as a mediator to enable the efficient production of Z-1336mzz through controlled chemical transformations, improving both manufacturing efficiency and cost-effectiveness
2Manufacturing precision
If existing synthesis routes are used, then the production process is complex, but the yield and purity are insufficient
Solution Approach 1:
The patent divides the synthesis process into distinct sequential steps: (1) formation of the intermediate compound with specific chlorine and fluorine substitution, and (2) conversion to Z-1336mzz through dehydrochlorination. This segmentation allows each step to be optimized independently, achieving high yield and purity while managing process complexity
Solution Approach 2:
The intermediate compound 1,1,1,3,3-pentachloro-4,4,4-trifluorobutane serves as a structured mediator that enables controlled transformation to the final product, ensuring high manufacturing precision through well-defined chemical pathways and intermediate purification steps
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 process provides a cost-effective synthesis route to Z-1336mzz, achieving high yields and purity, which is essential for its applications as a refrigerant and in other industrial uses.
Implementation Method 1
contacting a halogenated alkane with an olefin in the presence of a mononitrile and a catalyst comprising copper (II) chloride
Implementation Method 2
contacting 333jfa, produced as set forth hereinabove, with hydrogen fluoride (HF) in the gas phase or liquid phase, in the presence of a fluorination catalyst under conditions to produce a product mixture comprising 2,2-dichloro-1,1,1,4,4,4-hexafluorobutane
Implementation Method 3
contacting 336mfa, produced as set forth hereinabove, with base, and optionally a phase transfer catalyst, to produce a product mixture comprising 1,1,1,4,4,4-hexafluorobutyne
Implementation Method 4
1,1,1,4,4,4-hexafluoro-2-butyne is reacted with hydrogen and a hydrogenation catalyst to produce a product mixture comprising Z-1,1,1,4,4,4-hexafluoro-2-butene (Z-1336mzz)
Data Source
AI summary
A method of producing (Z)-1,1,1,4,4,4-hexafluoro-2-butene (Z-1336mzz) is described. The method utilizes readily available halogenated starting materials, including 1,1,1-trichloro-2,2,2-trifluoroethane (CFC-113a) and carbon tetrachloride.