HFO-1132E Production via Hydrogenation and Cis-Trans Isomerization
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Solution Overview
Problem
There is a need for improved methods to produce trans-1,2-difluoroethylene (HFO-1132E) with minimized production of undesired byproducts from chlorotrifluoroethylene (CTFE) and/or trifluoroethylene (HFO-1123).
Innovation Solution
A three-step process involving hydrogenation, dehydrohalogenation, and isomerization of chlorotrifluoroethylene and/or trifluoroethylene, using specific catalysts and conditions to maximize desired intermediates and minimize byproducts, including the use of palladium, platinum, and other metals on alumina supports.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If conventional hydrogenation methods are used to produce 1,1,2-trifluoroethane from chlorotrifluoroethylene and/or trifluoroethylene, then the production of desired intermediates can be achieved, but undesired byproducts are formed in significant amounts
Solution Approach 1:
The patent applies parameter changes by optimizing reaction temperature (75-225°C), pressure (1-100 psig), hydrogen to feed material mole ratio (2:1 to 20:1), and contact time (0.1-120 seconds) to achieve high selectivity to desired intermediates while minimizing undesired byproducts. The catalyst loading (0.01-10 wt%) and type (Pd, Pt, Rh, Ru, Ir) are also carefully controlled parameters
Solution Approach 2:
The patent employs feedback control by monitoring reaction conditions and adjusting catalyst selection, conditioning, and operating parameters in real-time to maximize production of desired intermediates (1-chloro-1,1,2-trifluoroethane, 1-chloro-1,2,2-trifluoroethane, and trifluoroethylene) while minimizing byproducts such as ethane, chloroethane, and HCFC-142 isomers
2Productivity
If the hydrogenation step is optimized to maximize desired intermediates, then production efficiency improves, but the complexity of process control increases
Solution Approach 1:
The patent segments the complex hydrogenation process into distinct operational phases with specific parameter ranges for each phase. The process is divided into controlled steps involving catalyst selection, conditioning, and reaction conditions (temperature, pressure, residence time) that can be independently optimized and controlled
Solution Approach 2:
The patent uses catalysts (Pd, Pt, Rh, Ru, Ir on alumina supports) as intermediaries to facilitate the hydrogenation reaction. These catalysts mediate between hydrogen and the feed material (chlorotrifluoroethylene and/or trifluoroethylene), enabling controlled production of desired intermediates while simplifying the overall process control by providing a reliable reaction pathway
3Manufacturing precision
If dehydrohalogenation and isomerization steps are used to produce trans-1,2-difluoroethylene, then product purity improves, but additional process steps and catalysts are required
Solution Approach 1:
The patent applies preliminary action by first producing pure 1,1,2-trifluoroethane intermediate with high selectivity through optimized hydrogenation, then using this pure intermediate as the starting material for subsequent dehydrohalogenation and isomerization steps. This preliminary purification simplifies the overall process by ensuring high product purity from the outset
Solution Approach 2:
The patent uses parameter changes in the dehydrohalogenation and isomerization steps (temperature, catalyst type, pressure) to selectively produce trans-1,2-difluoroethylene with high purity. The isomerization step specifically converts cis-1,2-difluoroethylene to trans-1,2-difluoroethylene through controlled parameter adjustment
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 effectively produces trans-1,2-difluoroethylene with controlled production of desirable intermediates while reducing the formation of unwanted byproducts, enhancing the overall efficiency and purity of the process.
Implementation Method 1
hydrogenating a feed material (e.g., reactant composition) comprising chlorotrifluoroethylene (CTFE) and/or trifluoroethylene (HFO-1123) by reaction with hydrogen in the presence of a catalyst
Implementation Method 2
dehydrohalogenating 1,1,2-trifluoroethane (HFC-143) in the presence of a catalyst to produce trans-1,2-difluoroethylene (HFO-1132E) and cis-1,2-difluoroethylene (HFO-1132Z)
Implementation Method 3
isomerizing cis-1,2-difluoroethylene (HFO-1132Z) to produce trans-1,2-difluoroethylene (HFO-1132E)
Data Source
AI summary
Production of HFO-1132 and, in particular, HFO-1132E, is produced from chlorotrifluoroethylene (CTFE) and/or trifluoroethylene (HFO-1123). In a first step, 1,1,2-trifluoroethane (HFC-143) is produced by hydrogenating chlorotrifluoroethylene (CTFE) and/or trifluoroethylene (HFO-1123) by reaction with hydrogen in the presence of a catalyst at a temperature of between about 75° C. and about 225° C. The 1,1,2-trifluoroethane (HFC-143) may then be dehydrohalogenated in the presence of a catalyst to produce trans-1,2-difluoroethylene (HFO-1132E) and cis-1,2-difluoroethylene (HFO-1132Z). The cis-1,2-difluoroethylene (HFO-1132Z) may then be isomerized to produce trans-1,2-difluoroethylene (HFO-1132E).