Fluorinated Cyclobutane Production via Catalytic Cyclodimerization
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Solution Overview
Problem
Current methods for producing 1,1,2-trifluoro-2-(trifluoromethyl)cyclobutane (TFMCB) are not cost-effective and are not amenable to large-scale commercial production due to issues such as complex mixtures, unwanted by-products, and poor conversions/selectivities, especially under high temperature and excess ethylene conditions.
Innovation Solution
A continuous catalytic process involving the reaction of hexafluoropropene and ethylene in the presence of a metal catalyst and oligomerization/polymerization inhibitors, with controlled reaction conditions to produce TFMCB, followed by pyrolysis of TFMCB to yield 2,3,3,3-tetrafluoropropene and vinylidene fluoride with high purity and selectivity.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Quantity of substance
If thermal dimerization is conducted at high temperature (200-600°C) for extended time (4-1000 hours), then conversion of reactants improves, but complex mixtures and unwanted by-products increase
Solution Approach 1:
The patent applies parameter changes by optimizing temperature (200-600°C range), time (4-1000 hours range), and reactant ratio (0.1:1 to 100:1 range) to achieve high conversion while controlling by-product formation. This resolves the contradiction by finding optimal parameter windows that balance conversion efficiency with product purity.
Solution Approach 2:
The patent employs preliminary anti-action by adding polymerization inhibitors to prevent oligomerization and polymerization side reactions before they can significantly occur. This proactive measure counteracts the tendency toward complex mixtures while maintaining high conversion conditions.
2Quantity of substance
If excess ethylene is used in the cyclodimerization reaction, then conversion of hexafluoropropene improves, but selectivity and product purity deteriorate
Solution Approach 1:
The patent optimizes the ethylene to hexafluoropropene ratio parameter within the range of 0.1:1 to 100:1 (preferably 1:1 to 10:1) to achieve the desired balance. By adjusting this critical parameter, the process achieves high conversion while maintaining acceptable selectivity and product purity.
Solution Approach 2:
The patent employs feedback control by monitoring the reaction mixture composition and adjusting reaction conditions (temperature, time, reactant feed rates) to maintain optimal conversion and selectivity. This allows dynamic adjustment to compensate for the effects of excess ethylene.
3Ease of manufacture
If metathesis catalyst is used in organic solvent, then HFO-1234yf production is achieved, but process cost and complexity increase
Solution Approach 1:
The patent extracts and eliminates the expensive metathesis catalyst and organic solvent components from the process by using alternative cyclodimerization chemistry. This substitution removes the sources of high cost and complexity while achieving the same ultimate product through a different reaction pathway.
Solution Approach 2:
The patent replaces expensive, sensitive metathesis catalysts with simpler, more robust catalytic systems that can be used under milder conditions without requiring expensive organic solvents. This substitution with cheaper, more stable alternatives reduces overall process cost and complexity.
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 process achieves high yields and selectivity of TFMCB and its subsequent conversion to valuable fluorinated compounds, such as HFO-1234yf and VDF, with improved atom efficiency and reduced by-product formation, making it commercially viable.
Implementation Method 1
reacting the hexafluoropropene and ethylene in the reaction vessel in the presence of at least one metal catalyst
Implementation Method 2
reacting the hexafluoropropene and ethylene in the reaction vessel in the presence of at least one oligomerization/polymerization inhibitor
Implementation Method 3
pyrolysis of TFMCB to yield 2,3,3,3-tetrafluoropropene and vinylidene fluoride
Data Source
AI summary
The production of 1, 1, 2-trifluoro-2-(trifluoromethyl)cyclobutane (TFMCB). More specifically, the present invention relates to a process for making 1, 1, 2-trifluoro-2-(trifluoromethyl)cyclobutane via a continuous catalytic reaction from commercially available raw materials ethylene and hexafluoropropene.