Integrated HFO-1234yf Synthesis with Fluorination and Dehydrochlorination
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Solution Overview
Problem
Existing methods for producing hydrofluoroolefins like HFO-1234yf are either hazardous, economically costly, or result in low yields with significant byproduct formation, necessitating a more efficient and economical production process.
Innovation Solution
An integrated manufacturing process involving three separate reaction steps, including vapor and liquid phase reactions, utilizing specific catalysts and reactors, with optional purification processes, which maximizes raw material utilization and product yields, and includes the ability to isolate by-products that are commercially valuable. The process includes the ability to recycle unreacted starting materials to maximize raw material utilization and product yields, and includes the ability to isolate by-products that are commercially valuable.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If hydrogen gas is used to contact fluorinated alcohols for producing HFOs, then the process achieves relatively high yield, but the process becomes hazardous due to commercial scale handling of hydrogen gas at high temperature and economically costly due to the need for on-site hydrogen plants
Solution Approach 1:
The patent extracts the hazardous hydrogen gas handling step from the process by using alternative fluorinating agents (such as sulfur tetrafluoride or gaseous fluorine) that can be delivered without requiring on-site hydrogen production facilities, thereby eliminating the associated hazards and infrastructure costs while maintaining high yields
Solution Approach 2:
The patent introduces intermediate compounds (fluorinated alcohols as starting materials) that can be converted to HFOs through fluorination reactions using safer, more manageable fluorinating agents, serving as intermediaries that avoid direct hydrogen gas handling while achieving the desired product
2Ease of manufacture
If pyrolysis of methyl chloride and tetrafluoroethylene is used to make fluorine containing olefins, then the process can be performed with available materials, but the process results in relatively low yield and significant formation of unwanted byproducts including carbon black that deactivates the catalyst
Solution Approach 1:
The patent performs preliminary fluorination of chlorinated hydrocarbons to create pre-fluorinated intermediates before the final olefin formation step, ensuring that fluorine atoms are already in place on the molecular structure, which directs the reaction toward the desired HFO product and prevents formation of carbon black and other unwanted byproducts
Solution Approach 2:
The patent changes the reaction parameters by using controlled fluorination conditions with specific fluorinating agents and catalysts, transitioning from uncontrolled pyrolysis conditions to a more selective chemical reaction environment that achieves high yields while minimizing byproduct formation
3Ease of manufacture
If pyrolysis process is used for producing fluorine containing olefins, then the process can proceed with available starting materials, but a very large percentage of organic starting material is converted to unwanted and unimportant byproducts
Solution Approach 1:
The patent converts the potential harm of excessive reactivity in pyrolysis processes into benefit by using controlled fluorination reactions where the high reactivity of fluorinating agents is directed toward specific positions on the chlorinated hydrocarbon molecules, ensuring that starting material is converted to desired HFO products rather than unwanted byproducts
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 maximizes raw material utilization and product yields, and includes the ability to isolate by-products that are commercially valuable, thereby achieving high yields and reducing production costs.
Implementation Method 1
contacting said starting composition with a first fluorinating agent to produce a first intermediate composition comprising 2-chloro-3,3,3-trifluoropropene
Implementation Method 2
contacting said first intermediate composition with a second fluorinating agent to produce a second intermediate composition comprising 2-chloro-1,1,1,2- tetrafluoropropane
Implementation Method 3
catalytically dehydrochlorinating at least a portion of said 2-chloro-1,1,1,2-tetrafluoropropane to produce a reaction product comprising 2,3,3,3-tetrafluoroprop-1-ene
Data Source
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AI summary
A method for preparing 2,3,3,3-tetrafluoroprop-1-ene comprising (a) providing a starting composition comprising at least one compound having a structure selected from Formulae I, II and III: CX2=CCl-CH2X (Formula I) CX3-CCl=CH2 (Formula II) CX3-CHCl-CH2X (Formula III) wherein X is independently selected from F, Cl, Br, and I, provided that at least one X is not fluorine; (b) contacting said starting composition with a first fluorinating agent to produce a first intermediate composition comprising 2-chloro-3,3,3-trifluoropropene and a first chlorine-containing byproduct; (c) contacting said first intermediate composition with a second fluorinating agent to produce a second intermediate composition comprising 2-chloro-1,1,1,2-tetrafluoropropane and a second chlorine-containing byproduct; and (d) catalytically dehydrochlorinating at least a portion of said 2-chloro-1,1,1,2-tetrafluoropropane to produce a reaction product comprising 2,3,3,3-tetrafluoroprop-1-ene.