Ionic Liquid Fluorination for HCFO-1233zd Yield
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Solution Overview
Problem
Current processes for producing 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) suffer from low yields and catalyst deactivation due to the formation of heavy by-products, leading to reduced productivity and the need for frequent reactor downtime.
Innovation Solution
The process involves fluorinating 1,1,1,3,3-pentachloropropane or 1,1,3,3-tetrachloropropene in the presence of an ionic liquid with hydrogen fluoride, allowing for improved dissolution and reaction, with optional catalysts like TiCl4, to produce HCFO-1233zd while minimizing by-product formation.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If a fluorination catalyst is used to increase the yield of HCFO-1233zd, then the manufacturing precision and productivity improve, but heavy by-products, oligomers, and tars build up in the reactor leading to catalyst deactivation and loss of productivity
Solution Approach 1:
The harmful by-products (heavy by-products, oligomers, and tars) are continuously extracted from the reactor system through a distillation column, preventing their accumulation that would otherwise lead to catalyst deactivation and productivity loss
Solution Approach 2:
The process operates continuously with the distillation column running alongside the reactor to continuously remove by-products, maintaining catalyst activity and productivity without periodic shutdowns for catalyst replacement or reactor cleaning
2Ease of manufacture
If the reaction is conducted in gas phase, then the process is simpler, but the yield of HCFO-1233zd is relatively low
Solution Approach 1:
The reaction phase is changed from gas phase to liquid phase, and a catalyst is introduced to change the reaction conditions, thereby significantly increasing the yield of HCFO-1233zd while maintaining process feasibility through continuous operation
3Reliability
If non-catalytic liquid phase reaction is used, then catalyst deactivation is avoided, but the yield and production rate of HCFO-1233zd remain low
Solution Approach 1:
By-products are continuously extracted from the reaction system, preventing catalyst deactivation, while the catalyst remains active at high concentrations to maintain high production rates
Solution Approach 2:
The system uses a composite approach combining a fluorination catalyst with a continuous distillation system, where the catalyst provides high reaction efficiency and the distillation system removes by-products that would cause deactivation, achieving both high productivity and catalyst stability
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 method enhances the yield of HCFO-1233zd, reduces catalyst deactivation, and minimizes downtime by facilitating a more efficient and continuous production process.
Implementation Method 1
reacting a starting material selected from the group consisting of 1,1,1,3,3-pentachloropropane (HCC-240fa), 1,1,3,3-tetrachloropropene, and 1,1,1,3-tetrachloropropene, alone or in combination, with anhydrous hydrogen fluoride in a liquid phase reactor in the presence of an ionic liquid, which facilitates the dissolution and reaction between the starting materials and hydrogen fluoride (HF)
Implementation Method 2
U.S. Pat. No. 6,844,475 describes a catalyzed liquid phase reaction of HCC-240fa with HF to produce 1233zd in higher yields
Data Source
AI summary
This invention relates to methods and systems for producing hydrochlorofluoro-olefins, particularly 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) by the fluorination of a starting material selected from the group consisting of 1,1,1,3,3-pentachloropropane (HCC-240fa), 1,1,3,3-tetrachloropropene, and 1,1,1,3-tetrachloropropene, alone or in combination, in an ionic liquid.