High Purity 1233zd(E) Production via Liquid Phase Fluorination
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Solution Overview
Problem
Existing methods for producing 1233zd(E) often result in impurities such as 2-chloro-3,3,3-trifluoropropene (1233xf), chlorotetrafluoropropene (1224), and 3,3,3-trifluoropropyne, which reduce yield and complicate the process, particularly due to their toxicity and explosive nature, and are difficult to separate from the desired product due to close boiling points.
Innovation Solution
The production of high purity 1233zd(E) is achieved by using pure 1,1,1,3,3-pentachloropropane as a starting material and employing a liquid phase manufacturing process, ensuring the reactor feed stream contains minimal impurities, and utilizing distillation and extraction methods to maintain impurity levels below 200 ppm, thereby avoiding the formation of toxic and explosive by-products.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If conventional production methods are used, then 1233zd(E) can be produced, but toxic and explosive impurities (1233xf, 1224, trifluoropropyne) are formed that reduce yield and complicate the process
Solution Approach 1:
The patent applies preliminary action by using high purity starting materials (1,1,1,3,3-pentachloropropane with purity ≥99.8%) before the fluorination reaction begins. This prevents the formation of toxic impurities 1233xf and 1224 at the source, rather than attempting to remove them afterward. The pure starting material ensures that the fluorination reaction produces minimal harmful by-products.
Solution Approach 2:
The patent changes the physical state parameter of the reaction system from vapor phase to liquid phase. By conducting the fluorination reaction in the liquid phase at temperatures below the boiling point of the reactants, the process achieves better selectivity and reduces formation of explosive impurity 3,3,3-trifluoropropyne, while maintaining production of desired 1233zd(E).
2Productivity
If impurities are present in the reactor feed, then the production process can proceed, but the purity of resulting 1233zd(E) is significantly reduced
Solution Approach 1:
The patent implements preliminary purification of the starting material 1,1,1,3,3-pentachloropropane to achieve purity of ≥99.8% before feeding it to the fluorination reactor. This preliminary action prevents impurities from contaminating the product stream, eliminating the need for complex post-reaction purification and maintaining both high productivity and high purity.
Solution Approach 2:
The patent applies local quality by ensuring that the starting material feed stream has exceptionally high purity (≥99.8%) compared to other process streams. This localized high purity requirement at the feed stage prevents impurity formation throughout the entire process, achieving both high productivity and high product purity without compromising either.
3Manufacturing precision
If 1233xf impurity is present in crude 1233zd(E), then yield losses occur during purification due to close boiling points
Solution Approach 1:
The patent prevents formation of impurity 1233xf through preliminary action by using high purity starting materials and optimized reaction conditions. By preventing 1233xf formation upfront rather than attempting to separate it later, the process avoids yield losses during purification that would otherwise be necessary due to the close boiling points of 1233xf and 1233zd(E).
Solution Approach 2:
The patent converts the potential harm of impurity formation into a benefit by using controlled liquid phase fluorination conditions that actually suppress 1233xf formation. The liquid phase reaction environment and controlled temperature profile transform what could be a harmful side reaction into a controlled process that minimizes unwanted by-products.
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 approach yields 1233zd(E) with a purity of greater than 99.6% by weight and impurity levels below 200 ppm, significantly improving the safety and efficiency of the production process by minimizing toxic and explosive impurities, and enhancing yield through effective separation techniques.
Implementation Method 1
the fluorination of 240fa to form 1233zd(E)
Implementation Method 2
utilizing distillation and extraction methods to maintain impurity levels below 200 ppm
Implementation Method 3
utilizing distillation and extraction methods to maintain impurity levels below 200 ppm
Data Source
AI summary
The present invention discloses high purity E-1-chloro-3,3,3-trifluoropropene (1233zd(E)) and methods to produce the same. More specifically, the present invention discloses the methods of making 1233zd(E) essentially free of toxic impurities (e.g. 2-chloro-3,3,3-trifluoropropene (1233xf), chlorotetrafluoro-propene (1224), and 3,3,3-trifluoropropyne). The present invention further provides methods for making high purity 1233zd(E) with concentration of 1233xf and 1224 at or below 200 parts per million (ppm) and 3,3,3-trifluoropropyne impurities at or below 20 ppm. Formation of 1233xf impurity can be avoided if pure 1,1,1,3,3-pentachloropropane is used as a starting material. It was also found that formation of 1233xf is avoided if a liquid phase manufacturing process is used.