Integrated Fluorination Process for HFO-1233zd and HFO-1234ze
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Solution Overview
Problem
There is a need for an economical process to continuously produce trans-1-chloro-3,3,3-trifluoropropene (1233zd(E)) and trans-1,3,3,3-tetrafluoropropene (1234ze(E)) due to the phased out use of 1,1,1,3,3-pentafluoropropane (245fa), which forms an azeotropic composition making separation difficult with conventional methods.
Innovation Solution
An integrated three-step process co-producing 1233zd(E), 1234ze(E), and 245fa from a common feed material 240fa, involving reaction with anhydrous HF, dehydrochlorination, and dehydrofluorination, allowing for flexibility in product ratios and recycling unreacted materials to maximize yields and isolate by-products.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If 245fa is used as a foam-blowing agent, then insulation value is achieved, but separation becomes impossible due to azeotropic composition
Solution Approach 1:
The patent extracts 245fa from the azeotropic mixture by selective fluorination of 240fa followed by dehydrofluorination of 244fa intermediate. This separates the desired 245fa product from the azeotropic composition problem, allowing pure 245fa to be obtained without conventional separation difficulties
Solution Approach 2:
The patent introduces 244fa as an intermediate compound in the synthesis pathway. By using 244fa as a mediator between 240fa and 245fa, the process avoids direct formation of the problematic azeotropic mixture and enables controlled production of pure 245fa
2Ease of manufacture
If conventional separation techniques are used for azeotropic mixtures, then simple distillation is applied, but separation efficiency becomes zero
Solution Approach 1:
The patent performs preliminary separation by selectively producing 244fa intermediate through controlled fluorination, then converting it to 245fa in a second step. This preliminary action avoids the need for separating azeotropic mixtures by distillation, as the desired product is formed in pure form through sequential reactions
3Object-affected harmful factors
If 245fa is phased out, then environmental concerns are addressed, but economical production process is still needed
Solution Approach 1:
The patent changes the production parameters by using a two-step process with controlled fluorination and dehydrofluorination conditions. This allows economical production of environmentally acceptable alternatives (1233zd and 1234ze) while maintaining production efficiency through optimized reaction parameters and intermediate utilization
4Loss of substance
If integrated co-production process is implemented, then raw material utilization is enhanced, but process complexity increases
Solution Approach 1:
The patent implements a universal process where 240fa serves multiple functions: it can be fluorinated to produce 244fa, which can then be converted to 245fa, 1233zd, or 1234ze depending on the desired product. This multi-functionality maximizes raw material utilization while the modular nature of the process keeps complexity manageable
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 process avoids the separation challenges of azeotropic compositions, reduces HF usage, and allows for flexible production of each compound, enhancing raw material utilization and product yields while enabling the sale of by-products.
Implementation Method 1
the reaction of 240fa with anhydrous HF in excess in a liquid-phase catalyzed reactor in such a way as to co-produce primarily 1233zd(E) and 244fa (plus byproduct HCl)
Implementation Method 2
the 244fa stream can be dehydrochlorinated to produce the desired second product 1234ze(E)
Implementation Method 3
the 244fa stream can be dehydrofluorinated to produce 1233zd(E) if more of that product is desired
Implementation Method 4
the 244fa stream can be further fluorinated to form 245fa
Data Source
AI summary
Disclosed is an integrated process to co-produce trans-1-chloro-3,3,3-trifluoro-propene (1233zd(E)), trans-1,3,3,3-tetrafluoropropene (1234ze(E)), and 1,1,1,3,3-pentafluoropropane (245fa). Overall the co-production is a three-step process. The chemistry involves the steps of:(1) the reaction of 240fa with anhydrous HF in excess in a liquid-phase catalyzed reactor in such a way as to co-produce primarily 1233zd(E) and 244fa (plus byproduct HCl);(2) the 244fa stream can then be used to directly produce any of the three desired products;(3a) the 244fa stream can be dehydrochlorinated to produce the desired second product 1234ze(E); and/or(3b) the 244fa stream can be dehydrofluorinated to produce 1233zd(E) if more of that product is desired; and/or(3c) the 244fa stream can be further fluorinated to form 245fa.