HFO-1447 Production via Staged Fluorination and Dehydrochlorination
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Solution Overview
Problem
Existing methods for producing 1,1,1,3,5,5,5-heptafluoro-2-pentene (HFO-1447) result in low yields of high-purity product due to the difficulty in separating by-products such as bis(trifluoromethyl) allene and unreacted starting materials, leading to resin deterioration.
Innovation Solution
A method involving the reaction of 3-chloro-hexafluoro-2-pentene with hydrogen fluoride at controlled temperatures in the presence of a metal halide catalyst, followed by dehydrochlorination with an activated carbon catalyst to produce high-purity HFO-1447.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If conventional defluorination reaction with high surface AlF3 catalyst is used to produce HFO-1447, then the production process is simple, but the yield of high-purity HFO-1447 is low due to difficult separation of by-products
Solution Approach 1:
The production process is divided into two distinct stages: first, fluorination reaction to produce 3-chloro-1,1,1,3,5,5,5-heptafluoropentane with high selectivity; second, dehydrochlorination reaction to produce HFO-1447. This segmentation allows each reaction to be optimized independently, achieving both high purity intermediate and high final yield.
Solution Approach 2:
The patent introduces 3-chloro-1,1,1,3,5,5,5-heptafluoropentane as an intermediate compound. This intermediary substance has a boiling point of 89°C, which is significantly different from HFO-1447 (52°C), enabling easy separation and purification before the final dehydrochlorination step.
2Ease of manufacture
If conventional defluorination reaction is used, then the process is straightforward, but separation of unreacted HFC-458 from (Z)-HFO-1447 is difficult
Solution Approach 1:
The fluorination reaction is performed first to convert the starting material into an intermediate compound with a different boiling point. This preliminary action creates a substance that can be easily separated from unreacted starting material through distillation before the final product is formed.
Solution Approach 2:
The patent changes the physical parameter (boiling point) of the intermediate compound to 89°C, which provides sufficient separation from both the starting material HFC-458 (boiling point 28°C) and the final product HFO-1447 (boiling point 52°C), enabling efficient purification at each stage.
3Ease of manufacture
If conventional production method is used, then the process is established, but allene compound by-product is generated and difficult to separate from (E)-HFO-1447
Solution Approach 1:
The patent converts the potential harm of by-product formation into a benefit by designing a reaction pathway where the intermediate compound's physical properties (boiling point 89°C) facilitate easy separation of any allene compound by-products through distillation before the final dehydrochlorination step.
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 efficiently produces HFO-1447 with a purity of over 99% without contamination from allene compounds or unreacted starting materials, preventing resin deterioration and expanding the range of applicable resins.
Implementation Method 1
reacting 3-chloro-hexafluoro-2-pentene with hydrogen fluoride at a temperature of more than −10° C. and 20° C. or less in the presence of a metal halide catalyst to produce 3-chloro-1,1,1,3,5,5,5-heptafluoropentane
Implementation Method 2
subjecting the 3-chloro-1,1,1,3,5,5,5-heptafluoropentane obtained in (a) to a dehydrochlorination reaction in the presence of an activated carbon catalyst to produce 1,1,1,3,5,5,5-heptafluoro-2-pentene
Data Source
AI summary
An object of the present invention is to provide a method for producing a high-purity 1,1,1,3,5,5,5-heptafluoro-2-pentene (HFO-1447), particularly with a purity of more than 99%. Another object of the present invention is to provide a high-purity 1,1,1,3,5,5,5-heptafluoro-2-pentene (HFO-1447) and uses thereof. A method for producing 1,1,1,3,5,5,5-heptafluoro-2-pentene, including: (a) reacting 3-chloro-hexafluoro-2-pentene with hydrogen fluoride at a temperature of more than −10° C. and 20° C. or less in the presence of a metal halide catalyst to produce 3-chloro-1,1,1,3,5,5,5-heptafluoropentane; and (b) subjecting the 3-chloro-1,1,1,3,5,5,5-heptafluoropentane obtained in (a) to a dehydrochlorination reaction in the presence of an activated carbon catalyst to produce 1,1,1,3,5,5,5-heptafluoro-2-pentene.