1,3-Butadiene Purification via Azide-Alkyne Cycloaddition
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Solution Overview
Problem
Current methods for purifying 1,3-butadiene from C4 hydrocarbon streams are energy intensive and involve large solvent use, with risks of explosion and inefficiencies in separating acetylenes, necessitating the need for improved purification techniques.
Innovation Solution
The method involves introducing a C4 hydrocarbon stream to an organic azide in the presence of a catalyst to generate a stream containing 1,3-butadiene and a triazole, followed by separation and distillation to produce a purified 1,3-butadiene stream, using azide-alkyne cycloaddition reactions and solvent distillation.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If extractive distillation is used to separate butanes and butenes to produce crude butadiene, then separation is achieved, but large amounts of solvent are required and energy consumption increases
Solution Approach 1:
The patent changes the chemical state of acetylenes by converting them into triazoles through azide-alkyne cycloaddition reactions. This chemical transformation fundamentally alters the properties of acetylenes, enabling their separation from butadiene without requiring extractive distillation and its associated high energy consumption and large solvent volumes.
Solution Approach 2:
The patent extracts acetylenes from the C4 hydrocarbon stream by converting them into triazoles that can be separated through distillation. This extraction approach eliminates the need for extractive distillation of butanes and butenes, thereby reducing both energy consumption and solvent usage while achieving the desired separation.
2Reliability
If extractive distillation is used to separate vinyl- and ethyl-acetylenes from crude butadiene, then acetylenes are removed, but large amounts of solvent are required and explosion risk increases
Solution Approach 1:
The patent changes the chemical identity of acetylenes by converting them into triazoles. This transformation eliminates the need to handle large volumes of solvent required for extractive distillation of acetylenes, thereby reducing explosion risks while achieving effective removal of vinyl- and ethyl-acetylenes from crude butadiene.
Solution Approach 2:
The patent converts the harmful or risky presence of acetylenes (which require dangerous extractive distillation processes) into beneficial triazole products through cycloaddition reactions. This conversion transforms a safety hazard into a separation opportunity, eliminating the need for large solvent volumes and reducing explosion risks.
3Manufacturing precision
If conventional distillation is used to remove methylacetylene, then purification is achieved, but the process remains highly energy intensive
Solution Approach 1:
The patent changes the chemical state of all acetylenes including methylacetylene by converting them into triazoles. This chemical transformation eliminates the need for conventional distillation to remove methylacetylene, thereby achieving the required purification quality without the high energy consumption associated with conventional distillation processes.
4Reliability
If separated acetylenes are sent to a flare, then safety is maintained, but valuable 1,3-butadiene must be diluted which reduces productivity
Solution Approach 1:
The patent converts acetylenes into valuable triazole products through cycloaddition reactions rather than flaring them. This conversion eliminates the need to dilute 1,3-butadiene with inert gases for safety, thereby maintaining safety while preserving productivity and avoiding the loss of valuable butadiene that would occur with dilution.
Solution Approach 2:
Instead of discarding acetylenes through flaring, the patent recovers them by converting them into triazoles that can be separated and potentially utilized. This recovery approach eliminates the need for safety dilution and maintains maximum productivity while still ensuring safe handling of the C4 stream.
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 enhances the recovery of 1,3-butadiene with greater than 90% efficiency, reduces solvent usage, and minimizes risks, providing a more efficient and cost-effective purification process.
Implementation Method 1
introducing the C4 hydrocarbon stream to an organic azide in the presence of a catalyst to generate a first stream including 1,3-butadiene and a triazole
Implementation Method 2
separating the triazole from the first stream to produce a second stream including 1,3-butadiene
Data Source
AI summary
The presently disclosed subject matter relates to methods and systems for purifying 1,3-butadiene from a C4 hydrocarbon stream. An example method includes introducing a C4 hydrocarbon stream including 1,3-butadiene and acetylenes to an organic azide in the presence of a catalyst to generate a first stream including triazole, separating triazole from the first stream to produce a second stream including 1,3-butadiene, and distilling 1,3-butadiene from the second stream to produce a purified 1,3-butadiene product stream.