Linear Internal Olefin Purification via Acid Catalyst Isomerization
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Solution Overview
Problem
Existing methods for producing high-purity linear internal olefins and linear alkanes face challenges due to the presence of vinylidenes, which are difficult to separate from linear olefins, leading to the production of methyl-branched alkanes that decrease the value of the desired linear alkane product.
Innovation Solution
A multistep process involving contacting an olefin feed with a first acid catalyst and carboxylic acid to form a reaction product, removing secondary esters, and then contacting the esters with a second acid catalyst to produce highly linear internal olefins, which can be further hydrogenated to form linear alkanes.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If vinylidenes are separated from linear olefins by distillation, then separation is achieved, but the process becomes extremely difficult and costly
Solution Approach 1:
The patent introduces an acid catalyst as an intermediary substance that facilitates the isomerization of vinylidenes into linear olefins. This mediator enables the conversion process without requiring direct separation, thereby resolving the technical contradiction between achieving high purity and avoiding complex separation processes
Solution Approach 2:
The patent changes the chemical parameter of the olefin molecules by catalyzing isomerization reactions. This transforms the structural parameters of vinylidene molecules, converting them from branched to linear configurations, thus achieving high purity linear olefins without complex separation
2Ease of manufacture
If vinylidenes are not separated and are directly hydrogenated, then the process is simplified, but methyl branched alkanes are produced that decrease product value
Solution Approach 1:
The patent applies preliminary isomerization action to convert vinylidenes into linear olefins before the hydrogenation step. This preliminary transformation ensures that when hydrogenation occurs, the resulting alkanes are linear rather than branched, thus maintaining both process simplicity and product quality
Solution Approach 2:
The patent creates a continuous process where isomerization and hydrogenation occur in sequence without interruption. This continuous action transforms vinylidenes to linear olefins and then to linear alkanes in one integrated flow, maintaining both ease of manufacture and high product linearity
3Productivity
If a single-step hydrogenation process is used, then productivity is high, but the presence of vinylidenes leads to branched alkane formation
Solution Approach 1:
The patent segments the production process into two distinct but connected steps: isomerization followed by hydrogenation. This segmentation allows each step to perform its specific function optimally - isomerization converts vinylidenes to linear olefins, and hydrogenation converts them to linear alkanes - thereby maintaining both high productivity and high product purity
Solution Approach 2:
The patent maintains continuous production flow through the two-step process, where the output of isomerization immediately feeds into hydrogenation. This continuity ensures high productivity while the intermediate isomerization step guarantees high product purity by eliminating branched structures before hydrogenation
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
The process significantly reduces branching, resulting in high-purity linear internal olefins and alkanes with minimal branched products, enhancing the value of the final alkane product.
Implementation Method 1
contacting an olefin feed comprising C10 to C20 vinylidenes and a C10 to C20 normal alpha olefin and/or C10 to C20 linear internal olefins, a first acid catalyst, and a C1 to C18 carboxylic acid to form a first reaction product
Implementation Method 2
contacting an olefin feed comprising C10 to C20 vinylidenes and a C10 to C20 normal alpha olefin and/or C10 to C20 linear internal olefins, a first acid catalyst, and a C1 to C18 carboxylic acid to form a first reaction product comprising linear internal olefins, trisubstituted olefins, and secondary esters
Implementation Method 3
contacting the secondary esters and a second acid catalyst to form a second reaction product comprising linear internal olefins
Implementation Method 4
further comprising a step (e) of hydrogenating the linear internal olefin product to form a linear alkane product
Data Source
AI summary
Processes for producing a linear internal olefin product include the steps of contacting an olefin feed containing C10-C20 vinylidenes and a C10-C20 normal alpha olefin and/or C10-C20 linear internal olefins, a first acid catalyst, and a C1 to C18 carboxylic acid to form a first reaction product containing linear internal olefins, trisubstituted olefins, and secondary esters, then removing all or a portion of the secondary esters from the first reaction product, followed by contacting the secondary esters and a second acid catalyst to form a second reaction product comprising linear internal olefins, and then removing all or a portion of the linear internal olefins from the second reaction product to form the linear internal olefin product. Linear alkanes subsequently can be produced by hydrogenating the linear internal olefin product to form a linear alkane product.