Cyclohexanone Production via Phenol Hydrogenation
Find Innovative SolutionsGenerate Solutions
Solution Overview
Problem
The production of cyclohexanone through the oxidation of cyclohexylbenzene to cyclohexylbenzene hydroperoxide followed by cleavage results in an azeotropic mixture with phenol, making separation costly and inefficient, and there is a need to balance the supply and demand between cyclohexanone and phenol.
Innovation Solution
A process involving the oxidation of cyclohexylbenzene to cyclohexylbenzene hydroperoxide, followed by cleavage, and then subjecting a portion of the effluent to a selective hydrogenation step to convert phenol into additional cyclohexanone, allowing for cost-effective purification and potential conversion of cyclohexanone back to phenol based on market demand.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If cyclohexylbenzene is oxidized and cleaved to produce cyclohexanone and phenol, then cyclohexanone is produced, but an azeotropic mixture is formed making separation costly and inefficient
Solution Approach 1:
The patent extracts phenol from the azeotropic mixture through selective hydrogenation, converting it to cyclohexanone. This removes the problematic phenol component that causes separation difficulties, allowing the cyclohexanone to be obtained more easily without complex separation equipment.
Solution Approach 2:
The patent changes the chemical state of phenol by hydrogenating it to cyclohexanone. This parameter change (chemical transformation) converts the separation problem into a production advantage, as the hydrogenated phenol adds to the cyclohexanone yield rather than requiring separation.
2Productivity
If phenol is separated from the effluent before hydrogenation, then hydrogenation efficiency is improved, but separation costs increase
Solution Approach 1:
The patent applies partial hydrogenation to the entire effluent stream rather than requiring complete phenol separation first. This partial action approach allows hydrogenation to proceed effectively on the phenol present in the mixture without requiring costly complete separation, achieving a balance between efficiency and cost.
Solution Approach 2:
The hydrogenation step serves multiple functions: it converts phenol to cyclohexanone, increases overall cyclohexanone yield, and simultaneously acts as a purification step by removing phenol from the mixture. This multi-functionality reduces the need for separate dedicated separation equipment.
3Quantity of substance
If the Hock process route is used to produce cyclohexanone and phenol, then both valuable products are obtained, but supply and demand balance becomes difficult to control
Solution Approach 1:
The patent introduces dynamic control by allowing selective hydrogenation of phenol to cyclohexanone based on market conditions. This dynamic adjustment capability enables the process to adapt product distribution to supply and demand balances, making the production system flexible rather than fixed at 1:1 ratios.
Solution Approach 2:
The patent changes the product ratio parameter by converting phenol to cyclohexanone through hydrogenation. This parameter change allows the output composition to be adjusted according to market requirements, transforming a fixed 1:1 production ratio into a flexible variable ratio system.
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 enhances the yield and cost-effectiveness of cyclohexanone production by converting phenol to cyclohexanone, reducing the need for expensive separation steps and allowing for flexible product distribution based on market requirements.
Implementation Method 1
contacting said effluent stream portion with hydrogen in the presence of a hydrogenation catalyst in said hydrogenation reaction zone under conditions effective to convert at least part of the phenol in said effluent portion into cyclohexanone
Implementation Method 2
oxidizing cyclohexylbenzene to produce cyclohexylbenzene hydroperoxide
Data Source
AI summary
In a process for producing cyclohexanone, cyclohexylbenzene is oxidized to produce cyclohexylbenzene hydroperoxide and then the resultant cyclohexylbenzene hydroperoxide is cleaved to produce an effluent stream comprising phenol and cyclohexanone. At least a portion of the effluent stream is then fed to at least one hydrogenation reaction zone, where the effluent stream portion is contacted with hydrogen in the presence of a hydrogenation catalyst under conditions effective to convert at least part of the phenol in the effluent portion into cyclohexanone.