Cyclododecanone Preparation with Controlled Epoxidation Selectivity
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Solution Overview
Problem
The existing methods for preparing cyclododecanone generate significant amounts of by-products such as cyclododecanol and cyclododecadiol, which hinder the efficiency and economy of the laurolactam production process.
Innovation Solution
A preparation method involving the use of a catalyst system with tungsten, phosphoric acid, and amine compounds to epoxidize cyclododecene, followed by a rearrangement reaction under an alkali metal halide catalyst, and purification with an aqueous organic acid solution, optimizing the addition form of hydrogen peroxide to achieve high conversion and selectivity.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If cyclododecanone is prepared by selective hydrogenation of cyclododecatriene followed by oxidation, then cyclododecanone can be produced, but significant amounts of by-products (cyclododecanol, cyclododecadiol) are generated
Solution Approach 1:
The patent changes the reaction parameters by using a specific catalyst system (tungsten compound, phosphoric acid compound, and amine compound) and controlling the addition rate of hydrogen peroxide according to a mathematical model. This ensures that hydrogen peroxide is consumed efficiently for epoxidation without excessive decomposition, thereby reducing by-product formation while maintaining high productivity
Solution Approach 2:
The patent introduces epoxidized cyclododecane as an intermediate compound. By using this intermediate and performing a rearrangement reaction under alkaline conditions, the process achieves high selectivity for cyclododecanone while minimizing the formation of unwanted by-products like cyclododecanol and cyclododecadiol
2Productivity
If hydrogen peroxide is added in large amounts to increase conversion rate, then reaction speed increases, but hydrogen peroxide decomposition increases and selectivity decreases
Solution Approach 1:
The patent applies periodic action by controlling the addition rate of hydrogen peroxide over time according to a mathematical model. The addition rate is adjusted dynamically - starting faster and then modulating based on conversion rate and selectivity measurements - to maintain optimal reaction conditions throughout the process, preventing both insufficient conversion and excessive decomposition
Solution Approach 2:
The patent implements feedback control by continuously monitoring the conversion rate and selectivity of hydrogen peroxide, and using this information to adjust the addition rate. The mathematical model incorporates real-time measurements to optimize the addition rate, ensuring high conversion while maintaining selectivity and preventing decomposition
3Manufacturing precision
If a complex separation process is used to remove by-products, then product purity increases, but process complexity and cost increase
Solution Approach 1:
The patent applies preliminary action by optimizing the reaction conditions and catalyst system to prevent by-product formation in the first place. By using the specific catalyst combination and controlled hydrogen peroxide addition, the process achieves high selectivity from the start, eliminating the need for complex separation and purification operations that would otherwise be required
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 method significantly reduces by-product formation, allows for a simplified process configuration, and enhances the conversion rate and selectivity of cyclododecanone production, making it suitable for commercial mass production and reducing the risk of explosive reactions.
Implementation Method 1
preparing an epoxidized cyclododecane by applying heat while additionally adding hydrogen peroxide to a mixture of cyclododecene and hydrogen peroxide under a catalyst system containing a tungsten compound, a phosphoric acid compound, and an amine compound
Implementation Method 2
preparing an epoxidized cyclododecane by applying heat while additionally adding hydrogen peroxide to a mixture of cyclododecene and hydrogen peroxide
Implementation Method 3
preparing a cyclododecanone through a rearrangement reaction without separation of a reaction mixture containing the epoxidized cyclododecane under an alkali metal halide catalyst
Implementation Method 4
purifying the cyclododecanone by mixing the reaction mixture containing the cyclododecanone with an aqueous organic acid solution and stirring them
Data Source
AI summary
The present invention relates to cyclododecanone and a preparation method therefor. According to the present invention, a cyclododecanone preparation method capable of achieving a high conversion rate and minimizing unreacted materials and the production of reaction byproducts can be provided. In addition, the present invention implements a high conversion rate and selectivity despite a simplified process, and thus can be helpfully utilized in economical laurolactam production methods that are easy to mass-produce commercially. According to the present invention, the proportions of cyclododecanol, cyclododecadiol, and the like, obtained as reaction byproducts, in the final product can be drastically reduced, and cyclododecanone can be produced at a high conversion rate.