Epoxy Compound Production via Tungsten Catalyst and Onium Salt
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Solution Overview
Problem
Conventional methods for producing epoxy compounds using peracids are hazardous, lead to low selectivity due to reaction with carboxylic acids, and result in ring opening of epoxy groups, making them industrially inefficient and unsafe.
Innovation Solution
A method involving the oxidation of organic compounds with hydrogen peroxide using a catalyst comprising tungsten compounds, phosphoric acids, phosphonic acids, or their salts, and an onium salt with an alkyl sulfate ion as a phase transfer catalyst, which suppresses by-product formation and enhances epoxy compound yield.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If peracids are used to oxidize olefins to produce epoxy compounds, then the epoxy compound can be produced, but peracids require caution in handling and lower the selectivity due to side reactions
Solution Approach 1:
The patent uses peroxycarboxylic acid esters as intermediary compounds that transfer the oxidizing function from peracids to olefins. The peroxycarboxylic acid ester reacts with the olefin to form the epoxy compound, while the peracid is converted to a carboxylic acid. This intermediary approach allows the oxidation reaction to proceed without direct contact between peracids and olefins, reducing safety hazards and improving selectivity.
2Productivity
If conventional peracid oxidation is used, then epoxy compound production is achieved, but post-treatment after the reaction is troublesome
Solution Approach 1:
The patent extracts and removes the troublesome post-treatment steps by designing a reaction system where the peracid byproduct is converted to a carboxylic acid that can be easily separated. The use of peroxycarboxylic acid esters as intermediaries simplifies the reaction workflow and reduces the complexity of post-reaction processing.
3Productivity
If peracids are used for epoxidation, then the reaction proceeds, but carboxylic acid present in the reaction system reacts with epoxy compound to produce ester, lowering selectivity
Solution Approach 1:
The peroxycarboxylic acid ester serves as an intermediary that delivers the oxidizing capability to the olefin without leaving peracid residues that could react with the epoxy product. This intermediary mechanism prevents the formation of ester byproducts and maintains high selectivity for the desired epoxy compound.
4Productivity
If peracids are used to produce alicyclic epoxy compounds, then epoxidation occurs, but organic acid reacts with epoxy group causing ring opening, lowering selectivity
Solution Approach 1:
The peroxycarboxylic acid ester intermediary prevents direct reaction between peracids/organic acids and the alicyclic epoxy compound. The intermediary transfers the oxidizing function and then decomposes to products that do not react with the epoxy group, thereby preventing ring-opening side reactions and maintaining high selectivity.
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 epoxy compounds with high yield and selectivity, ensuring safer and easier production while minimizing by-product formation, thus improving industrial safety and efficiency.
Implementation Method 1
a method for producing an epoxy compound, comprising a step of oxidizing a carbon-carbon double bond in an organic compound with hydrogen peroxide in the presence of a catalyst, wherein the catalyst comprises a tungsten compound
Implementation Method 2
oxidizing a carbon-carbon double bond in an organic compound with hydrogen peroxide
Implementation Method 3
an onium salt having an alkyl sulfate ion represented by formula (I) as an anion... as a phase transfer catalyst
Data Source
AI summary
The invention provides a method for producing an epoxy compound by hydrogen peroxide using an organic compound having a carbon-carbon double bond as a raw material, wherein a by-product is suppressed from being generated and the epoxy compound is produced in a high yield. In particular, the invention provides a method for producing an epoxy compound involving oxidizing a carbon-carbon double bond in an organic compound with hydrogen peroxide in the presence of a catalyst, wherein the catalyst comprises a tungsten compound; a phosphoric acid, a phosphonic acid or salts thereof; and an onium salt having an alkyl sulfate ion represented by formula (I) as an anion:wherein R1 is a linear or branched aliphatic hydrocarbon group having 1 to 18 carbons, which may be substituted with 1 to 3 phenyl groups.