Benzophenone Methacrylate Synthesis via Catalytic Acetate
Solution Overview
Problem
Existing methods for producing methacrylic acid esters of hydroxy-functional benzophenones are inefficient due to high salt loads, corrosive materials, and the need for neutralization steps, which increase costs and complexity.
Innovation Solution
A process using catalytic amounts of lithium or potassium acetates or their methacrylates to react hydroxybenzophenones with (meth)acrylic anhydrides, allowing for a molar ratio of 1.0:1.0 to 1.6:1.0, reducing salt load and eliminating the need for additional neutralization steps.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If triethylamine is used as a catalyst in the methacrylic anhydride process, then the reaction can proceed, but equimolar amounts of salt are formed as waste that must be disposed of
Solution Approach 1:
The patent changes the catalyst from triethylamine to catalytic amounts of lithium or potassium acetates or their methacrylates. This parameter change in catalyst identity and quantity transforms the stoichiometric reaction into a catalytic one, dramatically reducing salt waste from equimolar amounts to catalytic amounts while maintaining high reaction efficiency and yield
Solution Approach 2:
The patent employs catalytic amounts of salt that can be easily separated and where only a small salt load has to be carried. The catalyst serves its purpose and can be removed, avoiding the accumulation of large amounts of waste salt that would require disposal
2Productivity
If methacrylic acid chloride is used as a reactant, then the ester can be produced, but corrosive and caustic properties must be handled and HCl is released upon contact with water
Solution Approach 1:
The patent replaces the hazardous methacrylic acid chloride with methacrylic anhydride, which is less corrosive and does not release HCl upon contact with water. This substitution eliminates the harmful factors while maintaining the ability to produce the desired ester product
Solution Approach 2:
The patent uses methacrylic anhydride as an intermediary reagent that achieves the same esterification goal without the harmful properties of acid chloride. The anhydride serves as a safer mediator in the reaction process
3Productivity
If sulfuric acid is used as a catalyst, then the esterification can proceed, but the catalyst must be neutralized with sodium hydroxide solution and sodium sulfate filtered off
Solution Approach 1:
The patent extracts or removes the need for neutralization and filtration steps by using catalytic amounts of lithium or potassium acetates or their methacrylates as catalysts. These catalysts do not require neutralization and produce minimal salt waste that can be easily separated, eliminating the complex downstream processing required with sulfuric acid catalysis
Solution Approach 2:
The patent changes the catalyst from sulfuric acid to catalytic amounts of lithium or potassium acetates or their methacrylates. This parameter change in catalyst identity and quantity eliminates the need for neutralization steps and reduces salt load, simplifying the overall process
4Productivity
If large amounts of catalyst and/or acylating agent are required in salt-catalyzed esterification, then the reaction can proceed, but large amounts of salt load must be carried
Solution Approach 1:
The patent uses catalytic amounts of salt (lithium or potassium acetates or their methacrylates) rather than large amounts. The catalyst serves its function in small quantities and can be easily separated, minimizing the salt load that must be carried throughout the process
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 achieves high yield and purity of benzophenone (meth)acrylates with a small salt load, enabling easy separation and potential recycling of by-products, thus simplifying the production and reducing waste.
Implementation Method 1
hydroxybenzophenone and (meth)acrylic anhydride in the presence of catalytic amounts of salt selected from the group of lithium or potassium acetates or Li-, Na- or K-(meth)acrylates
Data Source
AI summary
The invention relates to a method for producing methacrylic acid esters from hydroxy-functional benzophenones and use thereof. According to the claimed method, methacrylated benzophenones (benzophenon(meth)acrylates) can be produced simply, with high purity and in high yield.