Terminally Unsaturated (Meth)acrylate Crosslinkers From Bottom Streams
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Solution Overview
Problem
Existing processes for preparing di(meth)acrylate diesters are inconvenient and costly, requiring high-purity starting materials and often result in incomplete esterification, primarily producing hydroxyalkyl (meth)acrylates rather than di(meth)acrylate diesters.
Innovation Solution
A process involving the reaction of (meth)acrylic acid with epoxides in the presence of a catalyst to form a hydroxyalkyl (meth)acrylate mixture, followed by distillation and subsequent reaction with (meth)acrylic acid or C1-C4-alkyl (meth)acrylate to produce a di(meth)acrylate diester mixture, allowing for efficient utilization of a previously discarded bottom stream and avoiding complex purification steps.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If conventional esterification processes are used to prepare di(meth)acrylate diesters, then high-purity starting materials are required, but the process becomes costly and complex
Solution Approach 1:
The patent changes the reaction parameters by using a specific catalyst system (tin(II) 2-ethylhexanoate with hydroquinone) and controlling the molar ratio of (meth)acrylic acid to epoxide between 1:0.95 and 1:1.5, along with temperature control (60-110°C) to achieve complete esterification and high di(meth)acrylate diester yield without requiring high-purity starting materials
Solution Approach 2:
The patent performs preliminary distillation of the reaction mixture to remove unreacted (meth)acrylic acid and water before the esterification reaction reaches completion, which prevents side reactions and drives the equilibrium toward complete esterification, thereby simplifying the overall process
2Productivity
If conventional processes are used, then esterification is incomplete, but this results in primary production of hydroxyalkyl (meth)acrylates instead of di(meth)acrylate diesters
Solution Approach 1:
The patent uses a dual-catalyst system where tin(II) 2-ethylhexanoate catalyzes the esterification reaction and hydroquinone acts as a polymerization inhibitor that prevents side reactions. This feedback mechanism ensures complete esterification while maintaining high selectivity for di(meth)acrylate diester formation
Solution Approach 2:
By optimizing the molar ratio of (meth)acrylic acid to epoxide to between 1:0.95 and 1:1.5 and controlling the reaction temperature (60-110°C), the patent ensures complete conversion of hydroxyalkyl (meth)acrylates to di(meth)acrylate diesters, achieving both high productivity and precise product composition
3Loss of energy
If the first bottom stream is discarded as waste, then resource utilization is poor, but this increases environmental impact and cost
Solution Approach 1:
Instead of discarding the first bottom stream containing unreacted (meth)acrylic acid and water, the patent recovers and reuses these components by performing distillation to separate and concentrate them, then adding them back to the reaction system to drive complete esterification, thereby improving resource utilization and reducing environmental impact
Solution Approach 2:
The patent converts the harmful waste stream into a beneficial resource by using the unreacted (meth)acrylic acid and water in the first bottom stream as reactants to drive the esterification equilibrium toward complete conversion, transforming a environmental problem into a process advantage
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 achieves a cost-effective and reproducible production of di(meth)acrylate diesters suitable for use as crosslinkers, with mechanical properties comparable to traditional crosslinkers, while being more sustainable and efficient in resource utilization.
Implementation Method 1
reacting (meth)acrylic acid with at least one epoxide selected from the group consisting of ethylene oxide and propylene oxide in the presence of a first catalyst to obtain a hydroxyalkyl (meth)acrylate mixture
Implementation Method 2
distilling the hydroxyalkyl (meth)acrylate mixture obtained in step a) to obtain a first top stream containing component (C), and a first bottom stream containing component (D) and residues of component (C) and the first catalyst
Implementation Method 3
reacting the first bottom stream obtained in step b) with (meth)acrylic acid and/or a C1-C4-alkyl (meth)acrylate in the presence of a second catalyst to obtain a mixture containing the di(meth)acrylate diester mixture
Data Source
AI summary
A process prepares a di(meth)acrylate diester mixture of at least one first di(meth)acrylate diester and at least one second di(meth)acrylate diester. (Meth)acrylic acid reacts with ethylene oxide or propylene oxide in the presence of a first catalyst to obtain a hydroxyalkyl (meth)acrylate mixture, followed by distilling the hydroxy (meth)acrylate mixture to obtain a first top stream component and a first bottom stream component. The bottom stream reacts with (meth)acrylic acid or C1-C4-alkyl (meth)acrylate in the presence of a second catalyst to obtain a mixture of the di(meth)acrylate diester mixture, the first catalyst and the second catalyst. Distilling of the resulting mixture leads to a second top stream of the di(meth)acrylate diester mixture and a second bottom stream of the first and second catalyst. The di(meth)acrylate diester mixture obtained can be used as a crosslinker in reactive resins and polymerization of alkyl(meth)acrylates.