Isosorbide Dimethacrylate Synthesis via Ti(IV) Catalysis
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Solution Overview
Problem
Existing methods for preparing isosorbide di(meth)acrylate through transesterification result in significant formation of by-products, leading to incomplete conversion and reduced purity of the target product.
Innovation Solution
A process involving the transesterification of alkyl (meth)acrylate with isosorbide in the presence of a titanium (IV) or zirconium (IV) containing catalyst and a stabilizer, with continuous distillation of an azeotrope and subsequent steps to separate and remove by-products, achieving high yields and purity of isosorbide di(meth)acrylate.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If transesterification is carried out with conventional catalysts, then the reaction proceeds, but significant by-products are formed and conversion is incomplete
Solution Approach 1:
The patent changes the catalyst parameter from conventional catalysts to titanium(IV) or zirconium(IV) alkoxides, which fundamentally alters the reaction pathway to minimize by-product formation. This parameter change in catalyst type enables complete conversion while maintaining high purity, directly resolving the contradiction between manufacturing precision and substance loss.
Solution Approach 2:
The patent converts the potentially harmful effect of catalyst residue into a benefit by selecting titanium(IV) or zirconium(IV) alkoxides that hydrolyze to form easily removable hydroxides. These hydroxides can be efficiently separated, turning what would be a contamination problem into an advantageous purification opportunity, thus improving purity while minimizing by-products.
2Productivity
If transesterification is carried out to high conversion, then yield increases, but by-product formation increases and purity decreases
Solution Approach 1:
The patent employs a specific catalyst system (titanium(IV) or zirconium(IV) alkoxides) with optimized alkoxide-to-isosorbide ratios that enables the reaction to proceed to complete conversion without generating significant by-products. This parameter optimization allows simultaneous achievement of high yield and high purity, resolving the contradiction between productivity and manufacturing precision.
Solution Approach 2:
The titanium(IV) or zirconium(IV) alkoxide acts as an intermediary that facilitates the transesterification reaction with high selectivity. This intermediary catalyst mediates between the reactants to produce the desired product with minimal by-products, enabling high conversion while maintaining purity, thus resolving the contradiction between yield and purity.
3Manufacturing precision
If multiple distillation steps are performed to remove by-products, then purity increases, but process complexity and time increase
Solution Approach 1:
The patent converts the potential harm of catalyst residue into a benefit by selecting titanium(IV) or zirconium(IV) alkoxides that hydrolyze to form water-soluble hydroxides. This allows a single water wash step to effectively remove the catalyst and associated by-products, dramatically simplifying the purification process while maintaining high purity, thus resolving the contradiction between manufacturing precision and device complexity.
Solution Approach 2:
The patent changes the purification approach from multiple sequential distillation steps to a single hydrolysis and filtration step. This parameter change in the purification methodology reduces process complexity and time while achieving the same or better purity levels, directly resolving the contradiction between manufacturing precision and device complexity.
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 effectively minimizes by-product formation, achieving high yields and purity of isosorbide di(meth)acrylate, with by-products comprising less than 4% of the final product, primarily isosorbide mono(meth)acrylates, and allowing for the use of the product as a resin component in two-component adhesives.
Implementation Method 1
Reacting alkyl(meth)acrylate with isosorbide in the presence of a titanium(IV) or zirconium(IV)-containing catalyst
Implementation Method 2
which forms an azeotrope with the alcohol bound in the alkyl(meth)acrylate
Implementation Method 3
continuously distilling off the azeotrope of entrainer and alcohol
Implementation Method 4
adding water to the isosorbide di(meth)acrylate-containing product mixture obtained in steps (i) and (ii) and separating hydrolysates of the titanium(IV) or zirconium(IV)-containing catalyst
Implementation Method 5
distilling off unreacted alkyl(meth)acrylate and entrainer from the product mixture
Data Source
AI summary
The invention relates to a method for producing isosorbide dimethacrylate by the transesterification of alkyl(meth)acrylate with isosorbide, comprising the following steps: (i) permitting alkyl(meth)acrylate to react with isosorbide in the presence of a catalyst containing titanium (IV) or zirconium (IV) and of a stabilizer in the presence of an entrainer, forming an azeotrope with the alcohol bonded in the alkyl(meth)alcylate; (ii) continuously distilling off the azeotrope that consists of entrainer and alcohol, steps (i) and (ii) being carried out simultaneously until isosorbide is substantially completely converted; (iii) adding water to the product mixture obtained in steps (i) and (ii) and containing isosorbide dimethacrylate, and separating the hydrolysate from the catalyst containing titanium (IV) or zirconium (IV); (iv) distilling off non-converted alkyl(meth)acrylate and entrainer from the product mixture; and (v) distilling off water from the product mixture, wherein step (iv) can also be carried out before step (iii), and the steps (iv) and (v) can also be carried out in a distillation step.