Dispiro Diol Synthesis for Thermal Stability
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Solution Overview
Problem
Existing diols, such as spiroglycol, lack sufficient thermal stability, which is a requirement for advanced applications.
Innovation Solution
A diol with a dispiro structure, represented by a specific formula, is synthesized through a dehydration cyclization reaction between a 1,4-cyclohexanedione derivative and a triol in the presence of an acid catalyst, followed by removal of water azeotropically with an organic solvent, resulting in a diol with improved thermal stability and a method for manufacturing a di(meth)acrylate.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If spiroglycol is used as a diol material, then good material properties are achieved, but thermal stability is insufficient
Solution Approach 1:
The patent modifies the molecular structure parameters of the diol by introducing a dispiro structure with specific R1 and R3 substituents. This structural parameter change directly improves thermal stability while the patent also reports that the melting point remains manageable, resolving the contradiction between thermal stability and ease of manufacture
Solution Approach 2:
The patent creates a composite molecular structure combining a dispiro core with various substituent groups (R1 and R3). This composite structure integrates the thermal stability benefits of the dispiro framework with the manageable physical properties provided by the substituent groups, achieving both high reliability and ease of manufacture
2Reliability
If thermal stability is improved through structural modification, then reliability increases, but the complexity of synthesis may increase
Solution Approach 1:
The patent divides the synthesis into two distinct stages: first forming the dispiro core structure, then introducing substituent groups. This segmentation of the synthesis process makes the overall complex structure achievable through manageable stepwise reactions, reducing the practical complexity despite the advanced molecular architecture required for thermal stability
3Reliability
If a dispiro structure is introduced to improve thermal stability, then reliability improves, but the melting point may change affecting handling
Solution Approach 1:
The patent applies local quality by strategically placing different substituent groups (R1 and R3) at specific positions on the dispiro structure. This localized modification allows the molecule to maintain high thermal stability from the dispiro core while the specific substituents adjust the melting point and other physical properties for ease of handling, resolving the contradiction between reliability and ease of operation
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 resulting diol exhibits enhanced thermal stability, lower melting points, and reduced likelihood of olefin production, making it suitable for handling and use in thermoplastic resins with improved physical properties.
Implementation Method 1
allowing a 1,4-cyclohexanedione derivative represented by the formula (2) below, and a triol represented by the formula (3) below to undergo a dehydration cyclization reaction
Implementation Method 2
the water resulted from the dehydration cyclization reaction is removed azeotropically with an organic solvent
Implementation Method 3
the dehydration cyclization reaction is allowed to proceed in the presence of an acid catalyst
Data Source
AI summary
Provided is a diol that excels in thermal stability; and, a method for manufacturing a diol, a di(meth)acrylate, and a method for manufacturing a di (meth) acrylate. The diol represented by the formula (1) below; wherein each of R1 and R2 independently represents a hydrocarbon group; and each R3 independently represents a hydrogen atom, hetero atom-containing group, halogen atom, straight chain alkyl group having 1 to 6 carbon atoms, branched alkyl group having 3 to 6 carbon atoms or, aryl group-containing group having 6 to 12 carbon atoms.