Electron Deficient Olefins via Imine Intermediates
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Solution Overview
Problem
Current methods for producing cyanoacrylate monomers, such as the Knoevenagel condensation reaction, face challenges in reliably and reproducibly producing pure difunctional monomers with reactive functional groups, particularly in the ester side chain, due to thermally sensitive and moisture-sensitive reagents, and require multi-step processes with low yields.
Innovation Solution
The development of novel electron deficient olefins, including 2-cyanoacrylates and methylidene malonates, using imine or iminium salts as reactants, which allows for the incorporation of reactive functional groups in the ester side chain, enabling the synthesis of compounds with improved yields and stability through controlled reaction conditions.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If Knoevenagel condensation reaction is used to produce cyanoacrylate monomers, then high yields of monofunctional cyanoacrylates can be obtained, but the production of difunctional monomers with reactive functional groups is unreliable and requires multi-step processes
Solution Approach 1:
The patent changes the chemical parameters of the reaction system by using imine or iminium salt intermediates instead of direct Knoevenagel condensation. This parameter change enables the formation of difunctional monomers with reactive functional groups in a more reliable and reproducible manner, reducing process complexity while maintaining high yields.
2Quantity of substance
If thermal depolymerisation of prepolymer is used, then cyanoacrylate monomer can be obtained, but the process is not reliable and reproducible for producing pure difunctional monomers
Solution Approach 1:
The patent applies preliminary action by forming imine or iminium salt intermediates before the final monomer formation. This preliminary step allows for better control over the reaction pathway, enabling reliable and reproducible production of pure difunctional monomers without relying on thermal depolymerisation of crosslinked prepolymers.
3Adaptability or versatility
If multi-step processes with protective group strategies are used to produce difunctional cyanoacrylates, then reactive functionality can be incorporated, but the yields are low and the process is complex
Solution Approach 1:
The patent extracts the need for protective group strategies by using imine or iminium salt intermediates that inherently protect the reactive functionality during the reaction. This extraction of the protective group requirement simplifies the process to a single step while maintaining the ability to incorporate reactive functional groups, thereby increasing yield.
4Quantity of substance
If Knoevenagel condensation is used for difunctional monomers, then monomer formation occurs, but the crosslinked prepolymer cannot be reliably depolymerised
Solution Approach 1:
The patent introduces imine or iminium salt intermediates as mediators in the reaction pathway. These intermediates facilitate monomer formation without creating crosslinked prepolymers that are difficult to depolymerise. The intermediary step allows for controlled monomer production with reliable and reproducible results.
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 approach facilitates the production of cyanoacrylates and methylidene malonates with reactive functional groups, offering higher yields and improved stability, overcoming the limitations of existing methods by using imine or iminium salts to form these compounds under controlled conditions.
Implementation Method 1
prepared using an imine or an iminium salt
Data Source
Figure 1~1(2)
Figure 2
Figure 3
AI summary
This invention relates to novel electron deficient olefins, such as certain 2-cyanoacrylates and methylidene malonates, prepared using an imine or an iminium salt.