Direct Di- or Polyformamide Synthesis from CO2 and Amines
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Solution Overview
Problem
Current methods for synthesizing di- or polyformamides containing Zerewitinoff active hydrogen atoms require additional synthesis and purification steps when using carbon dioxide as a reactant, complicating the process and leading to unwanted side reactions and discoloration in polymer applications.
Innovation Solution
A direct process involving the reaction of primary di- or polyamines with carbon dioxide in the presence of hydrogen, using either heterogeneous or homogeneous catalysts, such as transition metal-based catalysts or pincer-type ligand complexes, to form di- or polyformamides with reduced reactivity and minimized discoloration.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If formic acid or formic-acid derivatives are used as intermediates to synthesize di- or polyformamides from carbon dioxide, then the synthesis can proceed, but additional synthesis and purification steps are required which complicate the overall process
Solution Approach 1:
The invention extracts and eliminates the intermediate formic acid or formic-acid derivative steps from the synthesis pathway. By using a catalyst system that enables direct carboxylation of amines with carbon dioxide, the process removes the need for separate formic acid synthesis, purification, and subsequent reaction steps, thereby simplifying the overall manufacturing process.
Solution Approach 2:
The catalyst system is prepared in advance with specific properties (basicity and nucleophilicity) that enable it to directly activate carbon dioxide and facilitate its reaction with amines. This preliminary preparation of the catalyst eliminates the need for intermediate formic acid formation, as the catalyst directly mediates the carboxylation reaction.
2Object-affected harmful factors
If aromatic amines or substituted aromatic diamines are used to reduce reactivity and prevent discoloration, then nucleophilicity is reduced, but the amines still react fast with isocyanates and cause discoloration in polymer applications
Solution Approach 1:
The invention changes the chemical structure parameters of the amine by introducing electron-withdrawing groups (such as chloro, fluoro, or cyano groups) at specific positions on the aromatic ring. This structural modification reduces the nucleophilicity of the amine nitrogen, thereby controlling its reactivity toward isocyanates and preventing unwanted side reactions and discoloration in polymer applications.
Solution Approach 2:
The invention applies local quality modification by placing electron-withdrawing groups at specific positions (ortho, meta, or para positions) on the aromatic ring relative to the amino group. This localized structural change selectively reduces the electron density and nucleophilicity at the reaction site while maintaining the overall molecular structure and desired physical properties.
3Object-affected harmful factors
If aliphatic amines with Zerewitinoff active hydrogen atoms are used to achieve lower reactivity, then discoloration is reduced, but the reactivity with isocyanates remains high
Solution Approach 1:
The invention changes the electronic parameters of the amine by introducing electron-withdrawing groups that reduce the electron density on the nitrogen atom. This parameter change decreases the nucleophilicity and reactivity of the amine toward isocyanates, while the aliphatic structure maintains low discoloration potential, achieving both goals simultaneously.
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 simplifies the synthesis of di- or polyformamides, reduces unwanted side reactions, and minimizes discoloration, enabling the production of high-quality polyurethane or polyurea polymers with improved physical properties.
Implementation Method 1
by reacting at least one primary di- or polyamine with carbon dioxide in the presence of hydrogen and at least one catalyst selected from the group consisting of one or more heterogeneous and homogeneous catalysts or mixtures thereof
Implementation Method 2
by reacting at least one primary di- or polyamine with carbon dioxide in the presence of hydrogen
Data Source
AI summary
The invention relates to a process for preparing at least one di- or polyformamide comprising at least two -NHCHO groups by reacting at least one primary di- or polyamine with carbon dioxide in the presence of hydrogen and at least one catalyst selected from the group consisting of heterogeneous and homogeneous catalysts or mixtures thereof. The invention further relates to a di- or polyformamide and their use for different purposes as well as a two-component-system comprising the di- or polyformamide.