Purified 2,5-Furandicarboxylic Acid via In Situ Reduction
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Solution Overview
Problem
Current methods for producing furandicarboxylic acid (FDCA) often result in products containing impurities like 5-formylfuran-2-carboxylic acid, which are difficult to remove and lead to undesirable color bodies during polymerization, affecting the quality of FDCA products.
Innovation Solution
A process involving the reduction of FDCA pathway products using hydrogen in the presence of a heterogeneous reduction catalyst and a multi-component solvent, specifically contacting FDCA with hydrogen to convert 5-formylfurancarboxylic acid into hydroxymethylfurancarboxylic acid, achieving high purity levels of FDCA by reducing impurities such as 5-formylfurancarboxylic acid, 5-methyl-2-furoic acid, and tetrahydrofuran-2,5-dicarboxylic acid.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If conventional methods are used to produce FDCA, then production efficiency is maintained, but impurities like 5-formylfuran-2-carboxylic acid remain difficult to remove
Solution Approach 1:
The patent applies preliminary action by performing the reduction of 5-formylfuran-2-carboxylic acid to 5-hydroxymethylfuran-2-carboxylic acid immediately after the oxidation reaction, before the impurity has a chance to cause problems. This is achieved by adding the reduction catalyst and hydrogen donor to the oxidation reaction mixture and allowing the reduction to occur in situ, thereby removing the impurity at the earliest possible moment in the process.
Solution Approach 2:
The patent uses an intermediary approach by introducing a reduction catalyst and hydrogen donor as mediating substances that convert the harmful impurity (5-formylfuran-2-carboxylic acid) into a beneficial or harmless substance (5-hydroxymethylfuran-2-carboxylic acid). This intermediary chemical transformation effectively removes the impurity without requiring complex physical separation processes.
2Manufacturing precision
If impurities are not removed from FDCA, then production cost is reduced, but color bodies form during polymerization affecting product quality
Solution Approach 1:
The patent applies the blessing in disguise principle by converting the harmful impurity 5-formylfuran-2-carboxylic acid into a beneficial substance 5-hydroxymethylfuran-2-carboxylic acid through catalytic reduction. The harmful aldehyde group is transformed into a beneficial hydroxymethyl group, eliminating the color body formation problem while potentially creating a valuable co-product.
Solution Approach 2:
The patent uses parameter changes by altering the chemical state of the impurity through reduction reactions. By changing the oxidation state of the 5-formylfuran-2-carboxylic acid (reducing the aldehyde group), the chemical properties of the impurity are fundamentally changed, transforming it from a harmful substance that forms color bodies into a beneficial substance that does not cause polymerization problems.
3Manufacturing precision
If a reduction process is added to remove 5-formylfuran-2-carboxylic acid, then product purity is improved, but process complexity increases
Solution Approach 1:
The patent applies merging by combining the oxidation and reduction steps into a single integrated process. The oxidation reaction produces FDCA along with the impurity 5-formylfuran-2-carboxylic acid, and the reduction catalyst is then added to the same reaction mixture to convert the impurity. This merging of steps eliminates the need for separate purification units and reduces overall process complexity.
Solution Approach 2:
The patent applies preliminary action by performing the reduction of the impurity immediately after oxidation, before any separation or purification steps would be required. By addressing the impurity formation in situ and converting it promptly, the process eliminates the need for complex downstream purification equipment and operations.
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 high molar purity of FDCA, exceeding 90%, with significant reduction of impurities, thereby preventing the formation of color bodies and improving the quality of FDCA products for polymerization.
Implementation Method 1
contacting an FDCA pathway product comprising FDCA and 5-formylfurancarboxylic acid (FFCA) with hydrogen in the presence of a heterogeneous reduction catalyst under conditions sufficient to form a reaction mixture for reducing the FFCA to hydroxymethylfurancarboxylic acid (HMFCA)
Implementation Method 2
the heterogeneous reduction catalyst comprises a solid support and a metal selected from the group consisting of Cu, Ni, Co, Pd, Pt, Ru, Ag, Au, Rh, Os, Ir, and any combination thereof
Data Source
AI summary
The present disclosure provides processes for the purification of 2,5-furandicarboxylic acid (FDCA). The present disclosure further provides crystalline preparations of purified FDCA, as well as processes for making the same. In addition, the present disclosure provides mixtures used in processes for the purification of FDCA.