Purifying Crude FDCA via Selective Hydrogenation

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Solution Overview

Problem

Current methods for producing furan 2,5-dicarboxylic acid (FDCA) result in low yields and contain impurities like 5-formyl furan-2-carboxylic acid (FFCA) and colored bodies, which affect polymer quality and require costly purification processes.

Innovation Solution

A process involving catalytic hydrogenation of a solvated FDCA composition under mild conditions to selectively reduce FFCA and color bodies, improving yield and purity of FDCA.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If catalytic oxidation of 5-HMF is used to produce FDCA, then FDCA can be synthesized from renewable resources, but impurities like FFCA and colored bodies are produced that reduce polymer quality

Engineering Contradiction:
Improveuse of renewable resourcesVSAvoidpurity of FDCA
Core Design Contradiction:
Adaptability or versatilityVSManufacturing precision

Solution Approach 1:

The patent extracts and removes impurities (FFCA and colored bodies) from the crude FDCA reaction mixture through a multi-step purification process involving filtration, activated carbon treatment, and crystallization, thereby achieving high purity FDCA while maintaining the benefit of using renewable 5-HMF feedstock

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent uses intermediaries such as activated carbon and decolorizing carbon as mediators to adsorb and remove colored impurities from the reaction mixture, enabling purification without affecting the renewable resource advantage

Inventive Principle:
Principle #24Intermediary (Mediator)

2Manufacturing precision

If conventional purification methods are used to remove impurities, then colored bodies can be removed, but production costs increase due to additional processing steps

Engineering Contradiction:
Improveremoval of colored bodiesVSAvoidproduction cost
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The patent combines multiple purification functions (filtration of catalyst particles, adsorption of colored bodies, and crystallization of FDCA) into an integrated process sequence that achieves high purity while minimizing the number of separate unit operations and associated costs

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The patent discards harmful impurities (colored bodies and FFCA) through selective removal steps while recovering and recycling the catalyst and solvent systems, thereby reducing waste treatment costs and improving overall process economics

Inventive Principle:
Principle #34Discarding and recovering

3Manufacturing precision

If severe hydrogenation conditions are used to remove FFCA, then impurity reduction is achieved, but FDCA yield decreases due to over-hydrogenation

Engineering Contradiction:
Improvereduction of FFCAVSAvoidyield of FDCA
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The patent applies partial hydrogenation action using controlled amounts of hydrogen and mild catalysts (Pd/C or PtO2) at low temperatures and pressures, achieving sufficient removal of FFCA impurities without excessive hydrogenation that would degrade the desired FDCA product

Inventive Principle:
Principle #16Partial or excessive action

Solution Approach 2:

The patent carefully controls hydrogenation parameters (temperature, pressure, catalyst loading, and reaction time) to maintain conditions that selectively reduce FFCA while preserving FDCA, thereby optimizing both purity and yield

Inventive Principle:
Principle #35Parameter changes

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 achieves high yields of purified FDCA with reduced FFCA and color impurities, enhancing polymer quality and reducing production costs by minimizing energy consumption and byproduct formation.

Implementation Method 1

contacting the solvated FDCA composition with hydrogen and a catalyst under conditions sufficient to cause hydrogenation of at least a portion of the FFCA

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

catalytic hydrogenation of a solvated FDCA composition under mild conditions to selectively reduce FFCA and color bodies

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Implementation Method 3

contacting the solvated FDCA composition with activated carbon under conditions sufficient to cause adsorption of at least a portion of the colored bodies present in the solvated FDCA composition

Methodology Applied
Scientific EffectAdsorption: Adsorption

Data Source

PatentEP2864307B1Process for purifying crude furan 2,5-dicarboxylic acid using hydrogenation
Publication Date: 2018.03.07 EASTMAN CHEM CO
  • EP2864307B1 patent drawingFigure 1
  • EP2864307B1 patent drawingFigure 2
  • EP2864307B1 patent drawing

AI summary

A process to produce a dry purified furan-2,5-dicarboxylic acid (FDCA) is described. After oxidation of 5-(hydroxymethyl)furfural (5-HMF), a crude FDCA stream is produced that is fed to a crystallization zone followed by a solid-liquid displacement zone to form a low impurity slurry stream. The solids in the low impurity slurry stream are dissolved in a dissolution zone to produce a hydrogenation feed that is hydrogenated in a hydrogenation reactor to generate a hydrogenated FDCA composition. The hydrogenated FDCA composition is routed to a crystallization zone to form a crystallized produce stream that is separated from liquid in a solid-liquid separation zone to generate a purified wet cake stream containing FDCA that can be dried in a drying zone to generate a dry purified FDCA product stream