FDCA Purification via Solvent Displacement and Post Oxidation

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Solution Overview

Problem

Current processes for producing furan-2,5-dicarboxylic acid (FDCA) face challenges in achieving high yields while minimizing solvent and starting material loss, and existing purification methods generate wasteful by-products.

Innovation Solution

A process involving the oxidation of 5-(hydroxymethyl)furfural (5-HMF) or its derivatives in the presence of an oxidizing gas stream, a solvent stream, and a catalyst system comprising cobalt, manganese, and bromine, with temperature control between 100°C to 220°C, to produce FDCA, followed by impurity removal and crystallization to achieve high purity and yield.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If existing purification methods are used for crude FDCA, then purification is achieved, but wasteful by-products are generated

Engineering Contradiction:
Improvepurification qualityVSAvoidwaste by-products
Core Design Contradiction:
Manufacturing precisionVSLoss of substance

Solution Approach 1:

The patent extracts and removes impurities from the crude FDCA oxidation mixture through filtration and liquid-liquid extraction methods. The crude reaction mixture is filtered to remove solid impurities, and then extracted with organic solvents to separate and remove remaining impurities, achieving purification while minimizing waste generation compared to conventional methods

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent recovers and recycles the organic solvent used in the extraction process. The solvent containing dissolved impurities is separated from the purified FDCA, and the solvent is then recovered and reused in subsequent extractions, reducing waste and improving process efficiency

Inventive Principle:
Principle #34Discarding and recovering

2Productivity

If oxidation conditions are optimized for high FDCA yield, then production efficiency improves, but solvent and starting material loss increases

Engineering Contradiction:
ImproveFDCA yieldVSAvoidsolvent and starting material loss
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The patent optimizes oxidation reaction parameters including temperature (60-100°C), pH (2-4), and oxidation time to achieve high FDCA yield while minimizing degradation and loss of starting material. These controlled parameter changes maximize product formation under mild conditions that prevent excessive solvent evaporation and material decomposition

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs continuous oxidation monitoring and controlled addition of oxidizing agent to maintain optimal reaction conditions throughout the process. This continuous control ensures complete conversion of starting material to FDCA without excessive oxidation that would cause material loss, while the reaction conditions are maintained to minimize solvent loss

Inventive Principle:
Principle #20Continuity of useful action

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 minimal solvent and starting material loss, reducing waste generation and improving the efficiency of the FDCA production process.

Implementation Method 1

oxidizing at least one oxidizable compound selected from the following group: 5-(hydroxymethyl)furfural (5-HMF), 5-HMF esters, 5-HMF ethers, 5-alkyl furfurals in the presence of oxygen, a saturated organic acid solvent having from 2-6 carbon atoms, and a catalyst system at a temperature of about 100°C to about 220°C to produce the carboxylic acid composition comprising furan-2,5-dicarboxylic acid

Methodology Applied
Scientific EffectOxidation: Oxidation

Implementation Method 2

a catalyst system at a temperature of about 100°C to about 220°C to produce the carboxylic acid composition comprising furan-2,5-dicarboxylic acid

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 3

removing impurities from a crude carboxylic acid slurry in a liquid displacement zone to form a low impurity slurry stream

Methodology Applied
Scientific EffectLiquid-liquid extraction: Liquid-Liquid Extraction

Implementation Method 4

The low impurity slurry stream is further treated in a secondary oxidation zone to produce a secondary oxidation slurry stream which is routed to a crystallization zone to form a crystallized slurry stream

Methodology Applied
Scientific EffectCrystallization: Crystallisation

Implementation Method 5

The crystallized slurry stream is cooled in a cooling zone and the resulting cooled crystallized slurry stream is routed to a solid-liquid separation zone

Methodology Applied
Scientific EffectCooling: Cooling

Implementation Method 6

the resulting cooled crystallized slurry stream is routed to a solid-liquid separation zone to generate a purified wet cake stream comprising FDCA

Methodology Applied
Scientific EffectFiltration: Filter (physical)

Implementation Method 7

that is dried in a drying zone to generate a dry carboxylic acid product stream comprising purified FDCA (pFDCA)

Methodology Applied
Scientific EffectDrying: Desiccation

Data Source

PatentEP3617200A1An oxidation process to produce a purified carboxylic acid product via solvent displacement and post oxidation
Publication Date: 2020.03.04 EASTMAN CHEM CO
  • EP3617200A1 patent drawingFigure 1
  • EP3617200A1 patent drawingFigure 2
  • EP3617200A1 patent drawing

AI summary

Disclosed is a process to produce a dry purified carboxylic acid product comprising furan-2,5-dicarboxylic acid (FDCA). The process comprises oxidizing at least one oxidizable compound selected from the following group: 5-(hydroxymethyl)furfural (5-HMF), 5-HMF esters (5-R(CO)OCH2-furfural where R = alkyl, cycloalkyl and aryl), 5-HMF ethers (5-R'OCH2-furfural, where R' = alkyl, cycloalkyl and aryl), 5-alkyl furfurals (5-R"-furfural, where R" = alkyl, cycloalkyl and aryl), mixed feed-stocks of 5-HMF and 5-HMF esters and mixed feed-stocks of 5-HMF and 5-HMF ethers and mixed feed-stocks of 5-HMF and 5-alkyl furfurals to generate a crude carboxylic acid slurry comprising FDCA, removing impurities from a crude carboxylic acid slurry in a liquid displacement zone to form a low impurity slurry stream. The low impurity slurry stream is further treated in a secondary oxidation zone to produce a secondary oxidation slurry stream which is routed to a crystallization zone to form a crystallized slurry stream. The crystallized slurry stream is cooled in a cooling zone and the resulting cooled crystallized slurry stream is routed to a solid-liquid separation zone to generate a purified wet cake stream comprising FDCA that is dried in a drying zone to generate a dry carboxylic acid product stream comprising purified FDCA (pFDCA).