Supercritical CO2 Purification of FDCA from HMF Humins

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Solution Overview

Problem

The production of 2,5-furandicarboxylic acid and its esters is hindered by the presence of humins, highly colored polymeric impurities that contaminate hydroxymethyl furfural (HMF) derived from renewable resources, making it difficult to achieve high-quality, colorless poly(trimethylene furandicarboxylate) (PTF) for packaging applications.

Innovation Solution

A process involving the oxidation of HMF and humins to produce crude 2,5-furandicarboxylic acid (FDCA), followed by separation, esterification with an alcohol, and purification through distillation or sublimation to remove humins, ensuring the FDCA is substantially free from impurities.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If HMF from renewable resources is used to produce 2,5-furandicarboxylic acid, then the product is renewable and sustainable, but the product is contaminated with highly colored polymeric impurities called humins

Engineering Contradiction:

ImproverenewabilityVSAvoidhumin contamination

Core Design Contradiction:

Adaptability or versatilityVSObject-affected harmful factors

Solution Approach 1:

The patent applies extraction by dissolving FDCA in supercritical carbon dioxide and selectively removing humins through filtration, separating the desired product from the colored polymeric impurities while maintaining renewable sourcing

Inventive Principle:

Principle #2Taking out (Extraction)

Solution Approach 2:

The patent changes physical parameters by using supercritical carbon dioxide (high pressure and temperature conditions) to dissolve FDCA, then returning to ambient conditions to precipitate pure product, thereby changing the solubility parameters to achieve separation from humins

Inventive Principle:

Principle #35Parameter changes

2Productivity

If conventional oxidation processes are used to produce FDCA from HMF, then the production efficiency is maintained, but the color quality of the product deteriorates due to humin presence

Engineering Contradiction:

Improveproduction efficiencyVSAvoidcolor quality

Core Design Contradiction:

ProductivityVSManufacturing precision

Solution Approach 1:

The patent uses supercritical carbon dioxide as an intermediary solvent that selectively dissolves FDCA but not humins, acting as a mediator to separate the colored impurities from the desired product while maintaining production efficiency

Inventive Principle:

Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent exploits phase transitions of carbon dioxide between supercritical and gaseous states to control solubility: supercritical CO2 dissolves FDCA for separation, then returning to gaseous state precipitates pure product, achieving both efficiency and color quality

Inventive Principle:

Principle #36Phase transitions

3Manufacturing precision

If multiple purification steps are implemented to remove humins, then the purity of FDCA is improved, but the process complexity increases

Engineering Contradiction:

ImprovepurityVSAvoidprocess complexity

Core Design Contradiction:

Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent segments the purification process into distinct functional stages: oxidation reaction, supercritical CO2 dissolution, filtration, and precipitation, allowing each step to address specific purification needs without excessive overall complexity

Inventive Principle:

Principle #1Segmentation

Solution Approach 2:

The patent replaces complex mechanical purification systems with a chemical/physical solution using supercritical fluid extraction, substituting elaborate filtration and chromatography systems with a single supercritical CO2 treatment step

Inventive Principle:

Principle #28Mechanics substitution (Replace mechanical system)

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 effectively produces FDCA and its esters with minimal humin content, resulting in high-purity, colorless PTF suitable for packaging, enhancing oxygen and carbon dioxide barrier properties.

Implementation Method 1

oxidizing a feedstock comprising HMF and humins to produce a mixture comprising crude humins-containing FDCA

Methodology Applied

Scientific EffectOxidation: Oxidation

Implementation Method 2

purifying the crude ester of FDCA obtained in step c) by distillation or by sublimation to produce a purified ester of FDCA substantially free of humins

Methodology Applied

Scientific EffectDistillation: Distillation

Implementation Method 3

purifying the crude ester of FDCA obtained in step c) by distillation or by sublimation to produce a purified ester of FDCA substantially free of humins

Methodology Applied

Scientific EffectSublimation: Sublimation

Implementation Method 4

esterifying the solid FDCA/humins composition with an alcohol to produce a crude ester of FDCA

Methodology Applied

Scientific EffectEsterification:

Data Source

PatentUS10865190B2Processes for preparing 2,5-furandicarboxylic acid and esters thereof

Publication Date: 2020.12.15 EI DU PONT DE NEMOURS & CO

AI summary

A process for producing furan dicarboxylic acid or an ester thereof from a feedstock comprising hydroxymethyl furfural (HMF) and humins is disclosed. Humins are a byproduct from reactions forming HMF from sugars and are typically removed from the HMF prior to any further processing. A humins-containing HMF feedstock is utilized to produce furan dicarboxylic acids and ester substantially free from humins.