Heterogeneous Catalyst Oxidation for FDCA Production

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Solution Overview

Problem

Current processes for producing furan-2,5-dicarboxylic acid (FDCA) face challenges such as high by-product formation, catalyst deactivation due to FDCA precipitation, and inefficient use of solvents, leading to low yields and increased costs.

Innovation Solution

A process involving a starting mixture with at least 50 wt.% water and a pH of 4.0 to 7.0, using a heterogeneous catalyst with noble metals on a support to oxidize 5-(hydroxymethyl)furfural (HMF) and its dimer, di-HMF, in the presence of an oxygen-containing gas, optimizing the conversion to FDCA while allowing for catalyst separation and reuse.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of operation

If a heterogeneous catalyst is used to facilitate post-synthetic workup, then ease of operation is improved, but catalyst deactivation due to FDCA precipitation occurs, worsening reliability

Engineering Contradiction:
Improveease of operationVSAvoidreliability
Core Design Contradiction:
Ease of operationVSReliability

Solution Approach 1:

The patent changes the pH parameter of the reaction medium to maintain it in the range of 2-4, which prevents FDCA precipitation on the catalyst surface. This parameter adjustment resolves the contradiction by maintaining catalyst activity (reliability) while preserving the ease of operation benefits of heterogeneous catalysis.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces an intermediary substance (acidic additive such as H2SO4, HClO4, or CF3SO3H) that mediates between the oxidation process and the catalyst. This intermediary maintains the required pH level, preventing FDCA precipitation while allowing the heterogeneous catalyst to function effectively, thus resolving the reliability-ease of operation contradiction.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Productivity

If water content is increased to improve solubility and yield, then productivity is improved, but by-product formation increases, worsening manufacturing precision

Engineering Contradiction:
ImproveproductivityVSAvoidmanufacturing precision
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent adjusts the pH parameter to the range of 2-4, which changes the chemical environment to suppress by-product formation. This allows the process to operate with high water content (50-90 wt.%) for improved productivity while maintaining manufacturing precision by preventing unwanted side reactions.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The acidic additive acts as an intermediary that modifies the reaction pathway in the aqueous medium. It enables high water content operation for improved productivity while directing the reaction toward the desired FDCA product, preventing by-product formation and maintaining manufacturing precision.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Productivity

If oxidation conditions are intensified to increase conversion rate, then productivity is improved, but catalyst deactivation accelerates, worsening reliability

Engineering Contradiction:
ImproveproductivityVSAvoidreliability
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The patent changes the pH parameter to a lower range (2-4), which creates a protective environment for the heterogeneous catalyst during intensified oxidation. This allows higher conversion rates and improved productivity while the acidic medium prevents FDCA precipitation that would otherwise cause catalyst deactivation, thus maintaining reliability.

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 increases the yield of FDCA by efficiently converting both HMF and di-HMF, reduces catalyst deactivation, and simplifies the reactor setup, enabling economically viable production with improved catalyst activity and reduced by-product formation.

Implementation Method 1

subjecting said starting mixture to oxidation conditions in the presence of an oxygen-containing gas and a catalytically effective amount of a heterogeneous catalyst comprising one or more noble metals on a support so that both HMF and di-HMF react to give furane-2,5-dicarboxylic acid

Methodology Applied
Scientific EffectOxidation: Oxidation

Implementation Method 2

a catalytically effective amount of a heterogeneous catalyst comprising one or more noble metals on a support

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP3325457B1Process for preparing furan-2,5-dicarboxylic acid
Publication Date: 2020.01.01 BASF SE
  • EP3325457B1 patent drawing
  • EP3325457B1 patent drawing
  • EP3325457B1 patent drawing

AI summary

The present invention relates to a process forpreparingfuran-2,5-dicarboxylic acid, comprising the following steps: preparing or providing a starting mixture comprising5-(hydroxymethyl)furfural (HMF),5,5'-[oxy-bis(methylene)]bis-2-furfural (di-HMF), and water,subjecting said starting mixture to oxidation conditions in the presence of an oxygen-containing gas and a catalytically effective amount of a heterogeneous catalyst comprising one or more noble metals on a support so that both HMF and di-HMF react to give furane-2,5-dicarboxylic acid in a product mixture also comprising water and oxidation by-products. Moreover the present invention relates to the use of a catalyst comprising one or more noble metals on a support as an heterogeneous oxidation catalyst for catalyzing in an aqueous starting mixture the reaction of both HMF and di-HMF to furane-2,5-dicarboxylic acid.