FDCA Production via In-Situ Oxidation and Solvent Extraction

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Solution Overview

Problem

The production of 5-hydroxymethylfurfural (HMF) from glucose is hindered by low selectivity and high costs due to the need for expensive catalysts and complex separation processes, and there is a lack of research on integrating HMF production with downstream upgrading reactions to value-added chemicals like furandicarboxylic acid (FDCA), which requires simplifying or eliminating the separation of HMF from organic solvents.

Innovation Solution

A process converting HMF to FDCA without separating HMF from the reaction mixture, using a lactone solvent like gamma-valerolactone (GVL) and an aromatic solvent like toluene to create a two-phase system, allowing easy extraction and purification of FDCA, and employing supported metal catalysts for oxidation in the presence of molecular oxygen.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If HMF is produced from glucose using conventional methods, then HMF can be obtained, but the selectivity is low and separation costs are high

Engineering Contradiction:
ImproveHMF selectivityVSAvoidseparation cost
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The patent combines HMF production and FDCA upgrading into a one-pot reaction system. The reaction mixture containing HMF, catalysts, and solvents is directly subjected to oxidation without intermediate separation steps. This merging of production and upgrading operations eliminates the need for costly HMF isolation and purification, while the integrated system maintains high selectivity through controlled reaction conditions and catalyst design.

Inventive Principle:
Principle #5Merging (Combining)

2Manufacturing precision

If HMF is separated from organic solvents, then HMF can be purified, but the process becomes complex and costly

Engineering Contradiction:
ImproveHMF purityVSAvoidseparation process complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent performs preliminary oxidation of HMF to FDCA within the reaction mixture before any separation occurs. By converting HMF to FDCA in situ, the system eliminates the need for HMF isolation and subsequent purification steps. The FDCA product can then be directly separated from the reaction mixture through simple filtration or decantation, dramatically reducing process complexity while maintaining product purity.

Inventive Principle:
Principle #10Preliminary action

3Productivity

If conventional catalysts are used for HMF production, then dehydration can occur, but catalyst costs are high and corrosion problems arise

Engineering Contradiction:
Improvedehydration rateVSAvoidcatalyst cost
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The patent employs solid acid catalysts as intermediaries that provide the necessary dehydration function without the drawbacks of conventional homogeneous catalysts. These solid catalysts can be easily separated from the reaction mixture by filtration, eliminating corrosion issues and reducing catalyst costs. The solid catalyst surface provides active sites for efficient dehydration while being reusable and environmentally friendly.

Inventive Principle:
Principle #24Intermediary (Mediator)

4Manufacturing precision

If HMF is produced and then upgraded to FDCA in separate steps, then each reaction can be optimized, but the overall process becomes less efficient

Engineering Contradiction:
Improvereaction optimizationVSAvoidoverall process efficiency
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The patent merges HMF production and FDCA upgrading into a single integrated reaction system. Multiple catalysts and reaction conditions are optimized simultaneously to achieve both efficient dehydration and oxidation in one pot. This approach maintains high selectivity through careful catalyst design while dramatically improving overall process efficiency by eliminating intermediate separation and purification steps, reducing processing time and energy consumption.

Inventive Principle:
Principle #5Merging (Combining)

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 simplifies the production of FDCA by eliminating the need for HMF separation, reducing costs and improving the economic and environmental sustainability of the HMF production process, while enabling efficient conversion of biomass-derived sugars to value-added chemicals.

Implementation Method 1

The platform molecule 5-hydroxymethylfurfural (HMF), produced from the Brønsted acid-catalyzed dehydration of C6 sugars (hexoses)

Methodology Applied
Scientific EffectDehydration:

Implementation Method 2

oxidizing at least a portion of the HMF formed into FDCA

Methodology Applied
Scientific EffectOxidation: Oxidation

Data Source

PatentUS9617234B1Method to produce furandicarboxylic acid (FDCA) from 5-hydroxymethylfurfural (HMF)
Publication Date: 2017.04.11 WISCONSIN ALUMNI RES FOUND
  • US9617234B1 patent drawing
  • US9617234B1 patent drawing
  • US9617234B1 patent drawing

AI summary

A process to produce furandicarboxylic acid (FDCA). The process includes the steps of reacting a C6 sugar-containing reactant in a reaction solution comprising a first organic solvent selected from the group consisting of beta-, gamma-, and delta-lactones, hydrofurans, hydropyrans, and combinations thereof, in the presence of an acid catalyst for a time and under conditions wherein at least a portion of the C6 sugar present in the reactant is converted to 5-(hydroxymethyl)furfural (HMF); oxidizing the HMF into FDCA with or without separating the HMF from the reaction solution; and extracting the FDCA by adding an aprotic organic solvent having a dipole moment of about 1.0 D or less to the reaction solution.