Fructose to HMF Conversion via Partial Reaction and Membrane Separation

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Solution Overview

Problem

Current processes for converting fructose-containing feedstocks to 5-(hydroxymethyl)furfural (HMF) face challenges such as low overall process productivity due to the formation of unwanted acid by-products and polymerization, leading to reduced yields and increased complexity, especially when aiming for high conversion rates in the reaction zone.

Innovation Solution

The process involves partial conversion of fructose to HMF in a reaction zone with an acid catalyst and solvent, followed by separation and recycling of unconverted fructose and solvent, using techniques like selective membrane separation to control the yield and reduce off-path products like humins, thereby maintaining a high recovery and reutilization efficiency.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If fructose conversion to HMF is maximized in the reaction zone, then HMF yield increases, but formation of unwanted acid by-products and polymerization increases, reducing overall process yield and complicating recovery

Engineering Contradiction:
ImproveHMF production rateVSAvoidformation of unwanted acid by-products and polymerization
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The patent applies partial action by conducting the dehydration reaction only to partial conversion (30-70% fructose conversion) rather than complete conversion. This prevents excessive formation of humins and acid by-products while still achieving economically viable HMF yields. The reaction is intentionally stopped before maximum HMF formation to avoid degradation pathways.

Inventive Principle:
Principle #16Partial or excessive action

Solution Approach 2:

The patent extracts HMF from the reaction mixture at partial conversion using liquid-liquid extraction with organic solvents. This removes HMF from the aqueous phase where further degradation to humins and acid by-products would occur, effectively separating the desired product from the harmful degradation pathways.

Inventive Principle:
Principle #2Taking out (Extraction)

2Quantity of substance

If high conversion of fructose to HMF is achieved, then HMF yield increases, but process complexity and recovery difficulty increase

Engineering Contradiction:
ImproveHMF yieldVSAvoidprocess complexity and recovery difficulty
Core Design Contradiction:
Quantity of substanceVSDevice complexity

Solution Approach 1:

The patent employs liquid-liquid extraction to separate HMF from the reaction mixture at partial conversion. This extraction step simplifies the overall process by removing HMF early, avoiding the need for complex separation procedures that would be required if complete conversion were pursued, which would generate more by-products and require more elaborate purification systems.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent recovers and recycles the aqueous phase containing unconverted fructose and catalyst back to the reactor. This circular approach reduces waste and minimizes the need for complex disposal systems, while the organic extract containing HMF proceeds to simpler purification steps.

Inventive Principle:
Principle #34Discarding and recovering

3Productivity

If complete conversion of fructose is pursued, then HMF production is maximized, but formation of humins and acid by-products reduces overall yield

Engineering Contradiction:
ImproveHMF productionVSAvoidoverall process yield
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The patent deliberately limits the dehydration reaction to partial conversion (30-70% of fructose) rather than complete conversion. This partial action optimizes the balance between HMF formation rate and by-product formation, achieving maximum overall yield by stopping before degradation becomes significant.

Inventive Principle:
Principle #16Partial or excessive action

Solution Approach 2:

The patent converts the potential harm of unconverted fructose into a benefit by recycling it back to the reactor. The aqueous phase containing remaining fructose and catalyst is returned to the reaction zone, allowing further HMF production from the unconverted material without requiring additional fresh feedstock, thus improving overall process efficiency and yield.

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

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 approach allows for cost-effective and efficient production of HMF by controlling the conversion to a partial endpoint, reducing the formation of off-path products and enhancing the overall process yield while enabling the recovery and recycling of valuable constituents.

Implementation Method 1

HMF is primarily produced by dehydrating a carbohydrate feedstock, particularly monosaccharides such as glucose and fructose

Methodology Applied
Scientific EffectDehydration reaction: Chemical Bonding

Implementation Method 2

selective membrane separation techniques are employed for the separation and recovery of unconverted fructose and intermediates from the desired product

Methodology Applied
Scientific EffectSelective membrane separation: Semipermeable Membrane

Implementation Method 3

The post reaction zone separations also enable the effective recovery and reutilization of unconverted fructose and solvent

Methodology Applied
Scientific EffectRecycling:

Data Source

PatentUS10017486B2Conversion of fructose-containing feedstocks to HMF-containing product
Publication Date: 2018.07.10 ARCHER DANIELS MIDLAND CO
  • US10017486B2 patent drawing
  • US10017486B2 patent drawing
  • US10017486B2 patent drawing

AI summary

The present invention relates generally to processes for converting fructose-containing feedstocks to a product comprising 5-(hydroxymethyl)furfural (HMF) and water in the presence of water, solvent and an acid catalyst. In some embodiments, the conversion of fructose to HMF is controlled at a partial conversion endpoint characterized by a yield of HMF from fructose that does not exceed about 80 mol %. In these and other embodiments, the processes provide separation techniques for separating and recovering the product, unconverted fructose, solvent and acid catalyst to enable the effective recovery and reutilization of reaction components.