Furanic Compound Separation from DMSO via Liquid-Liquid Extraction

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Solution Overview

Problem

Current methods for separating furan compounds like 5-HMF from dimethoxysulfoxide (DMSO) using liquid-liquid extraction result in impure extracts with high DMSO content, leading to increased operating and investment costs due to solubility issues and delayed crystallization, which hampers industrial scalability.

Innovation Solution

Incorporating a counter-extraction step with water to enhance the purity of furan compounds, reducing DMSO content, and optimizing crystallization conditions, allowing for higher temperature and lower volume crystallization, thereby improving yield and efficiency.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If liquid-liquid extraction is used to separate furan compounds from DMSO, then separation is achieved, but the extract contains high DMSO content reducing purity

Engineering Contradiction:
Improvepurity of furan compound extractVSAvoidDMSO content in extract
Core Design Contradiction:
Manufacturing precisionVSQuantity of substance

Solution Approach 1:

The extraction process is divided into multiple sequential stages: initial extraction of furan compounds from DMSO, followed by counter-extraction with water to remove DMSO from the organic phase. This segmentation allows each stage to optimize for a specific function - first recovery of product, then removal of contaminant - achieving high purity without sacrificing yield

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

Water serves as an intermediary substance in the counter-extraction step. It selectively interacts with DMSO in the organic extract, forming a separate aqueous phase that carries DMSO away while leaving the furan compound in the organic phase. This intermediary enables selective removal of the unwanted substance without affecting the desired product

Inventive Principle:
Principle #24Intermediary (Mediator)

2Quantity of substance

If distillation is used to remove water from reaction medium, then water elimination is achieved, but DMSO and furan compounds concentrate at column bottom causing degradation

Engineering Contradiction:
Improvewater content in reaction mediumVSAvoidyield and quality of furan compound
Core Design Contradiction:
Quantity of substanceVSManufacturing precision

Solution Approach 1:

Instead of using distillation which concentrates all non-volatile components together, the invention uses liquid-liquid extraction to selectively take out the furan compound from the DMSO-water mixture. The organic solvent selectively dissolves the furan compound while leaving DMSO and water in the aqueous phase, avoiding the degradation that occurs when DMSO and furan compounds are concentrated together at the bottom of a distillation column

Inventive Principle:
Principle #2Taking out (Extraction)

3Manufacturing precision

If crystallization is performed on extract containing DMSO, then furan compound crystallization is achieved, but solubility increases and crystallization is delayed

Engineering Contradiction:
Improvecrystallization yield of furan compoundVSAvoidcrystallization time
Core Design Contradiction:
Manufacturing precisionVSDuration of action of moving object

Solution Approach 1:

The counter-extraction with water is performed as a preliminary action before crystallization. This removes DMSO from the organic extract in advance, eliminating its solvent effect that would otherwise increase furan compound solubility and delay crystallization. By performing this purification step beforehand, the subsequent crystallization proceeds rapidly and efficiently

Inventive Principle:
Principle #10Preliminary 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

The process achieves purity levels of 95% or more for furan compounds, reducing DMSO content, and enables more favorable crystallization conditions, leading to lower energy consumption and investment costs, thus enhancing the overall separation efficiency and industrial viability.

Implementation Method 1

a step b) of extracting the mixture produced in step a) by an organic solvent chosen from chlorinated solvents, ethers, ketones and aromatics, producing an aqueous raffinate enriched in DMSO and an organic extract intermediate enriched in furan compound(s)

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

Implementation Method 2

a step c) of counter-extracting the intermediate organic extract enriched in furan compound(s) produced in step b) with added water, producing an aqueous intermediate raffinate enriched in DMSO and a purified organic extract

Methodology Applied
Scientific EffectCounter-extraction: Liquid-Liquid Extraction

Implementation Method 3

d) optionally, a step d) of crystallization of the furan compound(s) contained in the purified organic extract produced in step c), followed by filtration

Methodology Applied
Scientific EffectCrystallization: Crystallisation

Data Source

PatentEP3684487B1Process for separating furanic compounds, in particular 5- hydroxymethylfurfural, from dimethoxysulfoxide by liquid-liquid extractions
Publication Date: 2021.08.25 IFP ENERGIES NOUVELLES
  • EP3684487B1 patent drawingFigure 1
  • EP3684487B1 patent drawingFigure 2

AI summary

The invention relates to a process for separating furanic compounds from a feedstock additionally containing dimethoxysulfoxide (DMSO). These furanic compounds are in particular 5-hydroxymethylfurfural (5-HMF), 2,5-diformylfuran (DFF), 2,5-furanedicarboxylic acid (FDCA) or dimethyl 2,5-furandicarboxylate (DMFDCA). The process successively comprises a) bringing the feedstock into contact with water originating from step c), then b) a liquid-liquid extraction with an organic solvent followed by a back extraction c) by the water added in order to obtain an organic extract rich in furanic compounds. The extract may then be subjected to a crystallization step d) and then a filtration in order to obtain the solid furanic compound. The water-rich or solvent-rich effluents are advantageously recycled respectively to the back extraction and the extraction.