DAFD Esterification Vapor Rectification for ACFC Removal

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Solution Overview

Problem

Current methods for producing dialkyl furan-2,5-dicarboxylate (DAFD) face challenges in achieving high purity and yield without the need for downstream separation of large volumes of high boiling compound intermediates like 5-(alkoxycarbonyl)furan-2-carboxylic acid (ACFC).

Innovation Solution

A process involving feeding furan-2,5-dicarboxylic acid to an esterification reactor with an alcohol compound, where an esterification reaction occurs, and the resulting vapor is subjected to rectification, converting ACFC into a liquid phase condensate which is then contacted with the liquid reaction mixture, thereby minimizing ACFC in the DAFD vapor composition and increasing the yield of DAFD.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If conventional esterification methods are used to produce DAFD, then the reaction can proceed with simple equipment, but the product requires complex downstream separation to remove large volumes of high boiling intermediates like ACFC

Engineering Contradiction:
Improvesimplicity of esterification processVSAvoidcomplexity of downstream separation
Core Design Contradiction:
Ease of manufactureVSDevice complexity

Solution Approach 1:

The patent combines the esterification reaction and rectification separation into a single integrated reactor system. The rectification zone is incorporated within the esterification reactor, allowing simultaneous reaction and separation of ACFC intermediate, thereby eliminating complex downstream separation equipment while maintaining process simplicity

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The esterification reactor is designed to perform multiple functions: conducting the esterification reaction, vaporizing the reaction mixture, and rectifying the vapor to separate ACFC. This multi-functional design eliminates the need for separate downstream separation equipment, resolving the contradiction between manufacturing simplicity and separation complexity

Inventive Principle:
Principle #6Universality (Multi-functionality)

2Productivity

If conventional esterification with excess alcohol is used, then the reaction can proceed to high conversion, but large volumes of high boiling intermediates must be separated downstream

Engineering Contradiction:
Improveconversion of FDCA to DAFDVSAvoidvolume of intermediates requiring separation
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The patent extracts the ACFC intermediate from the reaction mixture by vaporizing it and condensing it separately in the rectification zone. This continuous removal of ACFC prevents its accumulation and eliminates the need for downstream separation of large volumes of high boiling intermediates, while maintaining high FDCA conversion through continued reaction with excess alcohol

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The rectification process performs preliminary separation of ACFC from the reaction mixture during the esterification process itself. By removing ACFC early in the process rather than after completion, the system avoids the accumulation of large volumes of intermediates that would require downstream separation, while still allowing high conversion to proceed

Inventive Principle:
Principle #10Preliminary action

3Duration of action of stationary object

If ACFC accumulates in the reaction mixture, then the esterification can proceed continuously, but the purity of the DAFD product decreases

Engineering Contradiction:
Improvecontinuous operation of esterificationVSAvoidpurity of DAFD product
Core Design Contradiction:
Duration of action of stationary objectVSManufacturing precision

Solution Approach 1:

The rectification zone continuously monitors and removes ACFC from the vapor phase, creating a feedback loop that prevents ACFC accumulation in the liquid reaction mixture. This continuous removal mechanism maintains product purity while allowing the esterification reaction to proceed continuously without interruption

Inventive Principle:
Principle #23Feedback

Solution Approach 2:

The integrated rectification system operates continuously alongside the esterification reaction, continuously removing ACFC as it forms. This continuous separation action maintains constant product purity throughout the continuous reaction process, resolving the contradiction between continuous operation and product purity

Inventive Principle:
Principle #20Continuity of useful 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

This process enhances the yield and purity of DAFD by reducing the amount of ACFC in the vapor stream, simplifying downstream separation and improving the overall efficiency of the esterification process.

Implementation Method 1

in which at least a portion of the ACFC in the esterification vapor is converted to a liquid phase condensate

Methodology Applied
Scientific EffectCondensation: Condensation

Data Source

PatentEP3412662B1Esterification of furan-2,5-dicarboxylic acid to a dialkyl-furan-2,5-dicarboxylate vapor with rectification
Publication Date: 2020.09.16 EASTMAN CHEM CO
  • EP3412662B1 patent drawingFigure 1
  • EP3412662B1 patent drawingFigure 2
  • EP3412662B1 patent drawingFigure 3

AI summary

A process for the manufacture of dialkyl furan-2,5-dicarboxylate (DAFD) vapor composition by feeding furan-2,5-dicarboxylic acid ("FDCA") to an esterification reactor and in the presence of an alcohol compound such as methanol, conducting an esterification reaction to form an esterification vapor containing DAFD, unreacted alcohol compound, 5-(alkoxycarbonyl)furan-2-carboxylic acid (ACFC), and water, and continuously passing the esterification vapor through an ACFC condensing zone, that can be integral with the esterification reactor, in which at least a portion of the ACFC in the esterification vapor is converted to a liquid phase condensate, and continuously discharging the esterification vapor from the ACFC condensing zone as a DAFD vapor. There is also a DAFD vapor composition containing DAFD, water, unreacted alcohol, and by-products.