Low Color BEHFD Plasticizer via Catalytic Hydrogenation

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Solution Overview

Problem

The existing synthetic pathways for producing bis(2-ethylhexyl) furan-2,5-dicarboxylate (BEHFD) plasticizers result in highly colored products, making them less desirable for end-use applications due to their high APHA color values.

Innovation Solution

A method involving the hydrogenation of furan-2,5-dicarboxylate derivatives in the presence of a hydrogenation catalyst to produce low color furan-2,5-dicarboxylate derivative plasticizers with APHA values less than 100, which includes esterification of furan-2,5-dicarboxylic acid with an alcohol stream in the presence of an esterification catalyst followed by hydrogenation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If conventional esterification pathways are used to produce BEHFD plasticizers, then the production process is simple and direct, but the resulting plasticizers have high APHA color values making them less desirable for end-use applications

Engineering Contradiction:
Improvesimplicity of synthesis pathwayVSAvoidcolor of plasticizer
Core Design Contradiction:
Ease of manufactureVSObject-affected harmful factors

Solution Approach 1:

The patent introduces a hydrogenation catalyst as an intermediary substance that mediates between the colored BEHFD product and hydrogen gas. The catalyst (such as Pd/C, PtO2, or Raney nickel) facilitates the hydrogenation reaction that removes color-causing conjugated double bonds, transforming the harmful colored product into a desirable low-color or colorless product while maintaining the esterification pathway's simplicity

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent changes the chemical parameters of the BEHFD molecule by adding hydrogen across conjugated double bonds through catalytic hydrogenation. This parameter change (reducing the degree of unsaturation) directly addresses the color issue by eliminating the chromophores responsible for high APHA values, while the reaction conditions (temperature, pressure, catalyst loading) are optimized to maintain process simplicity

Inventive Principle:
Principle #35Parameter changes

2Object-affected harmful factors

If hydrogenation is applied to reduce color of BEHFD plasticizers, then the APHA color values decrease to less than 100, but the process complexity increases due to additional hydrogenation step

Engineering Contradiction:
Improvecolor of plasticizerVSAvoidnumber of synthesis steps
Core Design Contradiction:
Object-affected harmful factorsVSDevice complexity

Solution Approach 1:

The patent applies preliminary hydrogenation action during or immediately after the esterification process. By introducing the hydrogenation step early in the synthesis sequence (either concurrently with esterification or as a brief subsequent step), the color reduction is achieved before the product undergoes further processing, thereby minimizing the overall process complexity while ensuring low-color output

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The hydrogenation catalyst serves as a temporary intermediary that is introduced only when needed for color reduction and can be easily removed or deactivated afterward. This allows the process to remain relatively simple, as the catalyst can be filtered off or deactivated without requiring complex separation equipment or additional processing steps

Inventive Principle:
Principle #24Intermediary (Mediator)

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 effectively reduces the color of BEHFD plasticizers, resulting in products with improved fusion, lower volatility, and better efficiency for PVC applications compared to DEHP, with APHA values decreased to less than 20 or b* values less than 1.0, making them more suitable for industrial use.

Implementation Method 1

contacting the furan-2,5-dicarboxylate derivative with hydrogen in the presence of a hydrogenation catalyst to thereby produce a low color furan-2,5-dicarboxylate derivative plasticizer

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Implementation Method 2

contacting the furan-2,5-dicarboxylate derivative with hydrogen in the presence of a hydrogenation catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 3

contacting a furan-2,5-dicarboxylic acid composition and an alcohol stream in the presence of an esterification catalyst under esterification conditions to produce a furan-2,5-dicarboxylate derivative

Methodology Applied
Scientific EffectEsterification: Chemical Bonding

Data Source

PatentUS9029579B2Method of synthesizing low color furan diesters
Publication Date: 2015.05.12 EASTMAN CHEM CO
  • US9029579B2 patent drawing
  • US9029579B2 patent drawing

AI summary

The present invention relates to a method of making low colored bis(2-ethylhexyl) furan-2,5-dicarboxylate (BEHFD) plasticizer via mild hydrogenation of highly colored BEHFD.