Sulfonated Aromatic Monomer Purification via Salt Precipitation

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Solution Overview

Problem

Conventional methods for purifying sulfonated aromatic monomers are inefficient due to multiple salt precipitation steps, difficulty in controlling pH with strong bases, and excessive solvent use in recrystallization, leading to low yield and high costs.

Innovation Solution

A simplified method involving reduced salt precipitation steps, using a weak base for neutralization, and recrystallization from water, which reduces solvent usage and maintains reaction conditions, employing easily available and stable chemicals.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If multiple salt precipitation steps are used in conventional purification method, then purity of sulfonated aromatic monomer is improved, but process complexity and production cost increase

Engineering Contradiction:
Improvepurity of sulfonated aromatic monomerVSAvoidprocess complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The invention extracts and removes the neutralization step from the conventional purification process. By eliminating the neutralization step that used to be required before salt precipitation, the process is simplified while maintaining effective purification through direct salt precipitation of the sulfonated aromatic monomer from the reaction mixture.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention segments the purification process into distinct operational phases: direct salt precipitation followed by filtration and washing. This segmentation allows each step to be optimized independently, reducing overall process complexity while achieving the required purity level.

Inventive Principle:
Principle #1Segmentation

2Measurement precision

If strong base (NaOH) is used for neutralization in conventional method, then pH control is achieved, but side reactions occur and yield decreases

Engineering Contradiction:
ImprovepH controlVSAvoidyield of sulfonated aromatic monomer
Core Design Contradiction:
Measurement precisionVSProductivity

Solution Approach 1:

The invention converts the harmful effect of strong base-induced side reactions into a beneficial outcome by completely eliminating the neutralization step. The sulfonated aromatic monomer is directly precipitated as its salt form without requiring pH adjustment, thereby avoiding all side reactions associated with strong base usage while maintaining product purity.

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

3Manufacturing precision

If excessive amount of solvent is used for recrystallization in conventional method, then purity is improved, but solvent loss increases and cost rises

Engineering Contradiction:
Improvepurity of sulfonated aromatic monomerVSAvoidsolvent loss
Core Design Contradiction:
Manufacturing precisionVSLoss of substance

Solution Approach 1:

The invention extracts and removes the recrystallization step from the conventional purification process. By eliminating this step entirely and relying on direct salt precipitation followed by filtration and washing, the process achieves the required purity without requiring large amounts of solvent, thereby reducing solvent loss and associated costs.

Inventive Principle:
Principle #2Taking out (Extraction)

4Manufacturing precision

If conventional purification process is used, then high purity sulfonated aromatic monomer is obtained, but production cost increases due to multiple steps

Engineering Contradiction:
Improvepurity of sulfonated aromatic monomerVSAvoidproduction cost
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The invention merges the purification function into a single integrated salt precipitation step that combines what were previously separate operations (neutralization followed by precipitation). This consolidation achieves the required purity while significantly reducing the number of unit operations and associated costs.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The invention extracts and removes unnecessary steps (neutralization and recrystallization) from the conventional process, retaining only the essential salt precipitation step that delivers the required purity at lower cost.

Inventive Principle:
Principle #2Taking out (Extraction)

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 method achieves high-purity sulfonated aromatic monomers with reduced process complexity and cost, suitable for polymer electrolyte membrane synthesis, offering improved yield and molecular weight.

Implementation Method 1

adding a salt to the compound 2 to precipitate a crude compound 1-1

Methodology Applied
Scientific EffectSalt precipitation: Precipitation

Implementation Method 2

dissolving the crude compound 1-1 in water

Methodology Applied
Scientific EffectDissolution: Solvation

Implementation Method 3

neutralizing the aqueous solution containing the crude compound

Methodology Applied
Scientific EffectNeutralization:

Implementation Method 4

concentrating the neutralized aqueous solution and recrystallizing the concentrate from water

Methodology Applied
Scientific EffectRecrystallization: Crystallisation

Data Source

PatentUS9540319B2Method for purifying sulfonated aromatic monomer
Publication Date: 2017.01.10 KOREA RES INST OF CHEM TECH
  • US9540319B2 patent drawing
  • US9540319B2 patent drawing
  • US9540319B2 patent drawing

AI summary

The present invention relates to an improved method for purifying a sulfonated aromatic monomer. The method is an economical method capable of providing a highly pure sulfonated aromatic monomer, in which a salt precipitation step and a recrystallization step are simplified while maintaining the reaction conditions used in a conventional method for synthesizing the sulfonated aromatic monomer, and a purification process is carried out using an easily available and stable chemical substance. The sulfonated aromatic monomer obtained by the purification method will be useful for the preparation of a polymer for a polymer electrolyte membrane and will be advantageous to synthesize polymer with high molecular weight.