Terephthalic Acid Production via Ionic Liquid Oxidation

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Solution Overview

Problem

Conventional processes for producing terephthalic acid often result in crude products with high levels of impurities, such as 4-carboxybenzaldehyde, requiring costly purification steps and catalytic hydrogenation.

Innovation Solution

A process involving the oxidation of a substantially pure p-toluic acid stream using an ionic liquid solvent, a bromine source, and a catalyst to produce terephthalic acid with reduced impurities, eliminating the need for catalytic hydrogenation and achieving lower levels of contaminants.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If conventional oxidation processes are used to produce terephthalic acid, then the production cost is reduced through simpler processes, but the product purity deteriorates with high levels of impurities such as 4-carboxybenzaldehyde

Engineering Contradiction:
Improveproduction costVSAvoidproduct purity
Core Design Contradiction:
Ease of manufactureVSManufacturing precision

Solution Approach 1:

The patent changes the chemical parameters of the oxidation process by using an ionic liquid solvent system instead of conventional organic solvents, and by optimizing the catalyst composition (cobalt acetate and manganese acetate) and bromine source (sodium bromide) to achieve high selectivity for terephthalic acid while minimizing impurity formation

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces an ionic liquid as an intermediary solvent medium that facilitates the oxidation reaction. The ionic liquid serves as a unique reaction medium that enables better catalyst solubility and activity, leading to improved selectivity and reduced impurity formation compared to conventional oxidation processes

Inventive Principle:
Principle #24Intermediary (Mediator)

2Manufacturing precision

If multiple purification steps including catalytic hydrogenation are used to increase terephthalic acid purity, then the product quality improves to polymer grade, but the process complexity and cost increase

Engineering Contradiction:
Improveproduct purityVSAvoidpurification process complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent performs preliminary action by optimizing the oxidation reaction conditions to pre-minimize impurity formation before purification steps. By using the ionic liquid solvent system and optimized catalyst composition, the process achieves high selectivity that reduces impurity levels before any purification steps are applied

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent extracts or removes the need for complex catalytic hydrogenation steps by achieving sufficiently low impurity levels through the optimized oxidation process. The ionic liquid-based oxidation directly produces terephthalic acid with impurity levels low enough to eliminate or simplify subsequent hydrogenation purification steps

Inventive Principle:
Principle #2Taking out (Extraction)

3Ease of operation

If conventional oxidation conditions are used, then the reaction conditions are simpler to implement, but the impurity levels increase requiring additional purification steps

Engineering Contradiction:
Improvereaction conditions simplicityVSAvoidimpurity levels
Core Design Contradiction:
Ease of operationVSObject-generated harmful factors

Solution Approach 1:

The patent uses a composite catalyst system comprising cobalt acetate and manganese acetate in specific ratios, combined with sodium bromide as bromine source in an ionic liquid solvent. This composite material approach creates synergistic effects that enhance oxidation selectivity and reduce impurity formation while maintaining operationally simple reaction conditions

Inventive Principle:
Principle #40Composite materials

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 produces terephthalic acid with lower impurity levels, reducing purification costs and complexity, and allows for the production of polymer-grade terephthalic acid with improved efficiency.

Implementation Method 1

oxidation of a substantially pure p-toluic acid stream to terephthalic acid

Methodology Applied
Scientific EffectOxidation: Oxidation

Data Source

PatentUS9024059B2Process for producing terephthalic acid
Publication Date: 2015.05.05 UOP LLC
  • US9024059B2 patent drawing
  • US9024059B2 patent drawing
  • US9024059B2 patent drawing

AI summary

Methods of producing terephthalic acid are described. The methods involve using a substantially pure p-toluic acid stream. The substantially pure p-toluic acid stream, a solvent comprising an ionic liquid and optionally a carboxylic acid, a bromine source, a catalyst, and an oxidizing agent are contacted to produce a product comprising terephthalic acid.