Alkyl-Aromatic Oxidation via Ionic Liquid Catalyst

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Solution Overview

Problem

Current processes for oxidizing alkyl-aromatic compounds, such as terephthalic acid production, face challenges in reducing impurities and improving color, particularly high levels of 4-carboxybenzaldehyde (4-CBA) and color imperfections, which require additional purification steps and resources.

Innovation Solution

A process involving the use of a solvent comprising a carboxylic acid and an ionic liquid with a specific ratio, along with a bromine source and catalyst, to control the levels of impurities and color, achieving reduced 4-CBA levels and improved whiteness through controlled solvent composition and reaction conditions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional oxidation processes are used to produce terephthalic acid, then the oxidation reaction proceeds efficiently, but the product contains high levels of impurities (4-CBA) and color bodies requiring additional purification steps

Engineering Contradiction:
Improveoxidation reaction efficiencyVSAvoidproduct purity
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent changes the chemical parameters of the oxidation system by introducing an ionic liquid (specifically 1-butyl-3-methylimidazolium bromide) as a catalyst and using ammonium acetate as a promoter. This alters the reaction pathway and kinetics, enabling efficient oxidation while minimizing the formation of 4-CBA impurities and color bodies, thus achieving both high productivity and high purity simultaneously

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs a composite catalytic system consisting of ionic liquid (BMIMBr) combined with ammonium acetate promoter. This composite approach creates a synergistic effect where the ionic liquid provides catalytic activity and the ammonium acetate enhances the oxidation process, resulting in superior product purity without sacrificing reaction efficiency

Inventive Principle:
Principle #40Composite materials

2Manufacturing precision

If multiple purification steps are implemented to reduce impurities and improve color, then product purity increases, but process complexity and cost increase

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

Solution Approach 1:

The ionic liquid catalyst and ammonium acetate promoter perform a preliminary action during the oxidation phase itself, preventing the formation of impurities and color bodies at the source. This proactive approach eliminates the need for subsequent purification steps to remove these contaminants, thereby reducing process complexity while maintaining high product purity

Inventive Principle:
Principle #10Preliminary action

3Ease of operation

If conventional catalysts and solvents are used in oxidation, then the process is simple to operate, but impurity levels (4-CBA) and color bodies remain high

Engineering Contradiction:
Improveprocess simplicityVSAvoidimpurity and color body formation
Core Design Contradiction:
Ease of operationVSObject-generated harmful factors

Solution Approach 1:

The patent changes the physical and chemical parameters of the reaction system by employing an ionic liquid-based catalytic system with ammonium acetate promoter. This parameter change transforms the oxidation process into one that is equally simple to operate but produces significantly fewer impurities and color bodies, resolving the contradiction between operational simplicity and harmful factor reduction

Inventive Principle:
Principle #35Parameter changes

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 approach effectively minimizes impurities and enhances the whiteness of oxidation products, potentially reducing the need for additional purification steps and improving product quality by maintaining low 4-CBA levels and CIELAB b* values, resulting in a more efficient and cost-effective production process.

Implementation Method 1

the solvent comprises a carboxylic acid and an ionic liquid

Methodology Applied
Scientific EffectSolvation: Solvation

Implementation Method 2

a catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 3

oxidizing an alkyl-aromatic compound

Methodology Applied
Scientific EffectOxidation: Oxidation

Data Source

PatentUS8946471B2Process for oxidizing an alkyl-aromatic compound
Publication Date: 2015.02.03 UOP LLC
  • US8946471B2 patent drawing
  • US8946471B2 patent drawing
  • US8946471B2 patent drawing

AI summary

Processes for oxidizing an alkyl-aromatic compound are described. The processes include contacting an alkyl-aromatic compound, a solvent, a bromine source, a catalyst, and an oxidizing agent to produce a product comprising at least one of an aromatic alcohol, an aromatic aldehyde, an aromatic ketone, and an aromatic carboxylic acid. The composition of the solvent is controlled to reduce the impurities in the product.