Aromatic Methylating Process for Benzene Conversion

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Existing processes for converting benzene to higher substituted aromatics are costly and generate undesirable side products, requiring expensive catalysts and complex separation processes, while also failing to meet stringent environmental regulations for lower benzene content in motor fuels.

Innovation Solution

A process that increases the mole ratio of methyl to phenyl in aromatic compounds by reacting aromatic compounds with aromatic methylating agents, using non-aromatic compounds as alkylating or methylating agents, which are readily available in naphtha feeds, to produce higher valued products like para-xylene with improved aromatic ring recovery and reduced benzene content.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If existing processes are used to convert benzene to higher substituted aromatics, then conversion can occur, but expensive catalysts are required and undesirable side products are generated

Engineering Contradiction:
Improveconversion effectivenessVSAvoidundesirable side products
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent uses toluene as an intermediary substance in a two-step transalkylation process. First, benzene reacts with toluene to form xylenes. Then, the toluene produced in the first reaction serves as the alkylating agent for the second reaction. This intermediary approach allows selective conversion while minimizing side products.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent employs specific reaction conditions including temperature ranges (40-100°C for first reaction, 40-80°C for second reaction), pressure conditions (1-20 atm), and catalyst selection (acidic ion-exchange resins or solid acid catalysts) to optimize the conversion process and minimize undesirable side products while maintaining high selectivity for xylenes.

Inventive Principle:
Principle #35Parameter changes

2Reliability

If existing processes are used to convert benzene to higher substituted aromatics, then conversion can occur, but complex separation processes are required

Engineering Contradiction:
Improveconversion effectivenessVSAvoidseparation process complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

By using toluene as an intermediary that is consumed in the first reaction and regenerated in the second reaction, the process simplifies the overall separation requirements. The transalkylation reactions produce desired xylenes with minimal byproducts, reducing the complexity of downstream separation operations compared to direct alkylation methods.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent extracts and utilizes the toluene component separately in a two-step process, allowing for better control of reaction conditions and simplified separation. By taking out the toluene as a distinct intermediate species, the process avoids the formation of complex mixtures that would require elaborate separation systems.

Inventive Principle:
Principle #2Taking out (Extraction)

3Object-affected harmful factors

If existing processes are used to remove benzene from motor fuel, then benzene content can be reduced, but expensive catalysts and reactants are required

Engineering Contradiction:
Improvebenzene content in fuelVSAvoidprocess cost
Core Design Contradiction:
Object-affected harmful factorsVSEase of manufacture

Solution Approach 1:

The patent uses toluene as a readily available intermediary from naphtha feeds or existing aromatic complexes. This approach converts benzene to valuable xylenes using inexpensive toluene as the alkylating agent, avoiding the need for expensive specialized catalysts and reactants while simultaneously reducing benzene content and producing higher-value products.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent employs inexpensive acidic ion-exchange resins or solid acid catalysts that can be easily regenerated or replaced, rather than requiring expensive precious metal catalysts. The process uses readily available toluene from standard naphtha feeds, making the benzene removal and conversion economically viable.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

4Productivity

If aromatic compounds are converted to higher substituted compounds, then product value increases, but the process must maintain aromatic ring recovery

Engineering Contradiction:
Improveproduct valueVSAvoidaromatic ring recovery
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The patent carefully controls reaction parameters including temperature (40-100°C for first reaction, 40-80°C for second reaction), pressure (1-20 atm), and residence time to optimize both the conversion to higher-value xylenes and the preservation of aromatic ring structures. These controlled conditions ensure high aromatic ring recovery while achieving the desired product transformation.

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 process effectively converts benzene to higher substituted aromatics, such as xylenes, with increased methyl groups, enhancing product value and reducing benzene content, while minimizing side reactions and using cost-effective catalysts, thus addressing the limitations of existing methods.

Implementation Method 1

reacting an effective amount of one or more aromatic compounds and an effective amount of one or more aromatic methylating agents to form a product having a mole ratio of methyl to phenyl of at least about 0.1:1 greater than the feed

Methodology Applied
Scientific EffectAlkylation reaction: Chemical Bonding

Data Source

PatentUS9174892B2Process for increasing a mole ratio of methyl to phenyl
Publication Date: 2015.11.03 UOP LLC
  • US9174892B2 patent drawing
  • US9174892B2 patent drawing
  • US9174892B2 patent drawing

AI summary

One exemplary embodiment can be a process for increasing a mole ratio of methyl to phenyl of one or more aromatic compounds in a feed. The process can include reacting an effective amount of one or more aromatic compounds and an effective amount of one or more aromatic methylating agents to form a product having a mole ratio of methyl to phenyl of at least about 0.1:1 greater than the feed.