Cymene Conversion to BTX Aromatics via Flow Disproportionation

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Solution Overview

Problem

Current methods for producing BTX aromatic compounds rely on fossil-fuel sources, which are unsustainable and lack a simple, economic process for using renewable resources.

Innovation Solution

Converting cymene derived from terpenes, fusel oil waste, and citrus waste into BTX building blocks through dehydrogenation and flow disproportionation reactions using heterogeneous catalysts like Pd/C, Pd/Alumina, and acidic zeolites, such as ZSM-5, under controlled temperature and inert gas conditions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If fossil-fuel petroleum fractions are used as feedstock for BTX production, then established industrial processes can be utilized, but sustainability and renewability are compromised

Engineering Contradiction:
Improveprocess reliabilityVSAvoidfeedstock renewability
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The invention changes the fundamental parameter of feedstock origin from fossil-based to renewable biomass-based sources. By utilizing terpenes from citrus waste, fusel oil, and other renewable resources, the process maintains industrial reliability while achieving sustainability goals through parameter transformation of the feedstock source

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs cymene as an intermediary compound that bridges renewable biomass resources and BTX aromatic products. The multi-step conversion process (terpenes → cymene → BTX) uses cymene as a mediating substrate that enables transformation from renewable feedstock to desired aromatic products while maintaining process control

Inventive Principle:
Principle #24Intermediary (Mediator)

2Productivity

If conventional BTX recovery units and catalytic reforming processes are used, then high production efficiency is achieved, but process complexity and equipment requirements increase

Engineering Contradiction:
ImproveBTX production efficiencyVSAvoidprocess equipment complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The invention segments the BTX production process into distinct modular steps: (1) terpene dehydrogenation to cymene, (2) cymene disproportionation to xylenes, and (3) xylene isomer separation. This segmentation allows each step to be optimized independently with appropriate catalysts and reaction conditions, simplifying overall process design while maintaining high productivity

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The process extracts and utilizes specific chemical pathways from complex biomass feedstocks by isolating terpene components and directing them through controlled dehydrogenation and disproportionation reactions. This extraction approach simplifies the conversion of complex renewable feedstocks into targeted BTX products

Inventive Principle:
Principle #2Taking out (Extraction)

3Adaptability or versatility

If biomass conversion initiatives are implemented, then renewable feedstock utilization improves, but process simplicity and economic viability are compromised

Engineering Contradiction:
Improverenewable feedstock utilizationVSAvoidprocess simplicity
Core Design Contradiction:
Adaptability or versatilityVSEase of manufacture

Solution Approach 1:

The invention achieves universality by developing a multi-functional catalytic system that handles multiple renewable feedstocks (citrus waste, fusel oil, terpenes) through a common conversion pathway. The same dehydrogenation and disproportionation chemistry applies across different biomass sources, simplifying manufacturing while maintaining versatility in feedstock acceptance

Inventive Principle:
Principle #6Universality (Multi-functionality)

Solution Approach 2:

The process utilizes waste biomass materials (citrus waste, fusel oil byproducts) as feedstocks, effectively making the system self-service by converting available waste resources into valuable BTX products. This approach simplifies feedstock acquisition and improves economic viability by utilizing low-cost or waste materials

Inventive Principle:
Principle #25Self-service

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 achieves high yields of renewable BTX aromatics, such as toluene, benzene, and xylenes, reducing reliance on fossil fuels and promoting a circular economy by utilizing waste materials effectively.

Implementation Method 1

contacting monoterpenes with a dehydrogenation catalyst under conditions effective to produce cymenes and hydrogen

Methodology Applied
Scientific EffectDehydrogenation:

Implementation Method 2

contacting the cymene with a suitable catalyst under flow disproportionation reaction conditions effective to convert the cymene to the renewable aromatic backbone compound

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS11873277B2Circular economic methods for fragrance ingredients
Publication Date: 2024.01.16 INTERNATIONAL FLAVORS & FRAGRANCES INC
  • US11873277B2 patent drawing
  • US11873277B2 patent drawing
  • US11873277B2 patent drawing

AI summary

Disclosed is a method for converting cymene generated from renewable low value terpene streams into renewable benzene, toluene, xylenes, and cymene isomers (ortho and meta) under flow disproportionation reaction conditions, which compounds are basic building blocks for fragrance materials. This technology has potential to replace high volume petrochemical-based feedstocks with plant-based building blocks that can fill the renewability gap for key fragrance ingredients.