Fluid Catalytic Cracking of p-Cresol Dimer into Phenolic Monomers

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Solution Overview

Problem

There is no method available in the literature to convert p-cresol dimer into monomers through either thermal or catalytic approaches, posing a disposal challenge for the hazardous and non-flammable p-cresol dimer produced in aromatic industries.

Innovation Solution

A fluid catalytic cracking process using an equilibrium fluid catalytic cracking catalyst to convert p-cresol dimer into valuable phenolic monomers such as 2-methyl phenol, 4-methyl phenol, and 2,3-xylenol, avoiding incineration and environmental pollution.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If p-cresol dimer is produced as a by-product in the p-cresol process, then the main product yield is improved, but the disposal difficulty increases due to hazardous and non-flammable properties

Engineering Contradiction:
Improvep-cresol production yieldVSAvoidhazardous waste generation
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The invention converts the hazardous p-cresol dimer waste product into valuable phenolic monomers (p-cresol, o-cresol, m-cresol, phenol) through fluid catalytic cracking. This transforms the harmful waste into beneficial chemical products, eliminating disposal problems while creating additional value from the by-product stream.

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

2Use of energy by moving object

If traditional thermal or catalytic conversion methods are used, then energy recovery is improved, but the method availability is poor due to lack of established processes

Engineering Contradiction:
Improveenergy recovery from wasteVSAvoidprocess availability
Core Design Contradiction:
Use of energy by moving objectVSEase of manufacture

Solution Approach 1:

The invention employs fluid catalytic cracking with specific catalysts (zeolites, amorphous silica-alumina) at controlled temperatures (400-500°C) and catalyst-to-oil ratios (2:1 to 5:1) to convert p-cresol dimer. These parameter optimizations enable effective conversion without requiring established industrial processes, making the method both energy-efficient and practically implementable.

Inventive Principle:
Principle #35Parameter changes

3Loss of substance

If p-cresol dimer is incinerated for disposal, then the volume reduction is improved, but the environmental pollution increases due to combustion of highly condensed aromatic compounds

Engineering Contradiction:
Improvewaste volume reductionVSAvoidenvironmental pollution
Core Design Contradiction:
Loss of substanceVSObject-generated harmful factors

Solution Approach 1:

Instead of incinerating the p-cresol dimer which causes pollution, the invention uses catalytic cracking to convert it into valuable phenolic monomers. This eliminates the need for combustion, avoiding environmental pollution while still achieving waste utilization and volume reduction through product transformation.

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

4Productivity

If fluid catalytic cracking is applied to convert p-cresol dimer, then the value addition is improved, but the process complexity increases due to catalyst selection and reaction control requirements

Engineering Contradiction:
Improvevalue addition from wasteVSAvoidprocess complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The invention uses equilibrium FCC catalyst that can simultaneously crack various types of p-cresol dimer structures into multiple valuable phenolic products. This multi-functional catalyst approach achieves high value addition from a single waste stream without requiring multiple specialized processing units, thereby managing complexity while maximizing productivity.

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

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 effectively converts p-cresol dimer into phenolic monomers, providing value addition to the p-cresol process industry while avoiding environmental pollution, and allows for recycling of unconverted p-cresol dimer to improve conversion efficiency.

Implementation Method 1

fluid catalytic cracking process using an equilibrium fluid catalytic cracking catalyst to convert p-cresol dimer into valuable phenolic monomers

Methodology Applied
Scientific EffectCatalytic cracking: Catalysis

Implementation Method 2

Heating the fluidization gas at a temperature in the range between 350°C to 400°C

Methodology Applied
Scientific EffectConvection: Convection

Implementation Method 3

Condensing the catalytically cracked vapors as obtained in step (iii) in a condenser in the temperature range between 0°C to 100°C

Methodology Applied
Scientific EffectCondensation: Condensation

Data Source

PatentUS12275695B2Fluid catalytic cracking of p-cresol dimer into phenolic monomers and process thereof
Publication Date: 2025.04.15 COUNCIL OF SCI & IND RES
  • US12275695B2 patent drawing
  • US12275695B2 patent drawing
  • US12275695B2 patent drawing

AI summary

A fluid catalytic cracking process for p-cresol dimer to produce valuable phenolic monomers, i.e., 2-methyl phenol, 4-methyl phenol, 2,3-xylenol, and phenol, uses an equilibrium catalyst (E-cat) generated in the petroleum fluid catalytic cracking (FCC) unit. The p-cresol dimer can be processed under relatively mild conditions, while maximizing desired and minimizing undesired products. The process may include charging an equilibrium fluid catalytic cracking catalyst; heating to a predetermined cracking temperature and pressure; (c) charging a p-cresol dimer feed; (d) contacting the p-cresol dimer with the equilibrium fluid catalytic cracking catalyst; (e) condensing resulting phenolic monomer vapors to obtain phenolic monomer liquid and fluidization gas; (f) separating the phenolic monomer liquid from the fluidization gas; (g) collecting the separated phenolic monomer liquid; (h) separating the collected phenolic monomer liquid individual phenolic monomers; and (i) recycling any unconverted p-cresol dimer into the fluidized bed reactor.