Dehydrogenation Catalyst for Cyclohexane Conversion

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Solution Overview

Problem

Existing processes for producing cyclohexylbenzene through hydroalkylation of benzene suffer from low selectivity and the presence of impurities like cyclohexane and methylcyclopentane, which are difficult to separate due to similar boiling points with benzene, leading to inefficiencies and by-product formation.

Innovation Solution

A dehydrogenation process using a catalyst comprising 0.05 to 5 wt% of a Group 14 metal, such as tin, and 0.1 to 10 wt% of a Group 6 to 10 metal, like platinum or palladium, to convert cyclohexane and methylcyclopentane into benzene and paraffins, improving separation and selectivity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional distillation is used to separate cyclohexane and methylcyclopentane from benzene, then separation is attempted, but the separation is difficult due to similar boiling points

Engineering Contradiction:
Improveseparation efficiencyVSAvoidseparation process complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent changes the chemical parameter of the mixture by converting cyclohexane and methylcyclopentane into compounds with different boiling points through dehydrogenation and isomerization reactions. This transforms the separation problem from one requiring complex distillation to one that can be solved by simpler distillation methods.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces a catalyst as an intermediary substance that facilitates the chemical transformation of impurities. The catalyst enables selective dehydrogenation and isomerization reactions that convert the difficult-to-separate cyclic hydrocarbons into benzene and paraffins, which can then be easily separated.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Productivity

If dehydrogenation catalyst is used to convert cyclohexane to benzene, then cyclohexane conversion is improved, but catalyst selectivity and activity are insufficient with previous catalyst compositions

Engineering Contradiction:
Improvecyclohexane conversion rateVSAvoidcatalyst selectivity
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent employs a composite catalyst system containing multiple metal components (platinum group metals combined with nickel, cobalt, or iron) on a support material. This composite structure synergistically combines the dehydrogenation activity of platinum group metals with the isomerization capability of transition metals, achieving both high conversion and high selectivity.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent optimizes the local composition and distribution of metal components within the catalyst. By controlling the specific ratios and spatial arrangement of different metals, the catalyst achieves enhanced activity for cyclohexane dehydrogenation while maintaining high selectivity for the desired products.

Inventive Principle:
Principle #3Local quality

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 achieves high cyclohexane conversion and selectivity to benzene, overcoming the limitations of previous catalysts by enhancing the separation of impurities and improving the efficiency of benzene recovery.

Implementation Method 1

A dehydrogenation process using a catalyst comprising 0.05 to 5 wt% of a Group 14 metal, such as tin, and 0.1 to 10 wt% of a Group 6 to 10 metal, like platinum or palladium, to convert cyclohexane and methylcyclopentane into benzene and paraffins

Methodology Applied
Scientific EffectDehydrogenation:

Implementation Method 2

cyclohexane and methylcyclopentane have similar boiling points to that of benzene so that their separation by conventional distillation is difficult

Methodology Applied
Scientific EffectDistillation: Distillation

Data Source

PatentUS9580368B2Dehydrogenation process
Publication Date: 2017.02.28 EXXONMOBIL CHEMICAL PATENTS INC
  • US9580368B2 patent drawing
  • US9580368B2 patent drawing

AI summary

Disclosed herein is a process for dehydrogenating a saturated cyclic hydrocarbon and/or 5-membered ring compound with a dehydrogenation catalyst. The dehydrogenation catalyst comprises: (i) 0.05 wt % to 5 wt % of a metal selected from Group 14 of the Periodic Table of Elements; and (ii) 0.1 wt % to 10 wt % of a metal selected from Groups 6 to 10 of the Periodic Table of Elements. The process is conducted under dehydrogenation conditions effective to dehydrogenate at least a portion saturated cyclic hydrocarbon and/or 5-membered ring compound.