Phenol Purification via Selective Hydrogenation

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Solution Overview

Problem

Conventional phenol purification processes are inefficient in removing carbonyl compounds, leading to the loss of useful components like phenol and α-methylstyrene, as they react with impurities or form dimers, making it difficult to achieve high-purity phenol with reduced hydroxyacetone and other carbonyl compound levels.

Innovation Solution

A copper-based catalyst, comprising copper and oxides of silicon, aluminum, zinc, chromium, barium, or manganese, is used for selective hydrogenation of carbonyl compounds in phenol, converting them into corresponding alcohol compounds, which can then be separated by distillation, thereby preserving the useful components.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional purification methods (distillation, activated alumina, silica/alumina catalyst) are used to remove carbonyl compounds, then hydroxyacetone and other carbonyl compounds can be removed, but phenol and α-methylstyrene (useful components) are lost due to reactions with impurities or dimerization

Engineering Contradiction:
Improvepurity of phenol productVSAvoidloss of phenol and α-methylstyrene
Core Design Contradiction:
Manufacturing precisionVSLoss of substance

Solution Approach 1:

The invention changes the chemical parameter of the carbonyl compounds by selectively hydrogenating them to corresponding alcohols using a copper-based catalyst. This transformation modifies the boiling point and chemical properties of the impurities, enabling their removal through distillation without causing side reactions that would consume useful components like phenol and α-methylstyrene

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The copper-based catalyst acts as an intermediary that selectively promotes the hydrogenation of carbonyl compounds while leaving phenol and α-methylstyrene unaffected. The catalyst mediates the selective conversion of impurities to alcohols, which can then be separated by distillation, thus removing harmful impurities without losing valuable components

Inventive Principle:
Principle #24Intermediary (Mediator)

2Manufacturing precision

If activated alumina or silica/alumina catalyst is used at high temperatures (150-360°C) to convert carbonyl compounds, then some purification is achieved, but phenol and α-methylstyrene undergo addition reactions or dimerization to form cumylphenol and olefin dimers

Engineering Contradiction:
Improveremoval efficiency of carbonyl compoundsVSAvoidformation of cumylphenol and olefin dimers
Core Design Contradiction:
Manufacturing precisionVSObject-generated harmful factors

Solution Approach 1:

The invention changes the reaction parameter by using a copper-based catalyst that enables selective hydrogenation at lower temperatures, avoiding the high-temperature conditions (150-360°C) that cause unwanted side reactions. The copper catalyst provides a different reaction pathway that is selective for carbonyl compounds and does not promote addition reactions or dimerization of useful components

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention converts the harmful carbonyl compounds into beneficial alcohols through selective hydrogenation. The carbonyl groups are transformed into hydroxyl groups, creating alcohol compounds that have different distillation properties and can be easily separated from phenol, thus turning the harmful impurities into removable substances without generating harmful by-products

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

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 produces high-purity phenol by converting carbonyl compounds to alcohols, allowing for easy separation and preventing the loss of phenol and α-methylstyrene, thus enhancing the efficiency and quality of the purification process.

Implementation Method 1

A copper-based catalyst, comprising copper and oxides of silicon, aluminum, zinc, chromium, barium, or manganese, is used for selective hydrogenation of carbonyl compounds in phenol, converting them into corresponding alcohol compounds

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Implementation Method 2

A copper-based catalyst, comprising copper and oxides of silicon, aluminum, zinc, chromium, barium, or manganese, is used for selective hydrogenation of carbonyl compounds in phenol

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 3

separating the alcohol compounds and phenol by distillation

Methodology Applied
Scientific EffectDistillation: Distillation

Data Source

PatentUS9029609B2Phenol purification process
Publication Date: 2015.05.12 MITSUI CHEMICALS INC
  • US9029609B2 patent drawing

AI summary

The present invention provides an easy process for purifying phenol by separating carbonyl compounds through selective hydrogenation of the compounds to the corresponding alcohols then distillation. The phenol purification process of the present invention comprises bringing phenol into contact with a copper-based catalyst in the presence of hydrogen to convert carbonyl compounds contained in the phenol to the corresponding alcohol compounds, and separating the alcohol compounds and phenol by distillation.