Copper-Based Hydrogenation for Selective Isobutylphenyl Ethanol

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Solution Overview

Problem

Existing processes for producing 1-(4-isobutylphenyl)ethanol suffer from low selectivity, high formation of side-products like 1-ethyl-4-isobutylbenzene, and require the use of solvents or additives, making them inefficient and unsuitable for large-scale industrial production.

Innovation Solution

A catalytic hydrogenation process using a catalyst composition comprising copper and one or more metals other than copper, with copper ranging from 30 to 98% by mass, operates in a continuous process, minimizing solvent use and reducing side-product formation, particularly 1-ethyl-4-isobutylbenzene, while maintaining high selectivity and conversion.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional hydrogenation processes are used with traditional catalysts, then the reaction can proceed, but selectivity is low and side-products like 1-ethyl-4-isobutylbenzene are formed in high amounts

Engineering Contradiction:
ImproveselectivityVSAvoidside-product formation
Core Design Contradiction:
Manufacturing precisionVSObject-generated harmful factors

Solution Approach 1:

The patent applies parameter changes by modifying the catalyst composition parameters - using a copper-based catalyst with specific metal ratios (Cu:Zn:Al in 50-90:5-30:5-30 mass%) and controlling reaction parameters (temperature 80-150°C, pressure 1-10 bar) to achieve high selectivity (>95%) and minimize side-product formation

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent uses a composite catalyst material comprising copper, zinc, and aluminum in specific ratios, supported on a carrier material. This composite catalyst composition enables high selectivity for 1-(4-isobutylphenyl)ethanol while suppressing side reactions that produce 1-ethyl-4-isobutylbenzene

Inventive Principle:
Principle #40Composite materials

2Ease of manufacture

If solvents or additives are used in the hydrogenation process, then the reaction can be facilitated, but the process complexity increases and purification becomes more difficult

Engineering Contradiction:
Improveprocess efficiencyVSAvoidprocess complexity
Core Design Contradiction:
Ease of manufactureVSDevice complexity

Solution Approach 1:

The patent extracts and eliminates solvents and additives from the hydrogenation process. The reaction is performed in a solvent-free system using only the reactants (1-(4-isobutylphenyl)ethanone and hydrogen gas), which simplifies the process and eliminates the need for solvent removal and additional purification steps

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The catalyst composition is designed to be highly active and selective under mild conditions, enabling the reaction to proceed efficiently without requiring solvents or additives for facilitation. The system serves itself by using the reactants as the reaction medium

Inventive Principle:
Principle #25Self-service

3Adaptability or versatility

If batch processes are used for production, then flexibility is maintained, but productivity is low and the process is unsuitable for large-scale industrial production

Engineering Contradiction:
Improveprocess flexibilityVSAvoidproduction efficiency
Core Design Contradiction:
Adaptability or versatilityVSProductivity

Solution Approach 1:

The patent implements a continuous hydrogenation process where reactants are continuously fed through the reactor containing the copper-based catalyst, and products are continuously removed. This continuous operation significantly increases productivity compared to batch processes while maintaining process control and flexibility

Inventive Principle:
Principle #20Continuity of useful action

4Manufacturing precision

If extensive purification steps are used to remove side-products, then product purity can be achieved, but the process becomes more complex and time-consuming

Engineering Contradiction:
Improveproduct purityVSAvoidpurification time
Core Design Contradiction:
Manufacturing precisionVSLoss of time

Solution Approach 1:

The catalyst composition is designed to perform preliminary selective action during the reaction itself, converting >95% of the starting material to the desired product with minimal side-product formation. This preliminary selectivity eliminates the need for extensive downstream purification steps

Inventive Principle:
Principle #10Preliminary action

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 selectivity and conversion of 1-(4-isobutylphenyl)ethanone to 1-(4-isobutylphenyl)ethanol with minimal side-products, allowing for efficient large-scale production and simplified purification, and demonstrates long-term stability over 8000 operating hours.

Implementation Method 1

reacting 1-(4-isobutylphenyl)ethanone with hydrogen in the presence of a catalyst composition comprising copper and one or more metals other than copper

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

catalytic hydrogenation process for producing 1-(4-isobutylphenyl)ethanol from 1-(4-isobutylphenyl)ethanone

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Data Source

PatentUS12378174B2Process for producing 1-(4-isobutylphenyl)ethanol by hydrogenation of 1-(4-isobutyl-phenyl)ethanone in the presence of a catalyst composition comprising copper
Publication Date: 2025.08.05 BASF SE
  • US12378174B2 patent drawing
  • US12378174B2 patent drawing

AI summary

Described is a process for producing 1-(4-isobutylphenyl)ethanol by reacting 1-(4-isobutyl-phenyl)ethanone with hydrogen in the presence of a catalyst composition comprising cop-per and one or more metals other than copper, and a use of a respective composition and/or of a pre-composition, the pre-composition comprising a mixture of oxides of copper and oxides of one or more metals other than copper, in a catalytic hydrogenation process for producing 1-(4-isobutylphenyl)ethanol from 1-(4-isobutylphenyl)ethanone.