Rhodium Catalyst Synthesis Selectivity

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Solution Overview

Problem

Current synthesis methods for alkyl 2-acetyl-5,9,13-trimethyltetradeca-4,8,12-trienoates and 6,10,14-trimethylpentadeca-5,9,13-trien-2-one from beta-farnesene are inefficient due to long reaction times, high temperatures, and low selectivity, making them unsuitable for industrial-scale production.

Innovation Solution

A non-continuous process using a mixture of a rhodium complex and a water-soluble phosphine salt, such as sodium (m-sulfonatophenyl)diphenylphosphine or disodium bis(3-sulfonatophenyl)phenylphosphine, in the presence of water and an organic solvent, which allows for faster reactions with high yield and selectivity at low temperatures.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Extent of automation

If a continuous process using rhodium complexes and sulfonated triphenylphosphines is used, then the synthesis can be performed continuously, but the reaction time is long and very high reaction temperatures are required which decrease selectivity due to dimerization reactions

Engineering Contradiction:

Improvecontinuous process capabilityVSAvoidselectivity

Core Design Contradiction:

Extent of automationVSManufacturing precision

Solution Approach 1:

The patent changes the chemical parameters by using water-soluble phosphine salts with different sulfonation patterns (mono- or disulfonated instead of trisulfonated), which alters the catalyst's properties to enable high selectivity at lower temperatures while maintaining continuous process capability

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite catalyst system combining rhodium complexes with specifically designed water-soluble phosphine salts (mono- or disulfonated triphenylphosphines), which provides both the continuity of the process and the selectivity needed to prevent dimerization

Inventive Principle:

Principle #40Composite materials

2Productivity

If very high reaction temperatures are used to maintain continuous process operation, then the process can run continuously, but the selectivity clearly decreases significantly due to dimerization reactions

Engineering Contradiction:

Improvecontinuous production capabilityVSAvoiddimerization reactions

Core Design Contradiction:

ProductivityVSObject-generated harmful factors

Solution Approach 1:

The patent changes the temperature parameter from very high temperatures to lower temperatures (below 100°C) by introducing water-soluble phosphine salts with optimized sulfonation, which fundamentally alters the reaction conditions to eliminate dimerization while maintaining continuous production

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The patent uses water-soluble phosphine salts that can be easily separated and discarded after use in the continuous process, allowing for simplified cleanup and preventing catalyst-related dimerization side reactions

Inventive Principle:

Principle #27Cheap short-living objects (Disposable)

3Ease of operation

If trisulfonated triphenylphosphine salts are used, then water-soluble catalysts are obtained, but the reaction time is long and high temperatures are required

Engineering Contradiction:

Improvewater solubility of catalystVSAvoidreaction time

Core Design Contradiction:

Ease of operationVSDuration of action of moving object

Solution Approach 1:

The patent changes the degree of sulfonation from trisulfonated to mono- or disulfonated triphenylphosphines, which optimizes the balance between water solubility and catalytic activity, resulting in shorter reaction times and lower temperature requirements while maintaining ease of operation

Inventive Principle:

Principle #35Parameter changes

4Quantity of substance

If the synthesis process is optimized for high yield, then product yield is improved, but reaction time increases and high temperatures are required which reduce selectivity

Engineering Contradiction:

Improveproduct yieldVSAvoidselectivity

Core Design Contradiction:

Quantity of substanceVSManufacturing precision

Solution Approach 1:

The patent uses a composite catalyst system with water-soluble phosphine salts (mono- or disulfonated) and rhodium complexes that simultaneously achieves high yield and high selectivity by preventing dimerization side reactions through optimized catalyst structure and properties

Inventive Principle:

Principle #40Composite materials

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 approach significantly reduces reaction time, maintains high yield and selectivity, and minimizes dimerization products, making the process more cost-efficient and suitable for large-scale industrial production.

Implementation Method 1

reacting a compound of formula (II) and a compound of formula (III) in a non-continuous process in the presence of either i) a mixture of a rhodium complex and water-soluble phosphine salt

Methodology Applied

Scientific EffectCatalysis: Catalysis

Data Source

PatentEP3728174B1Synthesis of alkyl 2-acetyl-5,9,13-trimethyltetradeca-4,8,12-trienoates and derivatives by a non-continuous production process

Publication Date: 2022.11.30 DSM IP ASSETS BV

Figure 1
Figure 2~3

AI summary

The present invention relates to the manufacturing of a process of alkyl 2- acetyl-5,9,13-trimethyltetradeca-4,8,12-trienoates and alkyl 2-acetyl-9,13-di- methyl-5-methylenetetradeca-8,12-dienoate as well as 6,10,14-trimethylpenta- deca-5,9,13-trien-2-one and 10,14-dimethyl-6-methylenepentadeca-9,13-dien-2-5 one and 6,10,14-trimethylpentadecan-2-one.