Fluensulfone Synthesis via Low-Temp Catalytic Oxidation

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Solution Overview

Problem

Current processes for preparing fluensulfone, a potent nematicide, face challenges such as low yield, selectivity, and waste generation due to high temperatures and the use of expensive oxidizing agents like oxone, which are problematic especially in large-scale production.

Innovation Solution

A catalytic oxidation process at low temperatures using an oxidizing agent and a catalyst, such as sodium tungstate, to convert 5-chloro-2-[(3,4,4-trifluoro-3-buten-1-yl)thio]-thiazole into fluensulfone, optimizing reaction conditions to achieve high selectivity and yield while minimizing waste.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Speed

If high temperature oxidation is used to convert sulfide to sulfone, then reaction rate is improved, but selectivity deteriorates and yield decreases

Engineering Contradiction:
Improvereaction rateVSAvoidselectivity
Core Design Contradiction:
SpeedVSManufacturing precision

Solution Approach 1:

The patent applies parameter changes by conducting the oxidation reaction at low temperatures (0-25°C) instead of high temperatures, which improves selectivity and yield while maintaining acceptable reaction rates through the use of a catalyst system comprising sodium tungstate and phosphoric acid

Inventive Principle:
Principle #35Parameter changes

2Productivity

If expensive oxidizing agents like oxone are used, then oxidation efficiency is improved, but production cost increases and waste generation increases

Engineering Contradiction:
Improveoxidation efficiencyVSAvoidproduction cost
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The patent replaces expensive oxidizing agents like oxone with cheaper alternatives such as hydrogen peroxide or sodium percarbonate, which are more cost-effective for large-scale production while maintaining oxidation efficiency through the catalytic system

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

Solution Approach 2:

The patent reduces waste generation by using oxidizing agents that produce fewer salts and bypires the catalyst system that can be more easily handled and disposed of compared to oxone, reducing the environmental burden and waste treatment costs

Inventive Principle:
Principle #34Discarding and recovering

3Device complexity

If conventional oxidation methods are used, then process simplicity is maintained, but yield and selectivity are low

Engineering Contradiction:
Improveprocess simplicityVSAvoidyield
Core Design Contradiction:
Device complexityVSManufacturing precision

Solution Approach 1:

The patent introduces a catalyst system comprising sodium tungstate and phosphoric acid as intermediaries that mediate the oxidation reaction, enabling high yield and selectivity under mild conditions while maintaining process simplicity through the use of readily available chemicals and straightforward reaction conditions

Inventive Principle:
Principle #24Intermediary (Mediator)

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 conversion rates and chemical yields, reduces production costs, and minimizes salt waste, providing a more efficient and selective method for producing fluensulfone.

Implementation Method 1

reacting a compound of formula (II) with an oxidizing agent and a catalyst at a low temperature

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

preparing fluensulfone by the reaction of the corresponding sulfide with an oxidizing agent

Methodology Applied
Scientific EffectOxidation: Oxidation

Data Source

PatentUS11897853B2Synthesis of 1,1,2-trifluoro-4-(substituted sufonyl)-but-1-ene
Publication Date: 2024.02.13 ADAMA MAKHTESHIM LTD
  • US11897853B2 patent drawing
  • US11897853B2 patent drawing
  • US11897853B2 patent drawing

AI summary

The present invention provides a process for preparing a compound of formula [I] from a compound of formula [II] using an oxidizing agent and a catalyst, the process is carried out at a low temperature.