Fipronil Crystalline Modification V Preparation

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Solution Overview

Problem

Existing methods for preparing fipronil do not account for the existence of different crystalline modifications, which can affect solubility, stability, and filtration properties, leading to inefficiencies and challenges in large-scale production and use.

Innovation Solution

A novel crystalline modification of fipronil, referred to as 'crystalline modification V', is identified and characterized, with a specific preparation process involving a solution of fipronil in hot dimethylsulfoxide or acetonitrile, followed by crystallization and isolation, ensuring high yield and purity, and excluding other modification forms.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional preparation methods are used to produce fipronil, then production can proceed with standard procedures, but the product may contain mixed crystalline modifications leading to inconsistent solubility, stability, and filtration properties

Engineering Contradiction:

Improvecrystalline modification consistencyVSAvoidpreparation process complexity

Core Design Contradiction:

Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent applies parameter changes by controlling crystallization conditions including temperature range (cooling from elevated temperature), solvent selection (dimethylsulfoxide or acetonitrile), and cooling rate to obtain a specific crystalline modification (Form V) of fipronil with consistent properties

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The patent utilizes phase transitions during the crystallization process, where fipronil transitions from dissolved state in hot solvent to crystalline solid upon cooling, specifically forming the desired crystalline modification through controlled temperature reduction

Inventive Principle:

Principle #36Phase transitions

2Productivity

If no specific crystalline modification is targeted, then preparation is simpler, but filtration efficiency decreases due to poor filtration properties of certain crystalline forms

Engineering Contradiction:

Improvefiltration efficiencyVSAvoidcrystallization process complexity

Core Design Contradiction:

ProductivityVSEase of manufacture

Solution Approach 1:

The patent changes physical parameters during crystallization, specifically controlling temperature profiles and solvent conditions to produce crystals with optimal filtration properties, avoiding forms that clog filters

Inventive Principle:

Principle #35Parameter changes

3Reliability

If different crystalline modifications are not distinguished, then characterization is simpler using only melting point, but important properties like solubility and stability cannot be optimized

Engineering Contradiction:

Improveproduct stabilityVSAvoidcrystalline modification characterization

Core Design Contradiction:

ReliabilityVSDifficulty of detecting and measuring

Solution Approach 1:

The patent employs X-ray powder diffraction patterns as a characterization method, where different crystalline modifications produce distinct diffraction patterns that serve as fingerprints for identification and purity assessment

Inventive Principle:

Principle #32Color changes

Solution Approach 2:

The patent replaces simple melting point measurement with X-ray powder diffraction analysis to distinguish between different crystalline modifications, providing more reliable characterization of the crystalline form

Inventive Principle:

Principle #28Mechanics substitution (Replace mechanical system)

4Quantity of substance

If crystalline modifications are not controlled, then storage and packaging can proceed without special considerations, but bulk density variations cause inefficiencies

Engineering Contradiction:

Improvebulk density consistencyVSAvoidstorage and packaging complexity

Core Design Contradiction:

Quantity of substanceVSEase of manufacture

Solution Approach 1:

The patent controls crystallization parameters to produce a specific crystalline modification with consistent bulk density, ensuring predictable storage and packaging requirements without requiring special handling procedures

Inventive Principle:

Principle #35Parameter changes

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 novel crystalline modification V of fipronil provides enhanced stability, solubility, and filtration properties, improving the efficiency and reproducibility of fipronil production, storage, and use as a pesticide, effectively combating a wide range of pests and parasites.

Implementation Method 1

a solution of fipronil in hot dimethylsulfoxide or acetonitrile, followed by crystallization and isolation

Methodology Applied

Scientific EffectCrystallization: Crystallisation

Data Source

PatentUS9913473B2Crystalline modification of fipronil

Publication Date: 2018.03.13 BASF SE

AI summary

The present invention relates to a novel crystalline modification of fipronil, to a process for the preparation of the same, to pesticidal and parasiticidal mixtures and compositions comprising said crystalline modification and to their use for combating pests and parasites.