Sulfentrazone Crystalline Polymorph Solvent Entrapment

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Solution Overview

Problem

Technical grade sulfentrazone contains entrapped solvents like toluene, which pose issues during milling operations and usage due to volatile emissions, affecting its efficacy as an herbicide.

Innovation Solution

A new crystalline polymorphic form of sulfentrazone (sulfentrazone-1) is developed, obtained through crystallization from a polar, protic solvent, significantly reducing solvent content and enhancing stability, allowing for improved herbicidal performance.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If technical grade sulfentrazone is used, then it can be prepared commercially with existing processes, but it contains entrapped solvent that causes volatile emissions during milling and use

Engineering Contradiction:
Improvecommercial preparationVSAvoidvolatile solvent emissions
Core Design Contradiction:
Ease of manufactureVSObject-generated harmful factors

Solution Approach 1:

The patent changes the physical state parameter of sulfentrazone from amorphous/technical grade to a specific crystalline polymorphic form. This parameter change fundamentally alters the material's ability to trap solvents, eliminating the harmful volatile emissions while maintaining commercial manufacturability through controlled crystallization processes.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention utilizes phase transition from amorphous/technical grade sulfentrazone to a defined crystalline polymorphic form. This phase transition removes entrapped solvent molecules from the structure, preventing their subsequent volatile emissions during milling and application, while the crystalline form remains suitable for commercial preparation.

Inventive Principle:
Principle #36Phase transitions

2Productivity

If technical grade sulfentrazone with entrapped solvent is used, then it can be produced through conventional processes, but it presents problems with exposure during processing and use

Engineering Contradiction:
Improveproduction efficiencyVSAvoidexposure during processing
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The patent applies preliminary action by establishing a specific crystalline polymorphic form during the manufacturing process itself. This preliminary structuring of the material in its crystalline form prevents solvent entrapment before processing occurs, thereby eliminating exposure hazards during subsequent milling and application operations while maintaining production efficiency.

Inventive Principle:
Principle #10Preliminary action

3Quantity of substance

If conventional sulfentrazone is used, then it is available as technical grade material, but it has reduced herbicidal effectiveness compared to the new crystalline form

Engineering Contradiction:
ImproveavailabilityVSAvoidherbicidal effectiveness
Core Design Contradiction:
Quantity of substanceVSReliability

Solution Approach 1:

The patent changes the physical parameter of sulfentrazone from technical grade (amorphous/mixed form) to a specific crystalline polymorphic form. This parameter change enhances the herbicidal effectiveness and reliability of the substance, allowing for better performance at lower application rates while the substance remains readily available through conventional synthesis followed by crystallization.

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

Sulfentrazone-1 demonstrates increased herbicidal effectiveness at lower application rates, with reduced solvent content and improved stability, minimizing environmental impact and formulation challenges.

Implementation Method 1

A new crystalline polymorphic form of sulfentrazone (sulfentrazone-1) is developed, obtained through crystallization from a polar, protic solvent

Methodology Applied
Scientific EffectCrystallization: Crystallisation

Data Source

PatentUS11753383B2Polymorphs of herbicidal sulfonamides
Publication Date: 2023.09.12 FMC CORP
  • US11753383B2 patent drawing
  • US11753383B2 patent drawing
  • US11753383B2 patent drawing

AI summary

Solid polymorphic forms of sulfentrazone are described. Particularly, a new polymorphic form of sulfentrazone is described herein as sulfentrazone-1, having surprising property advantages over technical sulfentrazone. Processes for the preparation of sulfentrazone-1, herbicidal compositions comprising sulfentrazone-1, and methods of its use are described.