Crystalline L-glufosinate Monohydrate Production

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Solution Overview

Problem

Current methods for producing L-glufosinate, a herbicide, are not cost-effective and result in the use of racemic mixtures, where only half of the applied substance is active, while the other half is environmentally harmful without benefit.

Innovation Solution

The development of a method to prepare crystalline L-glufosinate ammonium monohydrate, which involves forming a mixture of glufosinate starting material and an aqueous solution, crystallizing L-glufosinate ammonium monohydrate, and separating the crystals, thereby obtaining purified L-glufosinate in a single step.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If racemic glufosinate is produced using conventional methods, then production cost is reduced and manufacturing is simplified, but only 50% of the applied substance is active while the other half is environmentally harmful

Engineering Contradiction:
Improveproduction simplicityVSAvoidenvironmental harm from inactive enantiomer
Core Design Contradiction:
Ease of manufactureVSObject-generated harmful factors

Solution Approach 1:

The patent applies preliminary action by using chiral pool synthesis to start with enantiomerically pure starting materials (L-glutamate or D-glutamate), which ensures that the final L-glufosinate product is obtained in high enantiomeric purity from the beginning of the synthesis process, avoiding the need for later resolution steps

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent uses chiral intermediates derived from natural amino acids (L-glutamate or D-glutamate) as mediators to transfer chirality through the synthesis pathway, ensuring enantiomeric purity is maintained throughout the conversion to L-glufosinate

Inventive Principle:
Principle #24Intermediary (Mediator)

2Ease of manufacture

If L-glufosinate is produced in stable solid form, then commercial viability and handling are improved, but previous solid forms were highly hygroscopic which complicates storage and processing

Engineering Contradiction:
Improvecommercial viabilityVSAvoidhygroscopicity
Core Design Contradiction:
Ease of manufactureVSStability of the object's composition

Solution Approach 1:

The patent changes the physical and chemical parameters of L-glufosinate by converting it to the ammonium salt form and obtaining it as a monohydrate crystal, which fundamentally alters its hygroscopic properties and stability characteristics compared to previous free acid forms

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent utilizes phase transition by crystallizing L-glufosinate ammonium as a monohydrate solid form, which provides a stable, low-hygroscopicity crystalline structure that is superior for commercial handling and storage compared to amorphous or anhydrous forms

Inventive Principle:
Principle #36Phase transitions

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 method allows for the efficient production of highly pure L-glufosinate, reducing environmental impact and improving commercial viability by utilizing a stable solid form that is less hygroscopic than previous forms.

Implementation Method 1

forming a mixture comprising a glufosinate starting material and an aqueous solution, wherein the aqueous solution comprises water, a water-miscible organic solvent

Methodology Applied
Scientific EffectSolvation: Solvation

Implementation Method 2

crystallizing L-glufosinate ammonium monohydrate from the mixture of step (i) to form L-glufosinate ammonium monohydrate crystals

Methodology Applied
Scientific EffectCrystallization: Crystallisation

Data Source

PatentUS12234254B2Methods for producing crystalline L-glufosinate ammonium monohydrate
Publication Date: 2025.02.25 BASF SE
  • US12234254B2 patent drawing
  • US12234254B2 patent drawing
  • US12234254B2 patent drawing

AI summary

Methods for preparing crystalline L-glufosinate ammonium monohydrate are disclosed. The methods include forming a mixture comprising water, a water-miscible organic solvent, ammonium hydroxide, and a glufosinate starting material containing L-glufosinate ammonium and D-glufosinate ammonium. L-Glufosinate ammonium monohydrate is crystallized and separated from the mixture, providing L-glufosinate ammonium monohydrate Form B. Compositions and methods employing the crystalline L-glufosinate ammonium monohydrate are also described.