Phosphorus Cyanohydrin Ester Synthesis via Radical Initiation

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Solution Overview

Problem

Existing processes for producing phosphorus-containing cyanohydrin esters face challenges such as low yields, high proportions of coupling products or byproducts, complex purification, and arduous reaction conditions, which affect safety, environmental impact, and quality.

Innovation Solution

A process involving the reaction of compounds of formula (II) and (III) in the presence of free-radical-forming substances, with specific mixture compositions and conditions, to produce phosphorus-containing cyanohydrin esters of formula (I) with improved yield and purity, and to facilitate the production of glufosinate/glufosinate salts.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional processes are used to produce phosphorus-containing cyanohydrin esters, then production is possible, but yields are insufficient and coupling products or byproducts are formed in excessively high proportions

Engineering Contradiction:
Improveyield of phosphorus-containing cyanohydrin estersVSAvoidproportion of coupling products or byproducts
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent applies parameter changes by modifying the reaction conditions including temperature range (40-120°C), pH range (2-12), and using specific molar ratios of reactants. The process also changes the physical state parameters by conducting the reaction in liquid phase with specific solvent systems, which optimizes the reaction pathway to improve yield and reduce byproduct formation.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces an intermediary substance - a radical initiator (such as peroxides or azo compounds) - that mediates the reaction between phosphorus-containing compounds and cyanohydrin esters. This intermediary facilitates the reaction through radical mechanisms, enabling better control over the reaction pathway and reducing unwanted coupling products while improving overall yield.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Productivity

If conventional processes are used to produce phosphorus-containing cyanohydrin esters, then production is possible, but purification/isolation is excessively complex

Engineering Contradiction:
Improveyield of phosphorus-containing cyanohydrin estersVSAvoidpurification/isolation complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent converts the potentially harmful radical reaction pathway into a beneficial process by carefully controlling the reaction conditions. The radical mechanism, which could lead to unwanted side reactions, is harnessed to selectively produce the desired cyanohydrin esters with high purity, thereby simplifying purification steps. The process design ensures that even though radicals are involved, the selectivity is maintained through controlled initiation and propagation steps.

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

3Productivity

If conventional processes are used to produce phosphorus-containing cyanohydrin esters, then production is possible, but reaction conditions are excessively arduous in terms of process/plant engineering

Engineering Contradiction:
Improveyield of phosphorus-containing cyanohydrin estersVSAvoidreaction conditions severity
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The patent significantly eases the reaction conditions by operating at moderate temperatures (40-120°C) and a wide pH range (2-12), eliminating the need for extreme conditions. The use of soluble radical initiators and liquid-phase reaction systems simplifies the engineering requirements compared to high-temperature or high-pressure processes, making the manufacturing more accessible and safer while maintaining high productivity.

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 process achieves higher yields and purity of phosphorus-containing cyanohydrin esters, reduces undesired secondary components, and simplifies reaction conditions, making the process more efficient and energy-saving while improving safety and environmental aspects.

Implementation Method 1

in the presence of one or more free-radical-forming substances (IV)

Methodology Applied
Scientific EffectFree radical formation:

Data Source

PatentUS10611785B2Process for producing phosphorus-containing cyanohydrin esters
Publication Date: 2020.04.07 BASF SE
  • US10611785B2 patent drawing
  • US10611785B2 patent drawing
  • US10611785B2 patent drawing

AI summary

The present invention primarily relates to a process for producing certain phosphorus-containing cyanohydrin esters of formula (I) and the use thereof for producing glufosinate/glufosinate salts. The present invention further relates to a process for producing glufosinate/glufosinate salts.