Dialkyl Diglycol Amide Synthesis Without Hazardous Solvents

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Solution Overview

Problem

Current methods for synthesizing dialkyl diglycol amic acid, a high-performance rare earth metal extractant, rely on expensive and hazardous reagents like diglycolic anhydride and dichloromethane, leading to low yields and high production costs, especially when scaled up beyond laboratory levels.

Innovation Solution

A method involving the reaction of diglycolic acid with an esterifying agent, followed by vacuum removal of unreacted materials, and subsequent reaction with dialkylamine in a nonpolar solvent to form a high-yielding dialkyl diglycol amic acid, eliminating the need for diglycolic anhydride and dichloromethane, thereby reducing costs and improving efficiency.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If diglycolic anhydride and dichloromethane are used as reagents in the synthesis method, then the separation efficiency of rare earth elements is improved, but the production cost increases and environmental harm increases

Engineering Contradiction:
Improveseparation efficiencyVSAvoidenvironmental harm
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent replaces expensive and hazardous reagents (diglycolic anhydride and dichloromethane) with cheaper, environmentally friendly alternatives (diglycolic acid and toluene). This substitution maintains the separation efficiency while eliminating environmental harm and reducing costs, directly applying the principle of using inexpensive, non-hazardous materials instead of expensive, harmful ones.

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

Solution Approach 2:

The patent converts the potentially harmful dichloromethane into a beneficial toluene solvent. Toluene is less hazardous to the environment while still providing the necessary solvent properties for the synthesis reaction. This transformation turns a harmful substance into a beneficial one, maintaining reaction effectiveness while eliminating environmental harm.

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

2Reliability

If diglycolic anhydride is used as a reagent, then the separation factor is improved, but the production cost increases

Engineering Contradiction:
Improveseparation factorVSAvoidproduction cost
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent substitutes expensive diglycolic anhydride with cheaper diglycolic acid. This replacement maintains the separation factor performance while significantly reducing reagent costs. The principle of using inexpensive materials instead of expensive ones is directly applied here to reduce production costs without sacrificing product performance.

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

3Productivity

If the synthesis method is scaled up from laboratory to industrial production, then the productivity is improved, but the yield decreases

Engineering Contradiction:
Improveproduction scaleVSAvoidyield
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The patent changes the reaction parameters by using toluene as the solvent instead of dichloromethane, and by adjusting the reaction conditions to be more suitable for large-scale production. This parameter change enables the synthesis to be scaled up while maintaining high yield, as toluene provides better scalability and safety characteristics for industrial processes.

Inventive Principle:
Principle #35Parameter changes

4Productivity

If dichloromethane is used as a solvent, then the reaction efficiency is improved, but the environmental harm increases

Engineering Contradiction:
Improvereaction efficiencyVSAvoidenvironmental harm
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The patent replaces dichloromethane with toluene as the solvent. Toluene is less harmful to the environment while maintaining the necessary solvent properties for efficient reactions. This substitution eliminates environmental harm while preserving reaction efficiency, directly applying the principle of replacing hazardous materials with safer alternatives.

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

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 enables the synthesis of dialkyl diglycol amic acid at high yields and low costs, suitable for industrial-scale production, with improved separation efficiency of rare earth elements like neodymium and praseodymium, and reduced environmental impact.

Implementation Method 1

reacting diglycolic acid with an esterifying agent

Methodology Applied
Scientific EffectEsterification reaction: Chemical Bonding

Implementation Method 2

removing in vacuum the unreacted esterifying agent and the reaction residue

Methodology Applied
Scientific EffectVacuum distillation: Vacuum Distillation

Implementation Method 3

reacting the intermediate product with a dialkylamine

Methodology Applied
Scientific EffectAmination reaction: Chemical Bonding

Implementation Method 4

in a nonpolar solvent which will serve as an organic solvent to form an organic phase in subsequent solvent extraction and which is capable of dissolving the dialkyl diglycol amic acid

Methodology Applied
Scientific EffectSolvation: Solvation

Implementation Method 5

the solvent extraction method capable of such efficient treatment is often used in industrial separation and purification of metal elements

Methodology Applied
Scientific EffectSolvent extraction: Liquid-Liquid Extraction

Data Source

PatentEP2592067B1Method for synthesizing rare earth metal extractant
Publication Date: 2017.10.11 SHIN ETSU CHEMICAL CO LTD
  • EP2592067B1 patent drawingFigure 1
  • EP2592067B1 patent drawingFigure 2
  • EP2592067B1 patent drawing

AI summary

A rare earth metal extractant containing, as the extractant component, dialkyldiglycol amide acid which is excellent in breaking down light rare earth elements is reacted in diglycolic acid (X mol) and an esterification agent (Y mol) at a reaction temperature of 70°C or more and for a reaction time of one hour or more such that the mol ratio of Y/X is 2.5 or more, and is subjected to vacuum concentration. Subsequently, a reaction intermediate product is obtained by removing unreacted products and reaction residue. Then a nonpolar or low-polar solvent which is an organic solvent for forming an organic phase during solvent extraction of the rare earth metal and which is capable of dissolving dialkyldiglycol amide acid is added as the reaction solvent, and the reaction intermediate product is reacted with dialkyl amine (Z mol) such that the mol ratio of Z/X is 0.9 or more. As a consequence, a rare earth metal extractant is efficiently synthesized at a low cost and at a high yield without having to use expensive diglycolic acid anhydride and harmful dichloromethane.