N,N-Dimethylglucamine Synthesis Using Formic Acid Catalyst

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Solution Overview

Problem

Current methods for producing N,N-dimethylglucamine solutions face challenges such as high production costs, poor product quality, and difficulty in meeting quality parameters like color and residual component content, due to multi-stage processes, expensive catalysts, and inefficient catalyst recycling.

Innovation Solution

A one-step process involving the reaction of formaldehyde and N-methylglucamine under hydrogen pressure with a nickel- or cobalt-containing catalyst, allowing for simultaneous reaction and post-hydrogenation steps, which results in a high-quality N,N-dimethylglucamine solution with improved color and reduced impurity levels.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If a multi-stage process with metallic hydrogenation catalyst (e.g., Raney-Ni) is used, then high yields can be achieved, but the production costs increase and product quality parameters (color, residual catalyst content) deteriorate

Engineering Contradiction:
ImproveyieldVSAvoidproduction cost
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The patent changes the fundamental parameters of the catalytic system by replacing traditional metallic hydrogenation catalysts (Raney-Ni, Raney-Co) with formic acid as a catalyst. This parameter change enables the reaction to proceed under milder conditions (lower temperature and pressure) while avoiding the contamination and cost issues associated with metallic catalysts, thus resolving the contradiction between yield and production cost/quality

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs formic acid as a disposable, inexpensive catalyst that does not require recovery or recycling like precious metal catalysts. This approach eliminates catalyst recycling costs and avoids residual catalyst contamination in the product, resolving the contradiction between achieving high yields and maintaining low production costs with high product quality

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

2Productivity

If high pressure hydrogenation (10-150 bar) is used, then reaction efficiency improves, but safety problems arise and equipment complexity increases

Engineering Contradiction:
Improvereaction efficiencyVSAvoidsafety risk
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The patent fundamentally changes the reaction parameters by replacing high-pressure hydrogenation (10-150 bar H2) with formic acid-catalyzed dehydration under atmospheric or low pressure conditions. This parameter change maintains reaction efficiency while eliminating the safety risks and equipment complexity associated with high-pressure hydrogen handling

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent substitutes the mechanical high-pressure hydrogenation system with a chemical catalysis system using formic acid. This substitution replaces the need for high-pressure equipment and hydrogen gas handling with a simpler liquid-phase catalytic process, resolving the contradiction between reaction efficiency and safety

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

3Manufacturing precision

If recrystallization is performed to improve product quality, then purity increases, but the product becomes a solid with melting point >100°C which is difficult to handle

Engineering Contradiction:
Improveproduct purityVSAvoidhandling ease
Core Design Contradiction:
Manufacturing precisionVSEase of operation

Solution Approach 1:

The patent changes the physical state parameters of the product by controlling the reaction conditions to produce N,N-dimethylglucamine in liquid form at room temperature. By using formic acid catalyst and avoiding excessive dehydration, the product maintains lower melting point characteristics, enabling it to remain liquid and easily handleable while still achieving high purity through the simplicity of the one-step process

Inventive Principle:
Principle #35Parameter changes

4Manufacturing precision

If expensive catalysts (e.g., Ag-Pd, Ru) are used, then reaction selectivity improves, but production costs increase

Engineering Contradiction:
Improvereaction selectivityVSAvoidproduction cost
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The patent replaces expensive, recoverable catalysts (Ag-Pd, Ru) with inexpensive formic acid that can be used in a one-step process without requiring recovery. The low cost of formic acid compensates for its single-use nature, achieving both high reaction selectivity and low production costs

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

Solution Approach 2:

The patent changes the catalyst type parameter from precious metals to organic acid (formic acid), which fundamentally alters the cost structure while maintaining or improving selectivity through the specific mechanism of formic acid-catalyzed dehydration

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 a cost-effective production of high-quality N,N-dimethylglucamine solutions with improved color and reduced impurity levels, enabling wider commercial applications by minimizing production costs and optimizing catalyst reuse.

Implementation Method 1

A one-step process involving the reaction of formaldehyde and N-methylglucamine under hydrogen pressure with a nickel- or cobalt-containing catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

the reaction of formaldehyde and N-methylglucamine under hydrogen pressure with a nickel- or cobalt-containing catalyst, allowing for simultaneous reaction and post-hydrogenation steps

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Data Source

PatentEP3601211B1Catalytic process for the manufacture of n,n-dimethylglucamin departing from n-methylglucamin
Publication Date: 2021.01.06 CLARIANT INT LTD

AI summary

The invention relates to a process for synthesizing an aqueous N,N-dimethyl glucamine solution, characterized in that a formaldehyde solution is metered into an N-methyl glucamine solution in the presence of a metal catalyst at hydrogen pressure.