N-Vinyl Carboxylic Acid Amide Monomer Purification via Solvent Crystallization

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Solution Overview

Problem

Existing methods for producing N-vinyl carboxylic acid amide monomers face challenges in efficiently purifying the monomer and achieving high polymerizability, leading to low productivity and high costs.

Innovation Solution

A method combining cooling crystallization with solvent crystallization using toluene and an aliphatic hydrocarbon with 6 to 7 carbon atoms is employed to produce a highly polymerizable N-vinyl carboxylic acid amide monomer, involving melting, cooling, solid-liquid separation, and subsequent solvent crystallization to achieve high purity and polymerizability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If pressure crystallization is used to purify N-vinyl carboxylic acid amide, then high polymerizability is achieved, but equipment investment is large and production cost is high

Engineering Contradiction:
ImprovepolymerizabilityVSAvoidproduction cost
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The invention changes the crystallization parameters by using a specific solvent system (alcohol and aliphatic hydrocarbon) with controlled temperature gradients. By adjusting the solvent composition ratios and temperature profiles during crystallization, the method achieves high polymerizability without requiring expensive pressure crystallization equipment, thus resolving the contradiction between reliability and ease of manufacture.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention introduces a specific solvent system as an intermediary medium to facilitate purification. The solvent system acts as a mediator that enables crystallization under ambient pressure conditions, replacing the need for expensive pressure crystallization equipment while maintaining high polymerizability of the product.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Manufacturing precision

If solvent crystallization with alcohol and aliphatic hydrocarbon is used, then purification is achieved, but large amount of poor solvent is required and volumetric efficiency is low

Engineering Contradiction:
ImprovepurityVSAvoidvolumetric efficiency
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The invention optimizes the solvent system parameters by selecting specific alcohol types (methanol, ethanol, propanol, or butanol) and controlling their ratios with aliphatic hydrocarbons. By adjusting these parameters, the method achieves effective purification with reduced solvent用量, thereby improving volumetric efficiency while maintaining high purity.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention applies local quality by using different types of solvents with specific properties in different stages of the crystallization process. The alcohol component provides selective dissolution while the aliphatic hydrocarbon component controls precipitation, achieving efficient purification with optimized solvent usage.

Inventive Principle:
Principle #3Local quality

3Ease of manufacture

If conventional purification methods are used, then production process is simple, but polymerizability is insufficient

Engineering Contradiction:
Improveprocess simplicityVSAvoidpolymerizability
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The invention merges cooling crystallization and solvent crystallization into a single integrated process. By combining these two crystallization methods, the invention achieves both high polymerizability and process simplicity, as the unified process eliminates the need for separate purification steps while maintaining effective removal of inhibitors.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The invention segments the crystallization process into distinct stages: cooling crystallization for initial precipitation and solvent crystallization for refined purification. This segmentation allows each stage to perform its specific function effectively, achieving high polymerizability while keeping the overall process simple and efficient.

Inventive Principle:
Principle #1Segmentation

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 significantly enhances the productivity of highly polymerizable N-vinyl carboxylic acid amide monomers, achieving high purity and excellent polymerizability, thereby reducing production costs and improving industrial scalability.

Implementation Method 1

melting a crude N-vinyl carboxylic acid amide monomer comprising 50 to 88 mass % of an N-vinyl carboxylic acid amide monomer by heating, followed by cooling for precipitation (cooling crystallization)

Methodology Applied
Scientific EffectMelting: Melting

Implementation Method 2

cooling for precipitation (cooling crystallization), and subjecting precipitated N-vinyl carboxylic acid amide monomer crystals to solid-liquid separation

Methodology Applied
Scientific EffectCrystallization: Crystallisation

Implementation Method 3

further dissolving the N-vinyl carboxylic acid amide monomer crystals separated in the step (A) in a mixed solvent of toluene and an aliphatic hydrocarbon having 6 to 7 carbon atoms, then performing crystallization (solvent crystallization)

Methodology Applied
Scientific EffectSolvent crystallization: Crystallisation

Implementation Method 4

dissolving the N-vinyl carboxylic acid amide monomer crystals separated in the step (A) in a mixed solvent of toluene and an aliphatic hydrocarbon having 6 to 7 carbon atoms

Methodology Applied
Scientific EffectSolvation: Solvation

Implementation Method 5

subjecting precipitated N-vinyl carboxylic acid amide monomer crystals to solid-liquid separation (step (A))

Methodology Applied
Scientific EffectSolid-liquid separation: Sedimentation

Data Source

PatentUS12297162B2Method for producing highly polymerizable N-vinyl carboxylic acid amide monomer
Publication Date: 2025.05.13 RESONAC CORP

AI summary

A method for producing a highly polymerizable N-vinyl carboxylic acid amide monomer includes (A) melting a crude N-vinyl carboxylic acid amide monomer comprising 50 to 88 mass % of an N-vinyl carboxylic acid amide monomer by heating, followed by cooling for precipitation, and subjecting precipitated N-vinyl carboxylic acid amide monomer crystals to solid-liquid separation (step (A)), and (B) further dissolving the N-vinyl carboxylic acid amide monomer crystals separated in step (A) in a mixed solvent of toluene and an aliphatic hydrocarbon having 6 to 7 carbon atoms, then performing crystallization, performing solid-liquid separation, and recovering an N-vinyl carboxylic acid amide monomer purified product (step (B)), wherein a mass ratio of toluene/N-vinyl carboxylic acid amide monomer crystal in step (B) is 0.01 to 0.5, and a mass ratio of aliphatic hydrocarbon having 6 to 7 carbon atoms/N-vinyl carboxylic acid amide monomer crystal in step (B) is 0.5 to 3.0.