Method for obtaining bio-sourced susbtituted alkyl(METH)acrylamide

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Solution Overview

Problem

Current methods for producing substituted alkyl(meth)acrylamides face challenges such as high temperature requirements, incomplete conversions, and the generation of by-products due to the reactive nature of these monomers, leading to reduced yield and productivity in polymerization processes.

Innovation Solution

The use of at least partially renewable and non-fossil (meth)acrylic acid or its esters, and alkylamines in a method that includes an enzymatic bioconversion step, improves the quality and performance of the monomers, reducing impurities and enhancing polymerization outcomes.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Temperature

If high temperature pyrolysis is used to generate the double bond in retro Michael reaction, then the double bond is formed, but by-products are generated and polymerizations are induced

Engineering Contradiction:
Improvereaction temperatureVSAvoidby-products and polymerizations
Core Design Contradiction:
TemperatureVSObject-generated harmful factors

Solution Approach 1:

The invention changes the temperature parameter from high temperature pyrolysis conditions to mild temperature conditions by introducing a catalyst, thereby avoiding the formation of by-products and unwanted polymerizations while still achieving the retro Michael reaction to generate the double bond

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

A catalyst is introduced as an intermediary substance to facilitate the retro Michael reaction at lower temperatures. The catalyst mediates the bond breaking between the terminal carbon and protecting agent, enabling the reaction to proceed without high temperature-induced side reactions

Inventive Principle:
Principle #24Intermediary (Mediator)

2Productivity

If high temperature pyrolysis is used for retro Michael reaction, then the reaction proceeds, but conversions are not complete and protective agent re-reacts with product

Engineering Contradiction:
Improvereaction rateVSAvoidconversion completeness
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The invention changes the temperature parameter from high to mild conditions and introduces a catalyst to achieve complete conversions. The catalytic mechanism allows the reaction to proceed to completion at lower temperatures, preventing the protective agent from re-reacting with the formed alkyl(meth)acrylamide product

Inventive Principle:
Principle #35Parameter changes

3Manufacturing precision

If distillation purification is used to separate Michael adducts, then separation is achieved, but productivity is reduced due to column stoppage for cleaning

Engineering Contradiction:
Improveseparation purityVSAvoidproduction efficiency
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The invention extracts and removes the need for distillation purification by using mild reaction conditions that prevent by-product formation in the first place. Without harmful by-products and polymerizations, the reaction mixture can be directly processed without requiring distillation column stoppage for cleaning, thereby maintaining high productivity

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The catalyst is used in advance to prevent the formation of problematic by-products and polymerizations during the retro Michael reaction. This preliminary catalytic action ensures that the reaction mixture remains clean and does not require subsequent distillation purification, thus avoiding productivity loss

Inventive Principle:
Principle #10Preliminary action

4Productivity

If conventional synthesis methods are used with fossil-based raw materials, then production is achieved, but environmental sustainability is compromised

Engineering Contradiction:
Improveproduction outputVSAvoidenvironmental impact
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The invention changes the raw material source parameter from fossil-based to renewable and non-fossil resources. This fundamental parameter change maintains production output while eliminating the environmental harm associated with depleting fossil resources, achieving sustainable production

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

This approach results in improved conversion rates, reduced impurities, and enhanced biodegradability of the polymers, along with better control of cement fluid loss and solid particles retention, leading to improved application performance.

Implementation Method 1

a) from (meth)acrylonitrile by hydrolysis in the presence of an enzyme

Methodology Applied
Scientific EffectEnzymatic hydrolysis: Hydrolysis

Data Source

PatentUS20240262786A1Method for obtaining bio-sourced susbtituted alkyl(METH)acrylamide
Publication Date: 2024.08.08 S P C M SA
  • US20240262786A1 patent drawing
  • US20240262786A1 patent drawing
  • US20240262786A1 patent drawing

AI summary

A method for obtaining substituted alkyl(meth)acrylamide includes reaction between (meth)acrylic acid or an ester thereof, and a primary or a secondary alkylamine. At least one of the two is at least partially renewable and non-fossil. The substituted alkyl(meth)acrylamide can have a bio-sourced carbon content of between 5 wt % and 100 wt % relative to the total carbon weight in the substituted alkyl(meth)acrylamide. The bio-sourced carbon content can be measured according to the standard ASTM D6866-21 Method B.