(Meth)Acrylic Acid Amide Synthesis in Immiscible Solvent Systems
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Solution Overview
Problem
Existing methods for producing (meth)acrylic acid amide compounds face challenges such as low yield and purity due to side reactions, vigorous foaming, and the need for additional purification steps, making them unsuitable for large-scale industrial production.
Innovation Solution
A method involving the addition of an amino group-containing compound or its neutralization salt to a mixture of (meth)acrylic acid halide and an organic solvent immiscible with water, followed by an alkali aqueous solution, creating a non-homogeneous mixed solvent system to suppress side reactions and enhance yield and purity.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If carboxylic acid halide is used to produce (meth)acrylic acid amide compound, then the reaction progresses quantitatively at low temperature without requiring condensing agents, but side reactions occur leading to low yield and purity
Solution Approach 1:
The patent introduces a specific organic solvent (immiscible with water, such as dichloromethane, chloroform, or carbon tetrachloride) as an intermediary medium to facilitate the reaction between carboxylic acid halide and amine. This solvent acts as a mediator that promotes the main reaction while suppressing side reactions, thereby improving both yield and purity without requiring additional condensing agents or complex purification steps.
Solution Approach 2:
The patent optimizes reaction parameters including temperature control (maintaining low temperature to prevent side reactions), solvent selection (using specific organic solvents immiscible with water), and reagent addition rates. These parameter changes enable the reaction to proceed quantitatively with high purity, resolving the contradiction between ease of manufacture and manufacturing precision.
2Productivity
If conventional methods are used for producing (meth)acrylic acid amide compounds, then production can proceed with standard reagents, but vigorous foaming occurs and additional purification steps are required
Solution Approach 1:
The organic solvent immiscible with water serves as an intermediary that prevents vigorous foaming during the reaction. By selecting specific solvents (dichloromethane, chloroform, carbon tetrachloride), the reaction proceeds smoothly without excessive foaming, eliminating the need for additional purification steps and simplifying the overall production process.
Solution Approach 2:
The patent changes the reaction medium from conventional aqueous or homogeneous organic systems to a specific heterogeneous system using water-immiscible organic solvents. This parameter change fundamentally alters the reaction behavior, suppressing foaming and simplifying product isolation, thereby improving productivity without increasing device complexity.
3Quantity of substance
If amino group-containing compound is added to conventional reaction systems, then the desired amide compound is formed, but side reactions reduce the overall yield and require more purification steps
Solution Approach 1:
The water-immiscible organic solvent acts as an intermediary that facilitates the formation of the desired amide compound while preventing side reactions. The solvent creates a favorable reaction environment that enhances product yield and simplifies the reaction mixture, reducing the time required for purification steps.
Solution Approach 2:
By changing the reaction medium to specific organic solvents immiscible with water and optimizing reaction conditions (temperature, addition rate), the patent maximizes product yield while minimizing side reactions. This reduces the time and effort required for purification, resolving the contradiction between quantity of substance and loss of time.
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 allows for the production of high-purity (meth)acrylic acid amide compounds with high yield, suitable for large-scale industrial applications, by minimizing side reactions and maintaining controlled reaction conditions.
Implementation Method 1
an organic solvent immiscible with water... creating a non-homogeneous mixed solvent system
Implementation Method 2
allow the (meth)acrylic acid halide and at least one selected from the group consisting of the amino group-containing compound and the neutralization salt of the amino group-containing compound to react with each other
Data Source
Figure 1A
Figure 1B
Figure 1C~2A
AI summary
A method for producing a (meth)acrylic acid amide compound, the method including: adding at least one selected from the group consisting of an amino group-containing compound and a neutralization salt of the amino group-containing compound to a mixture including a (meth)acrylic acid halide and an organic solvent immiscible with water to allow the (meth)acrylic acid halide and at least one selected from the group consisting of the amino group-containing compound and the neutralization salt of the amino group-containing compound to react with each other, to produce the (meth)acrylic acid amide compound.