Reactive Distillation for N,N-Dialkylaminoalkyl Acrylate Production

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Solution Overview

Problem

Current methods for preparing N,N-dialkylaminoalkyl (meth)acrylates are not cost-effective and do not allow for a continuous reaction process where reagents and catalysts can be added as needed, resulting in inefficient production and high yields.

Innovation Solution

A continuous transesterification process using a distillation reactor with a distillation column and reboiler, where an entrainer and catalyst are added to form N,N-dialkylaminoalkyl acrylate, with simultaneous removal of an azeotropic mixture of the entrainer and alcohol, allowing for continuous addition of reagents and catalysts, and achieving high chemical conversion.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If multiple serial distillation towers and reaction towers are used for continuous production, then productivity is improved, but device complexity increases

Engineering Contradiction:
Improvecontinuous production capabilityVSAvoidnumber of distillation towers and reaction towers
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent combines the reaction zone and distillation zone into a single reactive distillation column. The transesterification reaction occurs in the liquid phase on trays while simultaneous distillation removes the azeotropic mixture of entrainer and byproduct alcohol from the same column, eliminating the need for separate reaction towers and multiple distillation towers used in prior art

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The reactive distillation column performs multiple functions simultaneously: it serves as both a reaction vessel for transesterification and a distillation column for product separation and byproduct removal. The column handles reaction, separation, and purification in one unit, making the equipment highly versatile and reducing overall system complexity

Inventive Principle:
Principle #6Universality (Multi-functionality)

2Manufacturing precision

If water washing and decanter separation are used to remove entrainer, then manufacturing precision is improved, but loss of substance increases

Engineering Contradiction:
Improveproduct purityVSAvoidentrainer loss
Core Design Contradiction:
Manufacturing precisionVSLoss of substance

Solution Approach 1:

The patent utilizes phase transition through azeotropic distillation to separate the entrainer from the byproduct alcohol. The entrainer forms a low-boiling azeotrope with the byproduct alcohol that distills overhead, while the purified product remains in the liquid phase in the reboiler and lower column sections, achieving separation without water washing

Inventive Principle:
Principle #36Phase transitions

Solution Approach 2:

The entrainer acts as an intermediary substance that facilitates separation by forming a selective azeotrope with the byproduct alcohol. This azeotropic mixture serves as a vehicle to remove impurities from the system while the entrainer itself is largely recovered and recycled, minimizing substance loss

Inventive Principle:
Principle #24Intermediary (Mediator)

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 a high-yield, cost-effective continuous production of N,N-dialkylaminoalkyl acrylate with high chemical conversion (>88%) using lower amounts of reagents and catalysts, and allows for fine-tuning of the reaction conditions during operation.

Implementation Method 1

an azeotropic mixture of entrainer and byproduct alcohol is continuously removed from the transesterification

Methodology Applied
Scientific EffectAzeotropic mixture formation:

Implementation Method 2

a distillation column and a reboiler... Simultaneously removing an azeotropic mixture of the entrainer and the alcohol from the distillation column

Methodology Applied
Scientific EffectDistillation: Distillation

Implementation Method 3

a distillation column and a reboiler... removing the N,N-dialkylaminoalkyl acrylate and residual reactants from the reboiler

Methodology Applied
Scientific EffectHeating: Heating

Data Source

PatentEP2432758B1The production of n,n-dialkylaminoethyl (METH)acrylates
Publication Date: 2015.03.18 NALCO CO
  • EP2432758B1 patent drawing
  • EP2432758B1 patent drawing
  • EP2432758B1 patent drawing

AI summary

A method and apparatus for preparing a N,N-dialkylaminoalkyl acrylate in a continuous transesterification reaction. The reaction involves adding alkyl acrylates such as methacrylate or ethacrylate to a reboiler mechanism and efficiently removing alcohol co-products. Because the reaction is continuous, the alkyl acrylates can be added as needed to increase output, decrease output, or fine-tune the reaction dynamics. An entrainer is used to form a volatile azeotrope which contains both alcohol and entrainer and which is easily removed from the reboiler mechanism. This method reduces the amount of entrainer needed per unit of alkyl acrylate used and eliminates any need to purify the end product from entrainer contamination of the resulting N,N-dialkylaminoalkyl acrylate product.