Continuous Acrylate Esterification with In-Situ Adduct Dissociation

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Solution Overview

Problem

Existing processes for producing light acrylates from crude acrylic acid face challenges such as high costs due to purification requirements, formation of Michael adducts, and difficulties in recycling recoverable products, leading to inefficiencies and residue handling issues.

Innovation Solution

A continuous process for preparing methyl or ethyl acrylate using crude ester grade acrylic acid with a high content of Michael adducts, where thermal dissociation occurs within the reactor, optimizing productivity and simplifying the apparatus while maintaining high purity and fluidity of the final residue.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If purified acrylic acid is used for esterification, then the purity of light acrylate product is improved, but the process cost increases due to costly purification techniques

Engineering Contradiction:
Improvepurity of light acrylate productVSAvoidprocess cost
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The patent extracts and removes harmful impurities (polymerization products, Michael adducts, heavy compounds) from the crude acrylic acid stream through a purification train consisting of filtration, distillation, and extraction units, enabling the use of lower purity feedstock while maintaining product quality

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent changes the purity parameter of the acrylic acid feedstock from traditional high purity requirements to accept crude acrylic acid with 70-90% purity, fundamentally altering the input specification to reduce purification costs while implementing compensating purification steps for the esterification process

Inventive Principle:
Principle #35Parameter changes

2Ease of manufacture

If crude acrylic acid with high polymerization product content is used, then purification cost is reduced, but the formation of by-products increases

Engineering Contradiction:
Improvepurification costVSAvoidformation of by-products
Core Design Contradiction:
Ease of manufactureVSObject-generated harmful factors

Solution Approach 1:

The patent applies preliminary purification actions (filtration to remove polymerization products, distillation to separate light and heavy compounds) before esterification to prevent by-product formation during the reaction, addressing the impurity issue proactively rather than reactively

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent converts the previously harmful crude acrylic acid stream, which contained impurities requiring expensive purification, into a beneficial feedstock by implementing a targeted purification train that removes only the harmful components while retaining the acrylic acid, turning a cost center into a cost-saving opportunity

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

3Productivity

If thermal dissociation is applied within the reactor, then productivity is improved and apparatus complexity is reduced, but residence time requirements increase

Engineering Contradiction:
ImproveproductivityVSAvoidresidence time
Core Design Contradiction:
ProductivityVSLoss of time

Solution Approach 1:

The patent merges the thermal dissociation function with the esterification reactor by implementing heating zones within the reactor vessel, combining two previously separate operations (thermal treatment and chemical reaction) into a single integrated unit, thereby reducing apparatus complexity while maintaining productivity

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The patent changes the temperature parameter within the reactor to enable thermal dissociation of polymerization products and Michael adducts in situ, using temperature profiles that promote both the dissociation of unwanted compounds and the progression of esterification, optimizing residence time utilization

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 process achieves high yields of light acrylates with reduced residue viscosity, facilitating easy elimination and optimizing economic balance, thereby addressing the inefficiencies of existing methods.

Implementation Method 1

the apparatus comprises a reactor for carrying out the esterification reaction and for performing thermal dissociation of the Michael adducts

Methodology Applied
Scientific EffectThermal dissociation: Thermolysis

Implementation Method 2

reaction of the corresponding light alcohol chosen from methanol and ethanol, with a flow of crude ester grade acrylic acid, in the presence of at least one acid catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP3027586B1Method for continuous production of light acrylates by esterification of a raw ester-grade acrylic acid
Publication Date: 2020.02.26 ARKEMA FRANCE SA
  • EP3027586B1 patent drawing
  • EP3027586B1 patent drawing
  • EP3027586B1 patent drawing

AI summary

The present invention relates to methods by which the thermal dissociation of Michael adducts present in a stream of crude acrylic acid, called “crude ester grade”, and the esterification reaction of acrylic acid present in the stream of crude acrylic acid, or generated in situ by thermal dissociation, with a light alcohol, are carried out simultaneously.