Hydroxyalkyl Methacrylate Synthesis via Organometallic Catalyst Recycling

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Solution Overview

Problem

Current methods for producing hydroxyalkyl(meth)acrylate face challenges in reducing catalyst usage and by-product formation, leading to increased production costs and yield reduction, with existing recycling techniques being complex and costly.

Innovation Solution

Maintaining a specific molar ratio of acid components to catalysts in the reaction liquid and introducing dialkylene glycol mono(meth)acrylate into the reaction system to suppress catalyst inactivation and by-product formation, allowing for efficient catalyst recycling and improved yield of hydroxyalkyl(meth)acrylate.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If homogeneous catalysts such as chromium compounds and iron compounds are used to produce hydroxyalkyl(meth)acrylate, then the reaction efficiency is improved, but the harmfulness of catalyst disposal increases and production costs increase due to stricter environmental regulations

Engineering Contradiction:
Improvereaction efficiencyVSAvoidharmfulness of catalyst disposal
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The patent changes the chemical composition parameter of the catalyst from traditional homogeneous catalysts (chromium/iron compounds) to organometallic catalysts with specific ligand structures. This parameter change maintains high reaction efficiency while eliminating the harmful disposal issues associated with heavy metal catalysts, directly resolving the technical contradiction between productivity and environmental harm.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs organometallic catalysts that can be used in smaller amounts and potentially replaced or regenerated more easily than traditional catalysts. The use of soluble organometallic complexes allows for more flexible catalyst management, reducing the burden of harmful waste disposal while maintaining catalytic activity.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

2Productivity

If alkylene oxide is introduced independently to suppress by-product formation, then the yield of targeted product is improved, but the process complexity increases due to safety risks requiring (meth)acrylic acid to be introduced beforehand

Engineering Contradiction:
Improveyield of targeted productVSAvoidprocess complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent applies preliminary action by introducing (meth)acrylic acid into the reaction system before alkylene oxide to prevent safety hazards. However, it resolves the resulting process complexity by using an organometallic catalyst that maintains high activity and selectivity throughout the reaction, eliminating the need for additional process controls that would otherwise be required to manage by-product formation.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The organometallic catalyst acts as an intermediary that facilitates the reaction between (meth)acrylic acid and alkylene oxide with high selectivity. This intermediary catalytic system enables the reaction to proceed efficiently while suppressing by-product formation, thereby simplifying the overall process compared to conventional methods that require complex control mechanisms.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Productivity

If higher concentration of catalysts is used to suppress biadduct formation, then the yield of hydroxyalkyl(meth)acrylate is improved, but the production cost increases

Engineering Contradiction:
Improveyield of hydroxyalkyl(meth)acrylateVSAvoidamount of catalyst used
Core Design Contradiction:
ProductivityVSQuantity of substance

Solution Approach 1:

The patent changes the catalyst system from conventional homogeneous catalysts to organometallic catalysts with optimized ligand structures. This parameter change enables achieving high yields of hydroxyalkyl(meth)acrylate with lower catalyst concentrations, directly resolving the contradiction between productivity improvement and catalyst quantity reduction.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent replaces the conventional catalytic mechanism with an organometallic catalytic system that operates through different chemical mechanisms. This substitution allows for more efficient catalysis with lower catalyst loading, reducing the quantity of catalyst required while maintaining or improving product yield.

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

4Quantity of substance

If catalyst recycling processes such as distillation and additional catalyst supply are used, then the amount of fresh catalyst needed is reduced, but the process complexity and production costs increase

Engineering Contradiction:
Improveamount of catalyst usedVSAvoidprocess complexity
Core Design Contradiction:
Quantity of substanceVSDevice complexity

Solution Approach 1:

The organometallic catalyst system exhibits self-service characteristics through its high stability and reusability. The catalyst can be recovered and reused in subsequent reactions without requiring complex regeneration processes such as distillation or reactivation, thereby reducing both catalyst consumption and process complexity simultaneously.

Inventive Principle:
Principle #25Self-service

Solution Approach 2:

The patent implements a simplified catalyst recovery approach where the organometallic catalyst is easily separated from the reaction mixture and recovered for reuse. This recovering process is simpler than conventional methods, reducing both the amount of fresh catalyst needed and the complexity of recycling operations.

Inventive Principle:
Principle #34Discarding and recovering

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 reduces catalyst usage and costs, simplifies the recycling process, and enhances the yield of hydroxyalkyl(meth)acrylate by effectively suppressing by-product formation and maintaining catalytic activity.

Implementation Method 1

a reaction of (meth)acrylic acid and alkylene oxide in the presence of a catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS8203018B2Processes for producing hydroxyalkyl (meth) acrylate
Publication Date: 2012.06.19 NIPPON SHOKUBAI CO LTD

AI summary

Processes for producing a hydroxyalkyl(meth)acrylate which comprise reacting (meth)acrylic acid with an alkylene oxide in the presence of a catalyst. A first process is characterized in that the amount of the acid ingredient is kept, on calculation, at 0.010 or more in terms of molar ratio to the catalyst present in the liquid reaction mixture and that the liquid reaction mixture from which the hydroxyalkyl(meth)acrylate has been distilled off is used in the subsequent reaction. A second process is characterized in that a dialkylene glycol mono(meth)acylate is supplied to the reaction system to cause the dialkyleneglycol mono(meth)acylate to coexist in the liquid reaction mixture.