Quinone Methide Nitroxide Polyamine Additive for Butadiene Polymerization Control

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Solution Overview

Problem

The polymerization of butadiene during hydrocarbon processing leads to unwanted polymers and dimerization, resulting in yield loss and increased production costs, with existing inhibitor compositions requiring high doses of quinone methide derivatives and nitroxides that are costly and unstable.

Innovation Solution

An additive composition comprising quinone methide or its derivatives, nitroxides, and polyamines, such as polyether amines and oxide-treated tertiary amines, which reduces the dosage needed for effective polymerization and dimerization control, making the process more economical and environmentally friendly.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If higher amounts of quinone methide derivatives and nitroxides are used to achieve acceptable polymerization inhibition, then the control effectiveness is improved, but the cost of the process increases and unwanted products are formed due to instability

Engineering Contradiction:
Improvepolymerization inhibition effectivenessVSAvoidcost of process and formation of unwanted products
Core Design Contradiction:
ReliabilityVSLoss of substance

Solution Approach 1:

The patent introduces a synergistic combination of quinone methide derivatives, nitroxides, and amine compounds as intermediary substances that work together to inhibit polymerization. The amine compounds act as mediators that enhance the effectiveness of the quinone methide and nitroxides, allowing lower dosages to achieve the same inhibition level while reducing unwanted side reactions and costs.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The invention creates a composite inhibitor system by combining three different chemical components (quinone methide derivatives, nitroxides, and amine compounds) into a single additive composition. This composite approach leverages the synergistic effects of the components to achieve superior polymerization inhibition at reduced dosages compared to using individual inhibitors alone.

Inventive Principle:
Principle #40Composite materials

2Reliability

If quinone methide derivatives and nitroxides are used as polymerization inhibitors, then polymerization control is achieved, but the dosage required is high which increases cost and reduces economic viability

Engineering Contradiction:
Improvepolymerization controlVSAvoiddosage of inhibitor
Core Design Contradiction:
ReliabilityVSQuantity of substance

Solution Approach 1:

Amine compounds are introduced as intermediary substances that enhance the inhibitory action of quinone methide derivatives and nitroxides. These intermediaries facilitate the mechanism by which the primary inhibitors work, allowing the system to achieve effective polymerization control at lower concentrations of the expensive quinone methide and nitroxide components.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent changes the chemical composition parameters of the inhibitor system by adding amine compounds with specific functional groups. This parameter change creates a multi-component system where the combined chemical properties of all components produce synergistic effects, reducing the required dosage while maintaining control effectiveness.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If high doses of quinone methide derivatives and nitroxides are used for dimerization control, then dimerization inhibition is improved, but the stability of the composition deteriorates due to the unstable nature of these compounds

Engineering Contradiction:
Improvedimerization inhibitionVSAvoidstability of inhibitor composition
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

Amine compounds serve as stabilizing intermediaries that protect the unstable quinone methide derivatives and nitroxides from degradation. These intermediaries create a more stable chemical environment that preserves the activity of the sensitive inhibitor components while maintaining effective dimerization inhibition, allowing lower dosages to be used without compromising stability.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The invention forms a composite inhibitor composition where the amine compounds provide structural and chemical stability to the overall system. The composite structure distributes the functional load across multiple components, with the amine compounds acting as stabilizing agents that protect the less stable quinone methide and nitroxide components from decomposition.

Inventive Principle:
Principle #40Composite materials

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

The composition achieves substantial control of polymerization and dimerization of butadiene at reduced dosages, significantly lowering costs and minimizing the formation of unwanted products, while maintaining effectiveness across a wide temperature range.

Implementation Method 1

The polymerization of butadiene during processing of hydrocarbons is a matter of concern, because it causes formation of unwanted polymers... The prior art discloses use of quinone methide (QM) or its derivatives... and use of nitroxide (i.e. nitroxyl) compounds... as polymerization inhibitor

Methodology Applied
Scientific EffectFree radical inhibition:

Implementation Method 2

the present invention relates to use of an additive composition for controlling and inhibiting polymerization of aliphatic monomers including butadiene and for controlling and inhibiting dimerization of aliphatic monomers including butadiene

Methodology Applied
Scientific EffectChemical inhibition of dimerization:

Data Source

PatentEP2978735B1Additive composition for control and inhibition of polymerization of aliphatic monomers, and methods of use thereof
Publication Date: 2020.06.24 DORF KETAL CHEMICALS (INDIA) PRIVATE LIMITED

AI summary

The present invention relates to additive composition and method of use thereof for controlling and inhibition of polymerization and dimerization of aliphatic monomers including butadiene comprising A) one or more of first component selected from a group comprising a) quinone methide (QM), b) quinone methide (QM) derivative including ester derivative of quinone methide, c) nitroxide (i.e. nitroxyl) compounds, and d) mixture thereof; characterized in that the composition further comprises B) one or more of second component selected from amines or polyamines, wherein the amine and polyamine is selected from a group comprising i) oxide treated tertiary amines, ii) hydroxyl alkyl tertiary amines, iii) polyether amines, and iv) mixture thereof. In one embodiment, the present invention also relates to a method for controlling and inhibiting polymerization and dimerization of aliphatic monomers including butadiene by employing the presently provided compositions, and in another embodiment, the present invention relates to a method of preparation of the presently provided compositions.