Oxidative Dehydroxymethylation Catalyst for Olefin Production

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Solution Overview

Problem

Current methods for converting aldehyde and alcohol compounds into olefin compounds are inefficient, often resulting in low yields and significant production of byproducts such as alkanes and internal olefins.

Innovation Solution

Catalyst compositions comprising a Group VIII metal compound, a heteroatomic ligand compound, and a Bronsted acid compound, optionally with an acceptor, are used to promote oxidative dehydroxymethylation and dehydroformylation reactions, producing α-olefins with yields exceeding 90% while minimizing byproducts.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If current methods are used to convert aldehyde and alcohol compounds into olefin compounds, then the conversion process can be performed, but the yield is low and significant byproducts such as alkanes and internal olefins are produced

Engineering Contradiction:
Improveyield of olefinVSAvoidbyproducts (alkanes and internal olefins)
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The patent changes the chemical parameters of the reaction system by introducing a specific catalyst composition comprising a Group VIII metal compound, a heteroatomic ligand compound, and a Bronsted acid compound. This catalyst system fundamentally alters the reaction pathway to achieve high selectivity for α-olefins, converting the low-yield process into a high-yield process exceeding 90% while minimizing byproduct formation.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs a composite catalyst system that combines multiple components (Group VIII metal compound, heteroatomic ligand compound, and Bronsted acid compound) working synergistically. This composite catalyst composition enables the reaction to proceed with exceptional selectivity for α-olefins, simultaneously improving yield and reducing byproduct formation that plague conventional single-component catalytic systems.

Inventive Principle:
Principle #40Composite materials

2Manufacturing precision

If conventional catalytic systems are used for alcohol and aldehyde conversion, then the reaction can proceed, but selectivity over byproducts such as alkanes and internal olefins is poor

Engineering Contradiction:
Improveselectivity for α-olefinVSAvoidbyproducts (alkanes and internal olefins)
Core Design Contradiction:
Manufacturing precisionVSObject-generated harmful factors

Solution Approach 1:

The patent introduces a novel catalyst composition with specific chemical parameters: a Group VIII metal compound combined with a heteroatomic ligand compound and a Bronsted acid compound. This parameter change in the catalytic system achieves remarkable selectivity for α-olefins, producing yields exceeding 90% while suppressing formation of alkanes and internal olefins that are problematic in conventional systems.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The catalyst composition acts as an intermediary that mediates the conversion of alcohols and aldehydes to α-olefins. The specific combination of Group VIII metal compound, heteroatomic ligand compound, and Bronsted acid compound creates a highly selective reaction pathway that favors α-olefin formation, effectively mediating between the starting materials and desired product while minimizing byproduct generation.

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

The described catalyst compositions achieve high yields of α-olefins with reduced formation of byproducts, demonstrating improved selectivity and efficiency in converting alcohols and aldehydes to olefins.

Implementation Method 1

Catalyst compositions described herein can comprise a Group VIII metal compound, a heteroatomic ligand compound, and a Bronsted acid compound. These catalyst compositions can promote oxidative reaction pathways to produce α-olefins from alcohols and aldehydes

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

These catalyst compositions can further comprise an acceptor (e.g., N,N-dimethylacrylamide) capable of accepting a molecule of H2, for instance during oxidative dehydroxymethylation and oxidative dehydroformylation reaction steps

Methodology Applied
Scientific EffectAbsorption: Absorption (physical)

Data Source

PatentUS11123723B2Oxidative dehydroxymethylation of alcohols to produce olefins
Publication Date: 2021.09.21 CHEVRON PHILLIPS CHEMICAL COMPANY LP
  • US11123723B2 patent drawing
  • US11123723B2 patent drawing
  • US11123723B2 patent drawing

AI summary

Catalyst compositions for the conversion of aldehyde compounds and primary alcohol compounds to olefins are disclosed herein. Reactions include oxidative dehydroxymethylation processes and oxidative dehydroformylation methods, which are beneficially conducted in the presence of a sacrificial acceptor of H2 gas, such as N,N-dimethylacrylamide.