Cobalt Catalyst Oxidation in Expanded Liquid Solvents

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Solution Overview

Problem

The oxidation of hydrocarbon substrates under traditional methods, such as the Mid-Century Process, often requires high temperatures and pressures, uses harmful oxidants, and results in side products and solvent destruction, limiting efficiency and environmental sustainability.

Innovation Solution

A process utilizing cobalt tetrahydrate as a catalyst and N-hydroxysuccinimide, N-hydroxyphthalimide, or N-hydroxymaleimide as co-catalysts, with air or dioxygen as oxidants, under mild conditions of temperature and pressure, in organic solvents like acetic acid or carbon dioxide, to achieve efficient oxidation of hydrocarbons without prolonged initiation times and specialized equipment.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Temperature

If traditional Mid-Century Process is used for oxidation of hydrocarbons, then oxidation can be achieved, but high temperatures and pressures are required

Engineering Contradiction:
Improvereaction temperatureVSAvoidoxidation efficiency
Core Design Contradiction:
TemperatureVSProductivity

Solution Approach 1:

The patent changes the reaction parameters from high temperature and pressure to mild conditions (lower temperature and pressure) by introducing a specific catalyst system (cobalt complex with ligands) and co-catalyst (N-hydroxysuccinimide), enabling oxidation to proceed efficiently under environmentally benign conditions

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent uses a cobalt complex catalyst and N-hydroxysuccinimide co-catalyst as intermediaries to facilitate the oxidation reaction between hydrocarbon and oxygen, allowing the reaction to proceed at mild temperatures and pressures without requiring extreme conditions

Inventive Principle:
Principle #24Intermediary (Mediator)

2Object-generated harmful factors

If traditional oxidation processes are used, then oxidation reactions can be performed, but harmful oxidants and solvent destruction occur

Engineering Contradiction:
Improveharmful oxidants and solvent destructionVSAvoidprocess sustainability
Core Design Contradiction:
Object-generated harmful factorsVSReliability

Solution Approach 1:

The patent converts the potentially harmful oxidation process into a beneficial one by using oxygen (air) as a safe oxidant instead of harmful oxidants like chromium(VI) or manganese(VII), and by designing the catalyst system to prevent solvent destruction and side reactions, thereby eliminating harmful factors while maintaining oxidation efficiency

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

Solution Approach 2:

The patent changes the oxidant from harmful chemical oxidants to molecular oxygen (air), and adjusts reaction parameters (temperature, pressure, catalyst system) to enable this substitution, resulting in environmentally sustainable process that eliminates harmful oxidants and reduces solvent destruction

Inventive Principle:
Principle #35Parameter changes

3Loss of time

If traditional oxidation methods are used, then oxidation can be achieved, but prolonged initiation times and specialized equipment are required

Engineering Contradiction:
Improveinitiation timeVSAvoidspecialized equipment
Core Design Contradiction:
Loss of timeVSDevice complexity

Solution Approach 1:

The patent incorporates a pre-activated cobalt complex catalyst system that is ready to initiate oxidation immediately upon contact with the hydrocarbon and oxygen, eliminating prolonged initiation times. The catalyst system is designed to be activated in advance during preparation, so no special equipment or prolonged waiting periods are needed during the actual reaction

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent uses a cobalt complex with specific ligands as an intermediary catalyst that facilitates rapid initiation of the oxidation reaction. This catalyst system acts as a mediator between the hydrocarbon and oxygen, enabling the reaction to start quickly under mild conditions without requiring specialized equipment or prolonged initiation periods

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 rapid, high-yielding oxidation of hydrocarbons at ambient temperatures and pressures, reducing side products and solvent consumption, and is adaptable to various scales, from laboratory to industrial, with environmentally beneficial and economically advantageous outcomes.

Implementation Method 1

oxidation of hydrocarbon substrates... in the presence of an oxidation catalyst comprised of cobalt... and the co-catalyst selected from the group consisting of N-hydroxysuccinimide, N-hydroxyphthalimide, and N-hydroxymaleimide

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

oxidation of hydrocarbon substrates... by air or dioxygen

Methodology Applied
Scientific EffectOxidation: Oxidation

Implementation Method 3

compressed-gas expanded solvent systems... volumetrically expanded liquids by compressed gases

Methodology Applied
Scientific EffectVolumetric expansion:

Data Source

PatentUS8115029B2Cobalt-catalyzed oxidations in volumetrically expanded liquids by compressed gases
Publication Date: 2012.02.14 UNIVERSITY OF KANSAS
  • US8115029B2 patent drawing
  • US8115029B2 patent drawing
  • US8115029B2 patent drawing

AI summary

Oxidations of hydrocarbons, cycloalkanes and alkenes, arylalkanes, and a variety of other organic substrates are accomplished by cobalt-N-hydroxysuccinimide co-catalyzed reactions with dioxygen under unusually mild, near ambient conditions of temperature and pressure. The improved safety of the oxidation method and the high yields of product obtained make use of a unique combination of cobalt (II) complexes with N-hydroxysuccinimide. These autoxidation reactions do not have prolonged initiation times. Many of these reactions can be safely performed under normal chemical laboratory conditions and do not require specialized equipment or reagents.