Visible-Light Oxidation of Saturated Hydrocarbon Bonds

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Solution Overview

Problem

Existing methods for the direct oxidation of saturated hydrocarbon bonds in organic compounds require expensive transition metal catalysts, high temperatures, and pressures, and generate significant waste, limiting their efficiency and environmental sustainability.

Innovation Solution

A visible-light-induced direct oxidation method using a cerium complex and inexpensive additives under mild conditions, which activates hydrocarbon bonds to produce oxidation products with high yields and reduced waste, leveraging the energy of visible light and stable reagents.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If expensive transition metal catalysts are used for direct oxidation of hydrocarbon bonds, then oxidation reaction efficiency is improved, but catalyst cost increases

Engineering Contradiction:
Improveoxidation reaction efficiencyVSAvoidcatalyst cost
Core Design Contradiction:
ProductivityVSQuantity of substance

Solution Approach 1:

The patent replaces expensive transition metal catalysts with inexpensive cerium-based catalysts that can be used in small amounts. The cerium catalyst system achieves effective oxidation of hydrocarbon bonds without requiring large quantities of precious metals, directly addressing the cost-efficiency contradiction.

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

Solution Approach 2:

The patent changes the catalyst system from traditional expensive transition metals to cerium-based catalysts under visible light irradiation. This parameter change in catalyst composition and activation method maintains oxidation efficiency while dramatically reducing catalyst cost.

Inventive Principle:
Principle #35Parameter changes

2Productivity

If high temperatures and pressures are applied for hydrocarbon bond oxidation, then reaction rate is improved, but energy consumption and safety risks increase

Engineering Contradiction:
Improvereaction rateVSAvoidreaction temperature and pressure
Core Design Contradiction:
ProductivityVSTemperature

Solution Approach 1:

The patent replaces thermal activation (high temperature and pressure) with photochemical activation using visible light. The cerium catalyst absorbs visible light to generate reactive species that activate hydrocarbon bonds at mild temperatures, eliminating the need for harsh thermal conditions while maintaining reaction efficiency.

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

Solution Approach 2:

The patent utilizes photochemical phase transition from ground state to excited state in the cerium catalyst upon visible light absorption. This excited state enables the catalyst to activate hydrocarbon bonds under mild conditions, replacing the need for high temperature and pressure thermal activation.

Inventive Principle:
Principle #36Phase transitions

3Quantity of substance

If traditional oxidation methods are used, then oxidation products are obtained, but environmental pollution from heavy metals and peroxides increases

Engineering Contradiction:
Improveoxidation product yieldVSAvoidenvironmental pollution
Core Design Contradiction:
Quantity of substanceVSObject-generated harmful factors

Solution Approach 1:

The patent converts the previously harmful role of peroxides (as pollutants) into a beneficial intermediate species in the oxidation process. The cerium catalyst under visible light generates peroxides in situ that selectively oxidize hydrocarbon bonds, and the catalyst system is designed to minimize harmful byproducts, transforming the oxidation process into an environmentally friendly method.

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

Solution Approach 2:

The patent uses inexpensive cerium-based catalysts that replace expensive and environmentally problematic heavy metal catalysts. The cerium catalyst system is designed to be highly efficient at low loadings, reducing the amount of metal waste generated while maintaining high oxidation product yields.

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

4Object-affected harmful factors

If visible light catalysis is applied to hydrocarbon bond oxidation, then environmental friendliness is improved, but reaction efficiency needs to be enhanced

Engineering Contradiction:
Improveenvironmental friendlinessVSAvoidreaction efficiency
Core Design Contradiction:
Object-affected harmful factorsVSProductivity

Solution Approach 1:

The patent employs a composite catalyst system consisting of cerium-based compounds combined with organic ligands or co-catalysts. This composite structure enhances the visible light absorption capability and catalytic activity of cerium, enabling efficient hydrocarbon bond oxidation under visible light while maintaining environmental friendliness.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent optimizes parameters including cerium catalyst composition, ligand structure, visible light wavelength and intensity, and reaction conditions to maximize reaction efficiency. These parameter adjustments enable the visible light-catalyzed system to achieve high oxidation efficiency comparable to or exceeding traditional methods while maintaining green conditions.

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 method achieves high reaction efficiency at low temperatures with minimal environmental impact, utilizing low-cost cerium catalysts and stable reagents, avoiding pollution from heavy metals and peroxides, and providing a more economical and environmentally friendly synthesis route.

Implementation Method 1

visible-light-induced direct oxidation method

Methodology Applied
Scientific EffectVisible light absorption: Absorption (EM radiation)

Implementation Method 2

efficiently catalyzed by a cerium complex

Methodology Applied
Scientific EffectPhotocatalysis: Catalysis

Implementation Method 3

oxidizing the saturated hydrocarbon bond to afford an oxidation product

Methodology Applied
Scientific EffectOxidation: Oxidation

Data Source

PatentUS11008272B1Visible-light-induced direct oxidation method for saturated hydrocarbon bonds
Publication Date: 2021.05.18 SHANGHAI TECH UNIV
  • US11008272B1 patent drawing
  • US11008272B1 patent drawing
  • US11008272B1 patent drawing

AI summary

The present invention provides a direct oxidation method for saturated hydrocarbon bonds in an organic compound. The method allows an organic compound with a saturated hydrocarbon bond to react with an oxidizing reagent in the presence of cerium complex under visible light irradiation, thus oxidizing the saturated hydrocarbon bond to afford an oxidation product. The present reaction only needs to be carried out at room temperature, while the reaction efficiency remains high. In addition, only visible light is required to provide the energy for activation, rendering the present strategy is a milder and greener reaction method. The cerium catalyst used in the method is low in cost, simple and efficient, while the oxidizing reagent used is also stable in nature and low in industrial cost, rendering the catalytic system highly practical. Furthermore, environmental pollution caused by heavy transition metals and peroxides can be avoided in such strategy.