Epoxy Compound Synthesis via Tungsten-Phosphorus Catalyst
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Solution Overview
Problem
Conventional methods for epoxidizing organic compounds with carbon-carbon double bonds are not industrially advantageous due to safety concerns, high costs, and low efficiency, often requiring hazardous materials and generating harmful by-products.
Innovation Solution
A method involving the oxidation of carbon-carbon double bonds using hydrogen peroxide in the presence of a neutral inorganic salt and a mixed catalyst comprising a tungsten compound, phosphorus compound, and surfactant under mild conditions, which is inexpensive, safe, and efficient.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If percarboxylic acid is used for epoxidation, then the reaction proceeds efficiently, but safety issues arise due to explosibility and equimolecular wastes are generated
Solution Approach 1:
The patent converts the harmful percarboxylic acid into a beneficial system by using hydrogen peroxide (which generates only water as by-product) combined with a catalyst system (tungstic acid/phosphoric acid/surfactant) that enables efficient epoxidation without the safety hazards and waste problems of peracids
Solution Approach 2:
The patent changes the chemical parameters of the oxidation system by replacing percarboxylic acid with a hydrogen peroxide-based catalyst system, fundamentally altering the reaction pathway to eliminate harmful by-products while maintaining or improving reaction efficiency
2Object-generated harmful factors
If osmium salt or tungstic acid is used as catalyst with hydrogen peroxide, then only water is generated as by-product, but the osmium salt is highly toxic
Solution Approach 1:
The patent extracts and removes the toxic osmium salt from the catalyst system, replacing it with a non-toxic combination of tungstic acid, phosphoric acid, and surfactant that maintains the beneficial feature of generating only water as by-product
Solution Approach 2:
The patent employs inexpensive, non-toxic catalyst components (tungstic acid, phosphoric acid, surfactant) that can be easily disposed of or regenerated, replacing expensive and toxic osmium salts while maintaining environmental friendliness
3Productivity
If arsenic oxide and 3,5-di-tert-butyl-4-hydroxytoluene are used as catalysts, then styrene oxide is produced, but arsenic oxide is highly toxic
Solution Approach 1:
The patent removes the highly toxic arsenic oxide from the catalyst system and replaces it with non-toxic tungstic acid, phosphoric acid, and surfactant, eliminating the harmful factor while maintaining production capability
Solution Approach 2:
The patent uses inexpensive, non-toxic catalyst components that can be readily replaced or disposed of, contrasting with the expensive and highly toxic arsenic oxide while achieving the same production goal
4Productivity
If transition metal salts and inorganic promoters are used under high dilution conditions, then epoxidation occurs, but hydrogen peroxide utilization efficiency is poor and industrial productivity is inferior
Solution Approach 1:
The patent creates a composite catalyst system combining tungstic acid, phosphoric acid, and surfactant that works synergistically to dramatically improve hydrogen peroxide utilization efficiency and industrial productivity compared to conventional transition metal salt systems
Solution Approach 2:
The patent changes the reaction parameters by using a novel catalyst system that enables effective epoxidation without high dilution conditions, thereby improving both hydrogen peroxide efficiency and industrial productivity
5Productivity
If tungstophosphoric acid derivatives and aminomethylphosphonic acid are used as catalysts, then epoxidation is achieved, but these catalysts are difficult to produce
Solution Approach 1:
The patent segments the complex tungstophosphoric acid derivative catalyst into simpler, more easily manufactured components: tungstic acid, phosphoric acid, and surfactant, each of which can be obtained or synthesized more readily
Solution Approach 2:
The patent employs catalyst components that are inexpensive and easy to manufacture (tungstic acid, phosphoric acid, surfactant) replacing complex and difficult-to-produce tungstophosphoric acid derivatives
6Productivity
If methyltrioxorhenium and pyrazole are used as catalysts, then epoxidation occurs, but the catalyst is very expensive and difficult to use in industrial production
Solution Approach 1:
The patent replaces the very expensive methyltrioxorhenium catalyst with inexpensive, easily manufacturable catalyst components (tungstic acid, phosphoric acid, surfactant) that are suitable for industrial production
Solution Approach 2:
The patent extracts and removes the expensive methyltrioxorhenium from the catalyst system, replacing it with cost-effective alternatives that maintain epoxidation capability while enabling industrial scalability
7Productivity
If manganese porphyrin complex and imidazole are used as catalysts, then epoxidation is achieved, but the expensive manganese porphyrin complex makes industrial implementation problematic
Solution Approach 1:
The patent replaces the expensive manganese porphyrin complex with inexpensive catalyst components (tungstic acid, phosphoric acid, surfactant) that are economically viable for industrial production
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 allows for the high-yield, selective production of epoxy compounds without isomerization or decomposition, using only water as a by-product, making it suitable for industrial production.
Implementation Method 1
oxidizing a carbon-carbon double bond of an organic compound by hydrogen peroxide in the presence of a neutral inorganic salt and a mixed catalyst
Implementation Method 2
a mixed catalyst of a tungsten compound (a), at least one phosphorus compound selected from the group consisting of phosphoric acids, phosphonic acids, and salts thereof (b), and a surfactant (c)
Data Source
AI summary
The present invention provides a method for producing an epoxy compound, comprising oxidizing a carbon-carbon double bond of an organic compound by hydrogen peroxide in the presence of a neutral inorganic salt and a mixed catalyst of a tungsten compound (a), at least one phosphorus compound selected from the group consisting of phosphoric acids, phosphonic acids, and salts thereof (b) and a surfactant (c), and an epoxidizing method comprising oxidizing a carbon-carbon double bond by hydrogen peroxide in the presence of the catalyst and the neutral inorganic salt.