Phosphoric Acid Ester Production Without Halide Scavengers
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Solution Overview
Problem
Conventional methods for producing phosphorus compounds with aromatic substituents and phosphorinane backbones require expensive hydrogen halide scavengers like triethylamine, leading to high raw material costs, complex post-treatment processes, and reduced yield and purity.
Innovation Solution
A method involving the reaction of phosphorus oxytrihalide with phenol or naphthol compounds in the presence of metal halides, without using hydrogen halide scavengers, to produce phosphoric acid esters with improved yield and purity, utilizing specific molar ratios and reaction conditions.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If hydrogen halide scavengers like triethylamine are used in the synthesis method, then the reaction can proceed, but the raw material cost drastically increases and complex post-treatment processes are required
Solution Approach 1:
The invention extracts and eliminates the hydrogen halide scavenger component from the conventional synthesis system. By removing triethylamine and other amine-based scavengers, the patent achieves the reaction without requiring expensive additives or complex post-treatment processes for removing amine hydrohalide salts, thereby resolving the contradiction between reaction feasibility and manufacturing simplicity
Solution Approach 2:
The invention replaces expensive, reusable amine scavengers with a simple, disposable metal halide catalyst system. The metal halide can be used in catalytic amounts and does not require recovery or complex disposal procedures, reducing both material costs and process complexity while maintaining reaction effectiveness
2Productivity
If hydrogen halide scavengers are used to capture hydrogen halide, then the reaction proceeds, but hydrogen halide salt of the amine compound is produced as a by-product requiring filtration and water treatment
Solution Approach 1:
The invention extracts the hydrogen halide salt formation problem by eliminating the amine component from the system. Without triethylamine or other amine scavengers, no amine hydrohalide salt by-product is formed, thereby removing the need for filtration and water treatment steps entirely
Solution Approach 2:
The invention introduces metal halide as an intermediary catalyst that facilitates the reaction without forming problematic by-products. The metal halide mediates the reaction between phosphorus oxytrihalide and phenol/naphthol compounds, allowing hydrogen halide to be managed differently (through gas evolution or alternative scavenging) without creating soluble salts that require complex separation
3Ease of operation
If a large amount of reaction solvent is used to maintain stirring effect, then the reaction can proceed, but filtration and water treatment are required which reduce capacity efficiency
Solution Approach 1:
The invention extracts the need for large solvent volumes by removing the source of the problem (amine hydrohalide salt formation). Without amine scavengers, no salt by-product is formed, eliminating the need for extensive solvent use in filtration and water treatment operations, thereby improving capacity efficiency
Solution Approach 2:
The invention changes the chemical parameters of the reaction system by replacing amine-based chemistry with metal halide-catalyzed chemistry. This parameter change fundamentally alters the by-product profile, eliminating soluble salt formation and reducing the need for large solvent volumes in post-treatment operations
4Manufacturing precision
If water treatment is used to remove hydrogen halide salt, then the salt can be removed, but a large amount of water is required which greatly reduces capacity efficiency
Solution Approach 1:
The invention extracts the water treatment step entirely by eliminating the formation of amine hydrohalide salts. Without amine scavengers in the reaction, no salt by-product is generated, removing the need for water treatment operations and associated capacity losses
Solution Approach 2:
The metal halide catalyst serves as an intermediary that enables the reaction to proceed without forming water-soluble salt by-products. This intermediary approach allows the reaction to achieve high purity through simpler means, avoiding the need for large-scale water treatment that reduces capacity efficiency
5Ease of repair
If strong alkali aqueous solution is used to isolate amines from amine salt water, then amines can be recovered, but the cost increases and the aqueous solution becomes difficult to treat
Solution Approach 1:
The invention extracts the amine recovery problem by eliminating amine scavengers from the reaction system. Without triethylamine or other amines, no amine salt water is generated, removing the need for costly alkali treatment and complex waste water management
Solution Approach 2:
The invention replaces expensive, recoverable amine scavengers with a simple metal halide catalyst system that does not require recovery. The metal halide can be used in catalytic amounts and does not generate recoverable by-products, eliminating the need for costly isolation and waste treatment operations
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 the production of phosphorus compounds with aromatic substituents and phosphorinane backbones at lower costs and with higher yield and purity, eliminating the need for expensive scavengers and complex post-treatment processes.
Implementation Method 1
a step (1): a step of allowing phosphorus oxytrihalide represented by Formula (I) to react with a phenol compound or naphthol compound represented by Formula (II)
Data Source
AI summary
The present invention provides a novel production method which enables obtain a phosphorus compound having both an aromatic substituent and a phosphorinane backbone, without using an expensive hydrogen halide scavenger, without going through a complicated post treatment step or a step of recovering a solvent, and with a favorable yield and purity. In the present invention, step (1) of allowing phosphorus oxytrihalide to react with a phenol compound or naphthol compound at a molar ratio of 1.1-3.0:1 in the presence of metal halide, and removing unreacted phosphorus oxytrihalide, to produce a mono-substituted phosphorodihalidate; and step (2) of allowing the mono-substituted phosphorodihalidate obtained in the step (1) to react with a diol compound, at a 0. 90 to 0. 99 molar equivalent based on 1 mole of the halogen atom in the mono-substituted phosphorodihalidate so as to perform a dehydrohalogenation reaction, to obtain a phosphorus compound represented by Formula (V).