Alkoxymethyl Alkynyl Ether Synthesis via Dialkylaniline Base
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Solution Overview
Problem
Current methods for preparing alkoxymethyl alkynyl ether compounds with a terminal triple bond are environmentally hazardous, economically unfavorable, and have low yields due to the use of solvents like dichloromethane and lithium halide, and face challenges in separation and recovery of products.
Innovation Solution
A process involving the protection of a hydroxyl group of an alkynol compound with an alkoxymethyl group using a dialkylaniline compound as both a base and extraction solvent, eliminating the need for additional solvents and enabling high-yield production and easy recovery of the dialkylaniline for reuse.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If dichloromethane is used as a solvent and N,N-diisopropylethylamine is used as a base in large amount, then the alkoxymethylation reaction can proceed, but environmental hazard increases and recovery cost increases
Solution Approach 1:
The patent changes the chemical parameters by replacing dichloromethane with toluene or xylene as solvent, and replacing N,N-diisopropylethylamine with triethylamine or tributylamine as base. These parameter changes maintain reaction effectiveness while eliminating the environmental hazards associated with the original reagents.
Solution Approach 2:
The patent employs bases that can be easily disposed of or recovered without complex procedures. Triethylamine and tributylamine are less environmentally hazardous than N,N-diisopropylethylamine and can be handled more simply in waste treatment, reducing both environmental impact and recovery costs.
2Ease of operation
If diethyl ether is used as extraction solvent, then the product can be extracted into organic phase, but safety hazard increases due to low boiling point and flammability
Solution Approach 1:
The patent changes the physical parameters of the extraction solvent by replacing diethyl ether (low boiling point, flammable) with toluene or xylene (higher boiling point, less flammable). This maintains extraction efficiency while significantly reducing safety hazards in the workplace.
3Productivity
If a lower alkynol compound having 3 to 6 carbon atoms is used, then the reaction proceeds, but product loss into aqueous phase increases due to water solubility
Solution Approach 1:
The patent uses toluene or xylene as an intermediary extraction solvent that preferentially dissolves the water-soluble alkoxymethyl alkynyl ether product, pulling it from the aqueous phase into the organic phase. This intermediary solvent acts as a bridge to transfer the product without direct contact with water, minimizing product loss.
4Object-affected harmful factors
If toluene or xylene is used as solvent, then safety is improved, but product separation by distillation becomes difficult due to close boiling points
Solution Approach 1:
The patent exploits the local quality difference in boiling points between the solvent (toluene/xylene) and the product (alkoxymethyl alkynyl ether). Although the boiling points are close, the consistent temperature gradient during distillation allows for gradual separation, with the lower boiling product distilling first followed by the solvent.
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 approach results in a high-yield, economically viable, and environmentally friendly method for producing alkoxymethyl alkynyl ether compounds with improved separation and recovery efficiency, reducing waste and operational costs.
Implementation Method 1
subjecting an alkynol compound having a terminal triple bond of the following formula (1) to an alkoxymethylation with a halomethyl alkyl ether compound of the following formula (3) in the presence of a dialkylaniline compound
Implementation Method 2
a reaction mixture (organic phase) containing the alkoxymethyl alkynyl ether compound (4) obtained in the alkoxymethylation and the hydrogen halide salt of the dialkylaniline compound (2) is neutralized with a base in the presence of water to obtain an organic phase containing the alkoxymethyl alkynyl ether compound (4) and dialkylaniline compound (2)
Implementation Method 3
the alkoxymethyl alkynyl ether compound (4) obtained in the alkoxymethylation and the hydrogen halide salt of the dialkylaniline compound (2) is neutralized with a base in the presence of water
Data Source
AI summary
The present invention provides a process for preparing an alkoxymethyl alkynyl ether compound having a terminal triple bond of the following formula (4):H-C≡C(CH2)aOCH2OCH2R (4), wherein R represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, and "a" represents an integer of 1 to 10, the method comprising subjecting an alkynol compound having a terminal triple bond of the following formula (1): H-C≡C(CH2)aOH (1), wherein "a" is as defined above, to an alkoxymethylation with a halomethyl alkyl ether compound of the following formula (3): RCH2OCH2X (3), wherein X represents a halogen atom, and R is as defined above, in the presence of a dialkylaniline compound of the following formula (2): [CH3(CH2)b][CH3(CH2)c]NC6H5 (2), wherein b and c represent, independently of each other, an integer of 0 to 9, to form the alkoxymethyl alkynyl ether compound (4) having a terminal triple bond.