Fluorine-Containing Ether Monocarboxylic Acid Aminoalkyl Ester Synthesis
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Solution Overview
Problem
There is a lack of fluorine-containing ether carboxylic acid esters with an amino group at the end of the ester group, which are essential for providing flexibility in molecular chains and serving as synthetic intermediates or additives for lubricating oils.
Innovation Solution
A fluorine-containing ether monocarboxylic acid aminoalkyl ester is synthesized by reacting a perfluoroether carboxylic acid fluoride compound with a hydroxyalkyl amine in the presence of an alkali metal fluoride, forming a compound with an ether bond that imparts flexibility and is used as a synthetic intermediate and wear resistance improver.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Adaptability or versatility
If fluorine-containing ether carboxylic acid esters with terminal amino groups are synthesized, then flexibility in molecular chain and synthetic utility are improved, but such compounds have been hardly observed in prior art indicating a gap in existing technology
Solution Approach 1:
The patent performs preliminary action by synthesizing the fluorine-containing ether carboxylic acid aminoalkyl ester compound before it can be used as a synthetic intermediate. The compound is prepared in advance through reaction of perfluoroether carboxylic acid fluoride with hydroxyalkyl amine, making it available for subsequent applications in polymer synthesis and lubricant formulation where flexibility and synthetic utility are required.
2Productivity
If perfluoroether carboxylic acid fluoride reacts with hydroxyalkyl amine, then fluorine-containing ether monocarboxylic acid aminoalkyl ester is produced, but the reaction requires specific conditions including alkali metal fluoride catalyst
Solution Approach 1:
The patent employs an intermediary substance, specifically alkali metal fluoride (such as potassium fluoride or sodium fluoride), to mediate the reaction between perfluoroether carboxylic acid fluoride and hydroxyalkyl amine. The alkali metal fluoride acts as a catalyst that facilitates the esterification reaction, enabling the formation of the fluorine-containing ether monocarboxylic acid aminoalkyl ester under milder and more controllable conditions without requiring complex reaction setups.
3Reliability
If the compound is used as wear resistance improver for fluorine oils, then extreme pressure additive performance is improved, but the application requires supporting on silica gel or metal for water- and oil-repellency
Solution Approach 1:
The patent utilizes the compound's inherent molecular structure with ether bonds that provide flexibility in the molecular chain. This flexibility allows the compound to form effective protective films on metal surfaces, providing wear resistance and extreme pressure protection. The ether linkage enables the molecule to adapt to surface contours and maintain a flexible protective layer that reduces friction and wear without requiring rigid support structures.
Solution Approach 2:
The patent extracts and utilizes the water- and oil-repellency properties inherent in the fluorine-containing ether monocarboxylic acid aminoalkyl ester compound. By supporting the compound on silica gel or metal substrates, the invention separates and concentrates the water- and oil-repellent functionality, making it available as a coating or treatment layer that provides protection without requiring the bulk material to possess these properties.
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
The resulting fluorine-containing ether monocarboxylic acid aminoalkyl ester exhibits flexibility and is effectively used as a synthetic intermediate and wear resistance improver, offering water- and oil-repellency, making it suitable for forming flexible polymers and enhancing the properties of fluorine-containing oils.
Implementation Method 1
reacting a perfluoroether carboxylic acid fluoride compound with a hydroxyalkyl amine compound
Implementation Method 2
imparted with flexibility in a molecular chain due to an ether bond in a molecule
Implementation Method 3
Due to the water- and oil-repellency inherent therein
Data Source
AI summary
A fluorine-containing ether monocarboxylic acid aminoalkyl ester represented by the general formula: CnF2n+1O[CF(CF3)CF2O]aCF(CF3)COO(CH2)bNR1R2 (wherein R1 is a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an aryl group, or an aralkyl group, preferably an alkyl group having 1 to 6 carbon atoms or an aryl group; R2 is an alkyl group having 1 to 12 carbon atoms, an aryl group, or an aralkyl group, preferably an alkyl group having 1 to 6 carbon atoms or an aryl group; n is an integer of 1 to 3; a is an integer of 2 to 20, preferably an integer of 4 to 10; and b is an integer of 1 to 12, preferably an integer of 1 to 3). Such a fluorine-containing ether monocarboxylic acid ester having an amino group at the end of the ester group is produced by reacting a perfluoroether carboxylic acid fluoride compound CnF2n+1O[CF(CF3)CF2O]aCF(CF3)COF and a hydroxyalkyl amine compound HO(CH2)bNR1R2 in the presence of an alkali metal fluoride.