Fluorinated Alcohol Synthesis via Epoxide Ring Opening
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Solution Overview
Problem
Current methods do not effectively prepare fluorohydrins from fluorinated epoxides or produce fluorinated carbonate esters using fluorohydrins and carboxylating agents, which are valuable for applications in electronic devices and other materials.
Innovation Solution
A method involving the reaction of fluorinated epoxides with nucleophilic fluorinating agents, such as HF or Olah's reagent, to form partially fluorinated alcohols, which can then be used to synthesize fluorinated carbonate esters and other compounds suitable for battery solvents and intermediates.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If fluorinated epoxides are reacted with nucleophilic fluorinating agents, then fluorohydrins can be prepared, but the reaction pathway was previously unknown and unexplored in the art
Solution Approach 1:
The patent applies preliminary action by first identifying and characterizing the novel reaction between fluorinated epoxides and nucleophilic fluorinating agents before using it for practical synthesis. The inventors conducted preliminary experiments to establish that this reaction pathway produces fluorohydrins, which then enabled the development of reliable synthetic routes for fluorinated carbonate esters.
2Productivity
If fluorohydrins are reacted with carboxylating agents, then fluorinated carbonate esters can be produced, but this reaction pathway was previously unknown
Solution Approach 1:
The patent uses fluorohydrins as an intermediary substance that bridges the gap between fluorinated epoxides and fluorinated carbonate esters. The fluorohydrin serves as a stable intermediate that can be isolated and then converted to the desired carbonate ester product through reaction with carboxylating agents, enabling a two-step synthetic pathway where neither step was previously known.
3Adaptability or versatility
If conventional methods are used to prepare fluorinated compounds, then existing processes can be maintained, but fluorinated carbonate esters cannot be produced from fluorohydrins and carboxylating agents
Solution Approach 1:
The patent applies parameter changes by fundamentally altering the synthetic pathway parameters - instead of using conventional methods to prepare fluorinated compounds, the inventors changed the reaction sequence to involve fluorinated epoxide + nucleophilic fluorinating agent → fluorohydrin, followed by fluorohydrin + carboxylating agent → fluorinated carbonate ester. This parameter change enabled access to new products with desired 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
This method enables the production of fluorinated alcohols and carbonate esters with desirable physical and electrochemical properties, enhancing their utility in lithium ion batteries and other applications by providing stable, compatible, and low-flammability solvents.
Implementation Method 1
reacting a fluorinated epoxide with a nucleophilic fluorinating agent to form a partially fluorinated alcohol
Implementation Method 2
reacting a fluorohydrin with a carboxylating agent to prepare a fluorinated carbonate ester
Data Source
Figure 1
Figure 2
Figure 2a
AI summary
A method for preparing a partially fluorinated alcohol, comprises reacting an epoxide: wherein R1, R2, R3 and R4 are independently selected from the group comprising H, F, Cl, Br, I, CF3, alkyl, fluoroalkyl, haloalkyl with a fluorinating agent.