Fluorinated 1,3-Dioxolan-2-One Synthesis via Liquid-Liquid Reaction

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Solution Overview

Problem

Existing processes for preparing fluorinated 1,3-dioxolan-2-one require solid-liquid reactions with metallic fluorides, leading to slower reaction rates and the need for additional steps to remove solids, while maintaining low yields.

Innovation Solution

A liquid-liquid reaction process using amine hydrofluoride as a fluorinating agent with halogenated 1,3-dioxolan-2-one in an organic solvent, optimizing mole ratios and reaction conditions to enhance reactivity and yield, followed by rectification and antacid treatment to achieve high purity fluorinated EC.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If solid metallic fluoride is used as a fluorinating agent, then fluorinated EC can be produced, but the reaction rate is slow and additional solid removal steps are required

Engineering Contradiction:
Improvereaction rateVSAvoidprocess complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent changes the physical state parameter of the fluorinating agent from solid (metallic fluoride) to liquid (amine hydrofluoride). This parameter change transforms the reaction system from solid-liquid to liquid-liquid, dramatically increasing the reaction rate and eliminating the need for solid removal steps while maintaining high yield of fluorinated EC

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces an amine component as an intermediary that forms amine hydrofluoride complex. This intermediary facilitates the fluorination reaction by providing a liquid-phase fluorinating agent that is more reactive and easier to handle than solid metallic fluoride, while the amine component also helps in subsequent product isolation

Inventive Principle:
Principle #24Intermediary (Mediator)

2Ease of manufacture

If solid metallic fluoride is used as a fluorinating agent, then fluorinated EC can be produced, but additional steps for removing solids are required

Engineering Contradiction:
Improveease of purificationVSAvoidnumber of process steps
Core Design Contradiction:
Ease of manufactureVSDevice complexity

Solution Approach 1:

By changing the fluorinating agent from solid to liquid state, the patent eliminates the need for filtration or centrifugation steps required to remove solid residues. The liquid-liquid reaction system allows for simpler phase separation and purification processes, reducing the overall number of manufacturing steps

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent extracts the problematic solid component (metallic fluoride) from the reaction system and replaces it with a liquid alternative (amine hydrofluoride). This extraction of the solid phase eliminates the need for solid removal operations while maintaining the essential fluorination function

Inventive Principle:
Principle #2Taking out (Extraction)

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 process significantly reduces reaction time, maintains high yields (80-85%), and eliminates the need for solid removal steps, producing high-purity fluorinated EC with minimal halogen radicals, suitable for use in electrochemical devices.

Implementation Method 1

reacting a derivative of 1,3-dioxolan-2-one... with an amine hydrofluoride in an organic solvent

Methodology Applied
Scientific EffectNucleophilic substitution: Chemical Bonding

Implementation Method 2

followed by rectification and antacid treatment to achieve high purity fluorinated EC

Methodology Applied
Scientific EffectDistillation: Distillation

Data Source

PatentUS9067907B2Process for preparing fluorinated 1,3-dioxolan 2-one
Publication Date: 2015.06.30 DAIKIN INDUSTRIES LTD
  • US9067907B2 patent drawing
  • US9067907B2 patent drawing
  • US9067907B2 patent drawing

AI summary

The present invention provides a process for preparing fluorinated 1,3-dioxolan-2-one by reacting a derivative of 1,3-dioxolan-2-one having halogen atom other than fluorine with an amine hydrofluoride in an organic solvent, and in this preparation process, fluorinated 1,3-dioxolane-2-on can be prepared in a short period of time by liquid-liquid reaction while maintaining high yield, by using a derivative of 1,3-dioxolan-2-one having halogen atom other than fluorine as a starting material and fluorinating the derivative with a fluorinating agent.