Fluorolactone Synthesis for Single-Step Fluorodioxolane Production

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Solution Overview

Problem

Existing methods for producing fluorodioxolane derivatives, such as 2-(difluoromethylene)-4,4,5-trifluoro-5-(trifluoromethyl)-1,3-dioxolane, are inefficient and lack the production of novel compounds that can serve as raw materials or intermediates for polymer production.

Innovation Solution

A method involving the reaction of a compound of formula (6) with alkyl alcohol to produce a novel compound (7-1), where R1 are F or fluoroalkyl and R72 is alkyl, through specific reaction steps and conditions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If existing methods for producing fluorodioxolane derivatives are used, then production can be achieved, but the production efficiency is low and novel compounds cannot be produced

Engineering Contradiction:
Improveproduction efficiencyVSAvoidability to produce novel compounds
Core Design Contradiction:
ProductivityVSAdaptability or versatility

Solution Approach 1:

The production process is divided into multiple sequential steps: Step (A) reacts compound (2) with compound (3) to form compound (1); Step (B) reacts compound (1) with compound (4) to form compound (5); Step (C) reacts compound (5) with compound (6) to form the final fluorodioxolane derivative (7-1). This segmented approach allows each step to be optimized independently, improving overall production efficiency while enabling the synthesis of novel compounds with different R1 and R72 groups.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent employs parameter changes by varying the substituents R1 (F or fluoroalkyl) and R72 (alkyl) at different stages of the synthesis. By changing these molecular parameters in the starting materials and intermediates, the method can produce a family of novel fluorodioxolane derivatives rather than a single compound, thereby improving both productivity and chemical versatility.

Inventive Principle:
Principle #35Parameter changes

2Adaptability or versatility

If existing production methods are used, then known compounds can be produced, but novel fluorodioxolane derivatives cannot be synthesized

Engineering Contradiction:
Improveability to produce novel compoundsVSAvoidproduction efficiency
Core Design Contradiction:
Adaptability or versatilityVSProductivity

Solution Approach 1:

The multi-step synthesis method described in the patent serves multiple functions: it can produce various fluorodioxolane derivatives by changing the starting materials, it provides a systematic approach to compound synthesis, and it enables both known and novel compounds to be produced through the same general methodology. This universal approach improves adaptability without sacrificing productivity.

Inventive Principle:
Principle #6Universality (Multi-functionality)

3Productivity

If conventional synthesis routes are used, then production process is established, but the method lacks efficiency and cannot meet demand for fluororesin materials

Engineering Contradiction:
Improveproduction efficiencyVSAvoidmanufacturing process complexity
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The patent employs preliminary action by preparing intermediate compounds (compounds (1), (5), and (6)) through specific reactions before the final coupling step. Compound (1) is prepared by reacting compound (2) with compound (3), then compound (5) is formed by reacting compound (1) with compound (4). These preliminary preparations ensure that the final coupling reaction in Step (C) proceeds efficiently to produce the desired fluorodioxolane derivative (7-1).

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent uses intermediate compounds as mediators in the synthesis pathway. Compound (1) serves as an intermediary between the starting materials and the final product, as does compound (5). These intermediates facilitate the transformation by breaking down the complex synthesis into manageable steps, improving overall manufacturing efficiency while maintaining ease of manufacture through systematic progression.

Inventive Principle:
Principle #24Intermediary (Mediator)

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 method efficiently produces compound (7-1), which can be used as a raw material or intermediate for polymer production, enhancing the availability of fluororesin materials.

Implementation Method 1

step (D1-1) of reacting a compound of formula (6) with alkyl alcohol to produce the compound (7-1)

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Data Source

PatentEP3925954B1Fluorolactone and method for producing same
Publication Date: 2025.12.17 DAIKIN INDUSTRIES LTD
  • EP3925954B1 patent drawing
  • EP3925954B1 patent drawing
  • EP3925954B1 patent drawing

AI summary

The present disclosure provides, for example, a method that can produce a fluorolactone compound from hexafluoropropylene oxide or the like in a single step. The present disclosure relates to a method for producing a compound represented by formula (1): wherein two R1 are the same and each is a fluorine atom or a fluoroalkyl group, the method comprising step A of reacting a compound represented by formula (2): wherein R1 is as defined above, with a compound (3) represented by formula (3-1) or the like: wherein R31, R32, and R33 are the same or different and each is a hydrogen atom or a C1-10 alkyl group, or two of them are optionally linked to each other to form a ring optionally having one or more substituents, in the presence of a fluorine compound (4) represented by formula (4-1) or the like:         MHnFm     (4-1) wherein M is a metal atom, n is 0 or 1, and the sum of the valence number of M and n is m, and an organic solvent, provided that the compound represented by formula (3) is excluded from the organic solvent.