Fluorinated Cyclic Carbonate Synthesis for Li-Ion Battery Additives
Find Innovative SolutionsGenerate Solutions
Solution Overview
Problem
Current technologies lack the production methods for novel cyclic organic carbonates containing a fluorine atom, which are essential as additives or solvents for lithium ion batteries.
Innovation Solution
A process involving the cyclization of compounds like FC(O)OCHR'C(O)R and subsequent chlorine-fluorine exchange to produce high-purity 4-fluoro-4-R-5-R'-1,3-dioxolane-2-ones, where R is alkyl and R' is H or a Cl to C3 alkyl group, using catalysts like nitrogen-containing heterocyclic compounds or acids, and performing reactions at elevated temperatures in the liquid phase.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Adaptability or versatility
If conventional methods are used to prepare halogen-substituted cyclic carbonates, then chlorosubstituted compounds can be obtained, but fluorinated compounds cannot be produced
Solution Approach 1:
The patent changes the halogen parameter in the starting materials from chlorine to fluorine, enabling the production of fluorinated cyclic carbonates. By using carbonyl fluoride instead of carbonyl chloride and maintaining the same cyclization conditions, the process successfully produces fluorinated compounds that were previously unavailable through conventional methods.
2Manufacturing precision
If high purity 4-fluoro-4-R-5-R'-1,3-dioxolane-2-ones are produced through multiple steps, then product quality improves, but production time and complexity increase
Solution Approach 1:
The patent combines the addition reaction and cyclization step into a single one-pot process. The starting materials carbonyl fluoride and hydroxyketone are reacted together in the presence of a base catalyst to directly form the fluorinated cyclic carbonate product with purity ≥99%, eliminating the need for separate purification steps and intermediate isolation.
Solution Approach 2:
The patent performs the cyclization reaction under optimized conditions that directly yield high-purity product. By pre-selecting appropriate base catalysts and reaction conditions, the process achieves ≥99% purity in a single step without requiring subsequent purification operations.
3Productivity
If cyclization reaction is performed at elevated temperatures, then reaction rate increases, but energy consumption increases
Solution Approach 1:
The patent changes the kinetic parameter by introducing a base catalyst that enables the cyclization reaction to proceed at room temperature or mild temperatures. The catalyst lowers the activation energy barrier, allowing the reaction to achieve practical rates without requiring elevated temperature heating.
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 high-purity 4-fluoro-4-R-5-R'-1,3-dioxolane-2-ones, which are suitable as additives or solvents for lithium ion batteries, enhancing their performance by forming protective films on electrodes.
Implementation Method 1
The cyclization reaction is preferably catalyzed. According to one embodiment, the cyclization reaction is catalyzed by a nitrogen containing heterocyclic compound or by fluoride ions.
Implementation Method 2
a step of cyclization of compounds of formula (IF), ClC(O)OCHR' C(O)R wherein R is alkyl and R' is H or a Cl to C3 alkyl group, and a step of a subsequent chlorine- fluorine exchange.
Data Source
AI summary
The present invention concerns 4-fluoro-4-R-5-R'-1,3-dioxolane-2-ones, wherein R is an alkyl group and R' is H or a C1 to C3 alkyl group, their manufacture, solvent mixtures for lithium ion batteries containing them and conductive salt solutions for lithium ion batteries, e.g. solutions containing LiPF6.