| Identification | More | [Name]
4-Fluoro-1,3-dioxolan-2-one | [CAS]
114435-02-8 | [Synonyms]
4-FLUORO-1,3-DIOXOLAN-2-ONE
FLUOROETHYLENE CARBONATE
4-Fluoroethylene carbonate
FLUOROETHYLENE CARBONATE (FEC)
4-FLUORO-1,3-DIOXALAN-2-ONE | [EINECS(EC#)]
483-360-5 | [Molecular Formula]
C3H3FO3 | [MDL Number]
MFCD06247543 | [Molecular Weight]
106.05 | [MOL File]
114435-02-8.mol |
| Chemical Properties | Back Directory | [Melting point ]
18-23 °C | [Boiling point ]
212℃ | [density ]
1.454 | [vapor pressure ]
51Pa at 25℃ | [refractive index ]
1.3960 to 1.4000 | [Fp ]
>102°(216°F) | [storage temp. ]
2-8°C | [form ]
Liquid | [color ]
Colorless | [Water Solubility ]
Slightly miscible with water. | [Major Application]
battery manufacturing | [InChI]
InChI=1S/C3H3FO3/c4-2-1-6-3(5)7-2/h2H,1H2 | [InChIKey]
SBLRHMKNNHXPHG-UHFFFAOYSA-N | [SMILES]
O1CC(F)OC1=O | [LogP]
-0.435 at 20.1℃ | [CAS DataBase Reference]
114435-02-8(CAS DataBase Reference) | [EPA Substance Registry System]
1,3-Dioxolan-2-one, 4-fluoro- (114435-02-8) |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless liquid | [Uses]
4-Fluoro-1,3-dioxolan-2-one(114435-02-8) is used as an electrolyte additive in lithium ion batteries. It also enables the formation of thin, smooth and stable passive solid electrolyte interphase (SEI) layer, which increases the cycling efficiency and discharge capacity retention of the secondary battery. Further, it is used as an intermediate in organic synthesis.
| [Application]
Fluoroethylene carbonate (FEC,114435-02-8) can be used as organic solvents, synthetic intermediates, pharmaceutical intermediates, electronic chemicals and electrolyte additives, and is mainly used as electrolyte additives for lithium-ion batteries. FEC can inhibit the decomposition of the electrolyte, and form a tightly bonded improved SEI film on the anode, which enhances the low-temperature performance of the electrolyte and improves the specific capacity, cycle stability, and cycle life of lithium-ion batteries. It can improve the specific capacity, cycle stability and cycle life of lithium-ion battery. It plays a crucial role in improving the range, service life and safety of lithium-ion batteries.
| [Preparation]
The preparation of Fluoroethylene carbonate(114435-02-8) is as follows:Add 114g of liquid ethylene carbonate at 50, 1.14g of palladium acetate (II) and 114g of dry acetonitrile (water 100ppm) to a 500ml Monel reactor containing the monophenyl iodine difluoride prepared in step (1) , Stir at 50°C for 0.5h, raise the temperature to 70°C and react for 5h (the molar ratio of ethylene carbonate to hydrogen fluoride in step (1) is 1.1:2.5, the molar ratio of ethylene carbonate to acetonitrile is 1.1:2.8, palladium acetate (II) The dosage is 1.0% of the mass of ethylene carbonate). The tail gas during the reaction was absorbed by potassium hydroxide solution with a mass fraction of 10%. After the reaction, vacuum distillation was carried out under the condition of 3mmHg. The 65-71°C fraction was collected to obtain 103.3g of fluoroethylene carbonate with a GC content of 99.3%. The yield of FEC was 75%.
| [General Description]
We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for energy efficiency. Find details here. | [Flammability and Explosibility]
Notclassified | [Battery Materials]
Fluoroethylene carbonate (FEC) can inhibit the decomposition of the electrolyte, and form a tightly bonded improved SEI film on the anode, which enhances the low-temperature performance of the electrolyte and improves the specific capacity, cycle stability, and cycle life of lithium-ion batteries. It can improve the specific capacity, cycle stability and cycle life of lithium-ion battery. It plays a crucial role in improving the range, service life and safety of lithium-ion batteries. | [Synthesis]
1. 100 g of vinyl carbonate and 370 g of N-fluorotrifluoromethanesulfonamide were added to a sealed reactor and stirring was initiated.
2. Increase the temperature of the reaction system to 120 °C and maintain this temperature for the reaction.
3. The reaction process was monitored by HPLC until the reaction time of vinyl carbonate was undetectable (the reaction time was about 0.9 h) and the reaction was stopped.
4. The fluorinated vinyl carbonate product was obtained by distillation isolation with a purity of >99.9%, a yield of 97.8% and a color of 8 Hazen.
5. Alternative experiment: using 390 g of N-fluorobenzenesulfonamide as fluorination reagent, the reaction time was shortened to 0.5 h under the same reaction conditions. The purity of the product was >99.9%, the yield was 98.2% and the color was 8 Hazen. | [References]
[1] Yanting Jin. “Understanding Fluoroethylene Carbonate and Vinylene Carbonate Based Electrolytes for Si Anodes in Lithium Ion Batteries with NMR Spectroscopy.” Journal of the American Chemical Society 140 31 (2018): 9854–9867.
[2] Rod McMillan. “Fluoroethylene carbonate electrolyte and its use in lithium ion batteries with graphite anodes.” Journal of Power Sources 81 (1999): Pages 20-26.
[3] J. HEINE. Fluoroethylene Carbonate as Electrolyte Additive in Tetraethylene Glycol Dimethyl Ether Based Electrolytes for Application in Lithium Ion and Lithium Metal Batteries[J]. Journal of The Electrochemical Society, 2015, 162 1. DOI:10.1149/2.0011507JES.
[4] XUE-QIANG ZHANG. Fluoroethylene Carbonate Additives to Render Uniform Li Deposits in Lithium Metal Batteries[J]. Advanced Functional Materials, 2017, 27 10. DOI:10.1002/adfm.201605989.
[5] OKUNO Y, USHIROGATA K, SODEYAMA K, et al. Decomposition of the fluoroethylene carbonate additive and the glue effect of lithium fluoride products for the solid electrolyte interphase: an ab initio study?[J]. Physical Chemistry Chemical Physics, 2016, 12: 8643-8653. DOI:10.1039/C5CP07583A. |
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