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- Conflict of Interest
- In relation to this article, we declare that there is no conflict of interest.
- Publication history
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Received October 17, 2023
Accepted January 13, 2024
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This is an Open-Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/bync/3.0) which permits
unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
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Synthesis of Hexafluoropropylene Oxide from Hexafluoropropylene and Hypochlorite Using Hydrofluoroether Solven
Abstract
Hexafl uoropropylene oxide (HFPO) is a versatile fl uorochemical widely used in the synthesis of various fl uorinated compounds
and fl uorinated polymers. In this paper, we report on the successful synthesis of HFPO via the epoxidation of hexafl
uoropropylene (HFP) with NaOCl in a two-phase solvent system. Among the organic phase solvents tested, hydrofl uoroethers
such as C 4 F 9 OCH 3 , C 4 F 9 OC 2 H 5, and C 7 F 15 OC 2 H 5 showed high HFPO yields, indicating their potential to replace
conventional CFCl 2 CF 2 Cl (CFC-113), which is ozone depleting and global warming chemical. When the reaction was
carried out for 20 min at room temperature, the C 4 F 9 OCH 3 —water two-phase system produced HFPO with over 40% yield
and over 70% selectivity. To optimize the reaction conditions, various reaction parameters were investigated, including the
effects of NaOH and phase transition catalysts. Analysis of the by-products using 19 F and 13 C NMR and X-ray diff raction
(XRD) showed that HFP/HFPO decomposes during oxidation to F¯, CO 2 , oxalate, trifl uoroacetate, etc. Density functional
theory (DFT) calculations elucidated the reaction pathway of this epoxidation: with a lower E-barrier of 12.8 kcal/mol, the
nucleophilic attack of OCl¯ on the β-carbon of HFP is preferable to the α-carbon pathway.
