One stone two birds: Degradation of persistent organic pollutants to a valuable industrial chemical production of pentafluoropropionyl fluoride from HFPO oligomers catalyzed by cesium fluoride in tetraglyme

Hexafluoropropylene oxide (HFPO) oligomers are toxic, bioaccumulative, and persistent organic pollutants (POPs). Consuming the harmful chemicals to prevent them from releasing to nature is of serious significance as far as both natural environments and human health are concerned. In this study, investigation on degradation of HFPO oligomers to pentafluoropropionyl fluoride (PPF), a valuable industrial chemical, is reported. Different combinations of alkali metal fluoride in either diglyme or tetraglyme under both flask and batch autoclave conditions were examined. Under the optimal reaction conditions, HFPO oligomers (n = 2–10) were completely degraded to PPF in over 90% yield. Reactions on 200 g scale were tested and no deduction of efficiency was observed, which indicates the potential for practical industrial application of this chemistry.

Graphical abstractDegradation of HFPO oligomers, persistent organic pollutants harmful to human and natural environment, to pentafluoropropionyl fluoride (PPF), a valuable industrial chemical widely used for manufacture of important chemical products, such as Novec 1230, PPVE, GenX etc. is reported using CsF/tetraglyme as catalytic system under both flask and autoclave conditions.Figure optionsDownload full-size imageDownload as PowerPoint slide