Bisphenol AF (BPAF) is a fluorinated organic compound that is an analogue of bisphenol A in which the two methyl groups are replaced with trifluoromethyl groups. It exists as a white to light-gray powder.
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| Names | |
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| Preferred IUPAC name
4,4′-(1,1,1,3,3,3-Hexafluoropropane-2,2-diyl)diphenol | |
| Other names
Biphenol AF; Hexafluorobisphenol A; Hexafluorodiphenylolpropane; Bisphenol A hexafluoride; 4,4'-(Hexafluoroisopropylidene)diphenol; Hexafluoroacetone bisphenol A; 2,2-Bis(4-hydroxyphenyl)hexafluoropropane
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| Identifiers | |
3D model (JSmol)
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| Abbreviations | BPAF |
| ChemSpider | |
| ECHA InfoCard | 100.014.579 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C15H10F6O2 | |
| Molar mass | 336.233 g·mol−1 |
| Melting point | 162 °C[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Biological and Chemical Action
editBisphenol AF is an endocrine disrupting chemical.[2] Whereas BPA binds with human estrogen-related receptor gamma (ERR-γ), BPAF all but ignores ERR-γ. Instead, BPAF activates ERR-α and binds to and disables ERR-β.[3]
The chemical shifts in 1H, 13C and 19F NMR spectroscopy are given in the literature.[4]
Applications
editBisphenol AF is used as a crosslinking agent for certain fluoroelastomers and as a monomer for polyimides, polyamides, polyesters, polycarbonate copolymers and other specialty polymers. Polymers containing Bisphenol AF are useful in specialties such as high-temperature composites and electronic materials. Industries include cosmetics, chemical manufacturing, production of metals and rubber. It can also be a plastic additive.[5]
See also
editReferences
edit- ^ Hayasaka, Tatsuya; Katsuhara, Yutaka; Kume, Takashi; Yamazaki, Takashi (2011). "HF-mediated equilibrium between fluorinated ketones and the corresponding α-fluoroalcohols". Tetrahedron. 67 (12): 2215–2219. doi:10.1016/j.tet.2011.01.087.
- ^ Escrivá, Laura; Hanberg, Annika; Zilliacus, Johanna; Beronius, Anna (September 2019). "Assessment of the endocrine disrupting properties of Bisphenol AF according to the EU criteria and ECHA/EFSA guidance". EFSA Journal. 17 (EU‐FORA: Series 2): e170914. doi:10.2903/j.efsa.2019.e170914. PMC 7015508. PMID 32626472.
- ^ "Janet Raloff: Another plastics ingredient raises safety concerns, Science News, June 5th, 2010; Vol.177 #12 (p. 14)". Archived from the original on 2012-09-27. Retrieved 2010-06-11.
- ^ Hayasaka, Tatsuya; Katsuhara, Yutaka; Kume, Takashi; Yamazaki, Takashi (2011). "HF-mediated equilibrium between fluorinated ketones and the corresponding α-fluoroalcohols". Tetrahedron. 67 (12): 2215–2219. doi:10.1016/j.tet.2011.01.087.
- ^ "Bisphenol AF". PubChem. National Library of Medicine. Retrieved 20 January 2021.