Tetramethyl bisphenol F

Tetramethyl bisphenol F (TMBPF) is a new coating intended as a safer replacement for bisphenol A and bisphenol F to use in epoxy linings of aluminium cans and steel cans. It was previously suggested as an insulator in electronic circuit boards.[1]

Tetramethyl bisphenol F
Names
Preferred IUPAC name
4,4′-Methylenebis(2,6-dimethylphenol)
Other names
tetramethyl bisphenol F, valPure V70
Identifiers
3D model (JSmol)
ChEMBL
ECHA InfoCard 100.023.980
EC Number
  • 226-378-9
UNII
  • InChI=1S/C17H20O2/c1-10-5-14(6-11(2)16(10)18)9-15-7-12(3)17(19)13(4)8-15/h5-8,18-19H,9H2,1-4H3
    Key: AZZWZMUXHALBCQ-UHFFFAOYSA-N
  • CC1=CC(=CC(=C1O)C)CC2=CC(=C(C(=C2)C)O)C
Properties
C17H20O2
Molar mass 256.345 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Polymerisation of tetramethyl bisphenol F occurs with epichlorohydrin when heated between 40 and 70 °C using an alkali as a catalyst to form the resin used as a coating.

Health and Environmental Effects

Causes serious eye irritation. May cause respiratory and skin irritation. Very toxic to aquatic life.[2]

Human Endocrine Effects

According to tests TMBPF does not have any effect on the endocrine system; it does not leach out of cans because unlike BPA it is fully polymerized when deposited on the metal, so there is no free chemical to leach out.[1] Tetramethyl bisphenol F was tested on rats to see if there were effects like male or female hormones. It had almost no effects like this.[3] However, a different study did find effects.[4]

References
  1. Cornwall, Warren (23 January 2020). "To replace controversial plastic additive BPA, a chemical company teams up with unlikely allies". Science. doi:10.1126/science.aba9956. S2CID 213508417. Retrieved 8 December 2020.
  2. "Safety Data Sheet" (PDF). Toronto Research Chemicals Inc. October 11, 2019. Retrieved 8 December 2020.
  3. Maffini, Maricel V.; Canatsey, Ryan D. (January 2020). "An expanded toxicological profile of tetramethyl bisphenol F (TMBPF), a precursor for a new food-contact metal packaging coating". Food and Chemical Toxicology. 135: 110889. doi:10.1016/j.fct.2019.110889. PMID 31629790.
  4. "TMBPF as BPA alternative for coating epoxies | Food Packaging Forum". www.foodpackagingforum.org.
  5. "Preparation method of tetramethyl bisphenol F epoxy resin". Google Patents. Google Patents. Retrieved 2020-08-11.
  6. Szafran, Adam T.; Stossi, Fabio; Mancini, Maureen G.; Walker, Cheryl L.; Mancini, Michael A. (2017-07-13). "Characterizing properties of non-estrogenic substituted bisphenol analogs using high throughput microscopy and image analysis". PLOS ONE. 12 (7): e0180141. Bibcode:2017PLoSO..1280141S. doi:10.1371/journal.pone.0180141. PMC 5509144. PMID 28704378.
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