Tetramethyl bisphenol F

Tetramethyl bisphenol F
Names
	Preferred IUPAC name 4,4′-Methylenebis(2,6-dimethylphenol)
	Other names TMBPF, TM-BFP, tetramethyl bisphenol F, valPure V70
Identifiers
CAS Number	5384-21-4;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL593206;
ECHA InfoCard	100.023.980
EC Number	226-378-9;
PubChem CID	79345;
UNII	JH6FV2EG7J ;
CompTox Dashboard (EPA)	DTXSID4063820 ;
	InChI 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;
	SMILES CC1=CC(=CC(=C1O)C)CC2=CC(=C(C(=C2)C)O)C;
Properties
Chemical formula	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

Tetramethyl bisphenol F (TMBPF) is a new coating intended as a safer replacement^[1] 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.^[2]

Polymerization 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.^[3]

Health and environmental effects

Causes serious eye irritation. May cause respiratory and skin irritation. Very toxic to aquatic life.^[4]

Human endocrine effects

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.^[2] 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.^[5] However, a different study did find effects.^[6]

References

^ 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.
^ ^a ^b 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.
^ "Preparation method of tetramethyl bisphenol F epoxy resin". Google Patents. Google Patents. Retrieved 2020-08-11.
^ "Safety Data Sheet" (PDF). Toronto Research Chemicals Inc. October 11, 2019. Retrieved 8 December 2020.
^ 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.
^ "TMBPF as BPA alternative for coating epoxies | Food Packaging Forum". www.foodpackagingforum.org. 30 November 2018.

[1] 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.

[Cornwall-2] 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.

[3] "Preparation method of tetramethyl bisphenol F epoxy resin". Google Patents. Google Patents. Retrieved 2020-08-11.

[4] "Safety Data Sheet" (PDF). Toronto Research Chemicals Inc. October 11, 2019. Retrieved 8 December 2020.

[5] 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.

[6] "TMBPF as BPA alternative for coating epoxies | Food Packaging Forum". www.foodpackagingforum.org. 30 November 2018.

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