Article · Wikipedia archive · Last revised Jul 6, 2026

Tetramethyl bisphenol F

Tetramethyl bisphenol F (TMBPF) is a bisphenol monomer intended as an alternative 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.

Last revised
Jul 6, 2026
Read time
≈ 2 min
Length
502 w
Citations
8
Source
Wikipedia ↗
Tetramethyl bisphenol F
source ↗
Names
Preferred IUPAC name
4,4′-Methylenebis(2,6-dimethylphenol)
Other names
TMBPF, TM-BFP, tetramethyl bisphenol F, valPure V70
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
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
Hazards
GHS labelling:[1]
GHS07: Exclamation markGHS09: Environmental hazard
Warning
H315, H319, H335, H400
P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tetramethyl bisphenol F (TMBPF) is a bisphenol monomer intended as an alternative for bisphenol A and bisphenol F to use in epoxy linings of aluminium cans and steel cans.1 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

Synthesis

TMBPF can be synthesised by a reaction of 2,6-xylenol and formaldehyde.4 Typically formalin is used, which is a 37% solution of formaldehyde. The reaction is acid-catalysed. As such, sulfuric acid is commonly added to the reaction mixture.

Health and environmental effects

Causes serious eye irritation. May cause respiratory and skin irritation. Very toxic to aquatic life.5

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.6 However, a different study did find effects.7

References

References

  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.
  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. Sundell, B.; Shaver, A.; Liu, Q.; Nebipasagil, A.; Pisipati, P.; Mecham, S.; Riffle, J.; Freeman, B.; McGrath, J. (23 October 2014). "Synthesis, oxidation and crosslinking of tetramethyl bisphenol F (TMBPF)-based polymers for oxygen/nitrogen gas separations". Polymer. 55 (22): 5623–5634. doi:10.1016/j.polymer.2014.09.010.
  5. "Safety Data Sheet" (PDF). Toronto Research Chemicals Inc. October 11, 2019. Retrieved 8 December 2020.
  6. 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.
  7. "TMBPF as BPA alternative for coating epoxies | Food Packaging Forum". www.foodpackagingforum.org. 30 November 2018.