Tetramethyl bisphenol F

Last updated
Tetramethyl bisphenol F
Tetramethyl bisphenol F.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 226-378-9
PubChem CID
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:
GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
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]

Contents

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

  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. 1 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.
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