Tetramethyl bisphenol F

Last updated
Tetramethyl bisphenol F
Tetramethyl bisphenol F.png
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 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
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 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]

Contents

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]

Related Research Articles

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Bisphenol F is an organic compound with the chemical formula (HOC
6
H
4
)
2
CH
2
. It is structurally related to bisphenol A (BPA), a popular precursor for forming plastics, as both belong to the category of molecules known as bisphenols, which feature two phenol groups connected via a linking group. In BPF, the two aromatic rings are linked by a methylene connecting group. In response to concern about the health effects of BPA, BPF is increasingly used as a substitute for BPA.

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Bisphenol A controversy centers on concerns and debates about the biomedical significance of bisphenol A (BPA), which is a precursor to polymers that are used in some consumer products, including some food containers. The concerns began with the hypothesis that BPA is an endocrine disruptor, i.e. it mimics endocrine hormones and thus has the unintended and possibly far-reaching effects on people in physical contact with the chemical.

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References

  1. 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.
  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.