Chemistry:Tetramethyl bisphenol F
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| Names | |
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| Preferred IUPAC name
4,4′-Methylenebis(2,6-dimethylphenol) | |
| Other names
TMBPF, TM-BFP, tetramethyl bisphenol F, valPure V70
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3D model (JSmol)
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| Properties | |
| C17H20O2 | |
| Molar mass | 256.345 g·mol−1 |
| Hazards | |
| GHS pictograms |  
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| GHS Signal word | Warning |
| H315, H319, H335, H400 | |
| P261, P264, P264+265Script error: No such module "Preview warning".Category:GHS errors, P271, P273, P280, P302+352, P304+340, P305+351+338, P319Script error: No such module "Preview warning".Category:GHS errors, P321, P332+317Script error: No such module "Preview warning".Category:GHS errors, P337+317Script error: No such module "Preview warning".Category:GHS errors, P362+364Script error: No such module "Preview warning".Category:GHS errors, P391, P403+233, P405, P501 | |
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 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
- ↑ 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). doi:10.1371/journal.pone.0180141. PMID 28704378. Bibcode: 2017PLoSO..1280141S.
- ↑ 2.0 2.1 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. https://www.science.org/content/article/replace-controversial-plastic-additive-bpa-chemical-company-teams-unlikely-allies. Retrieved 8 December 2020.
- ↑ "Preparation method of tetramethyl bisphenol F epoxy resin". Google Patents. https://patents.google.com/patent/CN104479105A/en.
- ↑ Sundell, B.; Shaver, A.; Liu, Q.; Nebipasagil, A.; Pisipati, P.; Mecham, S.; Riffle, J.; Freeman, B. et al. (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.
- ↑ "Safety Data Sheet". Toronto Research Chemicals Inc.. October 11, 2019. https://www.trc-canada.com/prod-img/MSDS/M304433MSDS.pdf.
- ↑ 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. doi:10.1016/j.fct.2019.110889. PMID 31629790.
- ↑ "TMBPF as BPA alternative for coating epoxies | Food Packaging Forum". 30 November 2018. https://www.foodpackagingforum.org/news/tmbpf-as-bpa-alternative-for-coating-epoxies.
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