Tetramethyl bisphenol F
Chemical compound
From Wikipedia, the free encyclopedia
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]
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| Names | |
|---|---|
| Preferred IUPAC name
4,4′-Methylenebis(2,6-dimethylphenol) | |
| Other names
TMBPF, TM-BFP, tetramethyl bisphenol F, valPure V70 | |
| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.023.980 |
| EC Number |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C17H20O2 | |
| Molar mass | 256.345 g·mol−1 |
| Hazards | |
| GHS labelling: | |
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| 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).
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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]