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
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 [1] 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. [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]

Health and environmental effects

Causes serious eye irritation. May cause respiratory and skin irritation. Very toxic to aquatic life. [4]

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. [5] However, a different study did find effects. [6]

Related Research Articles

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Epoxy is the family of basic components or cured end products of epoxy resins. Epoxy resins, also known as polyepoxides, are a class of reactive prepolymers and polymers which contain epoxide groups. The epoxide functional group is also collectively called epoxy. The IUPAC name for an epoxide group is an oxirane.

<span class="mw-page-title-main">Steel and tin cans</span> Sealed container for storage of foods

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<span class="mw-page-title-main">Polycarbonate</span> Family of polymers

Polycarbonates (PC) are a group of thermoplastic polymers containing carbonate groups in their chemical structures. Polycarbonates used in engineering are strong, tough materials, and some grades are optically transparent. They are easily worked, molded, and thermoformed. Because of these properties, polycarbonates find many applications. Polycarbonates do not have a unique resin identification code (RIC) and are identified as "Other", 7 on the RIC list. Products made from polycarbonate can contain the precursor monomer bisphenol A (BPA).

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<span class="mw-page-title-main">Bisphenol A</span> Chemical compound used in plastics manufacturing

Bisphenol A (BPA) is a chemical compound primarily used in the manufacturing of various plastics. It is a colourless solid which is soluble in most common organic solvents, but has very poor solubility in water. BPA is produced on an industrial scale by the condensation reaction of phenol and acetone. Global production in 2022 was estimated to be in the region of 10 million tonnes.

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Carbonless copy paper (CCP), non-carbon copy paper, or NCR paper is a type of coated paper designed to transfer information written on the front onto sheets beneath. It was developed by chemists Lowell Schleicher and Barry Green, as an alternative to carbon paper and is sometimes misidentified as such.

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<span class="mw-page-title-main">Bisphenol S</span> Chemical compound

Bisphenol S (BPS) is an organic compound with the formula (HOC6H4)2SO2. It has two phenol functional groups on either side of a sulfonyl group. It is commonly used in curing fast-drying epoxy resin adhesives. It is classified as a bisphenol, and a close molecular analog of bisphenol A (BPA). BPS differentiates from BPA by possessing a sulfone group (SO2) as the central linker of the molecule instead of a dimethylmethylene group (C 2), which is the case of bisphenol A.

<span class="mw-page-title-main">2,2,4,4-Tetramethyl-1,3-cyclobutanediol</span> Chemical compound

2,2,4,4-Tetramethyl-1,3-cyclobutanediol (CBDO) is an aliphatic diol. This diol is produced as a mixture of cis- and trans-isomers, depending on the relative stereochemistry of the hydroxyl groups. It is used as a monomer for the synthesis of polymeric materials, usually as an alternative to bisphenol A (BPA). CBDO is used in the production of tritan copolyester which is used as a BPA-free replacement for polycarbonate.

<span class="mw-page-title-main">Bisphenol A diglycidyl ether</span> Chemical compound

Bisphenol A diglycidyl ether is an organic compound and is a liquid epoxy resin. The compound is a colorless viscous liquid. It is a key component of many epoxy resin formulations. Addition of further Bisphenol A and a catalyst and heat can produce Bisphenol A glycidyl ether epoxy resins of higher molecular weight that are solid.

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<span class="mw-page-title-main">Bisphenol F</span> Chemical compound

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.

<span class="mw-page-title-main">Health effects of Bisphenol A</span> Controversy centering on concerns about the biomedical significance of bisphenol A (BPA)

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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. "Safety Data Sheet" (PDF). Toronto Research Chemicals Inc. October 11, 2019. Retrieved 8 December 2020.
  5. 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.
  6. "TMBPF as BPA alternative for coating epoxies | Food Packaging Forum". www.foodpackagingforum.org. 30 November 2018.