Chemistry:Bisphenol
The bisphenols (/ˈbɪsfɪnɒl/) are a group of industrial chemical compounds related to diphenylmethane; commonly used in the production of plastics and epoxy resins. They feature two hydroxyphenyl groups linked by a methylene bridge. Also included are bisphenol S, P, and M. "Bisphenol" is a common name; the letter following denotes the variant, which depends on the additional substituents. Bisphenol A is the most common representative of the group, with millions of metric tons produced globally in the past decade, often simply called "bisphenol".[1]
Bisphenols have attracted controversy because of their role as endocrine disruptors.[2][3]
List
| Structural formula | Name | CAS | Reactants | |
|---|---|---|---|---|
 |
Bisphenol A | 80-05-7 | Phenol | Acetone |
 |
Bisphenol AP | 1571-75-1 | Phenol | Acetophenone |
 |
Bisphenol AF | 1478-61-1 | Phenol | Hexafluoroacetone |
 |
Bisphenol B | 77-40-7 | Phenol | Butanone |
 |
Bisphenol BP | 1844-01-5 | Phenol | Benzophenone |
 |
Bisphenol C | 79-97-0 | o-cresol | Acetone |
 |
Bisphenol C 2 | 14868-03-2 | Phenol | Chloral |
 |
Bisphenol E | 2081-08-5 | Phenol | Ethanal |
 |
Bisphenol F | 620-92-8 | Phenol | Formaldehyde |
 |
Bisphenol G | 127-54-8 | 2-Isopropylphenol | Acetone |
 |
Bisphenol M | 13595-25-0 | ||
 |
Bisphenol S | 80-09-1 | Phenol | Sulfur trioxide |
 |
Bisphenol P | 2167-51-3 | ||
 |
Bisphenol PH | 24038-68-4 | 2-Phenylphenol | Acetone |
 |
Bisphenol TMC | 129188-99-4 | Phenol | 3,3,5-Trimethylcyclohexanone |
 |
Bisphenol Z | 843-55-0 | Phenol | Cyclohexanone |
 |
Dinitrobisphenol A | 5329-21-5 | Bisphenol A | Nitric acid |
 |
Tetrabromobisphenol A | 79-94-7 | Bisphenol A | Bromine |
 |
Tetramethyl bisphenol F | 5384-21-4 | 2,6-Xylenol | Formaldehyde |
Health effects
Bisphenols A (BPA), F (BPF) and S (BPS) have been shown to be endocrine disruptors, potentially relating to adverse health effects.[2][4] Due to its high production volumes, BPA has been characterised as a "pseudo-persistent" chemical,[5] leading to its spreading and potential accumulation in a variety of environmental matrices, even though it has a fairly short half-life.[6][7][8][2]
References
- ↑ "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2002. doi:10.1002/14356007.a19_313. ISBN 978-3-527-30673-2..
- ↑ 2.0 2.1 2.2 "Bisphenol A: Food Exposure and Impact on Human Health". Comprehensive Reviews in Food Science and Food Safety 17 (6): 1503–1517. November 2018. doi:10.1111/1541-4337.12388. PMID 33350146.
- ↑ "Bisphenol-A and the great divide: a review of controversies in the field of endocrine disruption". Endocrine Reviews 30 (1): 75–95. February 2009. doi:10.1210/er.2008-0021. PMID 19074586.
- ↑ "BPA-Free Plastic Containers May Be Just as Hazardous". 11 August 2014. http://www.scientificamerican.com/article/bpa-free-plastic-containers-may-be-just-as-hazardous/.
- ↑ "Bisphenol A and its structural analogues in household waste paper". Waste Management 44: 39–47. October 2015. doi:10.1016/j.wasman.2015.07.017. PMID 26194879. Bibcode: 2015WaMan..44...39P. https://backend.orbit.dtu.dk/ws/files/118749778/PostPrint_Davidsen_JoH_1_.pdf.
- ↑ See Bisphenol A for extensive discussion
- ↑ NTP Research Report on Biological Activity of Bisphenol A (BPA) Structural Analogues and Functional Alternatives: Research Report 4. NTP Research Reports. Research Triangle Park (NC): National Toxicology Program. 2017. https://www.ncbi.nlm.nih.gov/books/NBK538922/.
- ↑ "Bisphenol F affects neurodevelopmental gene expression, mushroom body development, and behavior in Drosophila melanogaster". Neurotoxicology and Teratology 102. 2024-03-01. doi:10.1016/j.ntt.2024.107331. PMID 38301979. Bibcode: 2024NTxT..10207331F.
Further reading
- For additional examples and alternate names, see: Polymer Science Dictionary. Springer. 2017. p. 77. ISBN 978-94-024-0893-5.
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