The bisphenols are a group of industrial chemical compounds related to diphenylmethane; commonly used in the creation of plastics and epoxy resins. Most are based on two hydroxyphenyl functional groups linked by a methylene bridge. Exceptions include 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 popular representative of the group, with millions of metric tons produced globally in the past decade, often simply called "bisphenol".
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| 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 | |
Health effects
Bisphenols A (BPA), F (BPF) and S (BPS) have been shown to be endocrine disruptors, potentially relating to adverse health effects.78 Due to its high production volumes, BPA has been characterised as a "pseudo-persistent" chemical,9 leading to its spreading and potential accumulation in a variety of environmental matrices, even though it has a fairly short half-life.10
Further reading
- For additional examples and alternate names, see: Alger M (2017). Polymer Science Dictionary. Springer. p. 77. ISBN 978-94-024-0893-5.
References
Pelch KE, Wignall JA, Goldstone AE, Ross PK, Blain RB, Shapiro AJ, et al. (2017). 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. PMID 31944638. http://www.ncbi.nlm.nih.gov/books/NBK538922/ ↩
Fishburn JL, Larson HL, Nguyen A, Welch CJ, Moore T, Penn A, et al. (2024-03-01). "Bisphenol F affects neurodevelopmental gene expression, mushroom body development, and behavior in Drosophila melanogaster". Neurotoxicology and Teratology. 102: 107331. Bibcode:2024NTxT..10207331F. doi:10.1016/j.ntt.2024.107331. PMID 38301979. https://doi.org/10.1016%2Fj.ntt.2024.107331 ↩
Almeida S, Raposo A, Almeida-González M, Carrascosa C (November 2018). "Bisphenol A: Food Exposure and Impact on Human Health". Comprehensive Reviews in Food Science and Food Safety. 17 (6): 1503–1517. doi:10.1111/1541-4337.12388. PMID 33350146. /wiki/Doi_(identifier) ↩
Almeida S, Raposo A, Almeida-González M, Carrascosa C (November 2018). "Bisphenol A: Food Exposure and Impact on Human Health". Comprehensive Reviews in Food Science and Food Safety. 17 (6): 1503–1517. doi:10.1111/1541-4337.12388. PMID 33350146. /wiki/Doi_(identifier) ↩
Vandenberg LN, Maffini MV, Sonnenschein C, Rubin BS, Soto AM (February 2009). "Bisphenol-A and the great divide: a review of controversies in the field of endocrine disruption". Endocrine Reviews. 30 (1): 75–95. doi:10.1210/er.2008-0021. PMC 2647705. PMID 19074586. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2647705 ↩
Fiege H, Voges HW, Hamamoto T, Umemura S, Iwata T, Miki H, et al. (2002). "Phenol Derivatives". Phenol Derivatives. Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN 978-3-527-30673-2.. 978-3-527-30673-2 ↩
Almeida S, Raposo A, Almeida-González M, Carrascosa C (November 2018). "Bisphenol A: Food Exposure and Impact on Human Health". Comprehensive Reviews in Food Science and Food Safety. 17 (6): 1503–1517. doi:10.1111/1541-4337.12388. PMID 33350146. /wiki/Doi_(identifier) ↩
Bilbrey J (11 August 2014). "BPA-Free Plastic Containers May Be Just as Hazardous". Scientific American. Retrieved 8 August 2015. http://www.scientificamerican.com/article/bpa-free-plastic-containers-may-be-just-as-hazardous/ ↩
Pivnenko K, Pedersen GA, Eriksson E, Astrup TF (October 2015). "Bisphenol A and its structural analogues in household waste paper" (PDF). Waste Management. 44: 39–47. Bibcode:2015WaMan..44...39P. doi:10.1016/j.wasman.2015.07.017. PMID 26194879. S2CID 217938141. https://backend.orbit.dtu.dk/ws/files/118749778/PostPrint_Davidsen_JoH_1_.pdf ↩
See Bisphenol A#Environmental effects for extensive discussion /wiki/Bisphenol_A#Environmental_effects ↩