Bisphenol

The bisphenols (/ˈbɪsfɪnɒl/) are a group of chemical compounds with two hydroxyphenyl functionalities. Most of them are based on diphenylmethane. The exceptions are bisphenol S, P, and M. "Bisphenol" is a common name; the letter following refers to one of the reactants. Bisphenol A is the most popular representative of this group, often simply called "bisphenol."[1]

List

Structural formula Name CAS Reactants Systematic name
Bisphenol A Bisphenol A 80-05-7 Phenol Acetone 2,2-Bis(4-hydroxyphenyl)propane
Bisphenol AP Bisphenol AP 1571-75-1 Phenol Acetophenone 1,1-Bis(4-hydroxyphenyl)-1-phenyl-ethane
Bisphenol AF Bisphenol AF 1478-61-1 Phenol Hexafluoroacetone 2,2-Bis(4-hydroxyphenyl)hexafluoropropane
Bisphenol B Bisphenol B 77-40-7 Phenol Butanone 2,2-Bis(4-hydroxyphenyl)butane
Bisphenol BP Bisphenol BP 1844-01-5 Phenol Benzophenone Bis-(4-hydroxyphenyl)diphenylmethane
Bisphenol C Bisphenol C 79-97-0 o-cresol Acetone 2,2-Bis(3-methyl-4-hydroxyphenyl)propane
Bisphenol CII Bisphenol C 2 14868-03-2 Phenol Dichloromethane Bis(4-hydroxyphenyl)-2,2-dichlorethylene
Bisphenol E Bisphenol E 2081-08-5 Phenol Acetaldehyde 1,1-Bis(4-hydroxyphenyl)ethane
Bisphenol F Bisphenol F 620-92-8 Phenol Formaldehyde Bis(4-hydroxyphenyl)methane
Bisphenol G Bisphenol G 127-54-8 2-Isopropylphenol Acetone 2,2-Bis(4-hydroxy-3-isopropyl-phenyl)propane
Bisphenol M Bisphenol M 13595-25-0 1,3-Bis(2-(4-hydroxyphenyl)-2-propyl)benzene
Bisphenol S Bisphenol S 80-09-1 Phenol Sulfur trioxide Bis(4-hydroxyphenyl)sulfone
Bisphenol P Bisphenol P 2167-51-3 1,4-Bis(2-(4-hydroxyphenyl)-2-propyl)benzene
Bisphenol PH Bisphenol PH 24038-68-4 2-Phenylphenol Acetone 5,5’ -(1-Methylethyliden)-bis[1,1’-(bisphenyl)-2-ol]propane
Bisphenol TMC Bisphenol TMC 129188-99-4 Phenol 3,3,5-Trimethylcyclohexanone 1,1-Bis(4-hydroyphenyl)-3,3,5-trimethyl-cyclohexane
Bisphenol Z Bisphenol Z 843-55-0 Phenol Cyclohexanone 1,1-Bis(4-hydroxyphenyl)-cyclohexane
Dinitrobisphenol A Dinitrobisphenol A 5329-21-5 Bisphenol A nitric acid 2,2-Bis(4-hydroxy-3-nitrophenyl)propane
Tetrabromobisphenol A Tetrabromobisphenol A 79-94-7 Bisphenol A bromine 2,2-Bis(4-hydroxy-3,5-dibromophenyl)propane

Health effects

Bisphenols A (BPA) and S (BPS) have been shown to be endocrine disruptors.[2][3] Due to its high production volumes, BPA has been characterised as a "pseudo-persistent" chemical,[4] leading to its spreading and potential accumulation in a variety of environmental matrices, even though it has a fairly short half-life.[5]

References

  1. ^ Helmut Fiege, Heinz-Werner Voges, Toshikazu Hamamoto, Sumio Umemura, Tadao Iwata, Hisaya Miki, Yasuhiro Fujita, Hans-Josef Buysch, Dorothea Garbe, Wilfried Paulus (2002). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN 978-3527306732.CS1 maint: Uses authors parameter (link).
  2. ^ "BPA-Free Plastic Containers May Be Just as Hazardous". Scientific American. Retrieved 8 August 2015.
  3. ^ "Bisphenol A (BPA) & Bisphenol S (BPS)". SaferChemicals.org. Retrieved 8 August 2015.
  4. ^ Pivnenko, K.; Pedersen, G. A.; Eriksson, E.; Astrup, T. F. (2015-10-01). "Bisphenol A and its structural analogues in household waste paper". Waste Management. 44: 39–47. doi:10.1016/j.wasman.2015.07.017. PMID 26194879.
  5. ^ See Bisphenol A#Environmental effects for extensive discussion
  • For additional examples and alternate names, see: Alger, Mark (2017). Polymer Science Dictionary. Springer. p. 77. ISBN 9789402408935.