|Jmol-3D images||Image 1
|Molar mass||250.275 g/mol|
|Appearance||White colorless solid; forms needle shaped crystals in water|
|Density||1.3663 g/cm3, solid|
|Melting point||245 − 250 °C|
|Solubility in water||insoluble|
|Solubility||soluble in ethanol|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
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 as a reactant in epoxy reactions, and is used in curing fast-drying epoxy resin glues. It is an analog of bisphenol A (BPA) in which the dimethylmethylene group (C(CH3)2) is replaced with a sulfone group (SO2).
- 2 C6H5OH + H2SO4 → (C6H4OH)2SO2 + 2 H2O
This reaction can also produce 2,4'-sulfonyldiphenol.
History and use
Bisphenol S is used in curing fast-drying epoxy glues and as an anticorrosive. It is also commonly used as a reactant in polymer reactions.
Bisphenol S has become increasingly common as a plasticizing agent following the widespread bans on the use of BPA due to its estrogen-mimicking properties, and bisphenol S can now be found in a variety of common consumer products. Bisphenol S also has the advantage of being more stable to heat and light than BPA. In some cases, bisphenol S is used where the legal prohibition on BPA allows products containing bisphenol S to be labelled "BPA free".
- Liao, C.; Liu, F.; Kannan, K. (2012). "Bisphenol S, a New Bisphenol Analogue, in Paper Products and Currency Bills and Its Association with Bisphenol a Residues". Environmental Science & Technology 46 (12): 6515–22. doi:10.1021/es300876n. PMID 22591511.
- Liao, C.; Liu, F.; Guo, Y.; Moon, H. B.; Nakata, H.; Wu, Q.; Kannan, K. (2012). "Occurrence of Eight Bisphenol Analogues in Indoor Dust from the United States and Several Asian Countries: Implications for Human Exposure". Environmental Science & Technology 46 (16): 9138. doi:10.1021/es302004w.
- Kuruto-Niwa, R.; Nozawa, R.; Miyakoshi, T.; Shiozawa, T.; Terao, Y. (2005). "Estrogenic activity of alkylphenols, bisphenol S, and their chlorinated derivatives using a GFP expression system". Environmental Toxicology and Pharmacology 19 (1): 121–130. doi:10.1016/j.etap.2004.05.009. PMID 21783468.
- Jenna Bilbrey (Aug 11, 2014). "BPA-Free Plastic Containers May Be Just as Hazardous". Scientific American.
- Viñas, R.; Watson, C. S. (2013). "Bisphenol S Disrupts Estradiol-Induced Nongenomic Signaling in a Rat Pituitary Cell Line: Effects on Cell Functions". Environmental Health Perspectives 121 (3): 352–8. doi:10.1289/ehp.1205826. PMID 23458715.
- Ji, K.; Hong, S.; Kho, Y.; Choi, K. (2013). "Effects of Bisphenol S Exposure on Endocrine Functions and Reproduction of Zebrafish". Environmental Science & Technology: 130711134644006. doi:10.1021/es400329t.