Bisphenol S
| Bisphenol S | |
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4,4'-Sulfonyldiphenol |
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Other names
BPS, 4,4'-sulfonylbisphenol, |
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| Identifiers | |
| CAS number | 80-09-1  |
| PubChem | 6626 |
| ChemSpider | 6374 |
| KEGG | C14216 |
| ChEMBL | CHEMBL384441 |
| Jmol-3D images | Image 1 Image 2 |
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| Properties | |
| Molecular formula | C12H10O4S |
| 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[1] |
| Solubility in water | insoluble |
| Solubility | soluble in ethanol |
| Hazards | |
| R-phrases | R36 [1] |
| S-phrases | S26 [2] |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
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| Infobox references | |
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).
Synthesis[edit]
Bisphenol S is prepared by the reaction of two equivalents of phenol with one equivalent of sulfuric acid.
- 2 C6H5OH + H2SO4 → (C6H4OH)2SO2 + 2 H2O
This reaction can also produce 2,4'-sulfonyldiphenol.
History and use[edit]
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.[2][3] Bisphenol S also has the advantage of being more stable to heat and light than BPA.[4] In some cases, bisphenol S is used where the legal prohibition on BPA allows products containing bisphenol S to be labelled "BPA free".[5]
Toxicity[edit]
Bisphenol S has been shown to have similar in vitro estrogenic activity to BPA.[4][6][7]
See also[edit]
References[edit]
- ^ www.sigmaaldrich.com
- ^ 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. doi:10.1021/es300876n.
- ^ 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.
- ^ a b 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. doi:10.1289/ehp.1205826.
- ^ 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.
