Bisphenol S

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Bisphenol S
Bisphenol S
Identifiers
CAS number 80-09-1 YesY
PubChem 6626
ChemSpider 6374 YesY
KEGG C14216 YesY
ChEMBL CHEMBL384441 YesY
Jmol-3D images Image 1
Image 2
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)
 YesY (verify) (what is: YesY/N?)
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.

Chemical reaction to bisphenol S


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".[citation needed]

Toxicity[edit]

Bisphenol S has been shown to have similar in vitro estrogenic activity to BPA.[4][5][6]

See also[edit]

References[edit]

  1. ^ www.sigmaaldrich.com
  2. ^ 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.  edit
  3. ^ 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.  edit
  4. ^ 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.  edit
  5. ^ 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.  edit
  6. ^ 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.  edit