Bisphenol S

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Bisphenol S
Bisphenol S
Names
IUPAC name
4,4'-Sulfonyldiphenol
Other names
BPS, 4,4'-sulfonylbisphenol,
bis(4-hydroxyphenyl)sulfone
Identifiers
80-09-1 YesY
ChEMBL ChEMBL384441 YesY
ChemSpider 6374 YesY
Jmol-3D images Image
Image
KEGG C14216 YesY
PubChem 6626
Properties
C12H10O4S
Molar mass 250.27 g·mol−1
Appearance White colorless solid; forms needle shaped crystals in water
Density 1.3663 g/cm3
Melting point 245 to 250 °C (473 to 482 °F; 518 to 523 K)[1]
insoluble
Solubility soluble in ethanol
Hazards
R-phrases R36
S-phrases S26
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY verify (what isYesY/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 in curing fast-drying epoxy resin adhesives. It is an analog of bisphenol A (BPA) in which the dimethylmethylene group (C(CH3)2) is replaced with a sulfone group (SO2).

Use[edit]

BPS is used in curing fast-drying epoxy glues and as an corrosion inhibitor. It is also commonly used as a reactant in polymer reactions.

BPS has become increasingly common as a plasticizing agent following the widespread bans on the use of BPA due to its estrogen-mimicking properties, and BPS can now be found in a variety of common consumer products.[2][3] In some cases, BPS is used where the legal prohibition on BPA allows products containing BPS to be labelled "BPA free".[4] BPS also has the advantage of being more stable to heat and light than BPA.[5]

Toxicity[edit]

Bisphenol S has been shown to have similar in vitro estrogenic activity to BPA.[5][6][7]

History[edit]

BPS was first made in 1869 as a dye.[8]

Studies have shown that BPS is not a chemical that is newly incorporated into everyday consumer products, but one that is just being brought to public awareness.[9]

Regulation[edit]

It is difficult for consumers to determine if a product contains BPS due to limited labeling regulations.[10]

Synthesis[edit]

Bisphenol S is prepared by the reaction of two equivalents of phenol with one equivalent of sulfuric acid or oleum.[11]

2 C6H5OH + H2SO4 → (C6H4OH)2SO2 + 2 H2O
2 C6H5OH + SO3 → (C6H4OH)2SO2 + H2O

This reaction can also produce 2,4'-sulfonyldiphenol, a common isomeric complication in electrophilic aromatic substitution reactions.

Chemical reaction to bisphenol S

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): 6515–22. doi:10.1021/es300876n. PMID 22591511.  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): 9138–9145. doi:10.1021/es302004w.  edit
  4. ^ Jenna Bilbrey (Aug 11, 2014). "BPA-Free Plastic Containers May Be Just as Hazardous". Scientific American. 
  5. ^ 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
  6. ^ 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.  edit
  7. ^ Ji, K.; Hong, S.; Kho, Y.; Choi, K. (2013). "Effects of Bisphenol S Exposure on Endocrine Functions and Reproduction of Zebrafish". Environmental Science & Technology: 8793–8800. doi:10.1021/es400329t.  edit
  8. ^ Glausiusz, Josie. "Toxicology: The plastics puzzle". Nature Publishing Group. Retrieved 25 March 2015. 
  9. ^ Brian, Bienkowski. "BPA replacement alters hormones at low doses, study finds". Environmental Health News. Environmental Health Sciences. Retrieved 23 March 2015. 
  10. ^ Howard, Brian. "Chemical in BPA-Free Products Linked to Irregular Heartbeats". National Geographic. National Geographic. Retrieved 29 March 2015. 
  11. ^ METHOD OF PREPARATION OF 4,4′-DIHYDROXYDIPHENYLSULPHONE (Freepatentsonline).