Bisphenol S

Quality 0.50 · 1 view · Updated 2 months ago

title: "Bisphenol S" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["bisphenols", "endocrine-disruptors", "estrogens", "nonsteroidal-antiandrogens", "benzosulfones"] topic_path: "general/bisphenols" source: "https://en.wikipedia.org/wiki/Bisphenol_S" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Name = Bisphenol S | ImageFile = Bisphenol S.svg | ImageName = Bisphenol S | ImageSize = 220px | ImageFile2 = Bisphenol S 3D BS-fixed.png | ImageName2 = Bisphenol S 3D BS | ImageSize2 = 220px | OtherNames = BPS, 4,4′-sulfonylbisphenol, Bis(4-hydroxyphenyl)sulfone | PIN = 4,4′-Sulfonyldiphenol | Section1 = {{Chembox Identifiers |ChemSpiderID_Ref = |ChemSpiderID = 6374 |UNII_Ref = |UNII = 3OX4RR782R |PubChem = 6626 |KEGG_Ref = |KEGG = C14216 |EC_number = 201-250-5 |ChEBI = 34372 |InChI = 1/C12H10O4S/c13-9-1-5-11(6-2-9)17(15,16)12-7-3-10(14)4-8-12/h1-8,13-14H |SMILES = O=S(=O)(c1ccc(O)cc1)c2ccc(O)cc2 |InChIKey = VPWNQTHUCYMVMZ-UHFFFAOYAO |SMILES1 = c1cc(ccc1O)S(=O)(=O)c2ccc(cc2)O |ChEMBL_Ref = |ChEMBL = 384441 |StdInChI_Ref = |StdInChI = 1S/C12H10O4S/c13-9-1-5-11(6-2-9)17(15,16)12-7-3-10(14)4-8-12/h1-8,13-14H |StdInChIKey_Ref = |StdInChIKey = VPWNQTHUCYMVMZ-UHFFFAOYSA-N |CASNo_Ref = |CASNo = 80-09-1 | Section2 = {{Chembox Properties |C=12 | H=10 | O=4 | S=1 |Appearance = White colorless solid; forms needle shaped crystals in water |Density = 1.3663 g/cm3 |Solubility = 1100 mg/L |SolubleOther = Soluble in ethanol |MeltingPtC = 245 to 250 |MeltingPt_ref = | Section3 = {{Chembox Hazards |GHSPictograms = |GHSSignalWord = Warning |HPhrases = |PPhrases = | Watchedfields = changed | verifiedrevid = 408399736

Bisphenol S (BPS, dioxydiphenylsulfone) is an organic compound with the formula . 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 classified as a bisphenol, and a close molecular analog of bisphenol A (BPA). BPS differs from BPA in possessing a sulfone group as the central linker in the molecule instead of the dimethylmethylene group of bisphenol A.

History

German chemist Ludwig Glutz (1844–1873) first prepared the compound from phenol and hot sulfuric acid in 1867, designating it oxysulphobenzide. It was used starting in 1869 as a dye.

BPS received the modern name in the late 1950s.

Use

BPS is a precursor to the polyethersulfone called Victrex. BPS is also used as an anticorrosive agent in epoxy glues.

Occurrence in everyday life

BPS is used to a variety of common consumer products. In some cases, BPS is used as a replacement for BPA. BPS also has the advantage of being more stable to heat and light than BPA. BPS has also been reported to occur in canned foodstuffs, such as tin cans.

Paper products

Another study done on thermal receipt paper shows that 88% of human exposure to BPS from handling papers is through receipts.

The recycling of thermal paper can introduce BPS into the cycle of paper production and cause BPS contamination of other types of paper products.

In a 2015 study analyzing BPS in a variety of paper products worldwide, BPS was found in 100% of tickets, mailing envelopes, airplane boarding passes, and airplane luggage tags. In this study, very high concentrations of BPS were detected in thermal receipt samples collected from cities in the United States, Japan, Korea, and Vietnam. The BPS concentrations were large but varied greatly, from a few tens of nanograms per gram to several milligrams per gram. BPS is present in more than 70% of the household waste paper samples, potentially indicating spreading of BPS contamination through paper recycling.Nevertheless, concentrations of BPS used in thermal paper are usually lower compared to those of BPA. Finally, BPS can get into the human body through dermal absorption from handling banknotes.

Bisphenol-S concentrations within populations

A relationship to higher BPS concentrations is linked to individuals within certain socio-economic classes hence placing those individuals at greater risk of possible deleterious effects. Individuals with an annual income of less than $20,000 were found to have the highest concentrations of bisphenol and individuals with an annual income of $75,000 or more to have the lowest concentrations, suggesting a linear relationship between bodily concentrations of BPS and income. Black women had the highest concentrations of BPS with levels 93% higher than those of white women.

Biodegradation

BPS is more resistant to environmental degradation than BPA, and although not persistent cannot be characterised as readily biodegradable.

Regulation

In the United States, it can be difficult for consumers to determine if a product contains bisphenol S due to limited labeling regulations. As of December 2023, bisphenol S is recognized by the State of California as a reproductive toxicant.

In January 2023, the European Chemicals Agency added bisphenol S to the candidate list as a substance of very high concern, while under investigation for its potential to cause reproductive toxicity and endocrine disruption.

Synthesis

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

:

:

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

:[[File:bisphenol synthesis.svg|left|600px|Chemical reaction to bisphenol S]]

References

References

  1. (October 2015). "Bisphenol A and its structural analogues in household waste paper". Waste Management.
  2. "4,4′-Sulfonyldiphenol".
  3. Glutz, L.. (1868). "Ueber Oxysulfobenzid und einige Derivate desselben". Justus Liebigs Annalen der Chemie.
  4. Watts, Henry. (1875). "A Dictionary of Chemistry and the Allied Branches of Other Sciences. Second Supplement". Longmans, Green, and Company.
  5. (April 2014). "Toxicology: The plastics puzzle". Nature Publishing Group.
  6. Paquin, Alfred M.. (1958). "Epoxydverbindungen und Epoxydharze". Springer Berlin Heidelberg.
  7. (June 2012). "Bisphenol s, a new bisphenol analogue, in paper products and currency bills and its association with bisphenol a residues". Environmental Science & Technology.
  8. (August 2012). "Occurrence of eight bisphenol analogues in indoor dust from the United States and several Asian countries: implications for human exposure". Environmental Science & Technology.
  9. (June 2012). "Bisphenol S in urine from the United States and seven Asian countries: occurrence and human exposures". Environmental Science & Technology.
  10. Jenna Bilbrey. (Aug 11, 2014). "BPA-Free Plastic Containers May Be Just as Hazardous". [[Scientific American]].
  11. (January 2005). "Estrogenic activity of alkylphenols, bisphenol S, and their chlorinated derivatives using a GFP expression system". Environmental Toxicology and Pharmacology.
  12. (February 2002). "Acute toxicity, mutagenicity, and estrogenicity of bisphenol-A and other bisphenols". Environmental Toxicology.
  13. (May 2010). "Comparison of two derivatization-based methods for solid-phase microextraction-gas chromatography-mass spectrometric determination of bisphenol A, bisphenol S and biphenol migrated from food cans". Analytical and Bioanalytical Chemistry.
  14. (2013). "EHP – Thermal Reaction: The Spread of Bisphenol S via Paper Products". Environmental Health Perspectives.
  15. European Commission-Joint Research Centre. European Union Risk Assessment Report, 4,4′-Isopropylidenediphenol (Bisphenol-A). 2008, available from http://ecb.jrc.ec.europa.eu/documents/ExistingChemicals/RISK_ASSESSMENT/ADDENDUM/bisphenola_add_{{dead link. (November 2016)
  16. (October 2015). "Bisphenol A and its structural analogues in household waste paper". Waste Management.
  17. (2012-03-06). "Social disparities in exposures to bisphenol A and polyfluoroalkyl chemicals: a cross-sectional study within NHANES 2003-2006". Environmental Health.
  18. (April 2020). "A comprehensive analysis of racial disparities in chemical biomarker concentrations in United States women, 1999–2014". Environment International.
  19. (2006). "Biodegradation of a variety of bisphenols under aerobic and anaerobic conditions". Water Science and Technology.
  20. "Chemical in BPA-Free Products Linked to Irregular Heartbeats".
  21. (23 January 2024). "Bisphenol S (BPS) Added to Proposition 65 List Following 2023 Meeting of the Developmental and Reproductive Toxicant Identification Committee". Office of Environmental Health Hazard Assessment, State of California.
  22. (2025). "Bisphenols". [[European Chemicals Agency]].
  23. [http://www.freepatentsonline.com/EP0489788.html METHOD OF PREPARATION OF 4,4′-DIHYDROXYDIPHENYLSULPHONE (Freepatentsonline)].
  24. Vogel, Sarah A.. (November 2009). "The Politics of Plastics: The Making and Unmaking of Bisphenol A "Safety"". American Journal of Public Health.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

bisphenolsendocrine-disruptorsestrogensnonsteroidal-antiandrogensbenzosulfones