Bisphenol A

Bisphenol A
Names
Preferred IUPAC name
4,4′-(Propane-2,2-diyl)diphenol
Other names
  • Bisphenol acetone
  • BPA
  • Diphenylolpropane
  • p,p-Isopropylidenebisphenol
  • 2,2-Bis(4-hydroxyphenyl)propane
  • 2,2-Di(4-phenylol)propane
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.001.133
EC Number
  • 201-245-8
KEGG
PubChem CID
RTECS number
  • SL6300000
UNII
UN number 2430
InChI
  • InChI=1S/C15H16O2/c1-15(2,11-3-7-13(16)8-4-11)12-5-9-14(17)10-6-12/h3-10,16-17H,1-2H3 Y
    Key: IISBACLAFKSPIT-UHFFFAOYSA-N Y
  • InChI=1/C15H16O2/c1-15(2,11-3-7-13(16)8-4-11)12-5-9-14(17)10-6-12/h3-10,16-17H,1-2H3
    Key: IISBACLAFKSPIT-UHFFFAOYAI
SMILES
  • Oc1ccc(cc1)C(c2ccc(O)cc2)(C)C
  • CC(C)(c1ccc(cc1)O)c2ccc(cc2)O
Properties
Chemical formula
 C15H16O2
Molar mass 228.291 g·mol−1
Appearance White solid
Odor Phenolic, medical
Density 1.217 g/cm3[1]
Melting point 155 °C (311 °F; 428 K)[5]
Boiling point 250–252 °C (482–486 °F; 523–525 K)[5] at 13 torrs (0.017 atm)
Solubility in water
 0.3 g/L (25 °C)[2]
log P 3.41[3]
Vapor pressure 5×10−6 Pa (25 °C)[4]
Hazards[6]
GHS labelling:
Pictograms
Signal word
 Danger
Hazard statements
 H317, H318, H335, H360, H411[6]
Precautionary statements
 P201, P202, P261, P273, P302+P352, P304+P340, P305+P351+P338, P308+P313, P333+P313, P363, P403+P233[6]
NFPA 704 (fire diamond)
2
1
0
Flash point 227 °C (441 °F; 500 K)[6]
Autoignition
temperature
 510 °C (950 °F; 783 K)[6]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Bisphenol A (BPA) is a chemical compound primarily used in the manufacturing of various plastics. It is a colourless solid which is soluble in most common organic solvents, but has very poor solubility in water.[2][7] BPA is produced on an industrial scale by the condensation reaction of phenol and acetone. Global production in 2022 was estimated to be in the region of 10 million tonnes.[8]

BPA's largest single application is as a co-monomer in the production of polycarbonates, which accounts for 65–70% of all BPA production.[9][10] The manufacturing of epoxy resins and vinyl ester resins account for 25–30% of BPA use.[9][10] The remaining 5% is used as a major component of several high-performance plastics, and as a minor additive in polyvinyl chloride (PVC), polyurethane, thermal paper, and several other materials. It is not a plasticizer,[11] although it is often wrongly labelled as such.

The health effects of BPA have been the subject of prolonged public and scientific debate.[12][13][14] BPA is a xenoestrogen, exhibiting hormone-like properties that mimic the effects of estrogen in the body.[15] Although the effect is very weak,[16] the pervasiveness of BPA-containing materials raises concerns, as exposure is effectively lifelong. Many BPA-containing materials are non-obvious but commonly encountered,[17] and include coatings for the inside of food cans,[18] clothing designs,[19] shop receipts,[20] and dental fillings.[21] BPA has been investigated by public health agencies in many countries, as well as by the World Health Organization.[12]

While normal exposure is below the level currently associated with risk, several jurisdictions have taken steps to reduce exposure on a precautionary basis, in particular by banning BPA from baby bottles. There is some evidence that BPA exposure in infants has decreased as a result of this.[22] BPA-free plastics have also been introduced, which are manufactured using alternative bisphenols such as bisphenol S and bisphenol F, but there is also controversy around whether these are actually safer.[23][24][25]

  1. ^ Lim CF, Tanski JM (3 August 2007). "Structural Analysis of Bisphenol-A and its Methylene, Sulfur, and Oxygen Bridged Bisphenol Analogs". Journal of Chemical Crystallography. 37 (9): 587–595. Bibcode:2007JCCry..37..587L. doi:10.1007/s10870-007-9207-8. S2CID 97284173.
  2. ^ a b Shareef A, Angove MJ, Wells JD, et al. (11 May 2006). "Aqueous Solubilities of Estrone, 17β-Estradiol, 17α-Ethynylestradiol, and Bisphenol A". Journal of Chemical & Engineering Data. 51 (3): 879–881. doi:10.1021/je050318c.
  3. ^ Robinson BJ, Hui JP, Soo EC, et al. (2009). "Estrogenic Compounds in Seawater and Sediment from Halifax Harbour, Nova Scotia, Canada". Environmental Toxicology and Chemistry. 28 (1): 18–25. Bibcode:2009EnvTC..28...18R. doi:10.1897/08-203.1. PMID 18702564. S2CID 13528747.
  4. ^ "Chemical Fact Sheet – Cas #80057 CASRN 80-05-7". speclab.com. 1 April 2012. Archived from the original on 12 February 2012. Retrieved 14 June 2012.
  5. ^ a b Mitrofanova SE, Bakirova IN, Zenitova LA, et al. (September 2009). "Polyurethane varnish materials based on diphenylolpropane". Russian Journal of Applied Chemistry. 82 (9): 1630–1635. doi:10.1134/S1070427209090225. S2CID 98036316.
  6. ^ a b c d e Sigma-Aldrich Co., Bisphenol A.
  7. ^ Cite error: The named reference Fiege was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference production was invoked but never defined (see the help page).
  9. ^ a b Cite error: The named reference EU2008 was invoked but never defined (see the help page).
  10. ^ a b Cite error: The named reference Tom2021 was invoked but never defined (see the help page).
  11. ^ Cadogan DF, Howick CJ (2000). "Plasticizers". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a20_439. ISBN 3527306730.
  12. ^ a b Cite error: The named reference WHO was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference German2011 was invoked but never defined (see the help page).
  14. ^ Cite error: The named reference GLP was invoked but never defined (see the help page).
  15. ^ Egan M (2013). "Sarah A. Vogel. Is It Safe? BPA and the Struggle to Define the Safety of Chemicals". Isis. 105 (1). Berkeley: University of California Press: 254. doi:10.1086/676809. ISSN 0021-1753.
  16. ^ Cite error: The named reference Xenochemicals was invoked but never defined (see the help page).
  17. ^ Geens T, Aerts D, Berthot C, et al. (October 2012). "A review of dietary and non-dietary exposure to bisphenol-A" (PDF). Food and Chemical Toxicology. 50 (10): 3725–3740. doi:10.1016/j.fct.2012.07.059. PMID 22889897.
  18. ^ Noonan GO, Ackerman LK, Begley TH (July 2011). "Concentration of bisphenol A in highly consumed canned foods on the U.S. market". Journal of Agricultural and Food Chemistry. 59 (13): 7178–7185. Bibcode:2011JAFC...59.7178N. doi:10.1021/jf201076f. PMID 21598963.
  19. ^ Xue J, Liu W, Kannan K (May 2017). "Bisphenols, Benzophenones, and Bisphenol A Diglycidyl Ethers in Textiles and Infant Clothing". Environmental Science & Technology. 51 (9): 5279–5286. Bibcode:2017EnST...51.5279X. doi:10.1021/acs.est.7b00701. PMID 28368574. Archived from the original on 29 December 2022. Retrieved 12 April 2022.
  20. ^ Cite error: The named reference paper1 was invoked but never defined (see the help page).
  21. ^ Ahovuo-Saloranta A, Forss H, Walsh T, et al. (July 2017). "Pit and fissure sealants for preventing dental decay in permanent teeth". The Cochrane Database of Systematic Reviews. 2017 (7): CD001830. doi:10.1002/14651858.CD001830.pub5. PMC 6483295. PMID 28759120.
  22. ^ Cite error: The named reference auto was invoked but never defined (see the help page).
  23. ^ Thoene M, Dzika E, Gonkowski S, et al. (February 2020). "Bisphenol S in Food Causes Hormonal and Obesogenic Effects Comparable to or Worse than Bisphenol A: A Literature Review". Nutrients. 12 (2): 532. doi:10.3390/nu12020532. PMC 7071457. PMID 32092919.
  24. ^ Chen D, Kannan K, Tan H, et al. (7 June 2016). "Bisphenol Analogues Other Than BPA: Environmental Occurrence, Human Exposure, and Toxicity—A Review". Environmental Science & Technology. 50 (11): 5438–5453. Bibcode:2016EnST...50.5438C. doi:10.1021/acs.est.5b05387. PMID 27143250.
  25. ^ Eladak S, Grisin T, Moison D, et al. (2015). "A new chapter in the bisphenol A story: bisphenol S and bisphenol F are not safe alternatives to this compound". Fertility and Sterility. 103 (1): 11–21. doi:10.1016/j.fertnstert.2014.11.005. PMID 25475787.
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