Chemistry:Bisphenol

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The bisphenols (/ˈbɪsfɪnɒl/) are a group of industrial chemical compounds related to diphenylmethane; commonly used in the production of plastics and epoxy resins. They feature two hydroxyphenyl groups linked by a methylene bridge. Also included are bisphenol S, P, and M. "Bisphenol" is a common name; the letter following denotes the variant, which depends on the additional substituents. Bisphenol A is the most common representative of the group, with millions of metric tons produced globally in the past decade, often simply called "bisphenol".[1]

Bisphenols have attracted controversy because of their role as endocrine disruptors. Their estrogenic properties are weak, but the scale of their production is considerable.[2][3]

Partial inventory of bisphenols

Structural formula Name CAS Reactants
Bisphenol A Bisphenol A 80-05-7 Phenol Acetone
Bisphenol AP Bisphenol AP 1571-75-1 Phenol Acetophenone
Bisphenol AF Bisphenol AF 1478-61-1 Phenol Hexafluoroacetone
Bisphenol B Bisphenol B 77-40-7 Phenol Butanone
Bisphenol BP Bisphenol BP 1844-01-5 Phenol Benzophenone
Bisphenol C Bisphenol C 79-97-0 o-cresol Acetone
Bisphenol CII Bisphenol C 2 14868-03-2 Phenol Chloral
Bisphenol E Bisphenol E 2081-08-5 Phenol Ethanal
Bisphenol F Bisphenol F 620-92-8 Phenol Formaldehyde
Bisphenol G Bisphenol G 127-54-8 2-Isopropylphenol Acetone
Bisphenol M Bisphenol M 13595-25-0
Bisphenol S Bisphenol S 80-09-1 Phenol Sulfur trioxide
Bisphenol P Bisphenol P 2167-51-3
Bisphenol PH Bisphenol PH 24038-68-4 2-Phenylphenol Acetone
Bisphenol TMC Bisphenol TMC 129188-99-4 Phenol 3,3,5-Trimethylcyclohexanone
Bisphenol Z Bisphenol Z 843-55-0 Phenol Cyclohexanone
Dinitrobisphenol A Dinitrobisphenol A 5329-21-5 Bisphenol A Nitric acid
Tetrabromobisphenol A Tetrabromobisphenol A 79-94-7 Bisphenol A Bromine
Tetramethylbisphenol F Tetramethyl bisphenol F 5384-21-4 2,6-Xylenol Formaldehyde

Health effects

Many bisphenols, including Bisphenols A (BPA), F (BPF) and S (BPS), have been shown to be endocrine disruptors, potentially relating to adverse health effects.[2][4] Other implicated health effects include obesity and metabolic disorders.[5] The threat is of interest because the chemical is pervasive in everyday life, including food[2] and through the use of thermal paper.[6]

Occurrence in humans

Bisphenols have monitored in humans through analysis of serum and urine.[7][8] Workers who manufacture BPA-based thermal paper have high BPA levels.[6] BPS and BPF levels are elevated among workers dismantling e-waste in China.[9] Many analogues of BPA, such as bisphenol F (BPF), bisphenol S (BPS), bisphenol AP (BPAP), bisphenol AF (BPAF), bisphenol FL (BPFL), and bisphenol C (BPC) are less studied with respect to their hormone-disrupting potential and other health effects.[10][5][11][12]

Biodegradation

Due to its high production volumes, BPA has been characterised as "pseudo-persistent",[13] leading to its spreading and potential accumulation in a variety of environmental matrices. BPA has a fairly short half-life. A number of aerobic organisms degrade BPA.[14][15]

Precautions to reduce occupational exposures

Engineering controls to reduce exposure in the workplace have been applied such as process enclosure, local exhaust ventilation, and isolation of bisphenol-handling areas lower airborne and surface contamination in workplaces where bisphenols are used.[16][17]

Exposure to Bisphenol

Because bisphenol is largely used in everyday life such as in plastics, protective coating of packages, inner lining of food containers, and thermal paper of receipts, it can enter the body through multiple pathways (skin absorption, ingestion and inhalation).[18]

Exposure Pathways

Dietary Exposure

The main pathway of exposure is through ingestion of food that is contaminated with bisphenol. Bisphenol can leach slowly into the food from things like the inside lining of cans, plastic containers, packages, disposable tableware, and especially through wear and tear.[19] This means that even simply using or eating food that came in contact with product made from bisphenol could result in exposure.[20] Moreover, studies have found bisphenol residue in foods and beverages even when using containers that claimed to be "bisphenol free".[20][21][22]

Dermal (Skin) Exposure

Bisphenol can also enter the body through the skin via absorption and can result in skin irritation or allergic reactions in some individuals.[19][23] One well-known example is the handling of store receipts, which are often coated with bisphenol, and can transfer from the skin of the hands to the mouth, resulting in ingestion of the chemical.[24] Workers who handle receipts regularly, like cashiers and retail employees, may face higher dermal exposure.[19][25]

Inhalation Exposure

Due to its volatility, bisphenol do not easily evaporate into the air at room temperature according to their chemical properties.[25][23] However, bisphenol can attach to dust an small particles in the environment and be inhaled. Usually, inhalation exposure of bisphenol are more common under industrial and manufacture settings.[26][18][27]

References

  1. ↑ "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2002. doi:10.1002/14356007.a19_313. ISBN 978-3-527-30673-2. .
  2. ↑ 2.0 2.1 2.2 "Bisphenol A: Food Exposure and Impact on Human Health". Comprehensive Reviews in Food Science and Food Safety 17 (6): 1503–1517. November 2018. doi:10.1111/1541-4337.12388. PMID 33350146. 
  3. ↑ "Bisphenol-A and the great divide: a review of controversies in the field of endocrine disruption". Endocrine Reviews 30 (1): 75–95. February 2009. doi:10.1210/er.2008-0021. PMID 19074586. 
  4. ↑ "BPA-Free Plastic Containers May Be Just as Hazardous". 11 August 2014. http://www.scientificamerican.com/article/bpa-free-plastic-containers-may-be-just-as-hazardous/. 
  5. ↑ 5.0 5.1 Akash, M. S. H.; Alshahrani, S.; Alzahrani, A. (2023). "Toxicological evaluation of bisphenol analogues: Preventive measures and therapeutic interventions". Environmental Toxicology and Pharmacology 83. doi:10.1016/j.etap.2023.103545. 
  6. ↑ 6.0 6.1 Heinälä, M.; Ylinen, K.; Tuomi, T.; Santonen, T.; Porras, S. P. (2017). "Assessment of occupational exposure to bisphenol A in five different production companies in Finland". Annals of Work Exposures and Health 61 (1): 44–55. doi:10.1093/annweh/wxw006. PMID 28395312. 
  7. ↑ Hines, Cynthia J.; Jackson, Matthew V.; Deddens, James A.; Clark, John C.; Ye, Xiaoyun; Christianson, Annette L.; Meadows, Juliana W.; Calafat, Antonia M. (2017-03-01). "Urinary Bisphenol A (BPA) Concentrations among Workers in Industries that Manufacture and Use BPA in the USA" (in en). Annals of Work Exposures and Health 61 (2): 164–182. doi:10.1093/annweh/wxw021. ISSN 2398-7308. PMID 28395354. PMC 5577557. https://academic.oup.com/annweh/article/61/2/164/2769471. 
  8. ↑ Ribeiro, E.; Ladeira, C.; Viegas, S. (2017). "Occupational Exposure to Bisphenol A (BPA): A Reality That Still Needs to Be Unveiled". Toxics 5 (3): 22. doi:10.3390/toxics5030022. 
  9. ↑ "Bisphenols". https://echa.europa.eu/hot-topics/bisphenols. 
  10. ↑ Rifa, R. A.; Lavado, R. (2024). "Unveiling the next generation of bisphenol analogs and their impact on human health using in vitro methods". Emerging Contaminants 10 (2). doi:10.1016/j.emcon.2023.100296. 
  11. ↑ NTP Research Report on Biological Activity of Bisphenol A (BPA) Structural Analogues and Functional Alternatives: Research Report 4. NTP Research Reports. Research Triangle Park (NC): National Toxicology Program. 2017. https://www.ncbi.nlm.nih.gov/books/NBK538922/. 
  12. ↑ "Bisphenol F affects neurodevelopmental gene expression, mushroom body development, and behavior in Drosophila melanogaster". Neurotoxicology and Teratology 102. 2024-03-01. doi:10.1016/j.ntt.2024.107331. PMID 38301979. Bibcode: 2024NTxT..10207331F. 
  13. ↑ "Bisphenol A and its structural analogues in household waste paper". Waste Management 44: 39–47. October 2015. doi:10.1016/j.wasman.2015.07.017. PMID 26194879. Bibcode: 2015WaMan..44...39P. https://backend.orbit.dtu.dk/ws/files/118749778/PostPrint_Davidsen_JoH_1_.pdf. 
  14. ↑ Im, Jeongdae; Löffler, Frank E. (2016). "Fate of Bisphenol a in Terrestrial and Aquatic Environments". Environmental Science & Technology 50 (16): 8403–8416. doi:10.1021/acs.est.6b00877. PMID 27401879. 
  15. ↑ See Bisphenol A for extensive discussion
  16. ↑ "Occupational Exposure to Bisphenol A (BPA) in U.S. Manufacturing Companies". Centers for Disease Control and Prevention (CDC). 2017-01-05. https://blogs.cdc.gov/niosh-science-blog/2017/01/05/bpa/. 
  17. ↑ "Occupational Exposure to BPA". 2017-01-18. https://www.cbia.com/news/hr-safety/occupational-exposure-bpa/. 
  18. ↑ 18.0 18.1 Hines, C. J.; Jackson, M. V.; Deddens, J. A.; Clark, J. C.; Ye, X.; Christianson, A. L.; Meadows, J. W.; Calafat, A. M. (2017). "Urinary Bisphenol A concentrations among workers". Annals of Work Exposures and Health 61 (2): 164–182. doi:10.1093/annweh/wxw021. 
  19. ↑ 19.0 19.1 19.2 Lee, S. S.; Ryu, H. Y.; Ahn, K. S.; Lee, S.; Lee, J.; Lee, J. W.; Ko, S. M.; Son, W. C. (2022). "Toxicological profile of bisphenol F". Journal of Toxicology and Environmental Health Part A 85 (4): 163–174. doi:10.1080/15287394.2021.1997843. 
  20. ↑ 20.0 20.1 Benhamada, M.; Bouzid, D.; Boyron, O.; Taam, M. (2016). "Aging of polycarbonate and BPA release". European Food Research and Technology 242 (2): 227–232. 
  21. ↑ Agarwal, A.; Gandhi, S.; Tripathi, A. D.; Iammarino, M.; Homroy, S. (2022). "Bisphenol A migration from microwaveable cups". International Journal of Food Science & Technology 57: 7477–7485. 
  22. ↑ Ali, M.; Jaghbir, M.; Salam, M.; Al-Kadamany, G.; Damsees, R.; Al-Rawashdeh, N. (2019). "Testing baby bottles for BPA". Environmental Monitoring and Assessment 191 (1): 1–11. 
  23. ↑ 23.0 23.1 National Institute for Occupational Safety and Health (2011). NIOSH Skin Notation Profiles: Bisphenol A (BPA) (Report). U.S. Department of Health and Human Services. 
  24. ↑ Ehrlich, S.; Calafat, A. M.; Humblet, O.; Smith, T.; Hauser, R. (2014). "Handling of thermal receipts as a source of exposure to bisphenol A". JAMA 311 (8): 859–860. doi:10.1001/jama.2013.283735. 
  25. ↑ 25.0 25.1 National Institute of Environmental Health Sciences. "Bisphenol A (BPA)". https://www.niehs.nih.gov/health/topics/agents/sya-bpa. 
  26. ↑ European Chemicals Agency (2023). Scientific report for evaluation of limit values for Bisphenol A at the workplace (Report). https://echa.europa.eu/documents/10162/23ca2397-4387-e040-8070-b1fd27423fda. 
  27. ↑ Konieczna, A.; Rutkowska, A.; Rachoń, D. (2015). "Health risk of exposure to bisphenol A". Roczniki Państwowego Zakładu Higieny 66 (1). 

Further reading

  • For additional examples and alternate names, see: Polymer Science Dictionary. Springer. 2017. p. 77. ISBN 978-94-024-0893-5. 



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