Chemistry:Bisphenol A

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Short description: Chemical compound used in plastics manufacturing
Bisphenol A
Bisphenol-A-Skeletal.svg
Bisphenol A.png
Names
Preferred IUPAC name
4,4′-(Propane-2,2-diyl)diphenol
Other names
  • BPA
  • Diphenylolpropane
  • p,p-Isopropylidenebisphenol
  • 2,2-Bis(4-hydroxyphenyl)propane
  • 2,2-Di(4-phenylol)propane
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
EC Number
  • 201-245-8
KEGG
RTECS number
  • SL6300000
UNII
UN number 2430
Properties
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)
0.3 g/L (25 °C)[2]
log P 3.41[3]
Vapor pressure 5×10−6 Pa (25 °C)[4]
Hazards[6]
GHS pictograms GHS05: CorrosiveGHS07: HarmfulGHS08: Health hazardGHS09: Environmental hazard
GHS Signal word Danger
H317, H318, H335, H360, HH411Script error: No such module "Preview warning".Category:GHS errors[6]
P201, P202, P261, P273, P302+352, P304+340, P305+351+338, P308+313, P333+313, P363, P403+233[6]
NFPA 704 (fire diamond)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
1
2
0
Flash point 227 °C (441 °F; 500 K)[6]
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).
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Infobox references
Tracking categories (test):

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 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]

History

Bisphenol A was first reported in 1891 by the Russian chemist Aleksandr Dianin.[26]

In 1934, workers at I.G. Farbenindustrie reported the coupling of BPA and epichlorohydrin. Over the following decade, coatings and resins derived from similar materials were described by workers at the companies of DeTrey Freres in Switzerland and DeVoe and Raynolds in the US. This early work underpinned the development of epoxy resins, which in turn motivated production of BPA.[27] The utilization of BPA further expanded with discoveries at Bayer and General Electric on polycarbonate plastics. These plastics first appeared in 1958, being produced by Mobay, General Electric, and Bayer.[28]

In terms of the endocrine disruption controversy, the British biochemist Edward Charles Dodds tested BPA as an artificial estrogen in the early 1930s.[29][30][31] Subsequent work found that it bound to estrogen receptors tens of thousands of times more weakly than estradiol, the major natural female sex hormone.[32][16] Dodds eventually developed a structurally similar compound, diethylstilbestrol (DES), which was used as a synthetic estrogen drug in women and animals until it was banned due to its risk of causing cancer; the ban on use of DES in humans came in 1971 and in animals, in 1979.[29] BPA was never used as a drug.[29]

Production

The synthesis of BPA still follows Dianin's general method, with the fundamentals changing little in 130 years. The condensation of acetone (hence the suffix 'A' in the name)[33] with two equivalents of phenol is catalyzed by a strong acid, such as concentrated hydrochloric acid, sulfuric acid, or a solid acid resin such as the sulfonic acid form of polystyrene sulfonate.[34] An excess of phenol is used to ensure full condensation and to limit the formation of byproducts, such as Dianin's compound. BPA is fairly cheap to produce, as the synthesis benefits from a high atom economy and large amounts of both starting materials are available from the cumene process.[7] As the only by-product is water, it may be considered an industrial example of green chemistry. Global production in 2022 was estimated to be in the region of 10 million tonnes.[8]

Synthesis of bisphenol A from phenol and acetone

Usually, the addition of acetone takes place at the para position on both phenols, however minor amounts of the ortho-para (up to 3%) and ortho-ortho isomers are also produced, along with several other minor by‑products.[35] These are not always removed and are known impurities in commercial samples of BPA.[36][35]

Properties

BPA has a fairly high melting point but can be easily dissolved in a broad range of organic solvents including toluene, ethanol and ethyl acetate.[37] It may be purified by recrystallisation from acetic acid with water.[38] Crystals form in the monoclinic space group P 21/n (where n indicates the glide plane); within this individual molecules of BPA are arraigned with a 91.5° torsion angle between the phenol rings.[39][40][41] Spectroscopic data is available from AIST.[42]

Uses and applications

Bisphenol A is primarily used to make plastics, such as this polycarbonate water bottle.

Main uses

Polycarbonates

Main page: Physics:Polycarbonate

About 65–70% of all bisphenol A is used to make polycarbonate plastics,[9][10] which can consist of nearly 90% BPA by mass. Polymerisation is achieved by a reaction with phosgene, conducted under biphasic conditions; the hydrochloric acid is scavenged with aqueous base.[43] This process converts the individual molecules of BPA into large polymer chains, effectively trapping them.

Polycarbonatsynthese.svg

Epoxy and vinyl ester resins

About 25–30% of all BPA is used in the manufacture of epoxy resins and vinyl ester resins.[9][10] For epoxy resin, it is first converted to its diglycidyl ether (usually abbreviated BADGE or DGEBA).[44][45] This is achieved by a reaction with epichlorohydrin under basic conditions.

Diglycidether.svg

Some of this is further reacted with methacrylic acid to form bis-GMA, which is used to make vinyl ester resins. Alternatively, and to a much lesser extent, BPA may be ethoxylated and then converted to its diacrylate and dimethacrylate derivatives (bis-EMA, or EBPADMA). These may be incorporated at low levels in vinyl ester resins to change their physical properties[46] and see common use in dental composites and sealants.[47][48]

Minor uses

The remaining 5% of BPA is used in a wide range of applications, many of which involve plastic.[49] BPA is a main component of several high-performance plastics, the production of these is low compared to other plastics but still equals several thousand tons a year. Comparatively minor amounts of BPA are also used as additives or modifiers in some commodity plastics. These materials are much more common but their BPA content will be low.

Plastics

As a major component
  • Polycyanurates can be produced from BPA by way of its dicyanate ester (BADCy).[49] This is formed by a reaction between BPA and cyanogen bromide.[50] Examples include BT-Epoxy, which is one of a number of resins used in the production of printed circuit boards.
  • Polyetherimides such as Ultem can be produced from BPA via a nitro-displacement of appropriate bisnitroimides.[51][52] These thermoplastic polyimide plastics have exceptional resistance to mechanical, thermal and chemical damage. They are used in medical devices and other high performance instrumentation.
  • Polybenzoxazines may be produced from a number of biphenols, including BPA.[53][54]
  • Polysulfones can be produced from BPA and bis(4-chlorophenyl) sulfone forming poly(bisphenol-A sulfone) (PSF). It is used as a high performance alternative to polycarbonate.[49][55]
  • Bisphenol-A formaldehyde resins are a subset of phenol formaldehyde resins. They are used in the production of high-pressure laminates[49]
As a minor component
  • Polyurethane can incorporate BPA and its derivatives as hard segment chain extenders, particularly in memory foams.[56][57]
  • PVC can contain BPA and its derivatives through multiple routes. BPA is sometimes used as an antioxidant in phthalates,[58] which are extensively used as plasticizers for PVC. BPA has also been used as an antioxidant to protect sensitive PVC heat stabilizers. Historically 5–10% by weight of BPA was included in barium-cadmium types, although these have largely been phased out due health concerns surrounding the cadmium. BPA diglycidyl ether (BADGE) is used as an acid scavenger, particularly in PVC dispersions, such as organosols or plastisols,[59][60] which are used as coatings for the inside of food cans, as well as embossed clothes designs produced using heat transfer vinyl or screen printing machines.[19]
  • BPA is used to form a number of flame retardants used in plastics.[61] Bromination of BPA forms tetrabromobisphenol A (TBBPA), which is mainly used as a reactive component of polymers, meaning that it is incorporated into the polymer backbone. It is used to prepare fire-resistant polycarbonates by replacing some bisphenol A. A lower grade of TBBPA is used to prepare epoxy resins, used in printed circuit boards. TBBPA is also converted to tetrabromobisphenol-A-bis(2,3,-dibromopropyl ether) (TBBPA-BDBPE) which can be used as a flame retardant in polypropylene. TBBPA-BDBPE is not chemically bonded to the polymer and can leach out into the environment.[62] The use of these compounds is diminishing due to restrictions on brominated flame retardants. The reaction of BPA with phosphorus oxychloride and phenol forms bisphenol A diphenyl phosphate (BADP), which is used as a liquid flame retarder in some high performance polymer blends such as polycarbonate/ABS mixtures.[63]

Other applications

  • BPA is used as an antioxidant in several fields, particularly in brake fluids.[64]
  • BPA is used as a developing agent in thermal paper (shop receipts).[20] Recycled paper products can also contain BPA,[65] although this can depend strongly on how it is recycled. Deinking can remove 95% of BPA,[9] with the pulp produced used to make newsprint, toilet paper and facial tissues. If deinking is not performed then the BPA remains in the fibers, paper recycled this way is usually made into corrugated fiberboard.[9]
  • Ethoxylated BPA finds minor use as a 'levelling agent' in tin electroplating.
  • Several drug candidates have also been developed from bisphenol A, including ralaniten, ralaniten acetate, and EPI-001.

BPA substitutes

Concerns about the health effects of BPA have led some manufacturers replacing it with other bisphenols, such as bisphenol S and bisphenol F. These are produced in a similar manner to BPA, by replacing acetone with other ketones, which undergo analogous condensation reactions.[7] Thus, in bisphenol F, the F signifies formaldehyde. Health concerns have also been raised about these substitutes.[66][24] Alternative polymers, such as tritan copolyester have been developed to give the same properties as polycarbonate (durable, clear) without using BPA or its analogues.

Structural formula Name CAS Reactants
Bisphenol AF Bisphenol AF 1478-61-1 Phenol Hexafluoroacetone
Bisphenol F Bisphenol F 620-92-8 Phenol Formaldehyde
Bisphenol S Bisphenol S 80-09-1 Phenol Sulfur trioxide
Bisphenol Z Bisphenol Z 843-55-0 Phenol Cyclohexanone
Tetramethyl bisphenol F.png Tetramethyl bisphenol F 5384-21-4 2,6-xylenol Formaldehyde

Human safety

Exposure

The largest exposure humans have had to BPA is from food packaging, particularly the epoxy lining of metal food, beverage cans and plastic bottles.

As a result of the presence of BPA in plastics and other commonplace materials, most people are frequently exposed to trace levels of BPA.[67][68][69] The primary source of human exposure is via food, as epoxy and PVC are used to line the inside of food cans to prevent corrosion of the metal by acidic foodstuffs. Polycarbonate drinks containers are also a source of exposure, although most disposable drinks bottles are actually made of PET, which contains no BPA. Among the non-food sources, exposures routes include through dust,[10] thermal paper,[20] clothing,[19] dental materials,[70] and medical devices.[17] Although BPA exposure is common it does not accumulate within the body, with toxicokinetic studies showing the biological half-life of BPA in adult humans to be around two hours.[71][72] The body first converts it into more water-soluble compounds via glucuronidation or sulfation, which are then removed from the body through the urine. This allows exposure to be easily determined by urine testing, facilitating convenient biomonitoring of populations.[22][17][73] Food and drink containers made from Bisphenol A-containing plastics do not contaminate the content to cause any increased cancer risk.[74]

Health effects and regulation

Main page: Chemistry:Health effects of Bisphenol A

The health effects of BPA have been the subject of prolonged public and scientific debate,[12][13][14] with PubMed listing more than 18,000 scientific papers as of 2024.[75] Concern is mostly related to its estrogen-like activity, although it can interact with other receptor systems as an endocrine-disrupting chemical.[76] These interactions are all very weak, but exposure to BPA is effectively lifelong, leading to concern over possible cumulative effects. Studying this sort of long‑term, low‑dose interaction is difficult, and although there have been numerous studies, there are considerable discrepancies in their conclusions regarding the nature of the effects observed as well as the levels at which they occur.[12] A common criticism is that industry-sponsored trials tend to show BPA as being safer than studies performed by academic or government laboratories,[14][77] although this has also been explained in terms of industry studies being better designed.[13][78]

Public health agencies in the EU,[79][80][81] US,[82][83] Canada,[84] Australia[85] and Japan as well as the WHO[12] have all reviewed the health risks of BPA, and found normal exposure to be below the level currently associated with risk. Regardless, due to the scientific uncertainty, many jurisdictions have taken steps to reduce exposure on a precautionary basis. In particular, infants are considered to be at greater risk,[86] leading to bans on the use of BPA in baby bottles and related products by the US,[87] Canada,[88] and EU[89] amongst others. Bottle producers have largely switched from polycarbonate to polypropylene and there is some evidence that BPA exposure in infants has decreased as a result of this.[22] The European Chemicals Agency has added BPA to the Candidate List of substances of very high concern (SVHC), which would make it easier to restrict or ban its use in future.[90][91]

BPA exhibits very low acute toxicity (i.e. from a single large dose) as indicated by its LD50 of 4 g/kg (mouse). Reports indicate that it is a minor skin irritant as well, although less so than phenol.[7]

Pharmacology

Overlay of estradiol, the major female sex hormone in humans (green) and BPA (purple). This displays the structure–activity relationship which allows BPA to mimic the effects of estradiol and other estrogens.

BPA has been found to interact with a diverse range of hormone receptors, in both humans and animals.[76] It binds to both of the nuclear estrogen receptors (ERs), ERα and ERβ. BPA can both mimic the action of estrogen and antagonise estrogen, indicating that it is a selective estrogen receptor modulator (SERM) or partial agonist of the ER. Although, it is 1000- to 2000-fold less potent than estradiol, the major female sex hormone in humans. At high concentrations, BPA also binds to and acts as an antagonist of the androgen receptor (AR). In addition to receptor binding, the compound has been found to affect Leydig cell steroidogenesis, including affecting 17α-hydroxylase/17,20 lyase and aromatase expression and interfering with LH receptor-ligand binding.[92]

Bisphenol A's interacts with the estrogen-related receptor γ (ERR-γ). This orphan receptor (endogenous ligand unknown) behaves as a constitutive activator of transcription. BPA seems to bind strongly to ERR-γ (dissociation constant = 5.5 nM), but only weakly to the ER.[93] BPA binding to ERR-γ preserves its basal constitutive activity.[93] It can also protect it from deactivation from the SERM 4-hydroxytamoxifen (afimoxifene).[93] This may be the mechanism by which BPA acts as a xenoestrogen.[93] Different expression of ERR-γ in different parts of the body may account for variations in bisphenol A effects. BPA has also been found to act as an agonist of the GPER (GPR30).[94]

Environmental safety

Distribution and degradation

BPA has been detectable in the natural environment since the 1990s and is now widely distributed.[95] It is primarily a river pollutant,[96] but has also been observed in the marine environment,[97] in soils,[98] and lower levels can also be detected in air.[99] The solubility of BPA in water is low (~300 g per ton of water)[2] but this is still sufficient to make it a significant means of distribution into the environment.[98] Many of the largest sources of BPA pollution are water-based, particularly wastewater from industrial facilities using BPA. Paper recycling can be a major source of release when this includes thermal paper,[9][100] leaching from PVC items may also be a significant source,[96] as can landfill leachate.[101]

In all cases, wastewater treatment can be highly effective at removing BPA, giving reductions of 91–98%.[102] Regardless, the remaining 2–9% of BPA will continue through to the environment, with low levels of BPA commonly observed in surface water and sediment in the U.S. and Europe.[103]

Once in the environment BPA is aerobically biodegraded by a wide a variety of organisms.[95][104][105] Its half life in water has been estimated at between 4.5 and 15 days, degradation in the air is faster than this, while soil samples degrade more slowly.[98] BPA in sediment degrades most slowly of all, particularly where this is anaerobic. Abiotic degradation has been reported, but is generally slower than biodegradation. Pathways include photo-oxidation, or reactions with minerals such as goethite which may be present in soils and sediments.[106]

Environmental effects

BPA is an environmental contaminant of emerging concern.[101] Despite its short half-life and non-bioaccumulating character, the continuous release of BPA into the environment causes continuous exposure to both plant[107] and animal life. Although many studies have been performed, these often focus on a limited range of model organisms and can use BPA concentrations well beyond environmental levels.[108] As such, the precise effects of BPA on the growth, reproduction, and development of aquatic organism are not fully understood.[108] Regardless, the existing data shows the effects of BPA on wildlife to be generally negative.[109][110] BPA appears able to affect development and reproduction in a wide range of wildlife,[110] with certain species being particularly sensitive, such as invertebrates and amphibians.[109]

See also

Structurally related
Others

References

  1. ↑ Lim, Caitlin F.; Tanski, Joseph M. (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. doi:10.1007/s10870-007-9207-8. 
  2. ↑ 2.0 2.1 2.2 Shareef, Ali; Angove, Michael J.; Wells, John D.; Johnson, Bruce B. (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, Brian J.; Hui, Joseph P.M.; Soo, Evelyn C.; Hellou, Jocelyne (2009). "Estrogenic Compounds in Seawater and Sediment from Halifax Harbour, Nova Scotia, Canada". Environmental Toxicology and Chemistry 28 (1): 18–25. doi:10.1897/08-203.1. PMID 18702564. 
  4. ↑ "Chemical Fact Sheet – Cas #80057 CASRN 80-05-7". 1 April 2012. http://www.speclab.com/compound/c80057.htm. 
  5. ↑ 5.0 5.1 Mitrofanova, S. E.; Bakirova, I. N.; Zenitova, L. A.; Galimzyanova, A. R.; Nefed'ev, E. S. (September 2009). "Polyurethane varnish materials based on diphenylolpropane". Russian Journal of Applied Chemistry 82 (9): 1630–1635. doi:10.1134/S1070427209090225. 
  6. ↑ 6.0 6.1 6.2 6.3 6.4 Sigma-Aldrich Co., Bisphenol A.
  7. ↑ 7.0 7.1 7.2 7.3 "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2000. doi:10.1002/14356007.a19_313. 
  8. ↑ 8.0 8.1 "A review on sources and health impacts of bisphenol A". Reviews on Environmental Health 35 (2): 201–210. June 2020. doi:10.1515/reveh-2019-0034. PMID 31743105. 
  9. ↑ 9.0 9.1 9.2 9.3 9.4 9.5 9.6 European Commission. Joint Research Centre. Institute for Health Consumer Protection (2010). Updated European Union risk assessment report : 4,4'-isopropylidenediphenol (bisphenol-A) : environment addendum of February 2008. Publications Office. p. 6. doi:10.2788/40195. ISBN 9789279175428. 
  10. ↑ 10.0 10.1 10.2 10.3 10.4 "Bisphenol A and its analogues in outdoor and indoor air: Properties, sources and global levels". The Science of the Total Environment 789: 148013. May 2021. doi:10.1016/j.scitotenv.2021.148013. PMID 34323825. Bibcode: 2021ScTEn.789n8013V. 
  11. ↑ "Plasticizers". Ullmann's Encyclopedia of Industrial Chemistry. 2000. doi:10.1002/14356007.a20_439. ISBN 3527306730. 
  12. ↑ 12.0 12.1 12.2 12.3 12.4 (in en) Joint FAO/WHO expert meeting to review toxicological and health aspects of bisphenol A : final report, including report of stakeholder meeting on bisphenol A, 1-5 November 2010, Ottawa, Canada. World Health Organization. 2011. ISBN 978-92-4-156427-4. https://apps.who.int/iris/handle/10665/44624. Retrieved 23 March 2022. 
  13. ↑ 13.0 13.1 13.2 "Critical evaluation of key evidence on the human health hazards of exposure to bisphenol A". Critical Reviews in Toxicology 41 (4): 263–291. April 2011. doi:10.3109/10408444.2011.558487. PMID 21438738. 
  14. ↑ 14.0 14.1 14.2 "Why public health agencies cannot depend on good laboratory practices as a criterion for selecting data: the case of bisphenol A". Environmental Health Perspectives 117 (3): 309–315. March 2009. doi:10.1289/ehp.0800173. PMID 19337501. 
  15. ↑ "Sarah A. Vogel. Is It Safe? BPA and the Struggle to Define the Safety of Chemicals". Isis (Berkeley: University of California Press) 105 (1): 254. 2013. doi:10.1086/676809. ISSN 0021-1753. 
  16. ↑ 16.0 16.1 Blair, R. M. (1 March 2000). "The Estrogen Receptor Relative Binding Affinities of 188 Natural and Xenochemicals: Structural Diversity of Ligands". Toxicological Sciences 54 (1): 138–153. doi:10.1093/toxsci/54.1.138. PMID 10746941. 
  17. ↑ 17.0 17.1 17.2 "A review of dietary and non-dietary exposure to bisphenol-A". Food and Chemical Toxicology 50 (10): 3725–3740. October 2012. doi:10.1016/j.fct.2012.07.059. PMID 22889897. 
  18. ↑ "Concentration of bisphenol A in highly consumed canned foods on the U.S. market". Journal of Agricultural and Food Chemistry 59 (13): 7178–7185. July 2011. doi:10.1021/jf201076f. PMID 21598963. 
  19. ↑ 19.0 19.1 19.2 "Bisphenols, Benzophenones, and Bisphenol A Diglycidyl Ethers in Textiles and Infant Clothing". Environmental Science & Technology 51 (9): 5279–5286. May 2017. doi:10.1021/acs.est.7b00701. PMID 28368574. Bibcode: 2017EnST...51.5279X. http://ir.rcees.ac.cn/handle/311016/39260. 
  20. ↑ 20.0 20.1 20.2 "Bisphenol A and replacements in thermal paper: A review". Chemosphere 182: 691–706. September 2017. doi:10.1016/j.chemosphere.2017.05.070. PMID 28528315. Bibcode: 2017Chmsp.182..691B. https://research.vu.nl/en/publications/0c9480c5-48ce-4955-8d53-39b8b246802f. 
  21. ↑ "Pit and fissure sealants for preventing dental decay in permanent teeth". The Cochrane Database of Systematic Reviews 2017 (7): CD001830. July 2017. doi:10.1002/14651858.CD001830.pub5. PMID 28759120. 
  22. ↑ 22.0 22.1 22.2 "Bisphenol A concentrations in human urine, human intakes across six continents, and annual trends of average intakes in adult and child populations worldwide: A thorough literature review". The Science of the Total Environment 626: 971–981. June 2018. doi:10.1016/j.scitotenv.2018.01.144. PMID 29898562. Bibcode: 2018ScTEn.626..971H. 
  23. ↑ "Bisphenol S in Food Causes Hormonal and Obesogenic Effects Comparable to or Worse than Bisphenol A: A Literature Review". Nutrients 12 (2): 532. February 2020. doi:10.3390/nu12020532. PMID 32092919. 
  24. ↑ 24.0 24.1 Chen, Da; Kannan, Kurunthachalam; Tan, Hongli; Zheng, Zhengui; Feng, Yong-Lai; Wu, Yan; Widelka, Margaret (7 June 2016). "Bisphenol Analogues Other Than BPA: Environmental Occurrence, Human Exposure, and Toxicity—A Review". Environmental Science & Technology 50 (11): 5438–5453. doi:10.1021/acs.est.5b05387. PMID 27143250. Bibcode: 2016EnST...50.5438C. 
  25. ↑ Eladak, Soria; Grisin, Tiphany; Moison, Delphine; Guerquin, Marie-Justine; N'Tumba-Byn, Thierry; Pozzi-Gaudin, Stéphanie; Benachi, Alexandra; Livera, Gabriel et al. (2015). "A new chapter in the bisphenol A story: bisphenol S and bisphenol F are not safe alternatives to this compound" (in en). Fertility and Sterility 103 (1): 11–21. doi:10.1016/j.fertnstert.2014.11.005. PMID 25475787. 
  26. ↑ See:
  27. ↑ "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2012. doi:10.1002/14356007.a09_547.pub2. 
  28. ↑ Serini, Volker (2000). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a21_207. 
  29. ↑ 29.0 29.1 29.2 "The politics of plastics: the making and unmaking of bisphenol a "safety"". American Journal of Public Health 99 (Suppl 3): S559–S566. November 2009. doi:10.2105/AJPH.2008.159228. PMID 19890158. 
  30. ↑ "Synthetic Œstrogenic Agents without the Phenanthrene Nucleus". Nature 137 (3476): 996. 1936. doi:10.1038/137996a0. Bibcode: 1936Natur.137..996D. 
  31. ↑ "Molecular Structure in Relation to Oestrogenic Activity. Compounds without a Phenanthrene Nucleus". Proceedings of the Royal Society of London B: Biological Sciences 125 (839): 222–232. 1938. doi:10.1098/rspb.1938.0023. Bibcode: 1938RSPSB.125..222D. 
  32. ↑ Kwon, Jung-Hwan; Katz, Lynn E.; Liljestrand, Howard M. (October 2007). "Modeling binding equilibrium in a competitive estrogen receptor binding assay". Chemosphere 69 (7): 1025–1031. doi:10.1016/j.chemosphere.2007.04.047. PMID 17559906. Bibcode: 2007Chmsp..69.1025K. 
  33. ↑ Synthesis and Characterization of Oligomers. CRC Press. 1991. p. 103. ISBN 978-0-8493-4954-6. 
  34. ↑ "Solid Acid Catalysts for Industrial Condensations of Ketones and Aldehydes with Aromatics". Industrial & Engineering Chemistry Research 43 (5): 1169–1178. March 2004. doi:10.1021/ie030429+. 
  35. ↑ 35.0 35.1 "Impurities in industrial grade 4,4'-isopropylidene diphenol (bisphenol A): possible implications for estrogenic activity". Chemosphere 55 (6): 927–931. May 2004. doi:10.1016/j.chemosphere.2003.11.063. PMID 15041297. Bibcode: 2004Chmsp..55..927T. 
  36. ↑ "Occurrence, endocrine-related bioeffects and fate of bisphenol A chemical degradation intermediates and impurities: A review". Chemosphere 207: 469–480. September 2018. doi:10.1016/j.chemosphere.2018.05.117. PMID 29807346. Bibcode: 2018Chmsp.207..469P. 
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  57. ↑ Król, Piotr (2008). Linear polyurethanes : synthesis methods, chemical structures, properties and applications. Leiden: VSP. pp. 11–14. ISBN 9789004161245. 
  58. ↑ "European Union Summary Risk Assessment Report - Bis (2-ethylhexyl) Phthalate (DEHP)". European Commission. 16 July 2008. https://publications.jrc.ec.europa.eu/repository/handle/JRC45844. open access
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  61. ↑ "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_405. 
  62. ↑ Gauthier, Lewis T.; Laurich, Bruce; Hebert, Craig E.; Drake, Christine; Letcher, Robert J. (20 August 2019). "Tetrabromobisphenol-A-Bis(dibromopropyl ether) Flame Retardant in Eggs, Regurgitates, and Feces of Herring Gulls from Multiple North American Great Lakes Locations". Environmental Science & Technology 53 (16): 9564–9571. doi:10.1021/acs.est.9b02472. PMID 31364365. Bibcode: 2019EnST...53.9564G. 
  63. ↑ Pawlowski, Kristin H; Schartel, Bernhard (November 2007). "Flame retardancy mechanisms of triphenyl phosphate, resorcinol bis(diphenyl phosphate) and bisphenol A bis(diphenyl phosphate) in polycarbonate/acrylonitrile–butadiene–styrene blends". Polymer International 56 (11): 1404–1414. doi:10.1002/pi.2290. 
  64. ↑ "Alkylphenol and bisphenol A contamination of urban runoff: an evaluation of the emission potentials of various construction materials and automotive supplies". Environmental Science and Pollution Research International 25 (22): 21887–21900. August 2018. doi:10.1007/s11356-018-2272-z. PMID 29796891. Bibcode: 2018ESPR...2521887L. https://hal.science/hal-01813100/file/Lamprea2018_ESPR.pdf. 
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  66. ↑ "Bisphenol S and F: A Systematic Review and Comparison of the Hormonal Activity of Bisphenol A Substitutes". Environmental Health Perspectives 123 (7): 643–650. July 2015. doi:10.1289/ehp.1408989. PMID 25775505. 
  67. ↑ "Exposure of the U.S. population to bisphenol A and 4-tertiary-octylphenol: 2003-2004". Environmental Health Perspectives 116 (1): 39–44. January 2008. doi:10.1289/ehp.10753. PMID 18197297. 
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  69. ↑ "Human exposure to bisphenol A (BPA)". Reproductive Toxicology 24 (2): 139–177. August 2007. doi:10.1016/j.reprotox.2007.07.010. PMID 17825522. 
  70. ↑ Van Landuyt, K.L.; Nawrot, Tim; Geebelen, B.; De Munck, J.; Snauwaert, J.; Yoshihara, K.; Scheers, Hans; Godderis, Lode et al. (August 2011). "How much do resin-based dental materials release? A meta-analytical approach". Dental Materials 27 (8): 723–747. doi:10.1016/j.dental.2011.05.001. PMID 21664675. 
  71. ↑ "Development of Analytical Method for Determining Trace Amounts of BPA in Urine Samples and Estimation of Exposure to BPA.". Journal of Environmental Chemistry 14 (1): 57–63. 2004. doi:10.5985/jec.14.57. 
  72. ↑ "Physiologically based pharmacokinetics of bisphenol A". Journal of Toxicology and Environmental Health. Part A 67 (23–24): 1971–1985. December 2004. doi:10.1080/15287390490514615. PMID 15513896. Bibcode: 2004JTEHA..67.1971S. 
  73. ↑ Bousoumah, Radia; Leso, Veruscka; Iavicoli, Ivo; Huuskonen, Pasi; Viegas, Susana; Porras, Simo P.; Santonen, Tiina; Frery, Nadine et al. (August 2021). "Biomonitoring of occupational exposure to bisphenol A, bisphenol S and bisphenol F: A systematic review". Science of the Total Environment 783: 146905. doi:10.1016/j.scitotenv.2021.146905. PMID 33865140. Bibcode: 2021ScTEn.783n6905B. 
  74. ↑ "Does using plastic bottles and containers cause cancer?". Cancer Research UK. 23 December 2021. https://www.cancerresearchuk.org/about-cancer/causes-of-cancer/cancer-myths/does-using-plastic-bottles-and-containers-cause-cancer. 
  75. ↑ "bisphenol a - Search Results - PubMed" (in en). https://pubmed.ncbi.nlm.nih.gov/?term=bisphenol+a. 
  76. ↑ 76.0 76.1 MacKay, Harry; Abizaid, Alfonso (May 2018). "A plurality of molecular targets: The receptor ecosystem for bisphenol-A (BPA)". Hormones and Behavior 101: 59–67. doi:10.1016/j.yhbeh.2017.11.001. PMID 29104009. 
  77. ↑ "An extensive new literature concerning low-dose effects of bisphenol A shows the need for a new risk assessment". Environ. Health Perspect. 113 (8): 926–33. 2005. doi:10.1289/ehp.7713. PMID 16079060. 
  78. ↑ Teeguarden, Justin G.; Hanson-Drury, Sesha (December 2013). "A systematic review of Bisphenol A "low dose" studies in the context of human exposure: A case for establishing standards for reporting "low-dose" effects of chemicals". Food and Chemical Toxicology 62: 935–948. doi:10.1016/j.fct.2013.07.007. PMID 23867546. 
  79. ↑ "Bisphenol A - ECHA". https://echa.europa.eu/hot-topics/bisphenol-a. 
  80. ↑ European Food Safety Authority (2015). EFSA explains the Safety of Bisphenol A: scientific opinion on bisphenol A (2015).. European Food Safety Authority. doi:10.2805/075460. ISBN 9789291996421. 
  81. ↑ "Scientific Opinion on the risks to public health related to the presence of bisphenol A (BPA) in foodstuffs". EFSA Journal 13 (1): 3978. 21 January 2015. doi:10.2903/j.efsa.2015.3978. 
  82. ↑ OCSPP US EPA (21 September 2015). "Risk Management for Bisphenol A (BPA)" (in en). https://www.epa.gov/assessing-and-managing-chemicals-under-tsca/risk-management-bisphenol-bpa. 
  83. ↑ CLARITY-BPA Research Program (October 2021). NTP Research Report on the Consortium Linking Academic and Regulatory Insights on Bisphenol A Toxicity (CLARITY-BPA): A Compendium of Published Findings. pp. 18. doi:10.22427/NTP-RR-18. 
  84. ↑ Health Canada (16 April 2013). "Bisphenol A (BPA)". Government of Canada. https://www.canada.ca/en/health-canada/services/home-garden-safety/bisphenol-bpa.html. 
  85. ↑ "Bisphenol A (BPA)". Department of Health (Australia). https://www.foodstandards.gov.au/consumer/chemicals/bpa/Pages/default.aspx. 
  86. ↑ Bisphenol A and baby bottles : challenges and perspectives. The Publications Office of the European Union. 2010. doi:10.2788/97553. ISBN 9789279158698. 
  87. ↑ "Indirect Food Additives: Polymers". U.S. Government Publishing Office. https://www.federalregister.gov/documents/2012/07/17/2012-17366/indirect-food-additives-polymers. 77 FR 41899
  88. ↑ Legislative Services Branch (1 July 2020). "Consolidated federal laws of canada, Canada Consumer Product Safety Act". https://laws-lois.justice.gc.ca/eng/acts/C-1.68/index.html. 
  89. ↑ "EUR-Lex - 32011L0008 - EN - EUR-Lex" (in en). European Union. https://eur-lex.europa.eu/eli/dir/2011/8/oj. "COMMISSION DIRECTIVE 2011/8/EU of 28 January 2011 amending Directive 2002/72/EC as regards the restriction of use of Bisphenol A in plastic infant feeding bottles" 
  90. ↑ "MSC unanimously agrees that Bisphenol A is an endocrine disruptor - All news - ECHA" (in en-GB). European Chemicals Agency (ECHA). https://echa.europa.eu/-/msc-unanimously-agrees-that-bisphenol-a-is-an-endocrine-disruptor. 
  91. ↑ "EU court confirms BPA as substance of 'very high concern'". 12 July 2019. https://www.ehn.org/bisphenol-a-2639174350.html. 
  92. ↑ Akingbemi, Benson T.; Sottas, Chantal M.; Koulova, Anna I.; Klinefelter, Gary R.; Hardy, Matthew P. (1 February 2004). "Inhibition of Testicular Steroidogenesis by the Xenoestrogen Bisphenol A Is Associated with Reduced Pituitary Luteinizing Hormone Secretion and Decreased Steroidogenic Enzyme Gene Expression in Rat Leydig Cells". Endocrinology 145 (2): 592–603. doi:10.1210/en.2003-1174. PMID 14605012. 
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  94. ↑ "Estrogen biology: new insights into GPER function and clinical opportunities". Molecular and Cellular Endocrinology 389 (1–2): 71–83. May 2014. doi:10.1016/j.mce.2014.02.002. PMID 24530924. 
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  96. ↑ 96.0 96.1 "Global Assessment of Bisphenol A in the Environment: Review and Analysis of Its Occurrence and Bioaccumulation". Dose-Response 13 (3): 1559325815598308. 2015-07-29. doi:10.1177/1559325815598308. PMID 26674671. 
  97. ↑ Ozhan, Koray; Kocaman, Emel (February 2019). "Temporal and Spatial Distributions of Bisphenol A in Marine and Freshwaters in Turkey". Archives of Environmental Contamination and Toxicology 76 (2): 246–254. doi:10.1007/s00244-018-00594-6. PMID 30610254. Bibcode: 2019ArECT..76..246O. 
  98. ↑ 98.0 98.1 98.2 Cousins, I.T.; Staples, C.A.; Kleĉka, G.M.; Mackay, D. (July 2002). "A Multimedia Assessment of the Environmental Fate of Bisphenol A". Human and Ecological Risk Assessment 8 (5): 1107–1135. doi:10.1080/1080-700291905846. Bibcode: 2002HERA....8.1107C. 
  99. ↑ Vasiljevic, Tijana; Harner, Tom (October 2021). "Bisphenol A and its analogues in outdoor and indoor air: Properties, sources and global levels". Science of the Total Environment 789: 148013. doi:10.1016/j.scitotenv.2021.148013. PMID 34323825. Bibcode: 2021ScTEn.789n8013V. 
  100. ↑ Fürhacker, M; Scharf, S; Weber, H (September 2000). "Bisphenol A: emissions from point sources". Chemosphere 41 (5): 751–756. doi:10.1016/S0045-6535(99)00466-X. PMID 10834378. Bibcode: 2000Chmsp..41..751F. 
  101. ↑ 101.0 101.1 Qi, Chengdu; Huang, Jun; Wang, Bin; Deng, Shubo; Wang, Yujue; Yu, Gang (2018). "Contaminants of emerging concern in landfill leachate in China: A review". Emerging Contaminants 4 (1): 1–10. doi:10.1016/j.emcon.2018.06.001. 
  102. ↑ "An assessment of endocrine disrupting activity changes during wastewater treatment through the use of bioassays and chemical measurements". Water Environment Research 77 (1): 12–23. 2005. doi:10.2175/106143005x41573. PMID 15765931. Bibcode: 2005WaEnR..77...12D. 
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  104. ↑ Kang, J; Katayama, Y; Kondo, F (16 January 2006). "Biodegradation or metabolism of bisphenol A: From microorganisms to mammals". Toxicology 217 (2–3): 81–90. doi:10.1016/j.tox.2005.10.001. PMID 16288945. 
  105. ↑ Zhang, Chi; Li, Yi; Wang, Chao; Niu, Lihua; Cai, Wei (2 January 2016). "Occurrence of endocrine disrupting compounds in aqueous environment and their bacterial degradation: A review". Critical Reviews in Environmental Science and Technology 46 (1): 1–59. doi:10.1080/10643389.2015.1061881. Bibcode: 2016CREST..46....1Z. 
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  109. ↑ 109.0 109.1 Wu, Nicholas C.; Seebacher, Frank (July 2020). "Effect of the plastic pollutant bisphenol A on the biology of aquatic organisms: A meta-analysis". Global Change Biology 26 (7): 3821–3833. doi:10.1111/gcb.15127. PMID 32436328. Bibcode: 2020GCBio..26.3821W. 
  110. ↑ 110.0 110.1 "A critical analysis of the biological impacts of plasticizers on wildlife". Philosophical Transactions of the Royal Society B: Biological Sciences 364 (1526): 2047–62. 2009. doi:10.1098/rstb.2008.0242. PMID 19528055. 



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