Bisphenol A
Chemical compound used in plastics manufacturing / From Wikipedia, the free encyclopedia
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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.[3][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]
Names | |
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Preferred IUPAC name
4,4′-(Propane-2,2-diyl)diphenol | |
Other names
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Identifiers | |
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3D model (JSmol) |
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ChEBI | |
ChEMBL | |
ChemSpider |
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DrugBank |
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ECHA InfoCard | 100.001.133 |
EC Number |
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KEGG |
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PubChem CID |
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RTECS number |
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UNII | |
UN number | 2430 |
CompTox Dashboard (EPA) |
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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)[2] |
Boiling point | 250–252 °C (482–486 °F; 523–525 K)[2] at 13 torrs (0.017 atm) |
0.3 g/L (25 °C)[3] | |
log P | 3.41[4] |
Vapor pressure | 5×10−6 Pa (25 °C)[5] |
Hazards[6] | |
GHS labelling: | |
Danger | |
H317, H318, H335, H360, H411[6] | |
P201, P202, P261, P273, P302+P352, P304+P340, P305+P351+P338, P308+P313, P333+P313, P363, P403+P233[6] | |
NFPA 704 (fire diamond) | |
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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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]