Bisphenol A

[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.

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.

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.

[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.

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.

[36][35] 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.

[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.

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.

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.

[67][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.

Among the non-food sources, exposure routes include through dust,[10] thermal paper,[20] clothing,[19] dental materials,[71] and medical devices.

[22][17][75] Food and drink containers made from Bisphenol A-containing plastics do not contaminate the content to cause any increased cancer risk.

Regardless, due to the scientific uncertainty, many jurisdictions continued to take steps to reduce exposure on a precautionary basis.

In particular, infants were considered to be at greater risk,[88] leading to bans on the use of BPA in baby bottles and related products by the US,[89] Canada,[90] and EU[91] amongst others.

Bottle producers 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 Food Safety Authority completed a re-evaluation into the risks of BPA in 2023, concluding that its tolerable daily intake should be greatly reduced.

[92] This led the European Union to ban BPA in all the food contact materials, including plastic and coated packaging, in December of 2024.

[97] It is primarily a river pollutant,[98] but has also been observed in the marine environment,[99] in soils,[100] and lower levels can also be detected in air.

[103] In all cases, wastewater treatment can be highly effective at removing BPA, giving reductions of 91–98%.

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.

[111][112] BPA appears able to affect development and reproduction in a wide range of wildlife,[112][113] with certain species being particularly sensitive, such as invertebrates and amphibians.

NFPA 704 four-colored diamond Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen Special hazards (white): no code
Bisphenol A is primarily used to make plastics, such as this polycarbonate water bottle.
The largest exposure humans have had to BPA is from food packaging, particularly the epoxy lining of metal food, beverage cans and plastic bottles .
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.