Bisphenol A.

from Wikipedia, the free encyclopedia
Structural formula
Structural formula bisphenol A
Surname Bisphenol A.
other names
  • 4- [2- (4-hydroxyphenyl) propan-2-yl] phenol ( IUPAC )
  • 2,2-bis (4-hydroxyphenyl) propane
  • 4,4'-isopropylidenediphenol
  • p -Diphenol-2-propane
  • p -diphenol dimethyl methane
  • 4,4'-diphenol dimethyl methane
  • 4,4'-dimethylmethanediphenol
  • 2-propane-diphenol-4,4 ′
  • 4,4 '- (propane-2,2-diyl) diphenol
  • 4,4 '- (dihydroxybenzene) -2-propane
  • 4,4 '- (dihydroxybenzene) dimethyl methane
  • 4,4'-dibenzyldimethylmethane-1,1'-dihydroxide
  • 2-propane-diphenol-4
  • Dibenzolhydroxolpropane (old name)
Molecular formula C 15 H 16 O 2
Brief description

bright crystals, flakes, powder or flakes

External identifiers / databases
CAS number 80-05-7
EC number 201-245-8
ECHA InfoCard 100.001.133
PubChem 6623
ChemSpider 6371
DrugBank DB06973
Wikidata Q271980
Molar mass 228.28 g mol −1
Physical state



1.2 g cm −3

Melting point

155-156 ° C

boiling point

360 ° C

  • soluble in ethanol and alkalis
  • very heavy in water (300 mg l −1 )
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
05 - Corrosive 08 - Dangerous to health 07 - Warning 09 - Dangerous for the environment


H and P phrases H: 317-318-335-360F-411
P: 280-302 + 352-305 + 351 + 338-310-304 + 340
Authorization procedure under REACH

of particular concern : toxic for reproduction ( CMR ), serious effects on human health are considered likely


DFG / Switzerland: 5 mg m −3 (measured as inhalable dust )

Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Bisphenol A ( BPA ) is a chemical compound from the group of diphenylmethane - derivatives and one of the bisphenols . It is manufactured synthetically and is part of many products in daily use such as plastic bottles, plastic toys, thermal paper , the lining of cans , floor coatings made of epoxy resin and much more.

Endocrinological societies and the WHO categorize BPA as an endocrine disruptor , i.e. a substance with a hormone-like effect, and see it as proven that BPA in humans can cause diseases such as diabetes mellitus , obesity , thyroid disorders and developmental disorders (in particular in children) and infertility .


In 1891 the Russian chemist Alexander Dianin , who u. a. had studied in Jena , for the first time bisphenol A. Theodor Zincke , professor at the University of Marburg , published this synthesis in 1905. The British biochemists Edward Charles Dodds and Wilfrid Lawson searched in 1936 for substances with the effect of estrogen , because it was extracted from the urine of pregnant mares was too expensive. They treated rats with their ovaries removed with various chemicals and identified bisphenol A as a substance with weak estrogenic effects. However, they soon discovered far more effective synthetic estrogens, so that bisphenol A was no longer used for hormone therapy.


Bisphenol A is prepared from two equivalents of phenol and one equivalent of acetone shown . Hydrogen chloride (HCl) or polystyrene sulfonate serve as catalysts . In order to obtain the highest possible yield, an excess of phenol is used:

Synthesis of bisphenol A from phenol and acetone

The other representatives of the bisphenol group of substances , which in addition to the designation bisphenol, have a letter or a combination of letters for more detailed characterization, are also accessible through analogous syntheses . The A in bisphenol A stands for acetone.


BPA is primarily used as a raw material for the synthesis of polymeric plastics based on polyesters , polysulfones , polyether ketones , polycarbonates and epoxy resins . BPA is therefore of great economic and technical importance. BPA is also used as an antioxidant in plasticizers and to prevent polymerization in polyvinyl chloride (PVC).

Thermal papers such as receipt rolls etc. are coated with BPA so that they turn dark when exposed to heat. In addition, BPA is z. B. in the plastic of drinking bottles or food boxes as well as in the inner coating of food cans or the sealing surfaces of "twist-off" lids. According to the " Bund für Umwelt und Naturschutz Deutschland " (BUND), six million tons of BPA are produced worldwide every year, almost half a million of them in Germany.

Because of the health risks, various variants for replacing bisphenol A in polymers (polycarbonates, polyesters, epoxides and polyimides) are discussed in the scientific literature, including 2,2,4,4-tetramethyl-1,3-cyclobutanediol and isosorbide . At the beginning of 2018, some suppliers of receipts switched to bisphenol-A-free alternatives, including Aldi , Edeka , the dm drugstores and all companies in the Rewe Group .


In addition to the US companies Dow Chemical and Hexion Inc. (formerly: Momentive Performance Materials ), the Taiwanese company Nan Ya Plastics (part of the Formosa Plastics Group ) and Ineos Phenol are among the world's largest manufacturers. Other manufacturers are General Electric (GE) and Sunoco ( Bayer AG , Covestro since August 2015 ).


For the qualitative and quantitative determination of bisphenol A, after appropriate sample preparation , e.g. B. by solid phase extraction , the coupling of gas chromatography or HPLC can be used with mass spectrometry . The procedure has also been used to examine breast milk and child urine.

Occurrence and release

Plastics containing bisphenol A, in particular polycarbonate, vinyl ester resin and epoxy resin , are used to manufacture numerous items of daily use that come into direct contact with food and beverages . Epoxy resins are used to produce coatings for metallic containers, also for food such as food cans and for beverage containers and kettles. In addition, epoxy resins are used for varnishes , paints , adhesives , interior coatings for the renovation of drinking and waste water containers and pipes (see interior pipe renovation ) and for the production of swimming pool prefabricated pools and large wine storage tanks and much more. This is of relevance to health, since the polymer end products themselves are largely biologically inert , but the starting material BPA may be released from them again and can then cause damage to health.

Heat or heating, acids and alkalis favor the release of bisphenol A from the polymer. Boiling water speeds up the rate 55 times. The release can also occur when drinking water filled in polycarbonate bottles is stored too warm in hot areas, when food is prepared in polycarbonate containers and then washed off with hot water. The otherwise clear material becoming cloudy (without scratches) is an indication of the extraction of ingredients. Crockery made of polycarbonate, including blender jars from stand mixers, should therefore not be washed in dishwashers , since if bisphenols are dissolved out, all of the rinse water and all of the other crockery to be cleaned (after wetting and subsequent drying) will be contaminated. In order to reduce the bisphenol-A contamination of the food, containers made of polycarbonate should be rinsed with cold water shortly before use. The disinfection of drinking water by sunlight in recycled polycarbonate drinking water sales bottles and also the use of polycarbonate as a viewing window to indicate the level in kettles or coffee machines or for stand mixer containers and the heating of freezer containers made of PC in microwave ovens are therefore not without problems.

Certain filling and sealing compounds ( dental composites ) used in the dental field can release BPA during or as a result of dental treatment.

Some types of thermal paper also contain BPA in their coating, which means that it enters the paper cycle. Via this thermal paper, the substance also gets into the blood directly through the skin. A significantly increased burden on cashiers in supermarkets has been proven. Of 124 thermal papers examined in Switzerland between September 2013 and January 2014, BPA was detected in 100 samples and bisphenol S in 4 samples. In 2014 the US Environmental Protection Agency published a report with assessments of 19 different alternative substances for thermal paper production. No substance could be identified as definitely safer, mainly because insufficient toxicological data are usually available and, due to structural similarities, there are at least doubts as to its harmlessness. In the meantime, completely bisphenol-free thermal papers are also available.

Polyolefins such as B. Polypropylene and polyethylene , which are some of the most common plastics used in food packaging and shopping bags, do not contain bisphenol A.

Health hazard studies

Fertility problems


A Canadian study published in April 2015 reported no association between decreased fertility (longer time to pregnancy) and bisphenol-A levels in the urine of women.


A University of Michigan study (published 2010) of 190 men with fertility problems found no statistically significant association, statistical modeling suggests a possible association that requires further studies to confirm:

  • BPA was found in 89 percent of the urine samples.
  • In men who had high BPA concentrations, a 23 percent lower semen concentration and around 10 percent more DNA damage were found. The values ​​of the test persons in whom only little or no traces of BPA were present were significantly better.

According to evaluations by the Federal Environment Agency and the NGO CHEM Trust, new studies indicate a connection between diabetes , cardiovascular problems, a lack of libido or obesity and an increased BPA level in the blood.

US researchers found an increase in the BPA concentration to 20.8 micrograms per liter in the urine of test subjects through the consumption of canned soups, compared to the comparison group with 1.1 micrograms per liter. According to this, BPA diffuses from the inner coating of the can into the food, is consumed and ingested by the consumer and then excreted in the urine.

In experiments and under unfavorable environmental conditions in animals, including mammals, bisphenol A is a xenoestrogen with an estrogen-like effect (see endocrine disruptors ). So it not only disrupts sexual development, but also brain development in mice and birds. Male deer mice show female behavior after treatment with bisphenol A and are avoided by female conspecifics.

A study of factory workers who are regularly exposed to bisphenol A links the substance to disorders of male sexual function.

A panel of experts convened by the WHO came to the conclusion in November 2010 that in studies on reproductive toxicity, an effect from bisphenol A only occurs at a high dose. According to studies on neurodevelopment, among other things, the dangers already arise from the amount consumed by people. Because of the uncertainty in the research results, the panel recommended further research on the health hazard.

Other health effects

A scientific evaluation from 2010 found that BPA is not mutagenic .

According to a study by the University Hospital Bonn from December 2012, BPA can influence the hormonal balance and impair the function of enzymes and transport proteins. Experiments on tissue samples from mice and humans have shown that BPA reversibly blocks calcium channels in the cell membrane that are important for cell function.

Bisphenol A disrupts the function of proteins, which are crucial for growth processes in cells, and thus promotes GTPase- mediated tumors. Small GTPases are enzymes that exist in cells in two states. In active form, the GTP molecule is bound, in the inactive form the lower-energy GTP form GDP. These switch proteins are used to transmit signals in cells. Bisphenol A binds to the GTPases K-Ras and H-Ras and disrupts the exchange of GDP for GTP.

Bisphenol A is also suspected of causing molar incisor hypomineralization .

Government regulation

Australia, New Zealand

The Food Safety Authority of Australia and New Zealand ( FSANZ ) confirmed the American Food and Drug Administration (FDA) and European Food Safety Authority (EFSA) assessments of BPA in relation to young children in March 2009 , but emphasized that some manufacturers' move did not Using more in baby bottles is a voluntary decision, not a reaction to legal requirements.

European Union

Since March 1, 2011, the production and since June 1, 2011 the sale of baby bottles made of polycarbonate containing BPA has been banned in the EU. The manufacturers had already voluntarily withdrawn baby bottles containing BPA from the market.

On January 21, 2015, the re-evaluation of bisphenol A was presented by EFSA. EFSA found that with current consumer exposure, BPA does not pose a health risk to any age group (including unborn children, infants and adolescents). Exposure through diet or a combination of different sources (diet, dust, cosmetics and thermal paper) is well below the safe upper limit. In addition, the tolerable daily intake (TDI) was reduced from 50 micrograms per kilogram of body weight per day (µg / kg body weight / day) to 4 µg / kg body weight / day. The TDI is considered provisional as the results of a US long-term study are still to be taken into account.

The Scientific Committee on Emerging and Newly Identified Health Risks (SCENIHR) evaluated the use of bisphenol A in medical devices on behalf of the EU Commission . After a public consultation, the revised opinion was adopted on February 18, 2015. Accordingly, there are no health risks for the possible release of BPA from dental materials, while health risks for newborns in intensive care units and dialysis patients are considered possible. The SCENIHR therefore recommends replacing them with materials that do not release BPA.

In 2012, bisphenol A was included in the EU's ongoing action plan ( CoRAP ) in accordance with Regulation (EC) No. 1907/2006 (REACH) as part of substance evaluation . The effects of the substance on human health and the environment are re-evaluated and, if necessary, follow-up measures are initiated. Bisphenol A uptake was caused by concerns about consumer use , high (aggregated) tonnage and widespread use, and as a potential endocrine disruptor . The reassessment took place from 2012 and was carried out by Germany . As an interim result of the substance evaluation, ECHA published additional information requests from the German evaluation authorities in April 2014. In addition to a dermal absorption study, extensive information on emission paths into the environment was requested. Registrants had to submit this information and results to ECHA by December 20, 2015. The substance evaluation was completed in May 2017. The main conclusions of the final document are the following: The use of bisphenol A in thermal paper is not safe for the consumer. Furthermore, the use of items made of PVC and large items of polycarbonate is not safe for the consumer.

The classification proposal for France was implemented by the European Commission in early 2017. According to this, bisphenol A will be classified as reproductive toxic category 1B from March 1, 2018 . The labeling as reproductive toxic category 1B may be used before March 1, 2018. As a substance that is toxic to reproduction, bisphenol A was classified by the committees of the European Chemicals Agency (ECHA) as being of particular concern in January 2017 and was therefore placed on the list of candidates for possible authorization. In the meantime, the entry for bisphenol A has been expanded: in addition to the reproductive toxic properties, the endocrine disrupting properties of the substance have been named as particularly worrying; From 2020 the use of BPA for the coating of thermal paper (receipts, fax paper rolls , etc.) is prohibited.

EFSA is preparing a re-evaluation of bisphenol A in 2018, the evaluation strategy was published in December 2017.


On March 1, 2011, the Federal Ministry of Food, Agriculture and Consumer Protection (BMEL) banned the substance in connection with baby bottles ; the sale of bottles already made with this substance was permitted until the end of May 2011.


In the spring of 2010, bisphenol was banned in baby drinking bottles in France. In September 2011, ANSES published an assessment of bisphenol A and a call for further information on bisphenol A to be submitted. In autumn 2012, ANSES submitted a classification dossier to the European chemicals agency ECHA in order to achieve classification as category 1 (A or B) toxic to reproduction. The RAC followed the classification proposal and proposed classification as category 1B toxic for reproduction (see above, EU).

From 2013, there was already a ban on BPA in food packaging in France, initially for items for small children under 3 years of age. From January 1, 2015, the ban on all food packaging will apply. In 2014 France submitted a restriction dossier for bisphenol A in thermal paper to ECHA .

Le Monde stated that the following “gap” was clear when it came to bisphenol A: between the research results on the one hand and the behavior of the major regulatory agencies such as EFSA in Europe and FDA in the USA on the other. Several thousand scientific papers on BPA were published between 1996 and 2014, most of them exploring links between the chemical and a variety of diseases - type 2 diabetes, obesity, infertility, prostate cancer and the like. a. - determine or confirm. But the above-mentioned supervisory authorities have so far resisted this prevailing scientific opinion that France is a real role model (avant-garde), says the newspaper. The different points of view of ANSES and EFSA were discussed and documented at a meeting on December 3, 2014.


The Dutch Food Safety Agency took over the then EFSA assessment in November 2008.

At the request of the Dutch Ministry of Health, EFSA set up a working group to evaluate the possible effects of bisphenol A on the immune system. The findings were judged to be too limited to allow conclusions to be drawn about human health.


In 2004 a study by the Vienna Environment Agency found up to 8.8 mg / kg BPA in house dust . The production of soothers with bisphenol A was banned with an ordinance issued by the Federal Ministry of Health on October 6, 2011 .


Due to consumer concerns, the coatings on food cans have largely been switched from epoxy resin to PET film.


In April 2008, Canada had officially became the first country BPA as harmful classified (hazardous to human health) and banned the use of BPA for baby bottles. In 2009, official investigations revealed that products containing BPA had been declared BPA-free.


In February 2009 the Swiss Federal Office of Public Health (BAG) evaluated the scientific reports of various food safety authorities and summarized the result “that the consumption of bisphenol A through food does not pose a risk for the consumer. This also applies to newborns and infants. ”The authority argued in favor of BPA:“ A ban on BPA would inevitably mean that the manufacturers of packaging and consumer goods (products that come into contact with food) would have to switch to other substances that are less toxic is known. That would mean that a well-characterized risk would be replaced by a risk that is much more difficult to assess. "

United States of America

Unlike in previous years, there have been increasing voices of warning from authorities and public research institutions since 2008: The American “National Toxicology Program” (NTP) of the “National Institute of Environmental Health Sciences” (NIH-HHS) said in a summary from September 2008 some concerns (some concern) because of the effects of BPA on the brain , the behavior and the prostate gland in fetuses , infants and children under currently available environmental concentrations. At regional level, the consequence was pulled and banned in 2009 BPA in children's products, as in Chicago and Suffolk County, NY In January 2010, the US FDA announced were newer governmental investigations some concerns (some concern) about the impact of BPA in current products rendered on various human organs. Until further results are available, the FDA recommends reducing the intake of BPA through food, supports manufacturers in switching to BPA-free bottles and advocates more specific regulatory controls. The six largest manufacturers in the USA had already announced in March 2009 that they would discontinue the sale of baby bottles containing BPA and have started to switch production accordingly.

In cooperation with the NTP and NIEHS , the FDA has initiated several studies aimed at providing information on the possible health risks of bisphenol A.

In November 2014, in an update to its assessment of bisphenol A, the FDA determined that the currently approved uses of BPA in food packaging are safe.

People's Republic of China

Data on the situation in the People's Republic of China were published in 2012.


Several documentaries had, among other things, BPA on the subject and presented it as harmful to health:


Web links

German speaking

English speaking

Individual evidence

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  4. Entry in the SVHC list of the European Chemicals Agency , accessed on July 7, 2017.
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  47. EU coordination of German nature conservation ring (DNR): EU-wide ban on bisphenol A in baby bottles from June 2011. Report of November 26, 2010.
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  49. EFSA: No health risk for consumers from bisphenol A exposure , press release from January 21, 2015.
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  51. Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): 4,4′-isopropylidenediphenol , accessed on March 26, 2019.
  52. ECHA's request for information from November 2013 , accessed on December 21, 2017.
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  54. Regulation (EU) 2016/1179 (PDF)
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  56. ECHA decision of 6 July 2017 , accessed on 21 December 2017.
  57. EFSA press release of December 14, 2017: BPA: Plan for EFSA reassessment in 2018 is ready , accessed on December 20, 2017.
  58. ↑ Ban on the sale of baby bottles with bisphenol A on .
  59. ^ The French ban BPA in baby bottles from May 25, 2010.
  60. ANSES: Call for contributions by the French Agency for Food, Environmental and Occupational Health & Safety; Reports on the 'health effects and uses of bisphenol A' ( Memento from March 25, 2014 in the Internet Archive ) (PDF; 76 kB) from September 26, 2011 (accessed on January 21, 2013).
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  62. ECHA: France prepared a restriction report on bisphenol A in thermal paper .
  63. Bisphenol A: la France à l'avant-garde. In: Le Monde , January 5, 2015.
  64. Minutes of EFSA-ANSES Expert Meeting on Bisphenol A , Minutes of December 11, 2014, published January 21, 2015.
  65. ( Page no longer available , search in web archives: Communication from the Dutch Food Safety Agency )@1@ 2Template: Dead Link /
  66. EFSA: Bisphenol A: new knowledge on the immune system useful but limited. Communication dated October 13, 2016.
  67. House dust - an indicator for indoor pollution (PDF; 2.7 MB).
  68. Factsheet alkylphenols and bisphenol A and bisphenol F ( Memento from November 12, 2011 in the Internet Archive ) (PDF; 246 kB).
  69. Federal Law Gazette II No. 327/2011
  70. Jane Byrne: Consumers fear the packaging - a BPA alternative is needed now . September 22, 2008. Retrieved January 5, 2010.
  71. Health Canada makes it official: BPA is health hazard ( Memento of April 17, 2009 in the Internet Archive )
  72. ^ "Labeled as being free of bisphenol A" .
  73. Federal Office of Public Health (BAG): Fact sheet bisphenol A . ( Memento of March 2, 2009 in the Internet Archive ) As of February 24, 2009.
  74. ( Page no longer available , search in web archives: September 3, 2008: NTP Finalizes Report on Bisphenol A )@1@ 2Template: Dead Link /
  75. National Toxicology Program (NTP): Bisphenol A (ABPA). ( Memento of March 23, 2009 in the Internet Archive ) February 2010 factsheet.
  76. Chicago 2009: ban of BPA in empty beverage or food containers intended for use by children under the age of 3 .
  77. Suffolk County 2009: ban on baby bottles and cups that contain the potentially toxic BPA material ( Memento from April 9, 2009 in the Internet Archive )
  78. FDA Update on Bisphenol A for Use in Food Contact Applications Update from March 30, 2013.
  79. Washington Post 2009: No BPA For Baby Bottles In US .
  80. ^ Sunoco Will Stop Selling Bisphenol A for Use in Children's Food Products .
  81. ^ JJ Heindel, RR Newbold, JR Bucher et al .: NIEHS / FDA CLARITY-BPA research program update. Reprod Toxicol, 2015, 58, 33-44, doi: 10.1016 / j.reprotox.2015.07.075 .
  82. FDA: Questions & Answers on Bisphenol A (BPA) Use in Food Contact Applications , from November 5, 2014.
  83. Huang YQ, Wong CK, Zheng JS, Bouwman H, Barra R, Wahlström B, Neretin L, Wong MH: Bisphenol A (BPA) in China: a review of sources, environmental levels, and potential human health impacts. , Environ Int. 2012; 42: 91-99, Review, PMID 21596439 .
  84. ^ "The main thing is durable" , documentary by Inge Altemeier and Reinhard Hornung, 2010, 30 min.
  85. "Our daily poison" ( Memento of the original from February 22, 2011 in the Internet Archive ) Info: The archive link was inserted automatically and not yet checked. Please check the original and archive link according to the instructions and then remove this notice. , Documentary by Marie Monique Robin, co-production by Arte France and INA, France 2010, 113 min. @1@ 2Template: Webachiv / IABot /
  86. Plastic Planet is a documentary film by Werner Boote, Vienna 2009, 95 min.