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Revision as of 20:42, 4 June 2005 editWimvandorst (talk | contribs)Extended confirmed users, Pending changes reviewers, Rollbackers16,337 edits added full chembox← Previous edit Revision as of 20:48, 4 June 2005 edit undoWimvandorst (talk | contribs)Extended confirmed users, Pending changes reviewers, Rollbackers16,337 edits fill in table (limited data)Next edit →
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| 4,4'-(propan-2-ylidene)diphenol
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| Other names | Other names
| BPA
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| ? <!-- e.g. Na<sub>2</sub>CO<sub>3</sub> --> | C<sub>15</sub>H<sub>16</sub>O<sub>2</sub>
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| ?.?? g/mol | 228.29 g/mol
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Revision as of 20:48, 4 June 2005

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Bisphenol A
Bisphenol A
General
Systematic name 4,4'-(propan-2-ylidene)diphenol
Other names BPA
Molecular formula C15H16O2
Molar mass 228.29 g/mol
Appearance ?
CAS number
Properties
Density and phase ? g/cm, ?
Solubility in water ? g/100 ml (? °C)
Melting point 153 °C (? K)
Boiling point 220 °C (? K)
Viscosity ? cP at ? °C
Structure
Molecular shape ?
Coordination geometry ?
Crystal structure ?
Dipole moment ? D
Hazards
MSDS External MSDS
Main hazards ?
Flash point 227 °C
R/S statement R: ? S: ?
RTECS number ?
Supplementary data page
Structure & properties n, εr, etc.
Thermodynamic data Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Related compounds
Other anions ?
Other cations ?
Related ? ?
Related compounds ?
Except where noted otherwise, data are given for
materials in their standard state (at 25°C, 100 kPa)
Infobox disclaimer and references

Bisphenol A is a chemical compound that is prepared by reaction of two equivalents of phenol with one equivalent of acetone. Bisphenol A belongs to the phenol class of aromatic organic compounds; it has two phenol functional groups in its molecule.

History and use

Bisphenol A was first synthesized by Dianin in 1891,. Bisphenol A was investigated in the 1930s during the search for synthetic estrogens. At that time, another synthesized compound, diethylstilbestrol, turned out to be more powerful an estrogen, so bisphenol A was not used as a synthetic estrogen. Its current main uses are as a monomer in the manufacture of polycarbonate plastic and in the manufacture of epoxy resins. Bisphenol A is also used as an antioxidant in plasticizers, as an antioxidant in PVC, and as a polymerization inhibitor in PVC.

Polycarbonates are widely used in many consumer products, from sunglasses and CDs to water and food containers and shatter-resistant baby bottles. Some polymers used in dental fillings also contain bisphenol A, while epoxy resins containing bisphenol A are popular coatings for the inside of cans used for canning food.

Possible health risks

BPA has been known to leach from plastics which are cleaned with harsh detergents or used to contain acidic or high temperature liquids. The chemical has been found in nearly every human tested in the United States.

The first evidence of bisphenol A's estrogenicity came from experiments in the 1930s in which it was fed to ovariectomised rats,. Some hormone disrupting effects in studies on animals and human cancer cells have been shown to occur at levels as low as 2-5 ppb (parts per billion). It has been claimed that these effects lead to health problems such as, in men, lowered sperm count and infertile sperm.

The plastics industry has long claimed that bisphenol A is safe at typical levels of human exposure, minimizing or discounting all tests to the contrary. Eleven industry-funded studies found no risk from bisphenol A, while 90% of 104 independent studies showed possible risks, says a December 2004 report from scientists Frederick vom Saal and Claude Hughes. A previous report, released by the Harvard Center for Risk Analysis and funded by the American Plastics Council, called the evidence for risks "weak" and "inconsistent".

References

  • 1: Dianin, Zhurnal russkogo fiziko-khimicheskogo obshchestva, 23 (1891), pp. 492 ff.
  • 2: Th. Zincke, Mittheilungen aus dem chemischen Laboratorium der Universität Marburg, Justus Liebigs Annalen der Chemie, 343 (1905), pp. 75-131.
  • 3: Handbook of Chemistry and Physics, CRC Press, 76th edition (1995-1996).
  • 4: E. C. Dodds and Wilfrid Lawson, Nature, 137 (1936), 996.
  • 5: E. C. Dodds and W. Lawson, Proceedings of the Royal Society of London, Series B, Biological Sciences, 125, #839 (27-IV-1938), pp. 222-232.

External links