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Bisphenol A

Bisphenol A. Al Strickler Matt Moynihan Jose Mattos. Bisphenol A (BPA): Introduction. BPA is an organic molecule It is produced by a condensation reaction between acetone and phenol, catalyzed by an acid or a resin. (CH 3 ) 2 CO + 2 C 6 H 5 OH → (CH 3 ) 2 C(C 6 H 4 OH) 2 + H 2 O

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Bisphenol A

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  1. Bisphenol A Al Strickler Matt Moynihan Jose Mattos

  2. Bisphenol A (BPA): Introduction BPA is an organic molecule It is produced by a condensation reaction between acetone and phenol, catalyzed by an acid or a resin. (CH3)2CO + 2 C6H5OH → (CH3)2C(C6H4OH)2 + H2O The reaction is effecient and the only byproduct of the reaction is water. Properties: Molecular formula C15H16O2 Molar mass 228.29 g mol−1 Appearance White to light brown flakes or powder Density 1.20 g/cm³, solid Melting point 158 to 159 °C (430 K) Boiling point 220 °C (493 K) / 4 mmHg Solubility in water 120–300 ppm (at 21.5 °C)

  3. BPA: Hazards Risk and Safety Statements: A group of standardized codes that indicate the hazards of chemicals and compounds • Risk and Safety Statements R: 36, 37, 38, 43 S: 24, 26, 37: RISK • R36: Irritating to eyes • R37: Irritating to respiratory system • R38: Irritating to skin • R43: May cause sensitization by skin contact SAFETY • S24: Avoid contact with skin • S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice • S37: Wear suitable gloves BPA MSDS: http://msds.chem.ox.ac.uk/BI/bisphenol_A.html

  4. 0 BPA: Hazards 0 3 NFPA 704 National Fire Protection Association • Health (blue) • 4 Very short exposure could cause death or major residual injury • 3 Short exposure could cause serious temporary or moderate residual injury • 2 Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury • 1 Exposure would cause irritation with only minor residual injury • 0 Poses no health hazard, no precautions necessary. • Flammability (red) • 4 Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23°C (73°F) • 3 Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23°C (73°F) and 38°C (100°F) • 2 Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38°C (100°F) and 93°C (200°F) • 1 Must be heated before ignition can occurs. Flash point over 93°C (200°F) • 0 Will not burn • Instability/Reactivity (yellow) • 4 Readily capable of detonation or explosive decomposition at normal temperatures and pressures • 3 Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked • 2 Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water • 1 Normally stable, but can become unstable at elevated temperatures and pressures • 0 Normally stable, even under fire exposure conditions, and is not reactive with water • The white "special notice" area can contain several symbols.

  5. BPA: Uses There are seven plastic polymer groups. BPA is found in type 3 and type 7 Type 3 is PVC. BPA is used as a ‘plasticizer’ in this type Type 7 is a ‘catch all’ designation. Polycarbonates and epoxy resins use BPA and fall under this category. Other types that do not use BPA in production: 1 PET 2 HDPE 4 LDPE 5 polypropylene 6 polystyrene

  6. BPA: Uses BPA is used in: Synthesis of polyesters, Synthesis of polysulfones Synthesis of Polyether ketones Antioxidant in some plasticizers Polymerization inhibitor in PVC Monomer in production of epoxy resins Most common form of polycarbonate plastic. Polycarbonate plastic made from BPA is used in water bottles, baby bottles, sports equipment, medical and dental devices/sealant, eyeglass lenses, and disc media. Epoxy resins made from BPA are used as the liner in food and drink cans. Lexan (a polycarbonate), a polymer made using BPA

  7. BPA: Impact on Health • Postulated areas of negative health impact • Brain • Behavior • Reproduction • Endocrine system • Prostate gland • Mammary gland

  8. BPA: National Toxicology Program SOME Concern: there is insufficient human data to reach a conclusions - But there is LIMITED evidence in animal studies

  9. BPA: National Toxicology Program Conclusions • SOME CONCERN • Brain, Behavior, and Prostate gland • Fetuses, Infants, and Children at current human exposures to BPA • MINIMAL CONCERN • Mammary gland and an earlier age for puberty for females, in fetuses, infants, and children at current human exposures to BPA.

  10. BPA: National Toxicology Program Conclusions • NEGLIGIBLE CONCERN • fetal or neonatal mortality, birth defects, or reduced birth weight and growth • Exposure in pregnant women • NEGLIBILE CONCERN • Reproductive effects in non-occupationally exposed adults • MINIMAL CONCERN for occupationally exposed

  11. BPA: National Toxicology Program Conclusions • How where these conclusions reached? • WEIGHT of scientific evidence • Integration of toxicity and exposure data

  12. BPA: A Brief History • Was first synthesized in 1891 • BPA was investigated in the 1930s as a possible compound for synthetic estrogens, but was not used (DES was used instead) • After its discovery as a useful synthetic in plastics and other additives, its use skyrocketed in the manufacturing sector (global production of BPA was estimated to be over 2 million tons in 2003)

  13. BPA: Why Are People Concerned? • Human exposure to BPA is widespread • A large amount of BPA is produced in consumer goods every year • A study conducted by the CDC in 2003-2004 found detectable levels of BPA in 93% of urine samples said to be representative of exposures across the United States • There is an extensive database of animal studies on reproductive and developmental effects

  14. BPA: Prevention • If you are concerned about BPA, take precautions such as: • Don’t microwave polycarbonate plastic food containers • Avoid plastic containers with the number ‘7’ on the bottom • Don’t wash polycarbonate plastic containers in dishwasher with strong detergents • Reduce use of canned foods • Use containers labeled “BPA-free”

  15. BPA: Environmental Risk • Degradation of products containing BPA can contaminate the environment • It is a pollutant that can interfere with nitrogen fixation in plant soil • Over time, it has been found to affect reproduction and development in marine life and other organisms • Although low level releases of BPA into the environment from manufacturing sites is thought to be possible, recent comprehensive reviews of studies have concluded BPA pose virtually no risk to the environment (SOURCE: http://bisphenol-a.org/pdf/M4.pdf)

  16. References • http://en.wikipedia.org • http://www.niehs.nih.gov/health/docs/bpa-factsheet.pdf • http://www.cdc.gov/exposurereport/pdf/factsheet_bisphenol.pdf • Lang IA, et al. “Association of Urinary Bisphenol A Concentration with Medical Disorders and Laboratory Abnormalities in Adults”. JAMA, 300 (300): 1303.

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