Bisphenol AAl Strickler

Matt MoynihanJose Mattos

Bisphenol A (BPA): IntroductionBPA 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 mmHgSolubility in water 120–300 ppm (at 21.5 °C)

BPA: HazardsRisk 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

BPA: HazardsNFPA 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.

3

0

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BPA: UsesThere 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 typeType 7 is a ‘catch all’ designation. Polycarbonates and epoxy resins use BPA andfall under this category.

Other types that do not use BPA in production:

1 PET 2 HDPE4 LDPE5 polypropylene6 polystyrene

BPA: UsesBPA is used in:Synthesis of polyesters, Synthesis of polysulfonesSynthesis of Polyether ketonesAntioxidant in some plasticizersPolymerization inhibitor in PVC Monomer in production of epoxy resinsMost 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

BPA: Impact on HealthPostulated areas of negative health impact

BrainBehaviorReproductionEndocrine systemProstate glandMammary gland

BPA: National Toxicology Program

SOME Concern: there is insufficient human data to reach a conclusions - But there is LIMITED evidence in animal studies

BPA: National Toxicology Program Conclusions

SOME CONCERNBrain, Behavior, and Prostate gland

Fetuses, Infants, and Children at current human exposures to BPA

MINIMAL CONCERNMammary gland and an earlier age for puberty

for females, in fetuses, infants, and children at current human exposures to BPA.

BPA: National Toxicology Program Conclusions

NEGLIGIBLE CONCERN fetal or neonatal mortality, birth defects, or

reduced birth weight and growth Exposure in pregnant women

NEGLIBILE CONCERNReproductive effects in non-occupationally

exposed adults MINIMAL CONCERN for occupationally exposed

BPA: National Toxicology Program Conclusions

How where these conclusions reached?WEIGHT of scientific evidenceIntegration of toxicity and exposure data

BPA: A Brief HistoryWas first synthesized in 1891BPA 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)

BPA: Why Are People Concerned? Human exposure to BPA is widespreadA large amount of BPA is produced in

consumer goods every yearA 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

BPA: PreventionIf you are concerned about BPA, take

precautions such as:Don’t microwave polycarbonate plastic food

containersAvoid plastic containers with the number ‘7’ on

the bottomDon’t wash polycarbonate plastic containers in

dishwasher with strong detergentsReduce use of canned foodsUse containers labeled “BPA-free”

BPA: Environmental RiskDegradation of products containing BPA can

contaminate the environmentIt is a pollutant that can interfere with nitrogen

fixation in plant soilOver time, it has been found to affect reproduction

and development in marine life and other organismsAlthough 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)

Referenceshttp://en.wikipedia.orghttp://www.niehs.nih.gov/health/docs/bpa-fact

sheet.pdfhttp://www.cdc.gov/exposurereport/pdf/factsh

eet_bisphenol.pdfLang IA, et al. “Association of Urinary

Bisphenol A Concentration with Medical Disorders and Laboratory Abnormalities in Adults”. JAMA, 300 (300): 1303.