3D Mol Similar

Bisphenol A

: Iupac Name：4-[2-(4-hydroxyphenyl)propan-2-yl]phenol; CAS No.: 80-05-7; Molecular Weight：228.291; Modify Date.: 2022-11-06 03:22; Introduction: Bisphenol A (CAS 80-05-7, C15H16O2) is a widely used compound in the production of polycarbonate plastics and epoxy resins. It is known for its endocrine-disrupting properties and has been a subject of concern regarding its potential health effects. Bisphenol A is used in various consumer products, including food and beverage containers, thermal paper, and dental sealants. Research has linked Bisphenol A exposure to various health issues, leading to regulations and efforts to find alternative compounds with similar functionalities but lower toxicity profiles. Reports of bisphenol-A sensitization, particularly in workers at epoxyresin plants, are controversial. Bisphenol-A was alsoreported as an allergen in fiberglass, semisyntheticwaxes, footwear and dental materials. View more+

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1. Names and Identifiers

: 1.1 Name; Bisphenol A; 1.2 Synonyms; 2,2-Bis (4-hydroxyphenol) propane 2,2-Bis(4,4'-hydroxyphenyl)propane 2,2-Bis(4-hydroxyphenyl)-propa 2,2-Bis(4-hydroxyphenyl)propane 2,2-Bis(hydroxyphenyl)propane 4,4'-(1-Methylethane-1,1-diyl)diphenol 4,4'-(1-Methylethylidene)bisphenol 4,4'-(2,2-Propanediyl)diphenol 4,4’-(1-methylethylidene)bis-pheno 4,4’-(1-methylethylidene)bisphenol 4,4’-(1-methylethylidene)bis-Phenol 4,4″-isopropylidenediphenol 4,4'-Methylethylidendbisphenol 4,4'-propane-2,2-diyldiphenol b,b'-Bis(p-hydroxyphenyl)propane Bicifadino Bicifadinum Bis(p-hydroxyphenyl)propane BPA dimethyl bis(p-hydroxyphenyl)methane EINECS 201-245-8 Hidorin F 285 MFCD03427359 Parabis Phenol, 4,4'-(1-methylethylidene)bis-; View all

1.3 CAS No.: 80-05-7

1.4 CID: 6623

1.5 EINECS(EC#): 201-245-8

1.6 Molecular Formula: C15H16O2 (isomer)

1.7 Inchi: InChI=1S/C15H16O2/c1-15(2,11-3-7-13(16)8-4-11)12-5-9-14(17)10-6-12/h3-10,16-17H,1-2H3

1.8 InChIkey: IISBACLAFKSPIT-UHFFFAOYSA-N

1.9 Canonical Smiles: CC(C)(C1=CC=C(C=C1)O)C2=CC=C(C=C2)O

1.10 Isomers Smiles: CC(C)(C1=CC=C(C=C1)O)C2=CC=C(C=C2)O

2. Properties

2.1 Density: 1.195

2.1 Melting point: 152-158℃

2.1 Boiling point: 307 to 313° F (NTP, 1992)

2.1 Refractive index: 1.5542 (estimate)

2.1 Flash Point: 175° F (NTP, 1992)

2.1 Precise Quality: 228.11500

2.1 PSA: 40.46000

2.1 logP: 3.42370

2.1 Solubility: 0.12g/l insoluble

2.2 AnalyticLaboratory Methods: NIOSH Method 333. Analyte: Bisphenol A;. Matrix: Air. Procedure: High performance liquid chromatography. Method Evaluation: Method was validated over the range of 0.551 to 1.77 mg/cu m using a 288 liter sample. Method detection limit: 0.2. Precision (CVt): 0.018. Applicability: Under the conditions of sample size (288 liters) the useful range is 0.4 to 511 mg/cu m. Interferences: No specific interferences.

2.3 Appearance: Liquid

2.4 AutoIgnition: 510-570°C

2.5 Storage: Ambient temperatures.

2.6 Chemical Properties: Bisphenol A is a white or tan crystals or flakes with a mild phenolic odor and a very low vapor pressure (ECB, 2003). It is mildly soluble in water. It is not considered to be an explosive in the conventional sense but can pose a hazard as a finely powdered material in air (ECB, 2003). It is not considered to be a chemical oxidizer.

2.7 Color/Form: Clear light yellow to light orange

2.8 Contact Allergens: Bisphenol A is used with epichlorhydrin for thesynthesis of epoxy resins bisphenol-A type, forunsaturated polyester and polycarbonate resins, andepoxy di(meth)acrylates. In epoxy resins, it leads tobisphenol-A diglycidyl ether, which is the monomerof bisphenol-A-based epoxy resins. Reports ofbisphenol-A sensitization are rare and concernworkers at epoxy resin plants, after contact withfiber glass, semi-synthetic waxes, footwear, anddental materials. It is also a possible sensitizer invinyl gloves.

2.9 Decomposition: When heated to decomposition it emits acrid and irritating fumes.

2.10 Heat of Combustion: -7.465 J/kmol (est)

2.11 Odor: Phenol like

2.12 Physical: 4,4'-ISOPROPYLIDENEDIPHENOL; is a white to light brown flakes or powder. Has a weak medicine odor. Sinks in water;. (USCG, 1999)

2.13 pKa: 10.29±0.10(Predicted)

2.14 Water Solubility: <0.1 g/100 mL at 21.5 oC

2.15 Spectral Properties: MAX ABSORPTION (ALC): 227 NM (LOG E= 4.4); 275 NM (LOG E= 3.8); SADTLER REF NUMBER: 1070 (IR, PRISM); 216 (IR, GRATING); 325 (UV)
Intense mass spectral peaks: 213 m/z (100%), 228 m/z (26%), 119 m/z (25%), 214 m/z (14%)
IR: 2233 (Coblentz Society Spectral Collection)
UV: 325 (Sadtler Research Laboratories Spectral Collection)
1H NMR: 18699 (Sadtler Research Laboratories Spectral Collection)
MASS: 22777 (NIST/EPA/MSDC Mass SPectral database, 1990 version); 5205 (National Bureau of Standards)

2.16 StorageTemp: Store below +30°C.

3. Use and Manufacturing

3.1 Definition: ChEBI: A bisphenol that is 4,4'-methanediyldiphenol in which the methylene hydrogens are replaced by two methyl groups.

3.2 Environmental Fate: Bisphenol A can be released into the environment during the production, processing, and use of BPA-containing materials, although levels in environmental samples are generally very low or undetectable (ECB, 2003). This is because BPA has low volatility and a short half-life in the atmosphere, is rapidly biodegraded in water, and is not expected to be stable, mobile, or bioavailable from soils (ECB, 2003; Cousins et al., 2002).Most environmental releases of BPA are during the manufacture of BPA-containing products when residual BPA in wastewater is released from treatment plants into receiving streams (Cousins et al., 2002). BPA's half-life in soil and water is in the order of 4.5 days while in air it is <1 day (Cousins et al., 2002). It has a low bioconcentration factor and is rapidly metabolized in fish, with a half-life of <1 day (Cousins et al., 2002).

3.3 General Description: White to light brown flakes or powder. Has a weak medicine odor. Sinks in water.

3.4 GHS Classification: Signal: Danger
GHS Hazard Statements
H317: May cause an allergic skin reaction [Warning Sensitization, Skin]
H318: Causes serious eye damage [Danger Serious eye damage/eye irritation]
H335: May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
H360F: May damage fertility [Danger Reproductive toxicity]

Precautionary Statement Codes
P201, P202, P261, P271, P272, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P333+P313, P363, P403+P233, P405, and P501; View all

3.5 History: Bisphenol A (BPA) was first synthesized in 1891, but it was not used widely until applications in the plastics industry were identified in the 1950s (University of Minnesota, 2008). While the most prominent use of BPA is in the manufacture of polycarbonate plastic and epoxy resins, it is also used in the production and processing of polyvinyl chloride (PVC) and modified polyamide and in the manufacture of carbonless and thermal paper, wood filler, adhesives, printing inks, surface coatings, polyurethane, brake fluid, resin-based dental composites and sealants, flame retardants, paints, and tires (ECB, 2003; EFSA, 2006).

3.6 Methods of Manufacturing: ... Hydrogen chloride; or sulfonated cross-linked polystyrenes are used as the catalyst which are usually arranged as a fixed bed over which the reaction mixture is passed. The reaction of phenol; with acetone; takes place at 50 - 90 deg C, the molar ratio phenol; - acetone; is up to 15:1. Bisphenol A; crystallizes as an adduct with 1 mol phenol;, after separation of the hydrogen chloride; by distillation or neutralization. The use of ion exchangers is preferred to that of hydrogen chloride; because they are less corrosive. The yield is normally 80-95%.

3.7 Usage: A high-production-volume chemical used in manufacture of epoxy-phenolic resins (protective linings for food and beverage cans); monomer for polycarbonate resins (used in food contact materials such as returnable beverage bottles, infant feeding bottles, plates, and mugs); antioxidant in PVC plastics; inhibitor of end polymerization in PVC plastics

4. Safety and Handling

4.1 Symbol: GHS05, GHS07, GHS08, GHS09

4.1 Hazard Codes: Xn

4.1 Signal Word: Danger

4.1 Risk Statements: R37;R41;R43;R62

4.1 Safety Statements: S26;S36/37/39;S46

4.1 Exposure Standards and Regulations: 4,4'-Isopropylidenediphenol is an indirect food additive for use only as a component of adhesives.

4.2 Octanol/Water Partition Coefficient: log Kow = 3.32

4.3 Fire Hazard: Bisphenol A is combustible. Bisphenol A may form explosive dust clouds. Static electricity can cause its dust to explode.

4.4 Other Preventative Measures: SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

4.5 Hazard Declaration: H317-H318-H335-H361f-H411

4.5 Cleanup Methods: Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Vacuum cleaning is preferable to sweeping to keep dust levels down. Use special HEPA vacuum; not a shop vacuum. Ventilate area of spill or leak after cleanup is complete. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations. If employees are required to clean up spills, they must be properly trained and equipped. OSHA 1910.120(q) may be applicable.

4.6 DisposalMethods: SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

4.7 RIDADR: UN 3077 9 / PGIII

4.7 Fire Fighting Procedures: Foam, dry chemical, carbon dioxide.

4.8 FirePotential: Combustible

4.9 Caution Statement: P261-P273-P280-P305 + P351 + P338

4.9 Formulations/Preparations: ... 4,4'-DIHYDROXYDIPHENYLDIMETHYLMETHANE IS GENERALLY AVAIL AS THIN PLATES & HAS FOLLOWING PROPERTIES: BISPHENOL CONTENT GREATER THAN 99%; PHENOL CONTENT LESS THAN 0.1%; WATER CONTENT LESS THAN 1%; ASH LESS THAN 0.02%; & IRON LESS THAN 0.001%.
Available as flake, crystalline or prilled material

4.10 Incompatibilities: Incompatible with oxidizers (chlorates,nitrates, peroxides, permanganates, perchlorates, chlorine,bromine, fluorine, etc.); contact may cause fires or explosions.Keep away from alkaline materials, strong bases,strong acids, oxoacids, epoxides, acid chlorides and acidanhydrides. Bisphenol A Preparation Products And Raw materials Preparation Products

4.11 WGK Germany: 2

4.11 RTECS: SL6300000

4.11 Protective Equipment and Clothing: Wear protective gloves and clothing to prevent any reasonable probability of skin contact. Safety equipment suppliers/manufacturers can provide recommendations on the most protective glove/clothing material for your operation. All protective clothing (suits, gloves, footwear, headgear) should be clean, available for work each day, and put on before work. Contact lenses should not be worn when working with this chemical. Wear dust-proof chemical goggles and face shield unless full face-piece respiratory protection is worn. Employees should wash immediately with soap when skin is wet or contaminated. Provide emergency showers and eyewash.
Approved dust mask and clean, body covering clothing sufficient to prevent excessive or repeated exposure to dust, fumes, or soln. Safety glasses with side shields.

4.12 Reactivities and Incompatibilities: Strong oxidizers, strong bases, acid chlorides, and acid anhydrides.

4.13 Skin, Eye, and Respiratory Irritations: Solid irritating to skin & eyes. ... Dusts irritating to upper respiratory passages ... .

4.14 Safety: Safety Information about?Bisphenol A (CAS NO.80-05-7):
Hazard Codes: Xn
Risk Statements: 37-41-43-62
37:?Irritating to the respiratory system?
41:?Risk of serious damage to eyes?
43:?May cause sensitization by skin contact?
62:?Possible risk of impaired fertility?
Safety Statements:?26-36/37/39-45-46
26:?In case of contact with eyes, rinse immediately with plenty of water and seek medical advice?
36/37/39:?Wear suitable protective clothing, gloves and eye/face protection?
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)?
46:?If swallowed, seek medical advice immediately and show this container or label?
RTECS:? SL6300000
HS Code:? 29072300
Poison by intraperitoneal route. Moderately toxic by ingestion, inhalation, and skin contact. Experimental teratogenic and reproductive effects. A skin and eye irritant. When heated to decomposition it emits acrid and irritating fumes.; View all

4.15 Specification: General Information of?Bisphenol A (CAS NO.80-05-7): As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam.?
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Avoid ingestion and inhalation. Use only in a chemical fume hood.
Storage: Store in a cool, dry place. Store in a tightly closed container.

4.16 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
guinea pig	LD50	oral	4gm/kg (4000mg/kg)	AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 33(7), Pg. 25, 1968.
mammal (species unspecified)	LD50	oral	6500mg/kg (6500mg/kg)	?	"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 135, 1969.
mouse	LC	inhalation	> 1700mg/m³/2H (1700mg/m³)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Substances. For English translation, see TNICS*. Vol. 2, Pg. 50, 1961.
mouse	LD50	intraperitoneal	150mg/kg (150mg/kg)	?	National Technical Information Service. Vol. AD691-490,
mouse	LD50	oral	2400mg/kg (2400mg/kg)	AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 33(7), Pg. 25, 1968.
mouse	LDLo	subcutaneous	2500mg/kg (2500mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LIVER: FATTY LIVER DEGERATION	Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Substances. For English translation, see TNICS*. Vol. 2, Pg. 50, 1961.
rabbit	LD50	oral	2230mg/kg (2230mg/kg)	?	American Industrial Hygiene Association Journal. Vol. 28, Pg. 301, 1967.
rabbit	LD50	skin	3mL/kg (3mL/kg)	?	AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 4, Pg. 119, 1951.
rat	LD50	oral	3250mg/kg (3250mg/kg)	?	American Industrial Hygiene Association Journal. Vol. 28, Pg. 301, 1967.

View all

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Serious eye damage, Category 1

Skin sensitization, Category 1

Specific target organ toxicity \u2013 single exposure, Category 3

Reproductive toxicity, Category 1B

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H318 Causes serious eye damage H317 May cause an allergic skin reaction H335 May cause respiratory irritation H360F
Precautionary statement(s)
Prevention	P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P271 Use only outdoors or in a well-ventilated area. P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood.
Response	P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P310 Immediately call a POISON CENTER/doctor/\u2026 P302+P352 IF ON SKIN: Wash with plenty of water/... P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P308+P313 IF exposed or concerned: Get medical advice/ attention.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : in DMSO-d6

1H NMR : 400 MHz in DMSO-d6

IR : KBr disc

IR : nujol mull

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

80-05-7Total: 38 Synthesis Route

80-15-9 68 Suppliers

80-05-7 339 Suppliers

Literatures:
US2713072 , ;
Yield: null

108-95-2 253 Suppliers

80-05-7 339 Suppliers

Literatures:
US2779800 , ;
Yield: null

837-08-1 1 Suppliers

80-05-7 339 Suppliers

Literatures:
EP1985602 A1, ; Page/Page column 7-8 ;
Yield: null

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8. Precursor and Product

precursor:

2720-53-8

5026-12-0

463-49-0

5109-95-5

63661-69-8

2024-88-6

123-54-6

557-98-2

32565-67-6

80-15-9

837-08-1

108-22-5

14252-45-0

6497-29-6

3539-42-2

74-99-7

108-95-2

117-08-8

View all

product :

79-98-1

2444-90-8

29426-78-6

2065-16-9

1568-80-5

23197-55-9

18811-78-4

837-11-6

1745-89-7

5329-21-5

7418-16-8

79-95-8

79-94-7

17951-79-0

14151-65-6

99-89-8

599-64-4

53464-95-2

72471-05-7

1220-78-6

4621-04-9

6386-73-8

6627-84-5

3539-42-2

6627-83-4

View all

9. Other Information

9.0 Merck: 14,1297

9.1 BRN: 1107700

9.2 Chemical Properties: White prills

9.3 Chemical Properties: Bisphenol A is a white or tan crystals or flakes with a mild phenolic odor.

9.4 Uses: endocrine disruptor, plastic monomer

9.5 Uses: A monomer used for policarbonate and epoxy resins; exhibits estrogenic activity. BPA is also used as a building block in polycarbonate bottles and in the epoxy-resin liners of metal cans.

9.6 Definition: ChEBI: A bisphenol that is 4,4'-methanediyldiphenol in which the methylene hydrogens are replaced by two methyl groups.

9.7 General Description: White to light brown flakes or powder. Has a weak medicine odor. Sinks in water.

9.8 Air & Water Reactions: The finely powdered resin is a significant dust explosion hazard. Insoluble in water.

9.9 Reactivity Profile: Bisphenol A is incompatible with strong oxidizers. Bisphenol A is also incompatible with strong bases, acid chlorides and acid anhydrides.

9.10 Hazard: Poison; moderately toxic; teratogen; irritant.

9.11 Health Hazard: Dusts irritating to upper respiratory passages; may cause sneezing.

9.12 Fire Hazard: Bisphenol A is combustible. Bisphenol A may form explosive dust clouds. Static electricity can cause its dust to explode.

9.13 Contact allergens: Bisphenol A is used with epichlorhydrin for the synthesis of epoxy resins bisphenol-A type, for unsaturated polyester and polycarbonate resins, and epoxy di(meth)acrylates. In epoxy resins, it leads to bisphenol-A diglycidyl ether, which is the monomer of bisphenol-A-based epoxy resins. Reports of bisphenol-A sensitization are rare and concern workers at epoxy resin plants, after contact with fiber glass, semi-synthetic waxes, footwear, and dental materials. It is also a possible sensitizer in vinyl gloves.

9.14 First aid: If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit.

9.15 Shipping: UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9—Miscellaneous hazardous material, Technical Name Required.

9.16 Incompatibilities: Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, acid chlorides and acid anhydrides.

9.17 Usage: Bisphenol A is an important monomer used in the production of polycarbonate plastics which is utilized to make various consumer goods like water bottles, sports equipment, medical devices, eyeglass lenses, house hold electronics, compact discs (CDs) and digital versatile discs (DVDs). Bisphenol A containing epoxy resins are used to make lining in water pipes. It is used as a precursor to prepare flame retardant tetrabromobispheonl A, polysulfones and polyether ketones, which are antioxidants in some plasticizers. It acts as a polymerization inhibitor in poly vinyl chloride (PVC).

9.18 Uses: A high-production-volume chemical used in manufacture of epoxy-phenolic resins (protective linings for food and beverage cans); monomer for polycarbonate resins (used in food contact materials such as returnable beverage bottles, infant feeding bottles, plates, and mugs); antioxidant in PVC plastics; inhibitor of end polymerization in PVC plastics

9.19 Description: Reports of bisphenol- A sensitization, particularly in workers at epoxy resin plants, are controversial. Bisphenol-A was also reported as an allergen in fiberglass, semisynthetic waxes, footwear and dental materials.

9.20 Chemical Properties: Bisphenol A is a white or tan crystals or flakes with a mild phenolic odor and a very low vapor pressure (ECB, 2003). It is mildly soluble in water. It is not considered to be an explosive in the conventional sense but can pose a hazard as a finely powdered material in air (ECB, 2003). It is not considered to be a chemical oxidizer.

9.21 History: Bisphenol A (BPA) was first synthesized in 1891, but it was not used widely until applications in the plastics industry were identified in the 1950s (University of Minnesota, 2008). While the most prominent use of BPA is in the manufacture of polycarbonate plastic and epoxy resins, it is also used in the production and processing of polyvinyl chloride (PVC) and modified polyamide and in the manufacture of carbonless and thermal paper, wood filler, adhesives, printing inks, surface coatings, polyurethane, brake fluid, resin-based dental composites and sealants, flame retardants, paints, and tires (ECB, 2003; EFSA, 2006).

9.22 Uses: Bisphenol A (BPA) is used as the constitutional monomer or the monomeric building block of polycarbonate plastics, either by trans-esterification with diphenyl carbonate or via the interfacial process with a monohydroxylic phenol. Together with epichlorohydrin, BPA is also used as a major component of epoxy resins. Bisphenol A-polycarbonate plastics are in turn used in the manufacture of plastic food containers such as reusable water bottles, while epoxy resins are used as inner linings of tin cans. In addition, BPA is also used as an additive in other plastics and polymers, particularly as an antioxidant or stabilizer in polyvinyl chloride, printer ink, and in some other products.

9.23 Uses: Bisphenol A is used with epichlorhydrin for the synthesis of epoxy resins bisphenol-A type. It leads to bisphenol-A diglycidyl ether, which is the monomer of bisphenol-A based epoxy resins.

9.24 Preparation: The formation of bisphenol A is thought to proceed as follows:

Although the reaction theoretically requires the molar ratio of reactants to be 2: 1, an improved yield of bisphenol A is obtained if additional phenol is present; the optimum molar ratio is 4: 1. In a typical process, the phenol and acetone are mixed and warmed to 50°C. Hydrogen chloride (catalyst) is passed into the mixture for about 8 hours, during which period the temperature is kept below 70°C to suppress the formation of isomeric products. Bisphenol A precipitates and is filtered off and washed with toluene to remove unreacted phenol (which is recovered). The product is then recrystallized from aqueous ethanol. Since epoxy resins are oflow molecular weight and because colour is not normally particularly important, the purity of bisphenol A used in resin production is not critical. Material with a p,p'-isomer content of 95-98% is usually satisfactory; the principal impurities in such material are o,p'- and o,o'-isomers.; View all

9.25 Synthesis Reference(s): Journal of the American Chemical Society, 71, p. 2287, 1949 DOI: 10.1021/ja01175a004

9.26 Environmental Fate: Bisphenol A can be released into the environment during the production, processing, and use of BPA-containing materials, although levels in environmental samples are generally very low or undetectable (ECB, 2003). This is because BPA has low volatility and a short half-life in the atmosphere, is rapidly biodegraded in water, and is not expected to be stable, mobile, or bioavailable from soils (ECB, 2003; Cousins et al., 2002).
Most environmental releases of BPA are during the manufacture of BPA-containing products when residual BPA in wastewater is released from treatment plants into receiving streams (Cousins et al., 2002). BPA's half-life in soil and water is in the order of 4.5 days while in air it is <1 day (Cousins et al., 2002). It has a low bioconcentration factor and is rapidly metabolized in fish, with a half-life of <1 day (Cousins et al., 2002).

9.27 Toxicity evaluation: Bisphenol-A is a chemical substance with known oestrogenic action that is used in the manufacture of a wide range of products. The low-dose in utero exposure to bisphenol-A of experimental animals caused striking morphological changes in the vagina of postpubertal offspring. In addition, the oestrogen receptor alpha was not expressed during oestrus in the vagina of female offspring exposed to bisphenol-A and the altered vaginal morphology is attributed to the down regulation of oestrogen receptor alpha (Schonfelder et at., 2002). Another experiment on mice after intrauterine exposure to bisphenol-A showed differences in the rate of ductal migration into the stroma at 1 month of age and a significant increase in the percentage of ducts, terminal ducts, terminal end buds, and alveolar buds at 6 months of age. The changes in histoarchitecture, coupled with an increased presence of secretory product within alveoli, resemble those of early pregnancy. This suggests a disruption of the hypothalamic-pituitary-ovarian axis and/or mis-expression of developmental genes. It was concluded that the altered relationship in DNA synthesis between the epithelium and stroma and the increase in terminal ducts and terminal end buds are noteworthy, because these changes are associated with carcinogenesis in both rodents and humans (Markey et at., 2001).; View all

10. Computational chemical data

Molecular Weight: 228.291g/mol
Molecular Formula: C₁₅H₁₆O₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 228.115029749
Monoisotopic Mass: 228.115029749
Complexity: 209
Rotatable Bond Count: 2
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 40.5
Heavy Atom Count: 17
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceBwMAAAAAAAAAAAAAAAAAAAAAAAAAAwYAAAAAAAAAABQAAAGgAACAAADgSAmAAyBoAAAgCAAiBCAAACAAAgIAAIiAAGCIgIJiKCERKAcAAkwBEImAeAwPAPoAAAAAAAAABAAAAAAAAAAAAAAAAAAA==

11. Question & Answer

What is Bisphenol A and its Impact on Health? Aug 26 2024
Bisphenol A Overview Bisphenol A (BPA) is a synthetic estrogen used in the production of various plastic products worldwide. It can be found in everyday items such as food packaging, beverage containe..
What are the Implications of Bisphenol A (BPA) on Biological Processes? Jun 23 2022
Bisphenol A (BPA) is a chemical widely used in the production of polycarbonate plastics and epoxy resins. It is known for its environmental estrogen properties and its impact on various biological pro..
The Versatility and Controversy of Bisphenol A: Breaking Foreign Monopoly and Ensuring Health Safety? Feb 18 2022
Title: The Versatility and Controversy of Bisphenol A: Breaking Foreign Monopoly and Ensuring Health Safety Article: Bisphenol A: Breaking Foreign Monopoly and Ensuring Health Safety Bisphenol A (BPA)..
The Impact and Applications of Bisphenol A (BPA) in the Plastic Industry Can Bisphenol A (BPA) Revolutionize the Plastic Industry? Nov 26 2021
Bisphenol A (BPA), synthesized in 1891, gained widespread usage in the plastic industry during the 1950s. One production method involves condensing 2 mol of phenol with 1 mol of acetone while introduc..

12. Recommended Suppliers

Global317SuppliersView all >>

Hubei Jiutian Bio-medical Technology Co., Ltd Diamond member

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Factory Supply Bisphenol A Supplier Manufacturer with Competitive Price Worldwide Shipment

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13. Realated Product Infomation

181028-79-5 Bisphenol A diphosphate

1745-89-7 Diallyl bisphenol A

14868-03-2 Bisphenol C

37353-75-6 Propoxylated Bisphenol A

3253-39-2 BISPHENOL A DIMETHACRYLATE

32492-61-8 Ethoxylated Bisphenol A

10192-62-8 BISPHENOL A DIACETATE

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