80-05-7 Usage
Description
Bisphenol A, also known as BPA, is a high-production-volume chemical that serves as a monomer or building block for the synthesis of polycarbonate plastics and epoxy resins. It exhibits estrogenic activity and is used in various applications due to its versatile properties.
Uses
Used in Plastics and Polymers Industry:
Bisphenol A is used as a monomer for the production of polycarbonate plastics, either by trans-esterification with diphenyl carbonate or via the interfacial process with a monohydroxylic phenol. It is also used as a major component of epoxy resins, in conjunction with epichlorohydrin.
Used in Food and Beverage Industry:
Bisphenol A-polycarbonate plastics are used in the manufacture of plastic food containers such as reusable water bottles. Epoxy resins, which contain BPA, are used as inner linings of tin cans for food and beverage storage.
Used in PVC Plastics:
Bisphenol A is used as an antioxidant and inhibitor of end polymerization in polyvinyl chloride (PVC) plastics, contributing to the stability and longevity of these materials.
Used in Other Applications:
BPA is also used as an additive in other plastics and polymers, particularly as a stabilizer in printer ink and some other products. Additionally, it has been reported as an allergen in materials such as fiberglass, semisynthetic waxes, footwear, and dental materials, although reports of sensitization are controversial.
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).
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.
Synthesis Reference(s)
Journal of the American Chemical Society, 71, p. 2287, 1949 DOI: 10.1021/ja01175a004
Air & Water Reactions
The finely powdered resin is a significant dust explosion hazard. Insoluble in water.
Reactivity Profile
Bisphenol A is incompatible with strong oxidizers. Bisphenol A is also incompatible with strong bases, acid chlorides and acid anhydrides.
Hazard
Poison; moderately toxic; teratogen;
irritant.
Health Hazard
Dusts irritating to upper respiratory passages; may cause sneezing.
Fire Hazard
Bisphenol A is combustible. Bisphenol A may form explosive dust clouds. Static electricity can cause its dust to explode.
Flammability and Explosibility
Notclassified
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.
Potential Exposure
Workers engaged in the manufacture
of epoxy, polysulfone, polycarbonate and certain polyester
resins. It is also used in flame retardants, rubber chemicals,
and as a fungicide. Bisphenol A (BP A), an environmental
estrogen, is found in a wide variety of products, including
polycarbonate bottles food and drink containers. According
to 2008 research conducted at University of Cincinnati,
when it comes to BPA, it’s not whether polycarbonate
bottles are new or old but the liquid’s temperature that
has the greatest impact on how much BPA is released.
When exposed to boiling hot water, BPA was released
55 times more rapidly than exposure to cold water.
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).
Purification Methods
Crystallise bisphenol from acetic acid/water (1:1). It is used for making polycarbonate bottles and leaches out slowly on heating. It is a known “estrogenic chemical” shown to disrupt chemical signaling in the complex network of glands, hormones and cell receptors which make up the endocrine system. It causes low sperm count and damages the ecosystem by the feminisation of fish, reptiles and birds. [cf Chapter 1, p 3, Beilstein 6 IV 6717.]
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).
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.
Check Digit Verification of cas no
The CAS Registry Mumber 80-05-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 0 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 80-05:
(4*8)+(3*0)+(2*0)+(1*5)=37
37 % 10 = 7
So 80-05-7 is a valid CAS Registry Number.
80-05-7Relevant articles and documents
Selective synthesis of Bisphenol-A over mesoporous MCM silica catalysts functionalized with sulfonic acid groups
Das, Debasish,Lee, Jyh-Fu,Cheng, Soofin
, p. 152 - 160 (2004)
Mesoporous MCM-41 and -48 silicas anchored with sulfonic acid (-SO 3H) groups via postsynthesis modification are very effective for the synthesis of Bisphenol-A by liquid-phase condensation of phenol with acetone. Higher amounts of thiol groups can be incorporated in MCM-48 silicas presumably due to the presence of larger number of surface silanol groups. However sulfur K-edge XANES spectroscopy reveals that effective oxidation of the precursor thiol (-SH) groups to the sulfonic acid (-SO3H) groups was necessary for obtaining samples of good catalytic activity. It was noted that when sulfur loadings exceed 1.5 meq/g solid a part of the sulfur atoms remains in the reduced form even after prolonged oxidation. MCM-41 silica anchored with sulfonic acid groups has comparable catalytic activity to that of commercial ion-exchange resin Amberlite-120 and the former also showed higher selectivity toward the desired p,p′ isomer. MCM-48 silica-anchored samples are equally effective for selective synthesis of Bisphenol-A.
Hydrolysis of polycarbonate in sub-critical water in fused silica capillary reactor with in situ Raman spectroscopy
Pan, Zhiyan,Chou, I-Ming,Burruss, Robert C.
, p. 1105 - 1107 (2009)
The advantages of using fused silica capillary reactor (FSCR) instead of conventional autoclave for studying chemical reactions at elevated pressure and temperature conditions were demonstrated in this study, including the allowance for visual observation
Synthesis, characterization, and catalytic activity of sulfonic acid-functionalized periodic mesoporous organosilicas
Yang, Qihua,Liu, Jian,Yang, Jie,Kapoor, Mahendra P.,Inagaki, Shinji,Li, Can
, p. 265 - 272 (2004)
Sulfonic acid-functionalized periodic mesoporous organosilicas were synthesized directly by cocondensation of (R′O)3SiRSi(OR′ )3 (R = CH2CH2 and C6H4; R′ = CH3 and C2H5) with 3-mercaptopropyltrimethoxysilane (MeO)3SiCH2CH 2CH2SH in the presence of H2O2 using nonionic oligomeric polymer surfactant C18H37(OCH 2CH2)10OH in acidic medium. The sulfonic acid functionalities (SO3H) were generated in situ by oxidation of the propylthiol using H2O2 as oxidant during the synthesis process. Powder X-ray diffraction patterns and nitrogen sorption indicate the formation of well-ordered mesoporous material with uniform porosity. The highest acid-exchange capacity (acid-base titration methods) was 1.72 H+ mmol/g. Complete oxidation of SH to SO3H was observed as evidenced by X-ray photoelectron spectroscopy. For comparison, the sulfonic acid-functionalized mesoporous organosilicas were also prepared by a grafting method. The catalytic properties of the materials were investigated in liquid-phase condensation of phenol with acetone to form Bisphenol A. All sulfonic acid-functionalized mesoporous organosilicas show high catalytic activity. The highest TOF obtained for the mesoporous organosilica is 17.2.
Optimization of process parameters for preparing a solid catalyst for bisphenol synthesis
Kozlova,Tereshchuk,Myznikov,Antonenko,Zubritskaya,Bazanov
, p. 406 - 413 (2016)
The results of optimization of the process parameters for preparing high-performance heterogeneous catalysts for bisphenol synthesis show that the performance of the solid acid catalyst is determined by its exchange capacity, acidity, pore structure, and specific surface area. Optimum process parameters for preparing highly active solid acid catalysts were revealed.
Photocatalytic Degradation of 4,4′-Isopropylidenebis(2,6-dibromophenol) on Magnetite Catalysts vs. Ozonolysis Method: Process Efficiency and Toxicity Assessment of Disinfection By-Products
Balawejder, Maciej,Barylyak, Adriana,Bobitski, Yaroslav,Kisa?a, Joanna,Tomaszewska, Anna
, (2022/03/31)
Flame retardants have attracted growing environmental concern. Recently, an increasing number of studies have been conducted worldwide to investigate flame-retardant sources, environmental distribution, living organisms’ exposure, and toxicity. The presented studies include the degradation of 4,4′-isopropylidenebis(2,6-dibromophenol) (TBBPA) by ozonolysis and photocatalysis. In the photocatalytic process, nano-and micro-magnetite (n-Fe3 O4 and μ-Fe3 O4) are used as a catalyst. Monitoring of TBBPA decay in the photocatalysis and ozonolysis showed photocatalysis to be more effective. Significant removal of TBBPA was achieved within 10 min in photocatalysis (ca. 90%), while for ozonation, a comparable effect was observed within 70 min. To determine the best method of TBBPA degradation concentration on COD and TOC, the removals were examined. The highest oxidation state was obtained for photocatalysis on μ-Fe3 O4, whereas for n-Fe3 O4 and ozonolysis, the COD/TOC ratio was lower. Acute toxicity results show noticeable differences in the toxicity of TBBPA and its degradation products to Artemia franciscana and Thamnocephalus platyurus. The EC50 values indicate that TBBPA degradation products were toxic to harmful, whereas the TBPPA and post-reaction mixtures were toxic to the invertebrate species tested. The best efficiency in the removal and degradation of TBBPA was in the photocatalysis process on μ-Fe3 O4 (reaction system 1). The examined crustaceans can be used as a sensitive test for acute toxicity evaluation.
PROCESS FOR PREPARING BISPHENOLE A (BPA) IN THE PRESENCE OF HYDROXYACETONE
-
Page/Page column 12-15, (2021/03/05)
The present invention relates to a process for preparing bisphenol A in the presence of hydroxyacetone without poisoning the catalyst system comprising an ion exchange resin catalyst and a sulfur containing cocatalyst, wherein at least part of the sulfur containing cocatalyst is not chemically bound to the ion exchange resin catalyst. Moreover, the present invention provides a process for preparing polycarbonate and a composition comprising bisphenol A and at least one specific impurity which is formed in the production of bisphenol A.
A mild and practical method for deprotection of aryl methyl/benzyl/allyl ethers with HPPh2andtBuOK
Pan, Wenjing,Li, Chenchen,Zhu, Haoyin,Li, Fangfang,Li, Tao,Zhao, Wanxiang
, p. 7633 - 7640 (2021/09/22)
A general method for the demethylation, debenzylation, and deallylation of aryl ethers using HPPh2andtBuOK is reported. The reaction features mild and metal-free reaction conditions, broad substrate scope, good functional group compatibility, and high chemical selectivity towards aryl ethers over aliphatic structures. Notably, this approach is competent to selectively deprotect the allyl or benzyl group, making it a general and practical method in organic synthesis.