title: Acid and base-catalyzed hydrolysis of bisphenol A-related compounds.
abstract: In order to ascertain whether an estrogenic bisphenol A is produced from bisphenol A-related monomers by chemical-induced hydrolysis and to clarify their hydrolytic mechanisms, bisphenol A dimethacrylate (Bis-DMA) and bisphenol A bis(glycidyl methacrylate) (Bis-GMA) were reacted with phosphoric acid, hydrochloric acid, and sodium hydroxide in methanol or methanol/water mixed media at 37 degrees C. Amounts of monomethacrylate intermediates as well as bisphenol A (BPA) were determined by the use of high-performance liquid chromatography (HPLC), and time-conversion curves of hydrolytic products were prepared. BPA and bisphenol A monomethacrylate were produced by acid-catalyzed hydrolysis of Bis-DMA. Bis-GMA was partly converted into monomethacrylate by phosphoric acid and into monomethacrylate and 2,2-bis[4-(2,3-dihydroxypropoxy) phenyl]propane (BHP) by hydrochloric acid. Hydrolytic reactions by sodium hydroxide were completed almost within 1 day, resulting in the production of BPA from Bis-DMA, and BHP from Bis-GMA. No BPA was formed from Bis-GMA by chemical-induced hydrolysis. The hydrolytic behaviors of these monomers were discussed.
authors.affiliation: Department of Applied Functional Molecules, Division of Biofunctional Molecules, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10, Kanda-surugadai, Chiyoda-ku, Tokyo 101-0062, Japan.
authors.forename: Y
authors.initials: Y
authors.lastname: Kadoma
authors.forename: M
authors.initials: M
authors.lastname: Tanaka
mesh_terms: D001559:Benzhydryl Compounds / Q000138:chemical synthesis; D017438:Bisphenol A-Glycidyl Methacrylate / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D004968:Estrogens, Non-Steroidal / Q000138:chemical synthesis*; D006851:Hydrochloric Acid / Q000737:chemistry; D006868:Hydrolysis; D008689:Methacrylates / Q000138:chemical synthesis / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D010636:Phenols / Q000138:chemical synthesis*; D010756:Phosphoric Acids / Q000737:chemistry; D011407:Propane / Q000031:analogs & derivatives / Q000138:chemical synthesis; D012972:Sodium Hydroxide / Q000737:chemistry; D000098826:Bisphenol A Compounds
chemical_list: D001559:Benzhydryl Compounds; D017438:Bisphenol A-Glycidyl Methacrylate; D004968:Estrogens, Non-Steroidal; D006851:Hydrochloric Acid; D008689:Methacrylates; D010636:Phenols; D010756:Phosphoric Acids; D011407:Propane; D012972:Sodium Hydroxide; C422413:2,2-bis(4-(2,3-dihydroxypropoxy)phenyl)propane; C002462:4,4'-isopropylidenediphenol dimethacrylate; D000098826:Bisphenol A Compounds; C030242:phosphoric acid; C006780:bisphenol A