title: Effective and selective bisphenol A synthesis on a layered silicate with spatially arranged sulfonic acid.
abstract: The silylated derivatives of a layered alkali silicate, magadiite, modified with propylsulfonic or arylsulfonic acid were synthesized and used as catalysts for an acid-catalyzed condensation of phenol with acetone. The propylsulfonated magadiites with a different amount of the attached silyl group were synthesized by the silylation of the dodecylammonium-exchanged magadiite with the tuned amount of 3-(mercaptopropyl)trimethoxysilane and the subsequent oxidation of the attached thiol to sulfonic acid. The arylsulfonated magadiite was synthesized by the silylation of the dodecylammonium-exchanged magadiite with 2-(4-chlorosulfonylphenyl)ethyltrimethoxysilane and the subsequent hydrolysis of the attached sulfonyl chloride to sulfonic acid. The X-ray diffraction (XRD) patterns and elemental mappings of the products, and the photoluminescent spectra of the Eu(3+)-exchanged products suggested that propylsulfonic or arylsulfonic acid was homogeneously distributed in the interlayer space. When all the sulfonated materials were used as an acid catalyst for condensation between phenol and acetone, p,p' bisphenol A selectively formed over the o,p' isomer, and higher yield and selectivity were attained on the catalysts with larger amount of the attached sulfonic acid. When the interlayer space of the propylsulfonated magadiite was expanded by the co-attachment of octadecylsilyl group, lower selectivity was obtained. The arylsulfonated magadiite showed considerably higher p,p' bisphenol A yield than the propylsulfonated magadiites.
authors.affiliation: Department of Applied Chemistry, Graduated School of Engineering, Hiroshima University, Higashi-Hiroshima, Japan. ysuke-ide@hiroshima-u.ac.jp
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Ide
authors.forename: Noriko
authors.initials: N
authors.lastname: Kagawa
authors.forename: Masaya
authors.initials: M
authors.lastname: Itakura
authors.forename: Ichiro
authors.initials: I
authors.lastname: Imae
authors.forename: Masahiro
authors.initials: M
authors.lastname: Sadakane
authors.forename: Tsuneji
authors.initials: T
authors.lastname: Sano
mesh_terms: D001559:Benzhydryl Compounds; D002384:Catalysis; D015394:Molecular Structure; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry; D017640:Silicates / Q000737:chemistry*; D013451:Sulfonic Acids / Q000737:chemistry*; D000098826:Bisphenol A Compounds
chemical_list: D001559:Benzhydryl Compounds; D010636:Phenols; D017640:Silicates; D013451:Sulfonic Acids; C006780:bisphenol A; D000098826:Bisphenol A Compounds