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Synthesis of sulfonated polynaphthalene, polyanthracene, and polypyrene as strong solid acids via oxidative coupling polymerization
Author(s) -
Tanemura Kiyoshi,
Suzuki Tsuneo,
Horaguchi Takaaki
Publication year - 2012
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.38045
Subject(s) - oxidative coupling of methane , chemistry , dichloromethane , hydrolysis , polymer chemistry , anthracene , pyrene , polymerization , naphthalene , nitrobenzene , nitrogen , organic chemistry , solvent , polymer , catalysis
Oxidative coupling polymerization of naphthalene, anthracene, and pyrene with FeCl 3 in nitrobenzene under nitrogen gave polynaphthalene (PNP), polyanthracene (PAT), and polypyrene (PPR) in good yields, respectively. PNP, PAT, and PPR were transformed into sulfonated PNP (S‐PNP), S‐PAT, and S‐PPR by the treatment with chlorosulfonic acid in dichloromethane at 25°C for 24 h under nitrogen, respectively. The activities of S‐PPR were higher than those of S‐PNP and S‐PAT. For the hydrolysis of cyclohexyl acetate and oleyl acetate in water, activities of S‐PPR, S‐PAT, and S‐PNP were considerably higher than those of the other conventional solid acids. Rate constants of S‐PPR were 2.8 and 11.7 times larger than those of the sulfonated condensed polynuclear aromatic (S‐COPNA(PR)) resin (PR = pyrene) for the hydrolysis of cyclohexyl acetate and oleyl acetate, respectively. S‐PPR, S‐PAT, and S‐PNP were reused without significant loss of activities. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013