Synthesis of sulfonated polynaphthalene, polyanthracene, and polypyrene as strong solid acids via oxidative coupling polymerization

摘要

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.