Polymerization of benzene by aluminum chloride

Although the reaction of benzene with aluminum chloride has been quite thoroughly examined by prior investigators, the present report is the first one on formation of poly‐p‐phenylene in this system. Optimum conditions, which gave low yields, involved 7 days at 49–51deg;C. The presence of oxygen (oxidant) and presumably water (cocatalyst) was necessary in order for polymerization to occur. Physical and chemical properties, e.g., behavior toward Br2 and H2O2–CH3CO2H, indicate that the polymer structure is slightly different from that of the material from C6H6–AlCl3–CuCl2. The polymer from C6H6–AlCl3 may possess a lower molecular weight and exhibits a greater degree of structural irregularity in the form of dihydrobenzene, p‐quinoid, or polynuclear regions. In the chemical studies, various compounds were used as models (tetrahydroquaterphenyl, triphenylene, and lower p‐polyphenyls).

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Polymerization of aromatic nuclei. XVIII. Polymerization of benzene to poly‐p‐phenylene by aluminum chloride–air–water

Durham

McFarland

Kovacic

1978

J. Polym. Sci. Polym. Chem. Ed.

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Polymerization of aromatic nuclei. XIX. Polymerization of thiophene by aluminum chloride

Kovacic

McFarland

1979

J. Polym. Sci. Polym. Chem. Ed.

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Thiophene was polymerized in high yield on exposure to aluminum chloride in solvent under mild conditions. Experimental evidence [IR, NMR, UV, and mass spectra, elemental analyses, reductive desulfurization, and comparison with the literature trimer of thiophene (prepared with phosphoric acid)] suggests the following structure: From gel permeation chromatography an average weight of 1290 was obtained, which corresponded to the presence of 15 rings; the highest‐molecular‐weight chains contained about 192 rings. Mechanistically, participation of cationic intermediates is proposed. Apparently chain extension can occur by various routes, including participation of neutral oligomer molecules.

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Studies on the reaction of benzene and other hydrocarbons with aluminium trichloride: Effect of catalytically activated hydrogen

Lai

Benner

Vollhardt

1984

Fuel

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Polymerization of benzene by aluminum chloride

Cited by 4 publications

References 11 publications

Polymerization of aromatic nuclei. XVIII. Polymerization of benzene to poly‐p‐phenylene by aluminum chloride–air–water

Polymerization of aromatic nuclei. XVIII. Polymerization of benzene to poly‐p‐phenylene by aluminum chloride–air–water

Polymerization of aromatic nuclei. XIX. Polymerization of thiophene by aluminum chloride

Studies on the reaction of benzene and other hydrocarbons with aluminium trichloride: Effect of catalytically activated hydrogen

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