Recovery of organic carbon from wastewaters deriving from agroindustrial sources is studied using a low-cost catalytic system. This allows both to prevent pollution and to recycle organic materials. The bis(salicylideneimino)ethylenecobalt(II) catalyzed oxygenation of E-ferulic acid in methanol gives vanillic aldehyde, vanillic acid methyl ester and 2-hydroxyhomovanillic aldehyde. Also, methyl 2-hydroxy-3-oxo-(4-hydroxy-3-methoxyphenyl)propionate is formed from E-methyl ferulate. Electron Paramagnetic Resonance (EPR) measurements show that an organometallic radical is probably the intermediate when the reaction is run in chloroform and in methanol, while the Co(III) superoxo complex is present when the solvent is pyridine. The dependence of the conversion of E-Ferulic acid from the catalytic ratio is also studied. The cobalt-catalyzed oxidation of lignin model compounds, representative of the beta-arylether beta-O-4) and the phenylcoumaran (beta-5) structure, with dioxygen is studied. beta-O-4 dimers are cleaved into two fragments, whereas beta-5 dimers are oxygenated at the benzylic position with eventual cleavage of the dihydrofuran ring. Pollution prevention benefits could derive from the use of such systems in agroindustrial activities and in wood-processing industry.
Bassoli, A., Brambilla, A., Bolzacchini, E., Chioccara, F., Morazzoni, F., Orlandi, M., et al. (1996). Oxidation of phenolic phenylpropenoids with dioxygen using bis(salicylideneimino)ethylenecobalt(II). In Green Chemistry: Designing Chemistry For The Environment (pp.92-104). Oxford University Press [10.1021/bk-1996-0626.ch008].
Oxidation of phenolic phenylpropenoids with dioxygen using bis(salicylideneimino)ethylenecobalt(II)
BOLZACCHINI, EZIO;MORAZZONI, FRANCA;ORLANDI, MARCO EMILIO;RINDONE, BRUNO
1996
Abstract
Recovery of organic carbon from wastewaters deriving from agroindustrial sources is studied using a low-cost catalytic system. This allows both to prevent pollution and to recycle organic materials. The bis(salicylideneimino)ethylenecobalt(II) catalyzed oxygenation of E-ferulic acid in methanol gives vanillic aldehyde, vanillic acid methyl ester and 2-hydroxyhomovanillic aldehyde. Also, methyl 2-hydroxy-3-oxo-(4-hydroxy-3-methoxyphenyl)propionate is formed from E-methyl ferulate. Electron Paramagnetic Resonance (EPR) measurements show that an organometallic radical is probably the intermediate when the reaction is run in chloroform and in methanol, while the Co(III) superoxo complex is present when the solvent is pyridine. The dependence of the conversion of E-Ferulic acid from the catalytic ratio is also studied. The cobalt-catalyzed oxidation of lignin model compounds, representative of the beta-arylether beta-O-4) and the phenylcoumaran (beta-5) structure, with dioxygen is studied. beta-O-4 dimers are cleaved into two fragments, whereas beta-5 dimers are oxygenated at the benzylic position with eventual cleavage of the dihydrofuran ring. Pollution prevention benefits could derive from the use of such systems in agroindustrial activities and in wood-processing industry.
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