With an object of obtaining a compound containing no methoxy group from soda lignin of cryptomeria, the soda lignin was reacted at first with phosphorous oxychloride then oxidized with potassium permanganate and nitrobenzene, and the oxidation products were investigated.The result indicated that alkaline permanganate oxidation yielded benzoic acid and oxidation with nitrobenzene yielded protocatechualdehyde.Soda lignin from beech-wood and cryptomeria, and lignin sulfonate were treated with chlorine and subsequent treatment of oxidative decomposition with alkaline copper oxide yielded 2, 5-dihydroxybenzaldehyde.
The formation of alcohols from catalytic desulfurization decomposition of thiol ethyl esters or thiol benzyl esters of caprylic, capric, lauric and stearic acids has been investigated.In these cases, aldehydes are formed as intermediate products by regulating the conditions for reaction.The best yield of aldehyde in this experiment was obtained by reacting 10g. Raney nickel for0.009 mole of the thiol ester for2hours at room temperature.Also, the effect of ester group on the formation of aldehyde has been investigated and it was found that the yield of aldehyde was10% higher in thiol ethyl ester than thiol benzyl ester.
Reductive desulfurization decompositions have been investigated on two series of following compounds: [A] Monothiol benzyl esters of succinic, phthalic, and telephthalic acids, and salicylic acid thiol benzyl ester. [B] Ethyl thiol benzyl diesters of succinic, phthalic, and telephthalic acids, and thiol benzyl ester of o-methoxybenzoic acid. The result indicated that the compounds of [B] series showed far greater yield in reductive product than those of [A] series.The cause of this difference may be explained that thiol ester groups in [A] series with intramolecular or intermolecular hydrogen bonding have difficulty to be adsorbed on the catalyst than those of [B] series having thiol groups without such hydrogen bonding.