344259-23-0Relevant academic research and scientific papers
Imidazole Catalyzed Oxidations with Organic Peroxides: A Kinetic Study
Shawakfeh, Khaled Q.,Al-Ajlouni, Ahmad M.
, p. 313 - 319 (2004)
Imidazole and 1-methylimidazole catalyze the oxidation of indigo dyes with m-chloroperoxybenzoic acid (MCPBA) in organic and mixed aqueous solutions. The kinetics of these reactions were studied in CH3OH/CH3CN and CH3OH/H2O solvent systems. The reaction rates decreased with the solvent polarity. The catalytically active species is proposed as an MCPBA-Im adduct which is in equilibrium with MCPBA and the imidazole. The equilibrium constant (K ～ 70) for the formation of the MCPBA-Im adduct was determined in CH3OH/H2O (8:2). The catalyzed rates are at least three-orders of magnitude faster than the uncatalyzed rates. The electron-rich, 1-methylimidazole, increases the rate of oxidation of indigo blue via MCPBA more than imidazole itself. A mechanism similar to the Michaelis-Menten type was proposed for these reactions. The initial products from oxidation of indigo dyes by MCPBA are the epoxides, which undergo a slow ring-opening in the presence of water to form 1,2-diol products.
