The effect of manganese protoporphyrin, manganese halogenated porphyrins, polyethylene glycol (PEG)-linked manganese porphyrin and PEG-linked manganese halogenated porphyrins (Scheme 1), on the decoloration rates of C.I. Solvent Yellow 14 by m-chloroperbenzoic acid (mCPBA) at 25°C in non-aqueous solvent was examined. The decoloration rate of C.I. Solvent Yellow 14 by mCPBA was accelerated due to the presence of manganese porphyrin derivatives, depending on the structures of porphyrin derivatives. Interestingly, the decoloration rate decreased due to the presence of ligands such as imidazole, in comparison to the rate catalyzed by the manganese porphyrins in aqueous solution.
Ueda, M., and Yoshimura, Y., Characteristics of Non-aqueous Surfactant Solutions and their Applications to Cleaning of Fabrics, Dyeing Industry42(1), 2-11 (1994).
2.
Tokuda, J., Oura, R., and Nango, M., Effect of Surfactants on Decoloration of Various Dyes by Peroxide Bleaching Agents, Textile Res. J. 69(6), 456-462 (1999).
3.
Nango, M., Iwasaki, T., Takeuchi, Y., Kurono, Y., Tokuda, J., and Oura, R., Peroxide Decoloration of Azo Dyes Catalyzed by Polyethylene Glycol-Linked Manganese Halogenated Porphyrins, Langmuir14(12), 3272-3278 (1998).
4.
Tokuda, J., Oura, R., and Nango, M., Decoloration of Azo Dyes by Hydrogen Peroxide Catalyzed by Water-Soluble Manganese Porphyrins, Textile Res. J. 69(12), 956-960 (1999).
5.
Tokuda, J., Oura, R., Iwasaki, T., Takeuchi, Y., Nango, M., and Kashiwada, A., Decolorisation of Azo Dyes with Hydrogen Peroxide Catalyzed by Manganese Protoporphyrins , Journal of the Society of Dyers and Colourists116(2), 42-47 (2000).
6.
Hage, R., et al., Efficient Manganese Catalysts for Low-Temperature Bleaching , Nature369, 637-639 (1994).
7.
Namboodri, C.G. , and Walsh, W.K., Decolorizing Spent Dyebath with Hot Peroxide , Am. Dyest. Rep. 84(8), 86-95 (1995).
8.
Hodges, G.R. , Lindsay Smith, J.R., and Oakes, J., Mechanism of Oxidation of Azo Dyes by a Sterically Hindered Anionic Oxoiron(IV) Porphyrin in Aqueous Solution, J. Chem. Soc., Perkin Trans. 2, 617-627 (1998).
9.
Gürsoy, N., Lim, S., Hinks, D., and Hauser, P., Evaluating hydrogen peroxide bleaching with cationic bleach activators in a cold pad-batch process, Textile Res. J. 74(11), 970-976 (2004).
10.
Soares, G.M.B. , Amorim, M.T.P., Lageiro, M., and Costa-Ferreira , M., Pilot-scale Enzymatic Decolorisation of Industrial Dyeing Process Wastewater, Textile Res. J. 76(1), 4-11 (2006).
11.
Iida, K., Nango, M., Matsuura, M., Yamaguchi, M., Sato, K., Tamnaka, K., Akimoto, K., Yamashita, K., Tsuda, K., and Kurono, Y., Energy Transfer and Electron Transfer of Poly(ethylene glycol)-Linked Fluprinated Porphyrin Derivatives in Lipid Bilayers, Langmuir12(2), 450-458 (1996).
12.
Iida, K., et al., Synthesis and Characterization of Hybrid Porphyrin Dimers and Halogenated Porphyrin Dimers, Bull. Chem. Soc. Jpn68, 1959-1968 (1995).
13.
Nango, M., Kimura, Y., Ihara, Y., and Kuroki, N., Stereoselective Hydrolysis of Amino Acid Esters in Branched or Linear Poly(ethylenimine) Derivatives, Macromolecules21(8), 2330-2335 (1988).
14.
Chivukula, M., Spadarao, J.T., and Renganathan , V., Lignin Peroxidase-catalyzed Oxidation of Sulfonated Azo Dyes Generates Novel Sulfophenyl Hydroperoxides , Biochemistry34, 7765-7772 (1995 ).
15.
Battioni, P. , Renaud, J.P., Bartoli, J.F., Reina-Artiles , M., Fort, M., and Mansuy, D., Monooxygenase-like Oxidation of Hydrocarbons by H2O2 Catalyzed by Manganese Porphyrins and Imidazole: Selection of the Best Catalytic System and Nature of the Active Oxygen Species , J. Am. Chem. Soc. 110, 8462-8470 (1988 ).
