Volume 5, Issue 2, April 2017, Page: 29-34
N-Hydroxyphthalimide as a Catalyst of Cumene Oxidation with Hydroperoxide
Aleksandra Konopińska, Department of Chemical Organic Technology and Petrochemistry, Si
Beata Orlińska, Department of Chemical Organic Technology and Petrochemistry, Si
Danuta Gillner, Department of Organic, Bioorganic Chemistry and Biotechnology, S
Received: May 4, 2017;       Published: May 4, 2017
DOI: 10.11648/j.mc.20170502.12      View  2035      Downloads  68
Abstract
Cumene oxidation with 1-methyl-1-phenylethyl hydroperoxide catalyzed by N-hydroxyphthalimide or its derivatives and transition metal salts has been studied. Effects of the type of metal compound (Co(II), Mn(II) or Cu(II) chloride, acetate or acetylacetonate), amounts of N-hydroxyphthalimide and metal salt as well as temperature were established. The highest yields of dicumyl peroxide (48-54%) were obtained, when reaction was performed at 60-70°C, in the presence of the NHPI/CuCl2 catalytic system, in acetonitrile as a solvent. Similar yield of dicumyl peroxide (43%) was obtained in solvent-free medium.
Keywords
Oxidation, N-Hydroxyphthalimide, Cumene Hydroperoxide, Dicumyl Peroxide, Cumene, Copper(II) Chloride
To cite this article
Aleksandra Konopińska, Beata Orlińska, Danuta Gillner, N-Hydroxyphthalimide as a Catalyst of Cumene Oxidation with Hydroperoxide, Modern Chemistry. Vol. 5, No. 2, 2017, pp. 29-34. doi: 10.11648/j.mc.20170502.12
Reference
[1]
Kirk- Othmer Encyclopedia of Chemical Technology Vol. 18, Wiley, New York, 1990.
[2]
M. S. Kharasch, A. Fono, “New Metal Salt-Induced Homolytic Reactions. 2. Modification Of Free Radical Reactions By Copper Salts”, J. Org. Chem. 1959, 24, 72-78.
[3]
J. Kochi, “The Mechanism of the Copper Salt Catalysed Reactions of Peroxides”, Tetrahedron, 1962, 18, 483-497.
[4]
J. Zawadiak, D. Gilner, “Synthesis of t-Butyl-Cumyl Peroxide from t-Butyl Hydroperoxide and Cumene in the Presence of Cupric Chloride/Tetrabutylammonium Bromide Catalytic System”, Pol. J. Applied Chem., 1995, 39, 225-232.
[5]
J. Zawadiak, D. Gilner, R. Mazurkiewicz, “Copper salt - crown ether systems as catalysts for the oxidation of cumene with 1-methyl-1-phenylethylhydroperoxide to bis(1-methyl-1-phenylethyl)peroxide”, Tetrahedron Letters, 1999, 40(21), 4059-4062.
[6]
J. Zawadiak, D. Gilner, R. Mazurkiewicz, B. Orlinska, “Copper Salt-Crown Ether System as Catalysts for the Oxidation of Isopropyl Arenes with Tertiary Hydroperoxides to Peroxides”, Appl Catal A General, 2001, 205, 239-243.
[7]
G. Rothenberg, L. Feldberg, H. Wiener, Y. Sasson, “Copper-Catalyzed Homolytic and Heterolytic Benzylic and Allylic Oxidation using tert-Butyl Hydroperoxide”, J. Chem. Soc., Perkin Trans, 1998, 2, 2429–2434.
[8]
J. Zawadiak, Z. Stec, Z. Kulicki, A. Burghardt, B.Staniowski, G. Jóźwicki G. Stolarczyk, “The method of tertiary aralkyl peroxides production”, PL 156 813, 1992; “The method of dicumyl peroxide production from cumene and cumene hydroperoxide” PL 156 814, 1992; BR 88 06 302, 1989; BR 89 06 394, 1990; BR 89 06 395, 1990.
[9]
F. Recupero, C. Punta, Free Radical Functionalization of Organic Compounds Catalyzed by N-Hydroxyphthalimid”, Chem. Rev. 2007, 107, 3800-3842.
[10]
K. Chen, P. Zhang, Y. Wang, H. Lin, “ Metal-free allylic/ benzylic oxidation strategies with molecular oxygen: recnt advances and future prospects”, Green Chem. 2014, 16, 2344-2374.
[11]
S. Coseri, “Phthalimide‐N‐oxyl (PINO) Radical, a Powerful Catalytic Agent: Its Generation and Versatility Towards Various Organic Substrates”, Catal. Rev.-Sci. Eng., 2009, 51, 218-292.
[12]
R. Amorati, M. Lucarini, V. Mugnaini, G. Pedulli, F. Minisci, F. Recupero, F. Fontana, P. Astolfi, L. Greci, „Hydroxylamines as Oxidation Catalysts:  Thermochemical and Kinetic Studies”, J. Org. Chem., 2013, 68, 1747-1754.
[13]
J. Zawadiak, D. Gilner, Z. Kulicki, S. Baj, “Concurrent Iodimetric Determination of Cumene Hydroperoxide and Dicumenyl Peroxide Used for Reaction Control in Dicumenyl Peroxide Synthesis”, Analyst, 1993, 118, 1081-1083.
[14]
K. Kasperczyk, B. Orlińska, J. Zawadiak, " Aerobic Oxidation of Cumene Catalysed by 4-Alkyloxycarbonyl- N-Hydroxyphthalimide”, Cent. Eur. J. Chem. 2014, 12, 1176-1182.
[15]
Basudeb Saha, Nobuyoshi Koshino, James H. Espenson, "N-Hydroxyphthalimides and Metal Cocatalysts for the Autoxidation of p-Xylene to Terephthalic Acid”, J. Phys. Chem. A 2004, 108, 1176-431.
[16]
N. Koshino, B. Saha, J. H. Espenson, „Kinetic Study of the Phthalimide N-Oxyl Radical in Acetic Acid. Hydrogen Abstraction from Substituted Toluenes, Benzaldehydes, and Benzyl Alcohols”, J. Org. Chem. 2003, 68, 9364-9370.
[17]
N. Sawatari, S. Sakaguchi, Y. Ishii, „Oxidation of nitrotoluenes with air using N-hydroxyphthalimide analogues as key catalysts”, Tetrahedron Lett., 2003, 44, 2053-2056.
[18]
K. V. Novikova, M. O. Kompanets, O. V. Kushch, S. P. Kobzev, M. M. Khliestov, I. O. Opeida, “Substituted N-hydroxyphthalimides as oxidation catalysts”, Reac. Kinet. Mech. Cat., 2011, 103, 31–40.
Browse journals by subject