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N-Hydroxyphthalimide as a Catalyst of Cumene Oxidation with Hydroperoxide

Received: 4 May 2017     Published: 4 May 2017
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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.

Published in Modern Chemistry (Volume 5, Issue 2)
DOI 10.11648/j.mc.20170502.12
Page(s) 29-34
Creative Commons

This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2017. Published by Science Publishing Group

Keywords

Oxidation, N-Hydroxyphthalimide, Cumene Hydroperoxide, Dicumyl Peroxide, Cumene, Copper(II) Chloride

References
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[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.
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[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.
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Cite This Article
  • APA Style

    Aleksandra Konopińska, Beata Orlińska, Danuta Gillner. (2017). N-Hydroxyphthalimide as a Catalyst of Cumene Oxidation with Hydroperoxide. Modern Chemistry, 5(2), 29-34. https://doi.org/10.11648/j.mc.20170502.12

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    ACS Style

    Aleksandra Konopińska; Beata Orlińska; Danuta Gillner. N-Hydroxyphthalimide as a Catalyst of Cumene Oxidation with Hydroperoxide. Mod. Chem. 2017, 5(2), 29-34. doi: 10.11648/j.mc.20170502.12

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    AMA Style

    Aleksandra Konopińska, Beata Orlińska, Danuta Gillner. N-Hydroxyphthalimide as a Catalyst of Cumene Oxidation with Hydroperoxide. Mod Chem. 2017;5(2):29-34. doi: 10.11648/j.mc.20170502.12

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  • @article{10.11648/j.mc.20170502.12,
      author = {Aleksandra Konopińska and Beata Orlińska and Danuta Gillner},
      title = {N-Hydroxyphthalimide as a Catalyst of Cumene Oxidation with Hydroperoxide},
      journal = {Modern Chemistry},
      volume = {5},
      number = {2},
      pages = {29-34},
      doi = {10.11648/j.mc.20170502.12},
      url = {https://doi.org/10.11648/j.mc.20170502.12},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.mc.20170502.12},
      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.},
     year = {2017}
    }
    

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  • TY  - JOUR
    T1  - N-Hydroxyphthalimide as a Catalyst of Cumene Oxidation with Hydroperoxide
    AU  - Aleksandra Konopińska
    AU  - Beata Orlińska
    AU  - Danuta Gillner
    Y1  - 2017/05/04
    PY  - 2017
    N1  - https://doi.org/10.11648/j.mc.20170502.12
    DO  - 10.11648/j.mc.20170502.12
    T2  - Modern Chemistry
    JF  - Modern Chemistry
    JO  - Modern Chemistry
    SP  - 29
    EP  - 34
    PB  - Science Publishing Group
    SN  - 2329-180X
    UR  - https://doi.org/10.11648/j.mc.20170502.12
    AB  - 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.
    VL  - 5
    IS  - 2
    ER  - 

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Author Information
  • Department of Chemical Organic Technology and Petrochemistry, Si

  • Department of Chemical Organic Technology and Petrochemistry, Si

  • Department of Organic, Bioorganic Chemistry and Biotechnology, S

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