<i>N</i>-Hydroxyphthalimide as a Catalyst of Cumene Oxidation with Hydroperoxide

Aleksandra Konopińska; Beata Orlińska; Danuta Gillner

doi:doi:10.11648/j.mc.20170502.12

| Peer-Reviewed

N-Hydroxyphthalimide as a Catalyst of Cumene Oxidation with Hydroperoxide

Aleksandra Konopińska, Beata Orlińska, Danuta Gillner

Published in Modern Chemistry (Volume 5, Issue 2)

Received: 4 May 2017 Accepted: Published: 4 May 2017

Views: Downloads:

Download PDF

Share This Article

Twitter
Linked In
Facebook

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), 2024. Published by Science Publishing Group

Keywords

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

References

[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.

Cite This Article

Plain Text BibTeX RIS

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

Copy | Download

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

Copy | Download

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

Copy | Download

@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}
}

Copy | Download

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  -

Copy | Download

Author Information

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

Download PDF

Sections

Plain Text BibTeX RIS

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

Copy | Download

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

Copy | Download

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

Copy | Download

@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}
}

Copy | Download

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  -

Copy | Download