Research Article
BibTex RIS Cite

Oxidation of 2,6-Di-tert-Butylphenol Catalyzed by [5,10,15,20-Tetrakis(4-carboxyphenyl)porphyrinato]cobalt(II) in the Presence of Various Oxidants

Year 2017, , 1307 - 1316, 01.12.2017
https://doi.org/10.16984/saufenbilder.290357

Abstract

In this study, the
oxidation of 2,6-di-
tert-butylphenol (DTBP) catalyzed by
[5,10,15,20-tetrakis(4-carboxylphenyl)porphyrinato]cobalt(II) ([CoTCPP]) in the
presence of various oxidants has been investigated. Potassium peroxymonosulfate
(Oxone),
tert-butylhydroperoxide (ButOOH) or hydrogen
peroxide (H
2O2) were used as oxidants and the reactions
were carried out in 10-15% (v:v) of water-methanol solutions at room
temperature. The effects of the concentration of the substrate, catalyst and
oxidant on the outcome of the reactions were investigated. The products of the
reaction mixtures were identified using GC-MS and the amounts of the products and
unreacted DTBP were determined from the peak areas on GC chromatograms.
[CoTCPP] showed catalytic activity in the oxidation of DTBP when Oxone or Bu
tOOH
was used as oxidant. No catalytic activity of [CoTCPP] was observed when the oxidant
was H
2O2.

References

  • [1] X. Y. Wang, R. J. Motekaitis, and A. E. Martell, "Metallotetraphenylporphyrin-catalyzed oxidation of 2,6-di-tert-butylphenol," Inorg. Chem., vol. 23, pp. 271-275, 1984.
  • [2] M. T. Hassanein, S. S. Gerges, M. A. Abdo, and S. H. El-Khalafy, "Studies on the oxidation of 2,6-di-tert-butylphenol by molecular oxygen catalyzed by cobalt(II) tetraarylporphyrins bound to cationic latex," J. Porphyr. Phthalocya., vol. 09, pp. 621-625, 2005.
  • [3] B. Meunier, "Metalloporphyrin-catalysed oxygenation of hydrocarbons," Bull. Soc. Chim. Fr., pp. 578-594, 1986.
  • [4] F. P. Guengerich and T. L. Macdonald, "Chemical mechanisms of catalysis by cytochromes P-450: a unified view," Acc. Chem. Res., vol. 17, pp. 9-16, 1984.
  • [5] W. Sokol, “Uptake rate of phenol by pseudomonos putida grown in unsteady state” Biotech. Bioeng., vol. 32, 1097-1103, 1988.
  • [6] F. Cavani, G. Centi, S. Perathoner, and F. Trifirò, Sustainable Industrial Chemistry: Principles, Tools and Industrial Examples: John Wiley & Sons, 2009.
  • [7] R. A. Sheldon, I. Arends, and U. Hanefeld, Green chemistry and catalysis: John Wiley & Sons, 2007.
  • [8] E. I. Solomon, U. M. Sundaram, and T. E. Machonkin, "Multicopper oxidases and oxygenases," Chem. Rev., vol. 96, pp. 2563-2606, 1996.
  • [9] N. Kitajima and Y. Moro-oka, "Copper-Dioxygen Complexes. Inorganic and Bioinorganic Perspectives," Chem. Rev., vol. 94, pp. 737-757, 1994.
  • [10] R. Bernini, E. Mincione, M. Barontini, G. Fabrizi, M. Pasqualetti, and S. Tempesta, "Convenient oxidation of alkylated phenols and methoxytoluenes to antifungal 1, 4-benzoquinones with hydrogen peroxide (H2O 2)/methyltrioxorhenium (CH3ReO3) catalytic system in neutral ionic liquid," Tetrahedron, vol. 62, pp. 7733-7737, 2006.
  • [11] A. Pui and J.-P. Mahy, "Synthesis, characterization and catalytic activity of halo-methyl-bis(salicylaldehyde)ethylenediamine cobalt(II) complexes," Polyhedron, vol. 26, pp. 3143-3152, 2007.
  • [12] A. Pui, I. Berdan, I. Morgenstern-Badarau, A. Gref, and M. Perrée-Fauvet, "Electrochemical and spectroscopic characterization of new cobalt(II) complexes. Catalytic activity in oxidation reactions by molecular oxygen," Inorg. Chim. Acta, vol. 320, pp. 167-171, 2001.
  • [13] J. J. Bozell, J. O. Hoberg, and D. R. Dimmel, "Catalytic oxidation of para-substituted phenols with nitrogen dioxide and oxygen," Tetrahedron Lett., vol. 39, pp. 2261-2264, 1998.
  • [14] M. Hassanein, M. Sakaran, and S. Shendy, "Oxidation of 2,6-Di-tert-butylphenol by dioxygen catalyzed by tetrasodium phthalocyaninatocobalt(II) tetrasulfonate in aqueous micellar media," J. Iran. Chem. Soc., vol. 7, pp. 128-133, 2010.
  • [15] H. Türk and Y. Çimen, "Oxidation of 2,6-di-tert-butylphenol with tert-butylhydroperoxide catalyzed by cobalt(II) phthalocyanine tetrasulfonate in a methanol–water mixture and formation of an unusual product 4,4′-dihydroxy-3,3′,5,5′-tetra-tert-butylbiphenyl," J.Mol. Catal. A: Chem., vol. 234, pp. 19-24, 2005.
  • [16] Y. Çimen and H. Türk, "Oxidation of 2,6-di-tert-butylphenol with tert-butyl hydroperoxide catalyzed by iron phthalocyanine tetrasulfonate in a methanol–water mixture," J. Mol. Catal. A: Chem., vol. 265, pp. 237-243, 2007.
  • [17] H. Turk and W. T. Ford, "Autoxidation of 2, 6-di-tert-butylphenol in water catalyzed by cobalt phthalocyaninetetrasulfonate bound to polymer colloids," J. Org. Chem., vol. 53, pp. 460-462, 1988.
  • [18 W. T. Ford, R. Chandran, and H. Turk, "Catalysts supported on polymer colloids," Pure App. Chem., vol. 60, pp. 395-400, 1988.
  • [19] X. Y. Wang, R. J. Motekaitis, and A. E. Martell, "Metallotetraphenylporphyrin-catalyzed oxidation of 2, 6-di-tert-butylphenol," Inorg. Chem., vol. 23, pp. 271-275, 1984.
  • [20] F. R. Longo, M. G. Finarelli, and J. B. Kim, "The synthesis and some physical properties of ms-tetra(pentafluorophenyl)-porphin and ms-tetra(pentachlorophenyl)porphin," J. Heterocyc. Chem., vol. 6, pp. 927-931, 1969.
  • [21] R. F. Pasternack, L. Francesconi, D. Raff, and E. Spiro, "Aggregation of nickel(II), copper(II), and zinc(II) derivatives of water-soluble porphyrins," Inorg. Chem., vol. 12, pp. 2606-2611, 1973.

2,6-Di-tert-Bütilfenolün Çeşitli Oksidantlarla [5,10,15,20 Tetrakis(4 karboksifenil)porfirinato]kobalt(II) Katalizörlüğünde Oksidasyonu

Year 2017, , 1307 - 1316, 01.12.2017
https://doi.org/10.16984/saufenbilder.290357

Abstract

Bu çalışmada 2,6-di-tert-bütilfenolün
(DTBP) çeşitli oksidantlarla [5,10,15,20-tetrakis(4-karboksifenil)porfirinato]kobalt(II)
([CoTCPP]) tarafından katalizlenen oksidasyonu araştırılmıştır. Oksidant olarak
potasyum peroksimonosülfat (okzon),
tert-bütilhidroperoksit
(Bu
tOOH) veya hidrojen
peroksit (H
2O2) kullanılmış ve reaksiyonlar hacimce
%10-15 su içeren metanol çözeltilerinde oda sıcaklığında yürütülmüştür. Oksidasyona
substrat, katalizör ve oksidant derişimlerinin etkileri incelenmiştir.
Reaksiyon ürünleri gaz kromatografisi-kütle spektrometresiyle (GC-MS)
belirlenmiş ve ürünlerin ve reaksiyona girmemiş DTBP miktarları gaz
kromatografisi (GC) ile elde edilen kromatogramlardaki pik alanlarından
belirlenmiştir. DTBP oksidasyonunda oksidant olarak okzon ve Bu
tOOH kullanıldığında [CoTCPP]
katalitik aktivite göstermiştir. H
2O2 varlığında ise
[CoTCPP] katalitik aktivite göstermemiştir.

References

  • [1] X. Y. Wang, R. J. Motekaitis, and A. E. Martell, "Metallotetraphenylporphyrin-catalyzed oxidation of 2,6-di-tert-butylphenol," Inorg. Chem., vol. 23, pp. 271-275, 1984.
  • [2] M. T. Hassanein, S. S. Gerges, M. A. Abdo, and S. H. El-Khalafy, "Studies on the oxidation of 2,6-di-tert-butylphenol by molecular oxygen catalyzed by cobalt(II) tetraarylporphyrins bound to cationic latex," J. Porphyr. Phthalocya., vol. 09, pp. 621-625, 2005.
  • [3] B. Meunier, "Metalloporphyrin-catalysed oxygenation of hydrocarbons," Bull. Soc. Chim. Fr., pp. 578-594, 1986.
  • [4] F. P. Guengerich and T. L. Macdonald, "Chemical mechanisms of catalysis by cytochromes P-450: a unified view," Acc. Chem. Res., vol. 17, pp. 9-16, 1984.
  • [5] W. Sokol, “Uptake rate of phenol by pseudomonos putida grown in unsteady state” Biotech. Bioeng., vol. 32, 1097-1103, 1988.
  • [6] F. Cavani, G. Centi, S. Perathoner, and F. Trifirò, Sustainable Industrial Chemistry: Principles, Tools and Industrial Examples: John Wiley & Sons, 2009.
  • [7] R. A. Sheldon, I. Arends, and U. Hanefeld, Green chemistry and catalysis: John Wiley & Sons, 2007.
  • [8] E. I. Solomon, U. M. Sundaram, and T. E. Machonkin, "Multicopper oxidases and oxygenases," Chem. Rev., vol. 96, pp. 2563-2606, 1996.
  • [9] N. Kitajima and Y. Moro-oka, "Copper-Dioxygen Complexes. Inorganic and Bioinorganic Perspectives," Chem. Rev., vol. 94, pp. 737-757, 1994.
  • [10] R. Bernini, E. Mincione, M. Barontini, G. Fabrizi, M. Pasqualetti, and S. Tempesta, "Convenient oxidation of alkylated phenols and methoxytoluenes to antifungal 1, 4-benzoquinones with hydrogen peroxide (H2O 2)/methyltrioxorhenium (CH3ReO3) catalytic system in neutral ionic liquid," Tetrahedron, vol. 62, pp. 7733-7737, 2006.
  • [11] A. Pui and J.-P. Mahy, "Synthesis, characterization and catalytic activity of halo-methyl-bis(salicylaldehyde)ethylenediamine cobalt(II) complexes," Polyhedron, vol. 26, pp. 3143-3152, 2007.
  • [12] A. Pui, I. Berdan, I. Morgenstern-Badarau, A. Gref, and M. Perrée-Fauvet, "Electrochemical and spectroscopic characterization of new cobalt(II) complexes. Catalytic activity in oxidation reactions by molecular oxygen," Inorg. Chim. Acta, vol. 320, pp. 167-171, 2001.
  • [13] J. J. Bozell, J. O. Hoberg, and D. R. Dimmel, "Catalytic oxidation of para-substituted phenols with nitrogen dioxide and oxygen," Tetrahedron Lett., vol. 39, pp. 2261-2264, 1998.
  • [14] M. Hassanein, M. Sakaran, and S. Shendy, "Oxidation of 2,6-Di-tert-butylphenol by dioxygen catalyzed by tetrasodium phthalocyaninatocobalt(II) tetrasulfonate in aqueous micellar media," J. Iran. Chem. Soc., vol. 7, pp. 128-133, 2010.
  • [15] H. Türk and Y. Çimen, "Oxidation of 2,6-di-tert-butylphenol with tert-butylhydroperoxide catalyzed by cobalt(II) phthalocyanine tetrasulfonate in a methanol–water mixture and formation of an unusual product 4,4′-dihydroxy-3,3′,5,5′-tetra-tert-butylbiphenyl," J.Mol. Catal. A: Chem., vol. 234, pp. 19-24, 2005.
  • [16] Y. Çimen and H. Türk, "Oxidation of 2,6-di-tert-butylphenol with tert-butyl hydroperoxide catalyzed by iron phthalocyanine tetrasulfonate in a methanol–water mixture," J. Mol. Catal. A: Chem., vol. 265, pp. 237-243, 2007.
  • [17] H. Turk and W. T. Ford, "Autoxidation of 2, 6-di-tert-butylphenol in water catalyzed by cobalt phthalocyaninetetrasulfonate bound to polymer colloids," J. Org. Chem., vol. 53, pp. 460-462, 1988.
  • [18 W. T. Ford, R. Chandran, and H. Turk, "Catalysts supported on polymer colloids," Pure App. Chem., vol. 60, pp. 395-400, 1988.
  • [19] X. Y. Wang, R. J. Motekaitis, and A. E. Martell, "Metallotetraphenylporphyrin-catalyzed oxidation of 2, 6-di-tert-butylphenol," Inorg. Chem., vol. 23, pp. 271-275, 1984.
  • [20] F. R. Longo, M. G. Finarelli, and J. B. Kim, "The synthesis and some physical properties of ms-tetra(pentafluorophenyl)-porphin and ms-tetra(pentachlorophenyl)porphin," J. Heterocyc. Chem., vol. 6, pp. 927-931, 1969.
  • [21] R. F. Pasternack, L. Francesconi, D. Raff, and E. Spiro, "Aggregation of nickel(II), copper(II), and zinc(II) derivatives of water-soluble porphyrins," Inorg. Chem., vol. 12, pp. 2606-2611, 1973.
There are 21 citations in total.

Details

Primary Language Turkish
Subjects Chemical Engineering
Journal Section Research Articles
Authors

Yasemin Çimen

Tuğçe Günay This is me

Publication Date December 1, 2017
Submission Date February 6, 2017
Acceptance Date July 27, 2017
Published in Issue Year 2017

Cite

APA Çimen, Y., & Günay, T. (2017). 2,6-Di-tert-Bütilfenolün Çeşitli Oksidantlarla [5,10,15,20 Tetrakis(4 karboksifenil)porfirinato]kobalt(II) Katalizörlüğünde Oksidasyonu. Sakarya University Journal of Science, 21(6), 1307-1316. https://doi.org/10.16984/saufenbilder.290357
AMA Çimen Y, Günay T. 2,6-Di-tert-Bütilfenolün Çeşitli Oksidantlarla [5,10,15,20 Tetrakis(4 karboksifenil)porfirinato]kobalt(II) Katalizörlüğünde Oksidasyonu. SAUJS. December 2017;21(6):1307-1316. doi:10.16984/saufenbilder.290357
Chicago Çimen, Yasemin, and Tuğçe Günay. “2,6-Di-Tert-Bütilfenolün Çeşitli Oksidantlarla [5,10,15,20 Tetrakis(4 karboksifenil)porfirinato]kobalt(II) Katalizörlüğünde Oksidasyonu”. Sakarya University Journal of Science 21, no. 6 (December 2017): 1307-16. https://doi.org/10.16984/saufenbilder.290357.
EndNote Çimen Y, Günay T (December 1, 2017) 2,6-Di-tert-Bütilfenolün Çeşitli Oksidantlarla [5,10,15,20 Tetrakis(4 karboksifenil)porfirinato]kobalt(II) Katalizörlüğünde Oksidasyonu. Sakarya University Journal of Science 21 6 1307–1316.
IEEE Y. Çimen and T. Günay, “2,6-Di-tert-Bütilfenolün Çeşitli Oksidantlarla [5,10,15,20 Tetrakis(4 karboksifenil)porfirinato]kobalt(II) Katalizörlüğünde Oksidasyonu”, SAUJS, vol. 21, no. 6, pp. 1307–1316, 2017, doi: 10.16984/saufenbilder.290357.
ISNAD Çimen, Yasemin - Günay, Tuğçe. “2,6-Di-Tert-Bütilfenolün Çeşitli Oksidantlarla [5,10,15,20 Tetrakis(4 karboksifenil)porfirinato]kobalt(II) Katalizörlüğünde Oksidasyonu”. Sakarya University Journal of Science 21/6 (December 2017), 1307-1316. https://doi.org/10.16984/saufenbilder.290357.
JAMA Çimen Y, Günay T. 2,6-Di-tert-Bütilfenolün Çeşitli Oksidantlarla [5,10,15,20 Tetrakis(4 karboksifenil)porfirinato]kobalt(II) Katalizörlüğünde Oksidasyonu. SAUJS. 2017;21:1307–1316.
MLA Çimen, Yasemin and Tuğçe Günay. “2,6-Di-Tert-Bütilfenolün Çeşitli Oksidantlarla [5,10,15,20 Tetrakis(4 karboksifenil)porfirinato]kobalt(II) Katalizörlüğünde Oksidasyonu”. Sakarya University Journal of Science, vol. 21, no. 6, 2017, pp. 1307-16, doi:10.16984/saufenbilder.290357.
Vancouver Çimen Y, Günay T. 2,6-Di-tert-Bütilfenolün Çeşitli Oksidantlarla [5,10,15,20 Tetrakis(4 karboksifenil)porfirinato]kobalt(II) Katalizörlüğünde Oksidasyonu. SAUJS. 2017;21(6):1307-16.

30930 This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.