Abstract
The activity of the metal–organic framework (MOF) {[CuI(CN)(phen)2·CuII(CN)2·(phen)]·5H2O} containing 1,10-phenanthroline ligand (phen) has been investigated for the oxidation of 3,5-di-tert-butylcatechol (3,5-DTBCH2) to 3,5-di-tert-butyl-o-benzoquinone (3,5-DTBQ) with hydrogen peroxide. The effects of pH and concentration of catalyst, hydrogen peroxide and substrate on the oxidation reaction and yield of the reaction product have been studied. Kinetic studies indicate pseudo first-order rate with respect to the 3,5-DTBCH2 concentration (kobs = 0.113 min−1). Disodium salt of terephthalic acid photoluminescence probing technology indicated the formation of the hydroxyl radical as the reactive oxygen species in the MOF/H2O2—system. A mechanism for the oxidation reaction has been discussed.
Similar content being viewed by others
References
R.S. Himmelwright, N.C. Eickman, E.I. Solomon, Biochem. Biophys. Res. Commun. 101, 1576–1586 (1979)
R.S. Himmelwright, N.C. Eickman, E.I. Solomon, Proc. Nat. Acad. Sci. USA 76, 2094–2098 (1979)
D.B. Brown (ed.), Mixed Valance Compounds, Theory and Application in Chemistry, Physics, Geology and Biology (Reidel Publishing Co., Boston, 1980)
M. Dunaj-Jurco, G. Ondrejovic, M. Melnik, Coord. Chem. Rev. 83, 1–28 (1988)
S.R. Breeze, S. Wang, Inorg. Chem. 35, 3404–3408 (1996)
J. Manzur, A.M. Garcia, A. Vega, E. Spodine, polyhedron 18, 2399–2404 (1999)
S.H. Etaiw, S.A. Amer, M.M. El-Bendary, J. Inorg. Organomet. Polym. 21, 662–672 (2011)
Z. Han, Y. Li, Inorg. Chem. Commun. 22, 73–76 (2012)
P. Karsten, A. Neves, A.J. Bortoluzzi, J. Strähle, C.M. Mössmer, Inorg. Chem. Commun. 5, 434–438 (2002)
A. Neves, A.J. Botoluzzi, R. Jovito, R.A. Peralta, B. de Souza, B. Szpoganicz, C. Joussef, H. Terenzi, P.C. Serverino, F.L. Fischer, G. Schenk, M.J. Riley, S.J. Smith, L.R. Gahan, J. Braz. Chem. Soc. 21, 1201–1212 (2010)
J.L.C. Rowsell, O.M. Yaghi, Microporous Mesoporous Mater. 73, 3–14 (2004)
W.B. Lin, Z.Y. Wang, L. Ma, J. Am. Chem. Soc. 121, 11249–11250 (1999)
G. Ferey, C. Mellot-Draznieks, C. Seerre, F. Millange, Acc. Chem. Res. 38, 217–225 (2005)
O.M. Yaghi, M. O’Keeffe, N.W. Ockwing, H.K. Chae, M. Eddaoudi, J. Kim, Nature 423, 705–714 (2003)
S. Hasegawa, S. Horike, R. Matsuda, S. Furukawa, K. Mochizuki, Y. Kinoshita, S. Kitagawa, J. Am. Chem. Soc. 129, 2607–2614 (2007)
P. Horcajada, S. Surble, C. Serre, D.Y. Hong, Y.K. Seo, J.S. Chang, J.M. Grenche, I. Margiolaki, G. Ferey, Chem. Commun. 27, 2820–2822 (2007)
T. Dewa, T. Saiki, Y. Aoyama, J. Am. Chem. Soc. 123, 502–503 (2001)
F.X.L. Xamena, O. Casanova, R.G. Tailleur, H. Garcia, A. Corma, J. Catal. 255, 220–227 (2008)
Bo Xiao, Hongwei Hou, Yaoting Fan, J. Mol. Catal. A 288, 42–51 (2008)
L.G. Qiu, L. Gu, G. Hu, L. Zhang, J. Solid state Chem. 182, 502–508 (2009)
S.H. Cho, B. Ma, S.T. Nguyen, J.T. Hupp, T.E. Albrecht-Schmitt, Chem. Commun. 24, 2563–2565 (2006)
E. Angelescu, O.D. Pavel, R. Lonescu, R. Birjega, M. Badea, R. Zavoianu, J. Mol. Catal. A 352, 21–30 (2012)
M. Sabo, A. Henschel, H. Frode, E. Klemm, S. Kaskel, J. Mater. Chem. 17, 3827–3832 (2007)
J.S. Seo, D. Whang, H. Lee, S.I. Jun, J. Oh, Y.J. Jeon, K. Kim, Nature 404, 982–986 (2000)
Y. Zhou, J. Song, S. Liang, S. Hu, H. Liu, T. Jiang, B. Han, J. Mol. Catal. A 308, 68–72 (2009)
H. Kwak, S.H. Lee, S.H. Kim, Y.M. Lee, B.K. Park, Y.J. Lee, J.Y. Jun, C. Kim, S.J. Kim, Polyhedron 28, 553–561 (2009)
L. Pan, H. Liu, X. Lei, X. Huang, D.H. Olson, N.J. Turro, J. Li, Angew. Chem. Int. Ed. 42, 542–546 (2003)
S.H. Etaiw, A.S. Elsherbiny, A.S. Bader, El-din. Chin. J. Chem. 29, 1401–1410 (2011)
S.H. Etaiw, S.A. Amer, M.M. El-Bendary, J. Inorg. Organomet. Polym. 21, 662–672 (2011)
R.G. El-sharkawy, A.S. Bader El-din, S.H. Etaiw, Spectrochimica Acta Part A 79, 1969–1975 (2011)
S.H. Etaiw, M.M. El-Bendary, Appl. Catal. B 126, 326–333 (2012)
M. Hassanein, S.H. Etaiw, Eur. Polym. J. 29, 47–48 (1993)
V.K. Bhardwaj, N. Aliaga-Alcalalde, M. Corbella, G. Hundal, Inorg. Chim. Acta 363, 97–106 (2010). and references therein
P. Seth, M.G.B. Drew, A. Ghosh, J. Mol. Catal. A 365, 154–161 (2012)
V. Cherkasov, N. Druzhkov, T. Kocherova, G. Fukin, Tetrahedron 67, 80–84 (2011)
D.M. Kuzyaev, D.L. Vorohtsov, N.O. Druzhkov, M.A. Lopatin, E.V. Baranov, A.V. Cherasov, G.K. Fukin, G.A. Abakumov Bochkarev, J. Organomet. Chem. 698, 35–41 (2012)
L.Y. Ukhin, K.Y. Suponitsky, E.N. Shepelenko, L.V. Belousova, G.S. Borodkin, Tetrahedron Lett. 53, 67–70 (2012)
J.G. Yu, Q.J. Xiang, M.H. Zhou, Appl. Catal. B 90, 595–602 (2009)
M. Sahni, B.R. Locke, Ind. Eng. Chem. Res. 45, 5819–5825 (2006)
M.P. Titus, V.G. Molina, M.A. Banos, J. Gimenez, S. Esplugus, Appl. Catal. B 47, 219–256 (2004)
S.G. Schrank, J.N.R. Santos, D.S. Souza, E.E.S. Souza, J. Photochem. Photobiol. A 186, 125–129 (2007)
C. Galindo, A. Kalt, Dyes Pigm. 40, 27–35 (1998)
C. Flox, S. Ammar, C. Arias, E. Brillas, A. Vagas-Zaval, R. Abdehi, Appl. Catal. B 67, 93–104 (2006)
J. De Laat, T.G. Le, Appl. Catal. B 66, 137–146 (2006)
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Hassanein, M., Etaiw, S.Ed.H., El-Khalafy, S.H. et al. Activity of Mixed Valence Copper Cyanide Metal–Organic Framework in the Oxidation of 3,5-di-Tert-Butylcatechol with Hydrogen Peroxide. J Inorg Organomet Polym 25, 664–670 (2015). https://doi.org/10.1007/s10904-014-0139-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10904-014-0139-4