Catalytic Oxidation of 2-Mercaptoethanol by Cobalt(II)phthalocyanines Bearing Chalcone with Furan and Thiophene

Cobalt (II) phthalocyanines carrying on the four of the peripheral positions furan and thiophene as chalcones were sythesized. THF is used to investigate the catalytic oxidation of 2-mercaptoethanol. The synthesized phthalocyanines show catalytic activity on the oxidation of 2-mercaptoethanol. Cobalt (II) phthalocyanine derived by chalcone with furan has given catalytic specifications such as turnover number TON as 16.6, initial reaction rate as 0.293 μmol/sec and the oxygen consumption as 10.06 μmol/min. The other cobalt (II) phthalocyanine derived by chalcone with thiophene has given catalytic specifications such as turnover number TON as 15.9, initial reaction rate as 0.213 μmol/sec and the oxygen consumption as 9.88 μmol/min. So chalcone derived phthalocyanines can be used as catalyst is oxidation of mercaptan by air.

PDF

___

S.M.S. Chauhan, A. Gulati, A. Sahay, and P.N.H. Nizar, "Autooxidation of alkyl mercaptans catalysed by cobalt(II)phthalocyanine tetrasodium sulphonate in reverse micelles" J. of Molecular Catal. A: Chemical, 105, pp. 159-165. 1996.

M. Kimura, Y. Yamaguchi, T. Koyama, K. Hanabusa, and H. Shirai, "Catalytic oxidation of 2-mercaptoethanol by cationic water-soluble phthalocyaninatocobalt (II) complexes" J. of Porphyrins and Phthalocyanines, 1, pp. 309, 1997.

J.H. Zagal, M.A. Gulppi, C. Depretz, and D. Levievre, "Synthesis and electrocatalytic properties of octaalkoxycobalt phthalocyanine for the oxidation of 2-mercaptoethanol" J. of Porphyrins and Phthalocyanines, 3, pp. 355- 363, 1999.

D. Wöhrle, T. Buck, G. Schneider, G. Schulz- Ekloff, and H. Fischer, "Low molecular weight, polymeric and covalently bound Co(II)- phthalocyanines for the oxidation of mercaptanes" J. Inorg. Organomet. Polym., 1, pp. 115-129, 1991.

G.R. Hodges, J.R. Smith, and J. Oakes, "Mechanism of Oxidation of Azo Dyes by a Sterically Hindered Anionic Oxoiron(IV) Porphyrin in Aqueous Solution" J. Chem. Soc., Perkin Trans., 2, pp. 617-627, 1998.

G.R. Hodges, J.R. Smith, and J. Oakes, "The oxidation of azo dyes by peroxy acids and tertbutyl hydroperoxide in aqueous solution catalysed by iron(III) 5,10,15,20-tetra(2,6- dichloro-3-sulfonatophenyl) porphyrin: product studies and mechanism" J. Chem. Soc., Perkin Trans., 2, pp. 1943-1952, 1999.

A. Filippova , A. Vashurin, S. Znoyko , I. Kuzmin, M. Razumov, A. Chernova, G. Shaposhnikov, O. Koifman. " Novel Co(II) phthalocyanines of extended periphery and their water-soluble derivatives. Synthesis, spectral properties and catalytic activity" Journal of Molecular Structure, 1149, 17-26, 2017.

H. Karaca, M. Teker, A. Gül. " Catalytic Oxidation of 2-Mercaptoethanol by a Water- Soluble Porhphyrazinatocobalt (II) Complex" Chemistry Journal, Vol. 06, Issue 01, pp. 55-58, 2016.

H. Karaca, N. Akçay, M. Teker. "Porphyrazine immobilization on polyester fabric and heterogeneous catalytic application on oxidation of 2-mercaptoethanol" Fresenius Environmental Bulletin, Volume 25 – No. 5, pp 1714-1718, 2016.

H. Karaca. "Redox chemistry, spectroelectrochemistry and catalytic activity of novel synthesized phthalocyanines bearing four schiff bases on the periphery" Journal of Organometallic Chemistry, 822, pp. 39-45, 2016.

J. Jeong, R.S. Kumar, N. Mergu, Y.-A. Son. "Photophysical, electrochemical, thermal and aggregation properties of new metal phthalocyanines" Journal of Molecular Structure, 1147, pp. 469-479, 2017.

A.R. Karimi, Z. Jafarzadeh, M. Sourını, A. Zendehnam, A. Khodadadı, Z. Dalırnasab, M. Solımannejad, P. Zolgharneın. "Synthesis and computational studies of new metallophthalocyanines bearing dibenzoxanthenes and evaluation of their optical properties in solution and solid PMMA/ZnPc/Al nanocomposite films" Turkish Journal of Chemistry, 40, pp. 602-612, 2016.

A.R. Karimi, A. Khodadadi. "Synthesis and solution properties of new metal-free and metallo-phthalocyanines containing four bis(indol-3-yl)methane groups" Tetrahedron Letters 53,pp. 5223–5226, 2012.

A.A. Ramos, F.B. Nascimento, T.F.M. de Souza, A.T. Omori, T.M. Manieri, G. Cerchiaro and A.O. Ribeiro. " Photochemical and Photophysical Properties of Phthalocyanines Modified with Optically Active Alcohols" Molecules, 20, pp. 13575-13590, 2015.

A. Aktaş, İ. Acar, A. Koca, Z. Bıyıklıoglu, H. Kantekin. "Synthesis, characterization, electrochemical and spectroelectrochemical properties of peripherally tetra-substituted metal-free and metallophthalocyanines" Dyes and Pigments, 99, pp. 613-619, 2013.

A.R. Karimi, F. Bagherian and M. Sourinia."Synthesis and characterization of 1,4- dihydropyridinesubstituted metallophthalocyanines " Mendeleev Commun., 23, pp. 224–225, 2013.

F. Qiu, J. Liu, G. Cao,Y. Guan, Q. Shen, D. Yang & Q. Guo. "Synthesis, Thermo-Optic Properties, and Polymeric Thermo-Optic Switch Based on Novel Optically Active Polyurethane (Urea)" Soft Material, 11-3, pp. 233-243, 2013.

H. Karaca, B. Çayeğil, S. Sezer. "Synthesis characterization and metal sensing applications of novel chalcone substituted phthalocyanines" Synthetic Metals, 215, pp. 134–141, 2016.

E. Güzel, Ş. Çetin, A. Günsel, A. Bilgiçli, İ. Şişman, M.N. Yaraşır. "Comparative studies of photophysical and electrochemical properties of sulfur-containing substituted metal-free and metallophthalocyanines" Research on Chemical Intermediates, 44, 2, pp. 971-989. 2017.

P. Şen, D.K. Şimşek, S.Z. Yildiz. "Functional zinc(II) phthalocyanines bearing Schiff base complexes as oxidation catalysts for bleaching systems" Appl. Organometal. Chem., 29, pp. 509–516, 2015.

S.Z. Yildiz, S. Çolak, M. Tuna. "Non-ionic peripherally substituted soluble phthalocyanines: Synthesis characterization and investigation of their solution properties" Journal of Molecular Liquids, 195, pp. 22–29, 2014.