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

Year 2018, , 1699 - 1703, 01.12.2018

Hüseyin Karaca

https://doi.org/10.16984/saufenbilder.407781

Cited By: 1

Abstract

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.

Keywords

Catalysis, 2-mercaptoethanol, oxidation, phthalocyanine

References

• REFERENCES[1] 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.[2] 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.[3] 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.[4] 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.[5] 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.[6] G.R. Hodges, J.R. Smith, and J. Oakes, "The oxidation of azo dyes by peroxy acids and tert-butyl 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.[7] 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.[8] 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. [9] 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.[10] 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.[11] 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.[12] A.R. Karimi, Z. Jafarzadeh, M. Sourını, A. Zendehnam, A. Khodadadı, Z. Dalırnasab, M. Solımannejad, P. Zolgharneın. "Synthesis and computational studies of new metallo-phthalocyanines 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.[13] 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.[14] 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.[15] 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.[16] A.R. Karimi, F. Bagherian and M. Sourinia."Synthesis and characterization of 1,4-dihydropyridinesubstituted metallophthalocyanines " Mendeleev Commun., 23, pp. 224–225, 2013.[17] 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.[18] H. Karaca, B. Çayeğil, S. Sezer. "Synthesis characterization and metal sensing applications of novel chalcone substituted phthalocyanines" Synthetic Metals, 215, pp. 134–141, 2016.[19] 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.[20] 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.[21] 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.