Scaled-up, selective and green synthesis of sulfoxides under mild conditions using (CeIII-MoVI)Ox/aniline hybrid rods as an efficient catalyst
Aliyeh Feghhi
Department of Chemistry, University of Birjand, Birjand, Iran
Search for more papers by this authorCorresponding Author
Reihaneh Malakooti
Department of Chemistry, University of Birjand, Birjand, Iran
Correspondence
Reihaneh Malakooti, Department of Chemistry, University of Birjand, Birjand, Iran.
Email: [email protected]; [email protected]
Search for more papers by this authorSadeq Malakooti
Department of Mechanical Engineering, The University of Texas at Dallas, Richardson, TX, 75080 USA
Search for more papers by this authorAliyeh Feghhi
Department of Chemistry, University of Birjand, Birjand, Iran
Search for more papers by this authorCorresponding Author
Reihaneh Malakooti
Department of Chemistry, University of Birjand, Birjand, Iran
Correspondence
Reihaneh Malakooti, Department of Chemistry, University of Birjand, Birjand, Iran.
Email: [email protected]; [email protected]
Search for more papers by this authorSadeq Malakooti
Department of Mechanical Engineering, The University of Texas at Dallas, Richardson, TX, 75080 USA
Search for more papers by this authorAbstract
A novel hybrid material, (CeIII-MoVI)Ox/aniline, with rod-like morphology is synthesized through a wet chemical method using Mo3O10(C6H5NH3)2.2H2O nanowires as precursor. The synthesized materials are characterized by XRD, XPS, SEM, TEM, FTIR, Raman, UV–Vis, TGA, and elemental analysis. Also, their catalytic activities as a hybrid catalyst are tested in the selective oxidation of sulfides using hydrogen peroxide as a green oxidant. The proposed novel hybrid catalyst shows an excellent performance under green conditions at mild temperature. Furthermore, the scalability of the oxidation reaction is shown by making multi-gram quantities at optimized conditions.
REFERENCES
- 1Q. Gao, S. Wang, H. Fang, J. Weng, Y. Zhang, J. Mao, Y. Tang, J. Mater. Chem. 2012, 22, 4709.
- 2S. Wang, Q. Gao, Y. Zhang, J. Gao, X. Sun, Y. Tang, Chem. – Eur. J. 2011, 17, 1465.
- 3Y. Dong, Q. Peng, Y. Li, Inorg. Chem. Commun. 2004, 7, 370.
- 4W. T. Yao, S. H. Yu, Q. S. Wu, Adv. Funct. Mater. 2007, 17, 623.
- 5Q. Gao, P. Chen, Y. Zhang, Y. Tang, Adv. Mater. 2008, 20, 1837.
- 6L. Fan, H. Song, H. Zhao, G. Pan, H. Yu, X. Bai, S. Li, Y. Lei, Q. Dai, R. Qin, T. Wang, B. Dong, Z. Zheng, X. Ren, J. Phys. Chem. B 2006, 110, 12948.
- 7Z. Shi, K. Nie, Z. J. Shao, B. Gao, H. Lin, H. Zhang, B. Liu, Y. Wang, Y. Zhang, X. Sun, X. M. Cao, P. Hu, Q. Gao, Y. Tang, Energy Environ. Sci. 2017, 10, 1262.
- 8J. Polleux, A. Gurlo, N. Barsan, U. Weimar, M. Antonietti, M. Niederberger, Angew. Chem. 2005, 118, 267.
10.1002/ange.200502823 Google Scholar
- 9Y. X. Zhang, H. C. Zeng, Adv. Mater. 2009, 21, 4962.
- 10M. R. Gao, W. T. Yao, H. B. Yao, S. H. Yu, J. Am. Chem. Soc. 2009, 131, 7486.
- 11W. Yao, S. H. Yu, X. Y. Huang, J. Jiang, L. Q. Zhao, L. Pan, J. Li, Adv. Mater. 2005, 17, 2799.
- 12Q. Gao, S. Wang, Y. Tang, C. Giordano, Chem. Commun. 2012, 48, 260.
- 13Z. A. Zang, H. B. Yao, Y. X. Zhou, W. T. Yao, S. H. Yu, Chem. Mater. 2008, 20, 4749.
- 14R. Malakooti, A. Feghhi, New J. Chem. 2017, 41, 3405.
- 15M. C. Carreno, G. H. Torres, M. Ribagorda, A. Urbano, Chem. Commun. 2009, 0, 6129.
- 16G. E. O'Mahony, A. Ford, A. R. Maguire, J. Sulfur Chem. 2013, 34, 301.
- 17B. M. Trost, Chem. Rev. 1978, 78, 363.
- 18A. Fuerte, M. Iglesias, F. Sanchez, A. Corma, J. Mol. Catal. A: Chem. 2004, 211, 227.
- 19E. Dumitriu, C. Guimonc, A. Cordoneanu, S. Casenave, T. Hulea, C. Chelaru, H. Martinez, V. Hulea, Catal. Today 2001, 66, 529.
- 20W. Adam, C. M. Mitchell, C. R. Saha-Moller, T. Selvam, O. Weichold, J. Mol. Catal. A: Chem. 2000, 154, 251.
- 21J. M. Zen, S. L. Liou, A. S. Kumar, M. S. Hsia, Angew. Chem. 2003, 597, 115.
- 22E. Baciocchi, M. F. Gerini, A. Lapi, J. Org. Chem. 2004, 69, 3586.
- 23W. L. Xu, Y. Z. Li, Q. S. Zhang, H. S. Zhu, Synthesis 2004, 2004, 227.
- 24A. Y. Koposov, V. V. Zhdankin, Synthesis 2005, 2005, 22.
- 25S. S. Kim, G. Rajagopal, Synthesis 2003, 2003, 2461.
- 26H. Srour, P. L. Maux, S. Chevance, G. Simonneaux, Coord. Chem. Rev. 2013, 257, 3030.
- 27G. L. Sorella, L. Sperni, G. Strukul, A. Scarso, Adv. Synth. Catal. 2016, 358, 3443.
- 28R. Maggi, S. Chitsaz, S. Loebbecke, C. G. Piscopo, G. Sartori, M. Schwarzer, Green Chem. 2011, 13, 1121.
- 29B. Karimi, M. Khorasani, F. B. Rostami, D. Elhamifar, H. Vali, ChemPlusChem. 2015, 80, 990.
- 30A. Sedrpoushan, F. Hosseini, E. F. Mohanazadeh, M. Heydari, Appl Organometallic Chem. 2018, 32, e4004.
- 31D. A. F. Gonçalves, R. P. R. Alvim, H. A. Bicalho, A. M. Peres, I. Binatti, P. F. R. Batista, L. S. Teixeira, R. R. Resendecd, E. Lorençon, New J. Chem. 2018, 42, 5720.
- 32J. Zhu, P. C. Wang, M. Lu, New J. Chem. 2012, 36, 2587.
- 33N. Zohreh, S. H. Hosseini, A. Pourjavadi, R. Soleyman, C. Bennett, J. Ind. Eng. Chem. 2016, 44, 73.
- 34B. Karimi, M. Khorasani, ACS Catal. 2013, 3, 1657.
- 35M. Nikkhoo, M. Amini, S. Morteza, F. Farnia, A. Bayrami, M. Bagherzadeh, S. Gautam, K. H. Chae, Appl Organometal Chem. 2018, 32, e4358.
- 36C. J. Carrasco, F. Montilla, L. Bobadilla, S. Ivanova, J. A. Odriozola, A. Galindo, Catal. Today 2015, 255, 102.
- 37J. J. Boruah, S. P. Das, S. R. Ankireddy, S. R. Gogoi, N. S. Islam, Green Chem. 2013, 15, 2944.
- 38M. Jafarpour, A. Rezaeifard, M. Ghahramaninezhad, F. Feizpour, Green Chem. 2015, 17, 442.
- 39R. Fareghi-Alamdari, N. Zekri, A. Jamali Moghadam, M. Riahi Farsani, Catal. Commun. 2017, 98, 71.
- 40M. Khorshidifard, H. A. Rudbari, B. Askari, M. Sahihi, M. R. Farsani, F. Jalilian, G. Bruno, Polyhedron 2015, 95, 1.
- 41Y. Kon, T. Yokoi, M. Yoshioka, Y. Uesaka, H. Kujira, K. Sato, T. Tatsumi, Tetrahedron Lett. 2013, 54, 4918.
- 42M. Nikoorazm, A. Ghorbani-Choghamarani, M. Khanmoradi, Appl. Organomet. Chem. 2016, 30, 236.
- 43A. Fakhri, A. Naghipour, Mater. Technol. 2016, 31, 846.
- 44A. Rostami, F. Hassanian, A. Ghorbani-Choghamarani, S. Saadati, Phosphorus, Sulfur Silicon Relat. Elem. 2013, 188, 833.
- 45R. K. Sharma, A. Pandey, S. Gulati, Polyhedron 2012, 45, 86.
- 46Y. Leng, H. Ge, C. Zhou, J. Wang, Chem. Eng. J. 2008, 145, 335.
- 47S. E. Jacobson, D. A. Muccigrosso, F. Mares, J. Org. Chem. 1979, 44, 921.
- 48V. Palermo, P. I. Villabrille, P. G. Vazquez, C. V. Caceres, P. Tundo, G. P. Romanelli, J. Chem. Sci. 2013, 125, 1375.
- 49A. Feghhi, R. Malakooti, S. Malakooti, N. Hooshmand, ChemistrySelect 2019, 4, 2551.
- 50B. Rama Raju, S. Sarkar, U. Chandramoulali Reddy, A. K. Saikia, J. Mol. Catal. A: Chem. 2009, 308, 169.
- 51M. A. Zolfigol, K. Amani, M. Hajjami, A. Ghorbani-Choghamarani, Monatsh. Chem. 2008, 139, 895.
- 52M. Al-Hashimi, G. Roy, A. C. Sullivan, J. R. H. Wilson, Tetrahedron Lett. 2005, 46, 4365.
- 53K. L. Wong, Y. M. So, G. C. Wang, H. H. Y. Sung, I. D. Williams, W. H. Leung, Dalton Trans. 2016, 45, 8770.
- 54T. He, J. Yao, J. Photochem. Photobiol. C 2003, 4, 125.
- 55T. Siciliano, A. Tepore, E. Filippo, G. Micocci, M. Tepore, Mater. Chem. Phys. 2009, 114, 687.
- 56A. H. Ali Shah, R. Holze, Synth. Met. 2006, 156, 566.
- 57A. Quintana, A. Varea, M. Guerrero, S. Surinach, M. D. Baro, J. Sort, E. Pellicer, Electrochim. Acta 2015, 173, 705.
- 58D. Song, X. Feng, M. Sun, X. Ma, G. Tang, J. Rare Earth. 2012, 30, 383.
- 59Y. A. Teterin, A. Y. Teterin, A. M. Lebedev, I. O. Utkin, J. Electron Spectrosc. Relat. Phenom. 1998, 88-91, 275.
- 60L. Liu, S. M. Wang, W. L. Chen, Y. Lu, Y. G. Li, E. B. Wang, Inorg. Chem. Commun. 2012, 23, 14.
- 61K. V. Wood, D. J. Burinsky, D. Cameron, R. G. Cooks, J. Org. Chem. 1983, 48, 5236.
- 62H. Nasser, Á. Rédey, T. Yuzhakova, J. Kovács, J. Therm. Anal. Calorim. 2009, 95, 69.
- 63A. N. Desikan, L. Huang, S. T. Oyama, J. Phys. Chem. 1991, 95, 10050.
- 64X. Chen, F. Liu, X. Yan, Y. Yang, Q. Chen, J. Wan, L. Tian, Q. Xia, X. Chen, Chem. – Eur. J. 2015, 21, 18711.
- 65C. C. Williams, J. G. Ekerdt, J. M. Jehng, F. D. Hardcastle, A. M. Turek, I. E. Wachs, J. Phys. Chem. 1991, 95, 8781.
- 66H. Jezlorowski, H. Knoezinge, J. Phys. Chem. 1979, 83, 1166.
- 67Y. Wu, G. Hu, Y. Xie, M. Guo, M. Luo, Solid State Sci. 2011, 13, 2096.
- 68Y. Fan, W. Kuang, Y. Chen, Stud. Surf. Sci. Catal. 1997, 112, 121.
- 69W. Kuang, Y. Fan, Y. Chen, Catal. Today 2001, 68, 75.
- 70M. Xue, X. Gu, J. Chen, H. Zhang, J. Shen, Thermochim. Acta 2005, 434, 50.
- 71K. Bahrami, Tetrahedron Lett. 2006, 47, 2009.
- 72K. Jeyakumar, D. K. Chand, Tetrahedron Lett. 2006, 47, 4573.