Abstract
In this study, taking into account the principles of green chemistry and extension of economical and industrials catalysts (as the heart of the chemical processes), copper-grafted zagrosian natural asphalt sulfonate (Cu-Zagronas) was synthesized, identified and introduced as a new efficient heterogeneous nanocatalyst for the synthesis of phenols and anilines. For preparation of the Cu-Zagronas nanocatalyst, we transform Iranian natural asphalt as a green, cheap and available mineral material into a support for organic transformations. The Cu-Zagronas nanocatalyst was characterized by various techniques such as Fourier transform infrared spectroscopy, scanning electron microscopy, transmission electron microscope, energy-dispersive X-ray spectroscopy, thermogravimetric analysis, X-ray diffraction, inductively coupled plasma and N2 adsorption–desorption measurement. Some advantages of this heterogeneous nanocatalyst include: simple preparation from commercially available materials, simple operation, high catalytic activity, high yields, easy work-up and recyclability of the catalyst up to 6 times without significant loss in catalytic activity.
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References
- 1.
Xue X, Zhao Z, Wang Y (2018) Org Chem Front 4:3585
- 2.
Motahharifar N, Nasrollahzadeh M, Taheri-Kafrani A, Varma RS, Shokouhimehr M (2020) Carbohydr Polym 232:115819
- 3.
Singhania A, Gupta SM (2018) Mater Res Express 1:946
- 4.
Latos P, Szelwicka A, Boncel S, Jurczyk S, Swadzba-Kwasny M, Chrobok A (2019) ACS Sustain Chem Eng 8:5184
- 5.
Konwar LJ, Maki-Arvela P, Mikkola JP (2019) Chem Rev 119:11576
- 6.
Fernandes RA, Sampaio MJ, Da Silva ES, Serp P, Farias JL, Silva CG (2019) Catal Today 15:286
- 7.
Tokdemir E, Sakioglu E, Guzel A (2016) U.S. Patent. No. 15/115,072.
- 8.
Abiola OS, Wilson R, Barnard A, Hattingh S, Kupolati WK, Odunfa SO (2019) Eng Technol 4:22
- 9.
Kane M, Edmondson V (2018) Wear 400:100
- 10.
Kohzadi H, Soleiman- Beigi M (2020) New J Chem 44:12134
- 11.
Falah S, Soleiman-Beigi M, Kohzadi H (2020) Appl Organomet Chem 34:e5840
- 12.
Movassagh B, Soleiman-Beigi M (2009) Monatsh Chem 140:409
- 13.
Soleiman-Beigi M, Arzehgar Z (2015) Heteroatom Chem 26:355
- 14.
Roughley SD, Jordan AM (2011) J Med Chem 54:3451
- 15.
Cooper TW, Campbell IB, Macdonald SJF (2010) Angew Chem Int Ed 49:8082
- 16.
Buchwald SL, Mauger C, Mignani G, Scholz U (2006) Adv Synth Catal 348:23
- 17.
Magano J, Dunetz JR (2011) Chem Rev 111:2177
- 18.
Thaku KG, Sekar G (2011) ChemComm 23:6692
- 19.
Paul R, Ali MA, Punniyamurthy T (2010) Synthesis 24:4268
- 20.
Wu XF, Darcel C (2009) Eur J Org Chem 28:4753
- 21.
Neetha M, Saranya S, Ann Harry N, Anilkumar G (2020) ChemistrySelect 5:736
- 22.
Ghiasbeigi E, Soleiman-Beigi M (2019) ChemistrySelect 4:3611
- 23.
Henam SD, Ahmad F, Shah MA, Parveen S, Wane AH (2019) Spectrochim Acta A 15:337
- 24.
Reddy SK, Swamy B, Jayadevappa H (2012) Electrochim Acta 1:78
- 25.
Borah R, Saikia E, Bora SJ, Chetia B (2017) Tetrahedron Lett 58:1211
- 26.
Huang H, Wu Y, Zhang W, Feng C, Wang BQ, Cai WF, Hu P, Zhao KQ, Xiang SK (2017) J Org Chem 82:3094
- 27.
Jin Z, Xu D, Pan Y, Xu Y, Chiang MYN (2001) Mol Struct 559:1
- 28.
Sideri IK, Voutyritsa E, Kokotos CG (2018) Synlett 14:1324
- 29.
Xu HJ, Liang YF, Cai ZY, Qi HX, Yang CY, Feng YS (2011) Org Chem 76:2296
- 30.
Molander GA, Cavalcanti LN (2010) J Org Chem 76:623
- 31.
Xu J, Wang X, Shao C, Su D, Cheng D, Hu Y (2010) Org Lett 12:1964
- 32.
Keenan CS, Murphree SS (2017) Synth Commun 47:1085
- 33.
Wang AP, Li L (1992) Anal Chem 64:769
- 34.
Maejima T, Shimoda Y, Nozaki K, Mori S, Sawama Y, Monguchi Y, Sajiki H (2012) Tetrahedron 68:1712
- 35.
Aksenov AV, Lyakhovnenko AS, Kugutov MM (2011) Chem Heterocycl Compd 46:1262
- 36.
Kim J, Chang S (2008) ChemComm 3052
- 37.
Cheung CW, Surry DS, Buchwald SL (2013) Org Lett 15:3734
- 38.
Jorgensen EC, Berteau PE (1971) J Med Chem 14:1199
Acknowledgements
We thank the Iranian National Science Foundation (INSF, Grant No. 97017223), and Ilam University for their financial support.
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Kohzadi, H., Soleiman-Beigi, M. Copper-grafted Zagrousian natural asphalt sulfonate (Cu-Zagronas): as a novel heterogeneous carbonious nanocatalyst for the synthesis of anilines and phenols. Reac Kinet Mech Cat 132, 261–277 (2021). https://doi.org/10.1007/s11144-020-01918-1
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Keyword
- Amines
- Heterogeneous catalysis
- Natural
- Phenols