Abstract
An inexpensive and controllable CeMnOx composite oxides catalyst for the liquid-phase catalytic oxidation of toluene was conveniently prepared by ultrasound-assisted co-precipitation method. The physical–chemical properties of CeMnOx composite oxides catalyst have been systematically characterized. MnOx as catalytic active species was highly dispersed in the cubic fluorite structure CeO2. The cooperation of CeO2 and MnOx evidently improved the catalytic performance. CeMnOx composite oxides with a Ce/Mn molar ratio of 2:1 was showed the good catalytic performance. 7.0% of toluene conversion and 95.6% of overall selectivity to benzylalcohol, benzaldehyde and benzoic acid was acquired under optimal reaction conditions. The present catalyst has the advantages of low cost, good catalytic performance and stability. This work provides a simple, benign and controllable approach for the selective oxidation of toluene to valuable oxidation products.
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L. Kesavan, R. Tiruvalam, M.H.A. Rahim, M.I.B. Saiman, D.I. Enache, R.L. Jenkins, N. Dimitratos, J.A. Lopez-Sanchez, S.H. Taylor, D.W. Knight, C.J. Kiely, G.J. Hutchings, Science 331, 195 (2011)
A. Cai, H. He, Q. Zhang, Y. Xu, X. Li, F. Zhang, X. Fan, W. Peng, Y. Li, ACS Appl. Mater. Interfaces 13, 13087 (2021)
Q. Zheng, J. Chen, G. Rao, Russ. J. Org. Chem. 55, 569 (2019)
H. Kargar, M. Fallah Mehrjardi, R. Behjatmanesh Ardakani, K.S. Munawar, M. Ashfaq, M.N. Tahir, Transit. Met. Chem. 46, 437 (2021)
M. Nawab, S. Barot, R. Bandyopadhyay, New J. Chem. 43, 4406 (2019)
Y. Zhuang, Q. Lin, L. Zhang, L. Luo, Y. Yao, W. Lu, W. Chen, Particuology 24, 216 (2016)
H. Göksu, K. Cellat, F. Şen, Nature 10, 9656 (2020)
S. Gopinath, G. Kumar, S. Narayanan, C. Ragupathi, S.S. Kumar, K. Sivakumar, K. Saravanan, S. Ambika, SN Appl. Sci. 1, 520 (2019)
Y. Li, X. Huang, Y. Li, Y. Xu, Y. Wang, E. Zhu, X. Duan, Y. Huang, Sci. Rep. 3, 1787 (2013)
J. Jia, X. Chen, L. Zhai, Y. Niu, Monats. Chem. 151, 1549 (2020)
M. Mo, M. Zheng, J. Tang, Y. Chen, Q. Lu, Y. Xun, Res. Chem. Intermed. 41, 4067 (2015)
J. Lv, Y. Shen, L. Peng, X. Guo, W. Ding, Chem. Commun. 46, 5909 (2010)
J. Miki, Y. Osada, T. Konoshi, Y. Tachibana, T. Shikada, Appl. Catal. A: Gen. 137, 93 (1996)
S. Devika, B. Sundaravel, M. Palanichamy, V. Murugesan, J. Nanosci. Nanotechnol. 14, 3187 (2014)
G. Song, L. Feng, J. Xu, H. Zhu, Res. Chem. Intermed. 44, 4989 (2018)
N. Venkatathri, Indian J. Chem. A 43, 2325 (2004)
Y. Zhu, H. Wang, K. Jin, J. Gong, Chem. A Eur. J. 25, 6963 (2019)
G. Huang, J. Luo, C.C. Deng, Y.A. Guo, S.K. Zhao, H. Zhou, S. Wei, Appl. Catal. A: Gen. 338, 83 (2008)
K.H.C. Chen, P. Liu, T. Chen, J. Chen, Inorganics 6, 118 (2018)
T. Aneeja, M. Neetha, C.M.A. Afsina, G. Anilkumar, Catal. Sci. Technol. 11, 444 (2021)
M. Tan, L. Zhu, H. Liu, Y. Fu, S. Yin, W. Yang, Appl. Catal. A Gen. 614, 118035 (2021)
J.C.F. RodríguezReyes, C.M. Friend, R.J. Madix, Catal. Lett. 148, 1985 (2018)
P. Zhang, Y. Gong, H. Li, Z. Chen, Y. Wang, Nat. Commun. 4, 1593 (2013)
C. Ge, L. Xu, J. Sun, H. Liu, Q. Tong, W. Zou, C. Tang, H. Wan, L. Dong, Y. Chen, Res. Chem. Intermed. 47, 1239 (2021)
C. Guo, Q. Liu, X. Wang, H. Hu, Appl. Catal. A Gen. 282, 55 (2005)
W. Zhong, S.R. Kirk, D. Yin, Y. Li, R. Zou, L. Mao, G. Zou, Chem. Eng. J. 280, 737 (2015)
S.S. Acharyya, S. Ghosh, R. Tiwari, B. Sarkar, R.K. Singha, C. Pendem, T. Sasaki, R. Bal, Green Chem. 5, 2500 (2014)
Y. Sun, T. Zheng, G. Zhang, B. Liu, P. Wang, Environ. Sci. Pollut. Res. 25, 22818 (2018)
G. Picasso, R. Cruz, M.D.R.S. Kou, Mater. Res. Bull. 70, 621 (2015)
H. Cheng, J. Tan, Y. Ren, M. Zhao, J. Liu, H. Wang, J. Liu, Z. Zhao, Ind. Eng. Chem. Res. 58, 16427 (2019)
P. Zhang, H. Lu, Y. Zhou, L. Zhang, Z. Wu, S. Yang, H. Shi, Q. Zhu, Y. Chen, S. Dai, Nat. Commun. 6, 1 (2015)
R. Cano, K. Mackey, G.P. McGlacken, Catal. Sci. Technol. 8, 1251 (2018)
H. Azzi, L. Chérif, S. Siffert, Res. Chem. Intermed. 47, 1009 (2021)
W. Ni, K. You, L. Yi, F. Zhao, Q. Ai, P. Liu, H.A. Luo, Ind. Eng. Chem. Res. 60, 3907 (2021)
S. Liu, K. You, J. Jian, F. Zhao, W. Zhong, D. Yin, P. Liu, Q. Ai, H. Luo, J. Catal. 338, 239 (2016)
J. Jian, D. Kuang, X. Wang, H. Zhou, H. Gao, W. Sun, Z. Yuan, J. Zeng, K. You, H. Luo, Mater. Chem. Phys. 246, 122814 (2020)
P. Liu, K. You, R. Deng, Z. Chen, J. Jian, F. Zhao, P. Liu, Q. Ai, H. Luo, Mol. Catal. 466, 130 (2019)
G. Chen, K. You, X. Gong, F. Zhao, Z. Chen, H. Luo, React. Chem. Eng. 7, 898 (2022)
G. Qi, R.T. Yang, R. Chang, Appl. Catal. B Environ. 51, 93 (2004)
K.S.W. Sing, D.H. Everett, R.A.W. Haul, L. Moscou, R.A. Pierotti, J. Rouquerol, T. Siemieniewska, Pure Appl. Chem. 57, 603 (1985)
S.M. Vickers, R. Gholami, K.J. Smith, M.J. MacLachlan, ACS Appl. Mater. Interfaces 7, 11460 (2015)
M. Li, H. Zhu, J. Cheng, M. Zhao, W. Yan, J. Porous Mat. 24, 507 (2017)
W. Han, L. Wu, Y. Zhu, J. Am. Chem. Soc. 127, 12814 (2005)
J. Zhang, Y. Cao, C.A. Wang, R. Ran, ACS Appl. Mater. Interfaces 8, 8670 (2016)
M. Machida, M. Uto, D. Kurogi, T. Kijima, Chem. Mater. 12, 3158 (2000)
D. Jiang, M. Zhang, G. Li, H. Jiang, Catal. Commun. 17, 59 (2012)
G. Allaedini, S.M. Tasirin, P. Aminayi, Chem. Pap. 70, 231 (2016)
Y. Wang, X. Li, L. Zhan, C. Li, W. Qiao, L. Ling, Ind. Eng. Chem. Res. 54, 2274 (2015)
B. Bai, J. Li, J. Hao, Appl. Catal. B Environ. 164, 241 (2015)
F. Chen, T. Yang, S. Zhao, T. Jiang, L. Yu, H. Xiong, C. Guo, Y. Rao, Y. Liu, L. Liu, J. Zhou, P. Tu, J. Ni, Q. Zhang, X. Li, Chin. Chem. Lett. 30, 2282 (2019)
Y. Wang, C. Ge, L. Zhan, C. Li, W. Qiao, L. Ling, Ind. Eng. Chem. Res. 51, 116677 (2012)
F. Xia, Z. Song, X. Liu, Y. Yang, Q. Zhang, J. Peng, Res. Chem. Intermed. 44, 2703 (2018)
C. Sui, L. Xing, X. Cai, Y. Wang, Q. Zhou, M. Li, Catalysts 10, 243 (2020)
Y. Wang, W. Deng, Y. Wang, L. Guo, T. Ishihara, Mol. Catal. 459, 61 (2018)
G. Picasso, M. Gutierrez, M.P. Pina, J. Herguido, Chem. Eng. J. 126, 119 (2007)
L. Li, Y. Diao, X. Liu, J. Rare Earths 32, 409 (2014)
A. Chen, H. Guo, Y. Song, P. Chen, H. Lou, Int. J. Hydrogen Energy 42, 9577 (2017)
S.D. Gupt, R.L. Stewart, D. Chen, K.A. Abboud, H. Cheng, S. Hill, G. Christou, Inorg. Chem. 59, 8716 (2020)
G. Liu, R. Yue, Y. Jia, Y. Ni, J. Yang, H. Liu, Z. Wang, X. Wu, Y. Chen, Particuology 11, 454 (2013)
P. Raghavendrachar, S. Ramachandran, Ind. Eng. Chem. Res. 31, 453 (1992)
W. Partenheimer, J. Mol. Catal. A Chem. 206, 105 (2003)
Acknowledgements
The authors are grateful for the financial support of the National Natural Science Foundation of China (21676226), Key Research and Development Program in Hunan Province (2019GK2041), Outstanding Youth Project of Hunan Education Department (20B550), Natural Science Foundation of Hunan Province (2021JJ40531), Hunan Key Laboratory of Environment Friendly Chemical Process Integrated Technology and Collaborative Innovation Center of New Chemical Technologies for Environmental Benignity and Efficient Resource Utilization.
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Chen, G., You, K., Zhao, F. et al. Solvent-free catalytic oxidation of toluene over heterogeneous CeMnOx composite oxides. Res Chem Intermed 48, 2593–2606 (2022). https://doi.org/10.1007/s11164-022-04727-4
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DOI: https://doi.org/10.1007/s11164-022-04727-4