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Oxidation of NMST to NMSBA catalyzed by Co/Mn/Br together with porous carbon made from coconut shell with acetic acid as an activator

  • Feng Guo , Hua-jie Liu , Xin-zhi Zhou and Xiang-li Long EMAIL logo
Published/Copyright: October 28, 2022

Abstract

In this paper, a heterogeneous catalytic system consisting of Co/Mn/Br/activated carbon is used to catalyze 2-nitro-4-methylsulfonyl benzoic acid (NMSBA) production from the oxidation of 2-nitro-4-methylsulfonyltoluene (NMST) by oxygen. The activated carbon (AC) is made from coconut shell with acetic acid as an activator. The experiments indicate that the best AC is made by immersing coconut shell in 12 mol L−1 HAc solution at 50 °C for 32 h with a liquid/solid ratio (mL/g) of 5:1 and then being heated in nitrogen at 800 °C for 6 h. Compared with the Co/Mn/Br/H3PMo12O40@CAC (CAC, commercial activated carbon originated from coconut shell) catalytic system, the Co/Mn/Br/AC catalytic system is able to gain much higher NMSBA selectivity. In spite of holding smaller surface and less acidic groups, the AC owns much more carboxyl than CAC, which is the main reason for its better performance in the preparation of NMSBA.


Corresponding author: Xiang-li Long, State-Key Laboratory of Chemical Engineering, East China University of Science and Technology, Meilong Road 130, Shanghai, 200237, People’s Republic of China, E-mail:

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: None declared.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

Boehm, H. P. 1994. “Some Aspects of the Surface Chemistry of Carbon Blacks and Other Carbons.” Carbon 32 (5): 759–69, https://doi.org/10.1016/0008-6223(94)90031-0.Search in Google Scholar

Chavan, S. A., S. B. Halligudi, D. Srinivas, and P. Ratnasamy. 2000. “Formation and Role of Cobalt and Manganese Cluster Complexes in the Oxidation of p-Xylene.” Journal of Molecular Catalysis A: Chemical 161 (1–2): 49–64, https://doi.org/10.1016/s1381-1169(00)00361-7.Search in Google Scholar

Chen, C. J., X. Li, Z. F. Tong, Y. Li, and M. F. Li. 2014. “Modification Process Optimization, Characterization and Adsorption Property of Granular Fir-Based Activated Carbon.” Applied Surface Science 315: 203–11, https://doi.org/10.1016/j.apsusc.2014.07.111.Search in Google Scholar

Gómez-Serrano, V., M. Acedo-Ramos, A. J. López-Peinado, and C. V. Calahorro. 2016. “Oxidation of Activated Carbon by Hydrogen Peroxide. Study of Surface Functional Groups by FT-IR.” Fuel 73 (3): 387–95.10.1016/0016-2361(94)90092-2Search in Google Scholar

Gregory, J. A., and W. L. Dehany. 1992. “Method for the Preparation of 4-Methyl Sulfonyl Benzoic Acid Derivatives and Intermediates.” US5079381.Search in Google Scholar

Guedidi, H., L. Reinert, Y. Soneda, N. Bellakhal, and L. Duclaux. 2014. “Adsorption of Ibuprofen from Aqueous Solution on Chemically Surface-Modified Activated Carbon Cloths.” Arabian Journal of Chemistry 304 (Suppl. 2): S3584–94, https://doi.org/10.1016/j.arabjc.2014.03.007.Search in Google Scholar

Guo, H. J., and G. C. Yin. 2011. “Catalytic Aerobic Oxidation of Renewable Furfural with Phosphomolybdic Acid Catalyst: An Alternative Route to Maleic Acid.” Journal of Physical Chemistry C 115: 17516–22, https://doi.org/10.1021/jp2054712.Search in Google Scholar

Hagen, H. 1995. “Preparation of Methylsulfonylbenzoic Acids.” US5424481.Search in Google Scholar

He, H., Z. W. Fang, C. Zhang, and X. L. Long. 2018. “NMSBA Produced from NMST under the Catalysis of Supported H3PW12O40 and Co/Mn/Br Catalytic System.” Canadian Journal of Chemical Engineering 96: 1264–72, https://doi.org/10.1002/cjce.23085.Search in Google Scholar

Huang, C., R. Liu, C. T. Zhang, Q. P. Cheng, and H. J. Zhu. 2017. “Iron(II) and Copper(II) Phthalocyanine-Catalyzed Synthesis of 2-Nitro-4-methylsulfonylbenzoic Acid under Mild Conditions.” Journal of Chemical Sciences 129 (10): 1587–94, https://doi.org/10.1007/s12039-017-1373-4.Search in Google Scholar

Jacobson, S. E. 1997. “Process for Producing Ortho-Nitro Aromatic Acids by Oxidation of Ortho-Nitro Alkylaromatic Compounds.” US5591890.Search in Google Scholar

Kozhevnikov, I. V. 1998. “Catalysis by Heteropoly Acids and Multi-Component Polyoxometalates in Liquid-Phase Reactions.” Chemical Reviews 98: 171–98, https://doi.org/10.1021/cr960400y.Search in Google Scholar PubMed

Lu, Y., J. C. Tao, Z. L. Zhou, and Z. R. Zhang. 2017. “Green Synthesis of a Novel Herbicide Methyl Sulfoxone.” Pesticide Science and Management 38 (3): 29–33.Search in Google Scholar

Ludvik, C. N. 1991. “Preparation of Trisubstituted Benzoic Acid Precursors.” US 5055605.Search in Google Scholar

Li, X. L., J. B. Yang, and H. L. Pang. 2005. “Synthesis of 2-Nitro-4-sulfoxide Benzoic Acid by Sodium Dichromate Oxidation.” Fine Chemical Intermediates 35 (3): 5057–1.Search in Google Scholar

Long, X. L., C. Zhang, Y. Zhu, Z. L. Yang, and W. K. Yuan. 2016. “Production of NMSBA from the Oxidation of NMST with Oxygen Catalyzed by H3PW12O40/Co/Mn/Br Homogeneous Catalytic System.” Chemical Engineering Journal 286: 361–8, https://doi.org/10.1016/j.cej.2015.10.074.Search in Google Scholar

Long, X. L., B. B. Duan, H. X. Cao, M. L. Jia, and L. A. Wu. 2018. “Removal of NO with the Hexamminecobalt(II) Solution Catalyzed by the Activated Carbon Treated with Acetic Acid.” Journal of Industrial and Engineering Chemistry 62: 217–24, https://doi.org/10.1016/j.jiec.2017.12.060.Search in Google Scholar

Lowell, S., and J. E. Shields. 1991. Powder Surface Area and Porosity. Dordrecht: Springer.10.1007/978-94-015-7955-1Search in Google Scholar

Luo, J. J., J. Lu, Q. Niu, X. Chen, Z. Wang, and J. Zhang. 2015. “Preparation and Characterization of Benzoic Acid-Modified Activated Carbon for Removal of Gaseous Mercury Chloride.” Fuel 160: 440–5, https://doi.org/10.1016/j.fuel.2015.08.002.Search in Google Scholar

Mallick, S., S. Rana, and K. Parida. 2012. “Facile Method for the Synthesis of Phosphomolybdic Acid Supported on Zirconia-Ceria Mixed Oxide and its Catalytic Evaluation in the Solvent-Free Oxidation of Benzyl Alcohol.” Industrial & Engineering Chemistry Research 51: 7859–66, https://doi.org/10.1021/ie2022724.Search in Google Scholar

Michaely, W. J., W. J. Michaely, G. W. Kraatz, and S. Jose. 1988. “Certain Z-substituted Benzyl-1,3-cyclo Hexanediones and their Use as Herbicides.” US4780127.Search in Google Scholar

Moreno-Castilla, C., M. V. López-Ramón, and F. Carrasco-Marı́n. 2000. “Changes in Surface Chemistry of Activated Carbons by Wet Oxidation.” Carbon 38 (14): 1995–2001, https://doi.org/10.1016/s0008-6223(00)00048-8.Search in Google Scholar

Stavitskaya, S. S., V. M. Vikarchuk, N. N. Tsyba, N. I. Bogdanovich, V. F. Gaevskii, Y. P. Zaitsev, N. T. Kartel, and V. V. Strelko. 2006. “Structural and Sorption Characteristics of Carbon Adsorbents from Waste Formed in Wood Processing.” Russian Journal of Applied Chemistry 79 (2): 219–24.10.1134/S1070427206020108Search in Google Scholar

Wang, B., J. Zhang, X. Zou, H. G. Dong, and P. J. Yao. 2015. “Selective Oxidation of Styrene to 1,2-Epoxyethylbenzene by Hydrogen Peroxide over Heterogeneous Phosphomolybdic Acid Supported on Ionic Liquid Modified MCM-41.” Chemical Engineering Journal 260: 172–7, https://doi.org/10.1016/j.cej.2014.08.076.Search in Google Scholar

Wehrenberg, P. K. 1997. “Method for Preparation of Herbicide Intermediates.” US 5648525 A.Search in Google Scholar

Wen, D., Z. W. Fang, H. He, C. Zhang, and X. L. Long. 2018. “Production of NMSBA from NMST Catalyzed by Co/Mn/Br and HPW@C Modified with ZnCl2 Solution.” International Journal of Chemical Reactor Engineering 16 (8): 20170256, https://doi.org/10.1515/ijcre-2017-0256.Search in Google Scholar

Yuan, H. R., X. Fang, Q. Y. Ma, J. Y. Mao, K. X. Chen, Z. R. Chen, and H. R. Li. 2016. “New Mechanistic Insight into the Aerobic Oxidation of Methylaromatic Compounds Catalyzed by Co-Mn-Br and its Applications.” Journal of Catalysis 339: 284–91, https://doi.org/10.1016/j.jcat.2016.04.014.Search in Google Scholar

Zhi, Y., and J. Liu. 2016. “Surface Modification of Activated Carbon for Enhanced Adsorption of Perfluoroalkyl Acids from Aqueous Solutions.” Chemosphere 144: 1224–32, https://doi.org/10.1016/j.chemosphere.2015.09.097.Search in Google Scholar PubMed

Zhou, X. Z., Z. H. Wang, Z. W. Fang, H. J. Liu, and X. L. Long. 2018. “Production of Isophthalic Acid from m-Xylene Catalyzed by Co(II) and HPW@C Modified with Acetic Acid.” Industrial & Engineering Chemistry Research 57: 11893–902, https://doi.org/10.1021/acs.iecr.8b01820.Search in Google Scholar

Zhu, H. J., C. Huang, R. Liu, X. D. Jin, G. L. Song, Q. Liu, J. Xu, and Q. Y. Chu. 2015. “Preparation of 2-Nitro-4-sulfoxide Benzoic Acid by Catalytic Oxidation of 2-Nitro-4-sulfoxide Toluene.” CN 104844484A.Search in Google Scholar

Zielke, U., K. J. Hüttinger, and W. P. Hoffman. 1996. “Surface-Oxidized Carbon Fibers: I. Surface Structure and Chemistry.” Carbon 34 (8): 983–98, https://doi.org/10.1016/0008-6223(96)00032-2.Search in Google Scholar

Received: 2022-01-20
Accepted: 2022-09-18
Published Online: 2022-10-28

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