Hostname: page-component-848d4c4894-m9kch Total loading time: 0 Render date: 2024-05-31T23:48:29.627Z Has data issue: false hasContentIssue false
  • English
  • Français

One-Pot Synthesis of Sulfonated Carbon/Palygorskite Solid-Acid Catalyst for the Esterification of Oleic Acid with Methanol

Published online by Cambridge University Press:  01 January 2024

Jiadong Zhang ,
Wenbin Jiang ,
Jinlong Jiang ,
Mei Wu ,
Yingying Shi ,
Ping Mao  and
Qiulin Deng
Jiadong Zhang
Affiliation:
Faculty of Chemical Engineering, Key Laboratory for Palygorskite Science and Applied Technology of Jiangsu Province, National & Local Joint Engineering Research Center for Mineral Salt Deep Utilization, Huaiyin Institute of Technology, Huaian 223003, China School of Materials Science and Engineering, Southwest University of Science and Technology, Mianyang 621010, China
Wenbin Jiang
Affiliation:
Faculty of Chemical Engineering, Key Laboratory for Palygorskite Science and Applied Technology of Jiangsu Province, National & Local Joint Engineering Research Center for Mineral Salt Deep Utilization, Huaiyin Institute of Technology, Huaian 223003, China
Jinlong Jiang*
Affiliation:
Faculty of Chemical Engineering, Key Laboratory for Palygorskite Science and Applied Technology of Jiangsu Province, National & Local Joint Engineering Research Center for Mineral Salt Deep Utilization, Huaiyin Institute of Technology, Huaian 223003, China School of Materials Science and Engineering, Southwest University of Science and Technology, Mianyang 621010, China
Mei Wu
Affiliation:
Faculty of Chemical Engineering, Key Laboratory for Palygorskite Science and Applied Technology of Jiangsu Province, National & Local Joint Engineering Research Center for Mineral Salt Deep Utilization, Huaiyin Institute of Technology, Huaian 223003, China
Yingying Shi
Affiliation:
Faculty of Chemical Engineering, Key Laboratory for Palygorskite Science and Applied Technology of Jiangsu Province, National & Local Joint Engineering Research Center for Mineral Salt Deep Utilization, Huaiyin Institute of Technology, Huaian 223003, China
Ping Mao
Affiliation:
Faculty of Chemical Engineering, Key Laboratory for Palygorskite Science and Applied Technology of Jiangsu Province, National & Local Joint Engineering Research Center for Mineral Salt Deep Utilization, Huaiyin Institute of Technology, Huaian 223003, China
Qiulin Deng
Affiliation:
School of Materials Science and Engineering, Southwest University of Science and Technology, Mianyang 621010, China
*
*E-mail address of corresponding author: jiangjinlong75@163.com
Get access Rights & Permissions [Opens in a new window]

Abstract

Sulfonated carbon is a ‘green,’ solid-acid catalyst. For applications purposes, its surface area needs to be improved and its preparation needs to be made environmentally friendly. The objective of the present study was to provide a green and economical method of preparing a sulfonated carbon catalyst by using palygorskite (Plg) fiber as a support for sulfonated carbon. Sulfonated carbon/palygorskite solid-acid catalyst (SC-Plg) was synthesized via one-step carbonization-sulfonation by mixing palygorskite with sucrose as the carbon source and p-toluenesulfonic acid as the sulfonating agent. The catalyst was characterized by SEM, EDX, TEM, FTIR, and nitrogen adsorption-desorption isotherms. The results indicated that sucrose-derived carbon was loaded uniformly on the surface of Plg fibers and formed the SC-Plg catalyst. The inexpensive Plg fibers could replace sucrose-derived carbon and increase the surface area of the resulting catalyst. The SC-Plg shows significant catalytic performance and excellent stability when used in the esterification of oleic acid with methanol. The conversion of oleic acid reached 68.09%, even after five cycles. This work paves the way for the development of highly active, carbon-based, solid-acid composite catalysts using a natural Plg nanofiber template.

Keywords

CatalystEsterificationPalygorskiteSulfonated carbon
Type
Article
Information
Clays and Clay Minerals , Volume 69 , Issue 3 , June 2021 , pp. 389 - 396
Copyright
Copyright © Clay Minerals Society 2021

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

Alismaeel, Z. T., Abbas, A. S., Albayati, T. M., & Doyle, A. M. (2018). Biodiesel from batch and continuous oleic acid esterification using zeolite catalysts. Fuel, 234, 170–176.CrossRefGoogle Scholar
Araújo Melo, D. M., Ruiz, J. A. C., Melo, M. A. F., Sobrinbo, E. V., & Martinelli, A. E. (2002). Preparation and characterization of lanthanum palygorskite clays as acid catalysts. Journal of Alloys and Compounds, 344, 352–355.CrossRefGoogle Scholar
Budarin, V., Clark, J. H., Hardy, J. J. E., Luque, R., Milkowski, K., Tavener, S. J., & Wilson, A. J. (2006). Starbons: new starch-derived mesoporous carbonaceous materials with tunable properties. Angewandte Chemie International Edition, 45, 3782–3786.CrossRefGoogle ScholarPubMed
De Vyver, S. V., Peng, L., Geboers, J., Schepers, H., de Clippel, F. C., Gommes, J., Goderis, B., Jacobs, P. A., & Sels, B. F. (2010). Sulfonated silica/carbon nanocomposites as novel catalysts for hydrolysis of cellulose to glucose. Green Chemistry, 12, 1560–1563.CrossRefGoogle Scholar
Flores, K. P., Omega, J. L. O., Cabatingan, L. K., Go, A. W., Agapay, R. C., & Ju, Y. H. (2019). Simultaneously carbonized and sulfonated sugarcane bagasse as solid acid catalyst for the esterification of oleic acid with methanol. Renewable Energy, 130, 510–523.CrossRefGoogle Scholar
Geng, L., Wang, Y., Yu, G., & Zhu, Y. (2011). Efficient carbon-based solid acid catalysts for the esterification of oleic acid. Catalysis Communications, 13, 26–30.CrossRefGoogle Scholar
Geng, L., Yu, G., Wang, Y., & Zhu, Y. (2012). Ph-SO3H-modified mesoporous carbon as an efficient catalyst for the esterification of oleic acid. Applied Catalysis A: General, 427–428, 137–144.CrossRefGoogle Scholar
Guo, M. L., Yin, X. Y., & Huang, J. (2017). Preparation of novel carbonaceous solid acids from rice husk and phenol. Materials Letters, 196, 23–25.CrossRefGoogle Scholar
Jiang, J., Xu, Y., Duanmu, C., Gu, X., & Chen, J. (2012). Preparation and catalytic properties of sulfonated carbon-palygorskite solid acid catalyst. Applied Clay Science, 95, 260–264.CrossRefGoogle Scholar
Laohapornchaiphan, J., Smith, C. B., & Smith, S. M. (2017). One-step preparation of carbon-based solid acid catalyst from water hyacinth leaves for esterification of oleic acid and dehydration of xylose. Chemistry - An Asian Journal, 12, 3178–3186.CrossRefGoogle ScholarPubMed
Ma, H., Li, J., Liu, W., Cheng, B., Cao, X., Mao, J., & Zhu, S. (2014). Hydrothermal preparation and characterization of novel corncob-derived solid acid catalysts. Journal of Agricultural and Food Chemistry, 62, 5345–53530.CrossRefGoogle ScholarPubMed
Nakajima, K., & Hara, M. (2012). Amorphous carbon with SO3H groups as a solid Brønsted acid catalyst. ACS Catalysis, 2, 1296–1304.CrossRefGoogle Scholar
Nandan, D., Sreenivasulu, P., Saxena, S. K., & Viswanadham, N. (2011). Facile synthesis of sulfonated carbon-silica-meso composite and mesoporous silica. Catalysis Communications, 47, 11537–11539.Google ScholarPubMed
Ngaosuwan, K., Goodwin, J. G. Jr., & Prasertdham, P. (2016). A green sulfonated carbon-based catalyst derived from coffee residue for esterification. Renewable Energy, 86, 262–269.CrossRefGoogle Scholar
Okuhara, T. (2002). Water-tolerant solid acid catalysts. Chemical Reviews, 102, 3641–3666.CrossRefGoogle ScholarPubMed
Peng, L., Philippaerts, A., Ke, X., Noyen, J. V., Clippel, F. D., Tendeloo, G. V., Jacobs, P. A., & Sels, B. F. (2010). Preparation of sulfonated ordered mesoporous carbon and its use for the esterification of fatty acids. Catalysis Today, 150, 140–146.CrossRefGoogle Scholar
Suganuma, S., Nakajima, K., Kitano, M., Yamaguchi, D., Kato, H., Hayashi, S., & Hara, M. (2008). Hydrolysis of cellulose by amorphous carbon bearing SO3H, COOH, and OH groups. Journal of the American Chemical Society, 130, 12787–12793.CrossRefGoogle ScholarPubMed
Tang, X., & Niu, S. (2019). Preparation of carbon-based solid acid with large surface area to catalyze esterification for biodiesel production. Journal of Industrial and Engineering Chemistry, 69, 187–195.CrossRefGoogle Scholar
Tao, M. L., Guan, H. Y., Wang, X. H., Liu, Y. C., & Louh, R. F. (2015). Fabrication of sulfonated carbon catalyst from biomass waste and its use for glycerol esterification. Fuel Processing Technology, 138, 355–360.CrossRefGoogle Scholar
Toda, M., Takagaki, A., Okamura, M., Kondo, J. N., Hayashi, S., Domen, K., & Hara, M. (2005). Biodiesel made with sugar catalyst. Nature, 438, 178.CrossRefGoogle ScholarPubMed
Valle-Vigón, P., Sevilla, M., & Fuertes, A. B. (2012). Sulfonated mesoporous silica-carbon composites and their use as solid acid catalysts. Applied Surface Science, 261, 574–583.CrossRefGoogle Scholar
Wang, J., Xu, W., Ren, J., Liu, X., Lu, G., & Wang, Y. (2011a). Efficient catalytic conversion of fructose into hydroxymethylfurfural by a novel carbon-based solid acid. Green Chemistry, 13, 2678–2681.CrossRefGoogle Scholar
Wang, R., Jia, J., Li, H., Li, X., Wang, H., Chang, Y., Kang, J., & Lei, Z. (2011b). Nitrogen-doped carbon coated palygorskite as an efficient electrocatalyst support for oxygen reduction reaction. Eletrochimica Acta, 56, 4526–4531.CrossRefGoogle Scholar
Wang, Y., Wang, D., Tan, M., Jiang, B., Zheng, J., Tsubaki, N., & Wu, M. (2015). Monodispersed hollow SO3H-functionalized carbon/silica as efficient solid acid catalyst for esterification of oleic acid. ACS Applied Materials & Interfaces, 7, 26767–26775.CrossRefGoogle ScholarPubMed
Xiao, H., Guo, Y., & Liang, X. (2010). One-step synthesis of a novel carbon-based strong acid catalyst through hydrothermal carbonization. Monatshefte für Chemie, 141, 929–932.CrossRefGoogle Scholar
Xu, Y., Li, X., Zhang, X., Wang, W., Liu, S., Qi, W., Zhuang, X., Luo, Y., & Yuan, Z. (2016). Hydrolysis of corncob using a modified carbon-based solid acid catalyst. BioResources, 11, 10469–10482.CrossRefGoogle Scholar
Yang, Z., Niu, L., Jia, X., Kang, Q., Ma, Z., & Lei, Z. (2011). Preparation of silica-supported sulfate and its application as a stable and highly active solid acid catalyst. Catalysis Communications, 12, 798–802.CrossRefGoogle Scholar
Yang, J., Zhang, H., Ao, Z., & Zhang, S. (2019). Hydrothermal carbon enriched with sulfonic and carboxyl groups as an efficient solid acid catalyst for butanolysis of furfuryl alcohol. Catalysis Communications, 123, 109–113.CrossRefGoogle Scholar
Zhan, S., Tao, X., Cai, L., Liua, X., & Liu, T. (2014). The carbon material functionalized with NH2+ and SO3H groups catalyzed esterification with high activity and selectivity. Green Chemistry, 16, 4649–4653.CrossRefGoogle Scholar
Zhang, B., Ren, J., Liu, X., Guo, Y., Guo, Y., Lu, G., & Wang, Y. (2010a). Novel sulfonated carbonaceous materials from ptoluenesulfonic acid/glucose as a high-performance solid-acid catalyst. Catalysis Communications, 11, 629–632.CrossRefGoogle Scholar
Zhang, L., Jin, Q., Shan, L., Liu, Y., Wang, X., & Huang, J. (2010b). H3PW12O40 immobilized on silylated palygorskite and catalytic activity in esterification reactions. Applied Clay Science, 47, 229–234.CrossRefGoogle Scholar
Zhang, W., Tao, H., Zhang, B., Ren, J., Lu, G., & Wang, Y. (2011). One-pot synthesis of carbonaceous monolith with surface sulfonic groups and its carbonization/activation. Carbon, 49, 1811–1820.CrossRefGoogle Scholar