Abstract
A novel loaded copper ion catalyst, Cu/MCM-41-SH, was synthesized using CuI-modified thiol-functionalized MCM-41 silica-based materials, and the prepared catalysts were characterized by XPS, FT-IR, SEM and N2 adsorption–desorption techniques. The XPS results indicated that the chemical valence of the copper that adsorbed on the CuI/MCM-41-SH surface was + 1 valence. N2 adsorption–desorption showed that the adsorption–desorption isotherms of both MCM-41 and CuI/MCM-41-SH materials were type IV with H4-type hysteresis loops, and the pore size and specific surface area of the materials were reduced. This work demonstrates that that when the reaction time was 2 h, the reaction temperature was 80 ℃ and the catalyst dosage was 100 mg, the conversion of tetralin was obtained as 92.63% and the selectivity of α-tetralone was 84.84%. The catalyst showed good reusability in the three recovery experiments. These results show that the catalyst has potential applications for green and sustainable development.
Similar content being viewed by others
References
S.E. Dapurkar, H. Kawanami, T. Yokoyama, Y. Ikushima, Highly selective oxidation of tetralin to 1-tetralone over mesoporous CrMCM-41 molecular sieves catalyst using supercritical carbon dioxide†‡. New J. Chem. 33(3), 538–544 (2008)
J. Kim, S. Bhattacharjee, K.-E. Jeong, S.-Y. Jeong, M. Choi, R. Ryoo, W.-S. Ahn, CrAPO-5catalysts having a hierarchical pore structure for the selective oxidation of tetralin to 1-tetralone. New J. Chem. 34(12), 2971–2978 (2010)
M. Mureseanu, A. Reiss, I. Stefanescu, E. David, V. Parvulescu, G. Renard, V. Hulea, Modified SBA-15 mesoporous silica for heavy metal ions remediation. Chemosphere 73(9), 1499–1504 (2008)
K. Danish, Shaily, Synthesis and catalytic applications of organo-functionalized MCM-41 catalyst: a review. Appl. Organomet. Chem. 37(3), 7007 (2022)
S. Pasricha, P. Gahlot, K. Mittal, D. Rai, N. Avasthi, H. Kaur, S. Rai, Functionalized MCM-41: versatile catalysts for organic transformations. ChemistrySelect 7, 7 (2022)
L. Song, Z. Duan, L. Zhu, Y. Zhou, Y. Xiang, D. Xia, Selective functionalization of external and internal surface of MCM-41 for adsorptive desulfurization. J. Porous Mater. 23(5), 1181–1187 (2016)
J. Xiao, Y. Jing, Y. Yao, S. Xie, X. Wang, C. Shi, Y. Jia, Synthesis of amine-functionalized MCM-41 and its highly efficient sorption of U(VI). J. Radioanal. Nucl. Chem. 310(3), 1001–1011 (2016)
X. Xiaofei, S. Ke, G. Jie, L. Shima, Z. Xianwu, H. Jian, Adsorption behavior of amino functionalized MCM-41 on chlorogenic acid from Eucommia ulmoides leaves. J. Porous Mater. 30(1), 71–81 (2022)
S.D. Dhengale, T.R. Bhosale, S.B. Shinde, C.V. Rode, G.B. Kolekar, P.V. Anbhule, An efficient and convenient heterogeneous Cu/MCM-41 catalyst for the synthesis of 7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one derivatives. Res. Chem. Intermed. 49(4), 1581–1600 (2023)
R.A. Shaikh, G. Chandrasekar, K. Biswas, J.-S. Choi, W.-J. Son, S.-Y. Jeong, W.-S. Ahn, Tetralin oxidation over chromium-containing molecular sieves catalysts. Catal. Today 132(1–4), 52–57 (2008)
C. Mahendiran, P. Sangeetha, P. Vijayan, S.J. Sardhar Basha, K. Shanthi, Vapour phase oxidation of tetralin over Cr and Fe substituted MCM-41 molecular sievess. J. Mol. Catal. A: Chem. 275(1–2), 84–90 (2007)
B. Dai, B. Wen, M. Zhu, L. Kang, F. Yu, Nickel catalysts supported on amino-functionalized MCM-41 for syngas methanation. RSC Adv. 6, 66957–66962 (2016)
J. Zhang, G. Huang, C. Zhang, Q. He, C. Huang, X. Yang, H. Song, Z. Liang, L. Du, S. Liao, Immobilization of highly active Pd nano-catalysts on functionalized mesoporous silica supports using mercapto groups as anchoring sites and their catalytic performance for phenol hydrogenation. Chin. J. Catal. 34(8), 1519–1526 (2013)
J.C.S. Terra, A. Moores, F.C.C. Moura, Amine-functionalized mesoporous silica as a support for on-demand release of copper in the A3-coupling reaction: ultralow concentration catalysis and confinement effect. ACS Sustain. Chem. Eng. 7(9), 8696–8705 (2019)
A.A. Fadda, E.H. Tawfik, M. Abdel-Motaal, Y.A. Selim, Synthesis of novel cyanine dyes as antitumor agents. Arch. Pharm. 354(3), 2000186 (2020)
P. Funk, R.B. Richrath, F. Bohle, S. Grimme, A. Gansäuer, Oxidation under reductive conditions: from benzylic ethers to acetals with perfect atom-economy by titanocene(III) catalysis. Angew. Chem. Int. Ed. 60(10), 5482–5488 (2020)
B. Gauni, K. Mehariya, A. Shah, S.M. Duggirala, Tetralone scaffolds and their potential therapeutic applications. Lett. Drug Des. Discovery 18(3), 222–238 (2021)
N. Sadou, S. Aichouche-Bouzroura, R. Nechak, B. Nedjar-Kolli, V. Morizur, S. Poulain-Martini, E. Dunach, Acid-catalyzed synthesis of thiazolidin-4-ones. Polycyclic Aromat. Compd. 38(4), 311–321 (2016)
G.P. Kantin, M. Krasavin, Reaction of α-tetralone, 1 H -tetrazol-5-amine, and aromatic aldehydes upon microwave irradiation-a convenient method for the synthesis of 5,6,7,12-tetrahydrobenzo[h]tetrazolo[5,1- b]quinazolines. Chem. Heterocycl. Compd. 52, 918–922 (2017)
K. Sharma, D.K. Sharma, A.K. Arya, M. Kumar, An efficient and ecocompatible synthesis of annulated benzothiazoloquinazolines in SO3H-functionalized ionic liquid. Res. Chem. Intermed. 41(7), 4133–4139 (2014)
N. Afsar, D.R. Jonathan, B.K. Revathi, D. Satheesh, S. Manivannan, (2E)-2-(4-ethoxybenzylidene)-3,4-dihydro-2H-naphthalen-1-one single crystal: synthesis, growth, crystal structure, spectral characterization, biological evaluation and binding interactions with SARS-CoV-2 main protease. J. Mol. Struct. 1244, 130967 (2021)
V.S. Chaudhary, Sweta, Study of ethylbenzene oxidation over polymer-silica hybrid supported Co (II) and Cu (II) complexes. Catal. Today 375(1), 601–613 (2021)
D. Dhaneswara, J.F. Fatriansyah, A.B. Mahagnyana et al., The ROLE OF MODIFICATION SBA-15 mesoporous silica with CPTMS in Cd adsorptions[C]//IOP conference series. Mater. Sci. Eng. 299(1), 012063 (2018)
X.-F. Kong, B. Yang, H. Xiong, Y. Zhou, S.-G. Xue, B.-Q. Xu, S.-X. Wang, Selective removal of heavy metal ions from aqueous solutions with surface functionalized silica nanoparticles by different functional groups. J. Central South Univ. 21(9), 3575–3579 (2014)
N. Rao, M. Wang, Z. Shang, Y. Hou, G. Fan, J. Li, CO2 adsorption by amine-functionalized MCM-41: a comparison between impregnation and grafting modification methods. Energy Fuels 32(1), 670–677 (2018)
O.F. Odio, L. Lartundo-Rojas, E.G. Palacios, R. Martínez, E. Reguera, Synthesis of a novel poly-thiolated magnetic nano-platform for heavy metal adsorption. Role of thiol and carboxyl functions. Appl. Surf. Sci. 386, 160–177 (2016)
M. Lolage, M. Chaskar, A. Ghosh, Synthesis, characterization and application development of ordered mesoporous silica in wastewater remediation. J. Porous Mater. 28, 1867–1879 (2021)
S.S. Bhoware, A.P. Singh, Characterization and catalytic activity of cobalt containing MCM-41 prepared by direct hydrothermal, grafting and immobilization methods. J. Mol. Catal. A: Chem. 266(1–2), 118–130 (2007)
J.E. Sánchez-Velandia, A.L. Villa, Isomerization of α- and β- pinene epoxides over Fe or Cu supported MCM-41 and SBA-15 materials. Appl. Catal. A 580, 17–27 (2019)
J.J. Schwab, E.C. Wilkinson, S.R. Wilson, P.A. Shapley, Nitridoosmium(VI) and nitridoruthenium(VI) complexes of cysteine(2-) and related ligands. J. Am. Chem. Soc. 113(16), 6124–6129 (1991)
A. Jafarzadeh, S. Sohrabnezhad, M.A. Zanjanchi, M. Arvand, Synthesis and characterization of thiol-functionalized MCM-41 nanofibers and its application as photocatalyst. Microporous Mesoporous Mater. 236, 109–119 (2016)
R.P. Vasquez, CuI by XPS. Surf. Sci. Spectra 2(2), 149–154 (1993)
M. Ma, H. Liu, J. Cao, P. Hou, J. Huang, X. Xu, H. Yue, G. Tian, S. Feng, A highly efficient Cu/AlOOH catalyst obtained by in situ reduction: Catalytic transfer hydrogenation of ML into γ-GVL. Molecular Catalysis 467, 52–60 (2019)
S. Kreft, J. Radnik, J. Rabeah, G. Agostini, M.-M. Pohl, E. Gericke, A. Hoell, M. Beller, H. Junge, S. Wohlrab, Dye activation of heterogeneous Copper(II)-Species for visible light driven hydrogen generation. Int. J. Hydrogen Energy 44(53), 28409–28420 (2019)
Acknowledgements
This work was supported by the National Natural Science Foundation of China (21763015) and Kunming University of Science and Technology Test Fund (2020M20192111060, 2022M20212111110)
Author information
Authors and Affiliations
Contributions
Author 1 (First Author): Conceptualization, Methodology, Software,Investigation,Formal Analysis,Writing - Original Draft; Author 2: Data curation,Writing - Original Draft; Author 3 (Corresponding Author):Conceptualization, Funding Acquisition, Resources, Supervision,Writing - Review Editing. Author 4: Visualization,Validation; Author 5: Resources, supervision; Author 6: Review & Editing
Corresponding author
Ethics declarations
Competing Interests
The authors have no competing interests to declare that are relevant to the content of this article.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Wu, C., Li, Y., Ma, Y. et al. Synthesis of CuI-modified thiol-functionalized MCM-41 silica-based materials and their catalytic tetralin performance. J Porous Mater 31, 913–922 (2024). https://doi.org/10.1007/s10934-024-01560-5
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10934-024-01560-5