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Competent, selective and high yield of 7-hydroxy-4-methyl coumarin over sulfonated mesoporous silica as solid acid catalysts

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Abstract

Highly ordered mesoporous MCM-41 and SBA-15 have been synthesized and functionalized with different amounts of propyl sulfonic acid groups using 3-mercaptopropyltrimethoxysilane as sulfur source. The synthesized catalysts have been well-characterized by different techniques such as XRD, FTIR and BET surface area and pore size distribution by BJH method. FTIR spectra of chemisorbed pyridine and temperature programmed desorption of NH3 techniques have been successfully used to characterize the acidic sites. The results showed that, both surface area, mean pore diameter and pore volume decrease as the extent of sulfonation increase. XRD results and TEM images confirm the stability of mesoporous long range order even after sulfonation process done. In addition, the study also showed that, sulfonation enhances the surface acidity and new moderate and strong acid sites were created. All the sulfonated catalysts under investigations have been found to be highly active and selective for the Pechmann condensation reaction of resorcinol with ethyl acetoacetate. More than 98% yield of 7-hydroxy-4-methyl coumarin was obtained with 100% selectivity. Presence of high number of moderate and strong Brönsted acid sites in sulfonated catalysts help in achieving high yields. Furthermore, the MCM-41 sulfonated catalysts showed higher catalytic performance due to their higher surface acidities.

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Acknowledgements

The Authors are highly indebted to the Institute of Scientific Research and Revival of Islamic Heritage, Umm Al-Qura University for financial support of this work through the project number 43405052.

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Authors and Affiliations

  1. Chemistry Department, Faculty of Applied Science, Umm Al Qura University, Makkah, Saudi Arabia

    Abd El Rahman S. Khder, Saleh A. Ahmed, Khalid S. Khairou & Hatem M. Altass

  2. Chemistry Department, Faculty of Science, Mansoura University, Mansoura, Egypt

    Abd El Rahman S. Khder

  3. Chemistry Department, Faculty of Science, Assiut University, Assiut, 71516, Egypt

    Saleh A. Ahmed

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  1. Abd El Rahman S. Khder
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  2. Saleh A. Ahmed
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Correspondence to Abd El Rahman S. Khder or Saleh A. Ahmed.

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Khder, A.E.R.S., Ahmed, S.A., Khairou, K.S. et al. Competent, selective and high yield of 7-hydroxy-4-methyl coumarin over sulfonated mesoporous silica as solid acid catalysts. J Porous Mater 25, 1–13 (2018). https://doi.org/10.1007/s10934-017-0414-1

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