Potential applications of Zr-KIT-5: Hantzsch reaction, Meerwein–Ponndorf–Verley (MPV) reduction of 4-tert-butylcyclohexanone, and Prins reaction of citronellal

Vinju Vasudevan Srinivasan,Adeline Ranoux,Ulf Hanefeld,Bala Subramaniam,Rajamanickam Maheswari,Anand Ramanathan

doi:10.1007/s11164-015-2157-4

Vinju Vasudevan Srinivasan, Adeline Ranoux + Show 4 more

Open Access

https://doi.org/10.1007/s11164-015-2157-4

Copy DOI

Abstract

The acidity of Zr-incorporated large pore cubic mesoporous silicate, KIT-5, with Fm3m symmetry was explored as catalyst in the Hantzsch reaction for preparation of 1,4-dihydropyridine (DHP) derivatives, Meerwein–Ponndorf–Verley (MPV) reduction of 4-tert-butylcyclohexanone, and Prins reaction of citronellal. The catalyst showed ~82–94 % selectivity for formation of DHP derivatives based on substituted benzaldehydes. For the intramolecular cyclization of citronellal, the activity and isomer selectivity increased with Zr content. Both these reactions proceeded to nearly total conversion in relatively short reaction times of 3 h and 30 min, respectively. In sharp contrast, MPV reduction of 4-tert-butylcyclohexanone yielded 95 % conversion in 4 days, similar to those reported for Zr-TUD-1.

Highlights

Zirconium-containing mesoporous silica composites have been investigated as solid acid catalysts based on the presence of Lewis acid sites created by Zr4? incorporation in the framework and the large surface area, pore volume, and uniform pore size distribution [1–4]
The acidity of Zr-incorporated large pore cubic mesoporous silicate, KIT-5, with Fm3m symmetry was explored as catalyst in the Hantzsch reaction for preparation of 1,4-dihydropyridine (DHP) derivatives, Meerwein–Ponndorf–Verley (MPV) reduction of 4-tert-butylcyclohexanone, and Prins reaction of citronellal
We investigate in this work if the Lewis acidic Zr-KIT-5 materials may be used as promising and alternative green solid acid catalysts for reactions such as the synthesis of DHP derivatives (Hantzsch reaction), Prins reaction of citronellal, and Meerwein–Ponndorf–Verley (MPV) reduction of 4-tertbutylcyclohexanone

Summary

Introduction

Zirconium-containing mesoporous silica composites have been investigated as solid acid catalysts based on the presence of Lewis acid sites created by Zr4? incorporation in the framework and the large surface area, pore volume, and uniform pore size distribution [1–4]. Abstract The acidity of Zr-incorporated large pore cubic mesoporous silicate, KIT-5, with Fm3m symmetry was explored as catalyst in the Hantzsch reaction for preparation of 1,4-dihydropyridine (DHP) derivatives, Meerwein–Ponndorf–Verley (MPV) reduction of 4-tert-butylcyclohexanone, and Prins reaction of citronellal. We investigate in this work if the Lewis acidic Zr-KIT-5 materials may be used as promising and alternative green solid acid catalysts for reactions such as the synthesis of DHP derivatives (Hantzsch reaction), Prins reaction of citronellal, and Meerwein–Ponndorf–Verley (MPV) reduction of 4-tertbutylcyclohexanone.

Results

Conclusion