Fine-Tuning of Acidity in Hierarchical Zeolites for the Efficient Prins Cyclization Yielding Florol

Julián E. Sánchez-Velandia, Mykhailo Kurmach, Oleksiy Shvets, Hermenegildo Garcia Baldoví, Eduardo García-Verdugo, Dmitry Yu Murzin*, Nataliya Shcherban*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

Abstract

In this contribution, several hierarchical zeolites comprising mainly Brønsted acid sites with different morphologies (nanosheets, nanoparticles, nanorods) were synthesized and applied to the efficient synthesis of the perfume Florol (2-isobutyl-4-methyl-tetrahydro-2H-pyran-4-ol) via Prins cyclization of isoprenol and isovaraldehyde. Tuning the acidity in a zeolite was done by either incorporating metal centers or changing the initial composition and crystallization time. Furthermore, the interplay among the pore structure, specific mesoporosity, and accessibility of acidic sites is crucial for optimizing Florol synthesis. Strong Brønsted acid sites enhance the formation of the dehydration products, while mild-acidic Brønsted acid sites with a medium strength of accessible acid sites improve the formation of Florol. A maximum Florol yield of ca. 80% was achieved with Al-MFI and Al-FER (only 30 min) with typical nanosheet (nsh) morphology; in addition, values of TOF in the order of 1121 and 2655 h-1, respectively, were also achieved. Al-FER-nsh showed itself to be robust, because it can be reused several times without any apparent loss of its catalytic activity. Finally, different green chemistry parameters were also applied to the studied zeolites in the synthesis of Florol, suggesting the high efficiency of the best catalyst (Al-MFI-nsh).

Original languageEnglish
Pages (from-to)16283-16296
Number of pages14
JournalACS Sustainable Chemistry and Engineering
Volume12
Issue number44
DOIs
Publication statusPublished - 4 Nov 2024
MoE publication typeA1 Journal article-refereed

Keywords

  • acid sites
  • florol
  • hierarchical zeolites
  • Prins cyclization
  • tetrahydropyranol

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