Affiliations 

  • 1 Department of Chemistry, Faculty of Science, King Khalid University, Abha 61413, Saudi Arabia. mselvaraj@kku.edu.sa
  • 2 Department of Chemistry, School of Basic and Applied Sciences, RIMT University, Mandi Gobindgarh, Punjab 147301, India
  • 3 School of Chemical Sciences, Universiti Sains Malaysia, 11800 Penang, Malaysia
  • 4 Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi, Sangareddy, Telangana, India
  • 5 Department of Polymer Science and Engineering, Pusan National University, Busan 609-735, Republic of Korea
Dalton Trans, 2021 Jan 21.
PMID: 33475664 DOI: 10.1039/d0dt04158k

Abstract

The Prins cyclization of styrene (SE) with paraformaldehyde (PFCHO) was conducted with mesoporous ZnAlMCM-41 catalysts for the synthesis of 4-phenyl-1,3-dioxane (4-PDO) using a liquid phase heterogeneous catalytic method. For a comparison study, the Prins cyclization reaction was also conducted over different nanoporous catalysts, e.g. mesoporous solid acid catalysts, AlMCM-41(21) and ZnMCM-41(21), and microporous catalysts, USY, Hβ, HZSM-5, and H-mordenite. The recyclable mesoporous ZnAlMCM-41 catalysts were reused in this reaction to evaluate their catalytic stabilities. Since ZnAlMCM-41(75) has higher catalytic activity than other solid acid catalysts, washed ZnAlMCM-41(75)/W-ZnAlMCM-41(75) was prepared using an efficient chemical treatment method and used with various reaction parameters to find an optimal parameter for the highly selective synthesis of 4-PDO. W-ZnAlMCM-41(75) was also used in the Prins cyclization of olefins with PFCHO and formalin (FN, 37% aqueous solution of formaldehyde (FCHO)) under different reaction conditions to obtain 1,3-dioxanes, which are widely used as solvents or intermediates in organic synthesis. Based on the nature of catalysts used under different reaction conditions, a reasonable plausible reaction mechanism for the Prins cyclization of SE with PFCHO is proposed. Notably, it can be seen from the catalytic results of all catalysts that the W-ZnAlMCM-41(75) catalyst has higher 4-PDO selectivity with exceptional catalytic activity than other microporous and mesoporous catalysts.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.