Production of p-Methylstyrene and p-Divinylbenzene from Furanic Compounds

Maura Koehle, Erisa Sara�i, Paul Dauenhauer, Raul F. Lobo

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

A four-step catalytic process was developed to produce p-methylstyrene from methylfuran, a biomass-derived species. First, methylfuran was acylated over zeolite H-Beta with acetic anhydride. Second, the acetyl group was reduced to an ethyl group with hydrogen over copper chromite. Third, p-ethyltoluene was formed through Diels–Alder cycloaddition and dehydration of 2-ethyl-5-methyl-furan with ethylene over zeolite H-Beta. Dehydrogenation of p-ethyltoluene to yield p-methylstyrene completes the synthesis but was not investigated because it is a known process. The first two steps were accomplished in high yield (>88 %) and the Diels–Alder step resulted in a 67 % yield of p-ethyltoluene with a 99.5 % selectivity to the para isomer (final yield of 53.5 %). The methodology was also used for the preparation of p-divinylbenzene. It is shown that acylation of furans over H-Beta zeolites is a highly selective and high-yield reaction that could be used to produce other valuable molecules from biomass-derived furans.

Original languageEnglish (US)
Pages (from-to)91-98
Number of pages8
JournalChemSusChem
Volume10
Issue number1
DOIs
StatePublished - Jan 10 2017

Bibliographical note

Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Copyright:
Copyright 2021 Elsevier B.V., All rights reserved.

Keywords

  • acylation
  • furans
  • para selectivity
  • sustainable chemistry
  • zeolites

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