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

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

Research output: Contribution to journalArticle

8 Citations (Scopus)

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 1 2017

Fingerprint

divinyl benzene
Zeolites
Furans
furan
Biomass
Acylation
Chromite
Cycloaddition
Dehydrogenation
Dehydration
zeolite
Isomers
Ethylene
Copper
Hydrogen
Molecules
biomass
chromite
dehydration
ethylene

Keywords

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

Cite this

Production of p-Methylstyrene and p-Divinylbenzene from Furanic Compounds. / Koehle, Maura; Sara�i, Erisa; Dauenhauer, Paul; Lobo, Raul F.

In: ChemSusChem, Vol. 10, No. 1, 01.01.2017, p. 91-98.

Research output: Contribution to journalArticle

Koehle, Maura ; Sara�i, Erisa ; Dauenhauer, Paul ; Lobo, Raul F. / Production of p-Methylstyrene and p-Divinylbenzene from Furanic Compounds. In: ChemSusChem. 2017 ; Vol. 10, No. 1. pp. 91-98.
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