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

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.

• Authors: Maura Koehle, Erisa Saraçi, Paul Dauenhauer, Raul F Lobo
• Journal: ChemSusChem (ChemSusChem) Vol. 10 Issue 1 Pg. 91-98 (Jan 10 2017) ISSN: 1864-564X [Electronic] Germany
• PMID: 27943648 (Publication Type: Journal Article)
• Copyright: © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Chemical References

• Furans
• Styrenes
• Vinyl Compounds
• vinyltoluene
• divinyl benzene
• Oxygen

Topics

• Acetylation
• Catalysis
• Furans (chemistry)
• Isomerism
• Oxygen (chemistry)
• Styrenes (chemistry)
• Vinyl Compounds (chemistry)