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

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

Maura Koehle, Erisa Saraçi, Paul Dauenhauer, Raul F Lobo

ChemSusChem. 2017 Jan 10;10(1):91-98.

PMID: 27943648

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP105066	p-Divinylbenzene		105-06-6	Price

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