A new series of zeolite-catalyzed Diels-Alder cycloaddition and dehydrative aromatization reactions between oxygenated furan dienes and ethylene are reported. It is found that pure Lewis-acid zeolites (Sn-BEA) are catalysts for the conversion of 5-substituted furoic acid derivatives and ethylene to 4-substituted benzoic acid derivatives. For example, the diene, methyl 5-(methoxymethyl)-furan-2-carboxylate, is converted to the dehydrated Diels-Alder product upon reaction with high-pressure (1000 psig) ethylene at 190oC (selectivity can be over 50%). The aromatic product of this reaction, methyl 4-(methoxymethyl)benzoate, can be used to produce terephthalic acid or its diester via oxidation. This new reaction pathway opens a completely new route for the production of terephthalic acid starting from glucose-derived HMF (5-hydroxymethyl-2-furfural) and ethylene, and avoids any costly reduction steps. Figure 1. <img src='https://acs-archive-assets2.s3.amazonaws.com/241nm/uploads/64286_figure1.jpg' alt='' />

New route to glucose-derived terephthalic acid using zeolite catalysts

248th National Meeting (2014)

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