2-Pentenoic acid → Carbon Dioxide

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An appropriate (and preferred) compromise between obtaining a high rate of GVL conversion and maintaining stable catalyst operation is achieved using an aqueous feed solution containing about 60 wt % GVL at 648 K and at a pressure of about 36 bar (see Table 1, entry 5). Under these conditions, catalytic activity remains constant for over 100 h of time on stream (see FIG. 4 and the accompanying text in the Examples). Under these reaction conditions, the following yields were obtained: 85% conversion of the GVL feed to form butene and stoichiometric CO2 (67% yield), pentenoic acid isomers (15% yield), small oxygenates such as butanol and propionaldehyde (2% yield), and aromatization/oligomerization products including octene and ethylbenzene (1% yield). The butene yield is limited by the unconverted pentenoic acid intermediate, and yields in excess of 90% are achieved using a 60 wt % feed at lower space velocities (Table 1, entry 7) with 100% of GVL conversion. Under these reaction conditions, pentenoic acid was not observed, and 93% yield to butene was achieved. The fraction of butene converted to C8+ alkenes and aromatics increased and accounted for the remainder of products observed (7% yield). The percentage of butene present as 1-butene (33%) compared to cis/trans 2-butene (67%) was higher than thermodynamic equilibrium, suggesting that 1-butene is the primary product.

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