Article history: Supercritical ethanol was used as a solvent for the thermal cyclization of ethyl 3-(phenylimino)-butanoate Received 14 September 2015 to 2-methyl-4-hydroxyquinoline; the reaction is of great importance in pharmaceutical and color indus- Received in revised form 30 March 2016 tries but conventionally needs speciﬁc solvents with high boiling points. The mechanism and the kinetics Accepted 30 March 2016 were studied with a microreactor by measuring the yield of the product at various temperatures up to Available online 30 March 2016 ◦ ◦ 350 C. The reaction in ethanol completed in 27 s at 350 C and 10.0 MPa giving the quinoline in 97% GC yield, although it required higher temperature than that in acetonitrile. The results were explained Keywords: by the mechanism consisting of the two steps: (i) a reversible elimination of ethanol from the reactant Supercritical alcohol yielding ketene intermediate followed by (ii) an irreversible ring closure into the quinoline. On the basis The Conrad-Limpach thermal cyclization of the reaction mechanism, the rate constant and the activation energy were determined from the yield- High-temperature and high-pressure ◦ −3 time proﬁles measured at temperatures of 300–350 C and a constant ethanol density of 0.11 g cm . The
The Journal of Supercritical Fluids – Elsevier
Published: Aug 1, 2016
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