Conversion
of furfuryl alcohol to 4-hydroxy-2-cyclopentenone
was studied in a microreactor channel of 0.5 mm diameter and 1.5 m
length. Addition of 1 M N-methylpyrrolidinone as
a cosolvent significantly reduces the polymeric material normally
formed during the reaction in purely aqueous solution. The reaction
follows pseudo-first-order kinetics at constant pressure (200 bar)
with the values of ΔH
⧧ =
18 ± 2 kcal/mol and ΔS
⧧ = −38 ± 3 cal/mol/K. At 240 °C, 200 bar pressure,
and residence time of 1.5 min, the product is obtained with 98% conversion
and is isolated as a stable O-phenylacetyl derivative
in 80% yield. This racemic mixture was resolved into enantiomerically
pure forms by kinetic resolution with penicillin G acylase (E.C.3.5.1.11)
immobilized on epoxy-activated polymer in 90–92% theoretical
yield and >99% ee.
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